That may be the right path for you but I want to convince you that there might be another path.

I want to share my version of how I’m playing something Packy McCormick calls the “great online game.” A version that focuses on building a life where I can work in different ways to pay the bills, have plenty of time for creative pursuits, and don’t have to be tied to a full-time job.

What follows are five principles that have emerged that have guided my path. They have emerged slowly and organically. Only now do some of them seem obvious. I fully expect that they may morph over time. These principles serve as a compass for me as I navigate the infinite possibilities of the internet.

I think that nearly everyone, including people on the default path, should develop their own principles. This is because the stories of how we think about our work and lives are outdated, one based on a 1950s reality. This story worked in a time in which people worked for one company in their life when growth rates of 5% were normal, and most women didn’t work.

The trap of this story is that it actually works in the first few years of anyone’s career. Many companies still believe in this story and this is why the first five years of your career are still filled with promotions and a clear career path. Anyone that’s made it past that point, however, knows the truth. That there aren’t many clear career paths left and because of slowing growth rates, competition and politics are more central to getting ahead than some may think.

Developing your own principles and strategy is the only choice left if you don’t want to play those games. For the self-employed, developing your own game and set of principles is not a choice but a necessity. It is the only way to survive over the long term.

Here are five principles that help guide my path.

Principle #1: Coming Alive Over Getting Ahead

In April of 2020, my strategy consulting skills course started taking off. This was a weird moment because it took off at the same time I started dealing with extreme fatigue following complications from a tooth extraction. My course was selling like hotcakes and I was either wandering around the Canary Islands talking to doctors or sleeping in bed. This is one of the weird things about being a self-employed creator. Your financial reality can shift dramatically in a short period of time and often due to things outside of your control.

I had spent hundreds of hours to get it to that point but it was never my intention to hit a monthly revenue goal. I genuinely thought it would be fun to figure out how to create an online course (If you want to go much deeper, the full story is here). If you had talked to me in January of 2019 you might have thought my principles of keep doing stuff I like, give generously, and don’t work too much were pretty stupid because I had made less than $3,000 doing so in a year. Two years later I’ve somehow made a decent American salary for two straight years.

After a strong year of sales, I reflected on my success with StrategyU. My inner consultant knew that the obvious solution was to double down, add more courses, level up the marketing, create more content, and see where it goes. I was even invited to an accelerator program for proven course creators to make this happen. I could see the path and had a reasonable level of confidence that I could 4-5x my course sales if I wanted to.

But then I challenged myself, “what would you do once you had that money?” I realized I would write. I then reflected upon the fact that I could simply do that now. I was already making enough to support myself and still save a little money each year.

With this in mind, I decided to make a commitment. In 2021 I would write a book. This would be a way to commit to what I claimed to care about and also be a way of testing out this principle of “coming alive over getting ahead.”

My course has remained steady but has not grown much more than the previous year. However, the act of committing to writing a book has been one of the most thrilling commitments of my life. I’ve never felt so alive, challenged, and excited about anything I’ve worked on.

If a choice emerges between spending more time on making money but means I’ll have to cut back on some of the things I like doing like learning, writing, and connecting with people, I plan to walk away from that choice.

Principle #2: Don’t Be Attached

While my online course continued to succeed, I realized that I had come to expect that income.

With a few hours of maintenance per week, I was able to keep a profitable business running while writing my book and studying Chinese full-time for a three-month stretch. In one of those months, I even worked with a client to run a four-week consulting skills bootcamp which led to my best month since being self-employed. Then in May, the sales of my course tanked, likely driven by a change in the google search algorithm, people returning to the office after covid restrictions, and travel for the summer.

These kinds of ups and downs would be terrifying if I had a high fixed-cost lifestyle or if I had not experienced them before. To anyone that’s been self-employed for a long period of time, they learn to deal with these shifts. Here is an example of some various swings in different income sources I’ve experienced over the past five years.

With this in mind, I try to make sure that I’m not assuming that any of these income sources are permanent. I’ve embraced a visualization exercise where I go through an exercise of visualizing all my digital properties and revenue streams evaporating and then asking “am I okay?”

When my consulting course struggled for a couple of months after doing so well for more than a year, I was able to reflect on the fact that I’ve started from scratch in the past and I could do it again.

Principle #3: Build An Income Floor & Optimize For Income Streams

About a year into self-employment I realized I really want to stay on my path longer than my initial plans for a one-year experiment. I realized that if I wanted to commit to this path, I needed a better strategy for earning money than only freelancing.

Freelancing is one of the best ways to get started with self-employment. It enables you to leverage your existing skills while giving you more flexibility with time to spend on other things you want to work on or to simply work less. This worked well for me. I had much more time to work on creative projects but realized that following that path was a lower-income and precarious version of my previous path.

I wanted to embrace an antifragile approach, one in which I would not be as susceptible to stretches without income or to shocks in the broader economy. Freelancing is one of the best ways to make money in a strong economy, but it’s also one of the quickest things to disappear when companies are cutting costs.

With that in mind I set out to focus on two goals:

• Earn money in as many different ways as possible
• Build a portolio of income streams that act as a high probability “floor” of income

This lowered my income in the short term but boosted my confidence and resilience. Knowing how to make money in a number of different ways gave me practical skills and an expanded imagination about what I could do to make money.

While I had a hard time realizing it at the time, my overall income also steadily increased over time with this approach. I now have had at least three sources of income generate over $200 for more than a year and have had at least six income sources for longer than that.

In my first year of self-employment, I had high earnings but it was inconsistent. I had six months with less than $2,000 income and three months with more than $10,000 per month. The second year I shifted away from consulting and had seven months with less than $2k income. The last two years? I’ve made at least $2k every month.

This is much more valuable for the game I’m playing as it dramatically lowers the odds that I will run out of money and gives me more freedom to walk away from any type of work I don’t want to do without feeling like I might go broke

Principle #4: Start Slow & Keep Trying Things

I like trying a bunch of different things for a few reasons. First, I genuinely like creating new things and experimenting. I find the process of turning ideas into my head into things that can be helpful for others to be fun. This is a unique advantage in the world that is emerging and I’m fully aware of this.

Second, it keeps things interesting and also exposes me to a number of different ways of engaging in the world such that I can help others do the same.

Finally, it helps me build a portfolio of “small bets” as Dan Vassallo shared in this conversation with me – any one of which could have unexpected payoffs.

With my newsletter and podcast, both started as ways of sharing what I was up to and without any intentions of turning them into businesses. I didn’t promote them or share them widely because I wanted to be able to quit without people noticing. Tim Ferriss took this strategy with his podcast. He told himself that he would do six-episode and if he was having fun and didn’t hate it, he would keep going.

Conventional wisdom says to grow fast, to take advantage of every launch. However, that increases the odds that you end up doing something you don’t want to do. My approach has been to take a slower path. Five years into this journey, almost everything I’m doing I want to be doing and this has been from a series of incremental “yeses.”

I recently launched a freelance consulting skills course. This course was the result of helping a couple of freelancers that were doing work for me level up my skills. I realized I was having a lot of fun helping them be better and they were finding the information and feedback useful. I had validated both the idea and the feeling. That second part is often ignored. Too many people don’t think about the fact that once they build something that makes money, they have to spend a lot of time doing that thing. I only built the course because I enjoyed helping people become freelancers. Right now it’s still a small bet but when the opportunity emerges to take it somewhere else, I will consider it and if it feels right, I’ll say “yes.”

Principle #5 Make Friends. Be Helpful

This is the most important principle and the one that makes everything else more fun. Yet, it is also the one where I struggle the most.

I’ve always been the person that likes helping other people. In college, I proactively volunteered to help fix people’s computers and help with resumes, job searches, and interviewing. After I graduated I helped people make career changes and write essays for grad school. At my jobs I always took on extra roles to help with training and coaching.

It was fun. But the world tells you that these are silly things. People tell you, don’t get taken advantage of. Adam Grant writes books showing how to avoid being a pathological altruist and to make sure you balance yours gives with your takes. Others ask “why you don’t charge?” You spend your time at work helping your struggling colleague while you watch the skilled politician land another raise.

I was cynical about this for a while. I wanted the working world to change. I wished there were paths for people to progress and get raises while remaining a front-line manager. My first blog was called “better working world project.” Eventually, I realized it was better to create my own game rather than try to swim upstream.

So I experimented. I started a career coaching business on the side. I started writing. I eventually went out on my own and was able to be the kind of freelancer I wanted to be. I had more time to spend helping people for fun without feeling like an idiot (though sometimes it still feels silly to do things for free).

As I continued to do this and built an audience through my writing, people starting sending me thank you notes. I received one note from someone that I had a conversation with a few years earlier. She told me that her conversation with me completely changed her mind on what she wanted to do. Now she was doing something she loved and wanted to thank me for the inspiration. I’d be lying if I said that these moments are fucking awesome.

I did an exercise in which I had to rank my “yearnings” or the things we really crave. My top two were appreciation and freedom. Appreciation was something that surprised me but it felt true. Leaning into that and realizing that it is something I need but can also be fuel is a powerful thing to know.

A couple of years ago I did another exercise in which I had to write down my “purpose.” The person that created it said to keep writing versions until you cry. I thought it was silly but I’m always open to trying new things. It worked and this is what I landed on.

Connect as a real friend to people to give them the courage to create, help simplify the world to enable people to imagine new possibilities, and continuously be more brave in discovering the people and things that matter in my own life

I know that my desire to help others might be a little pathological and after reading Adam Grant’s Give and Take it seems that I’ll probably succeed financially a little less. But I don’t buy his argument that this is something to fix. I have realized that I want to design a life around making this weird quirk a great part of my life. I know that it undermines my ability to be financially successful sometimes and that’s okay.

I’ve just decided that it matters.

The Bottom Line

I don’t know what will be paying the bills next year but the longer I play this game the more confident I become. It could all blow up at any second, but the whole point of the game is to enjoy the journey.

I spent ten years on a path where I was always focused on the next project or the next step.

This is way more fun and I hope I’ve convinced you to find your own game worth playing.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Designing Your Own Infinite Game In The Creator Economy appeared first on Boundless by Paul Millerd.

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I connected with Visa on twitter, where he’s made many friends over the past several years. I wanted to interview Visa to talk about his leap to self-employment over the past couple of years, but we talked about so much more. We talk about:

• What the word “nourish” means to him
• His evolution on procrastination and getting started
• How to find like-hearted humans on twitter
• The “asshole problem”
• The curious humans of twitter
• How he creates his own work

Thinking On Twitter

Visa has gained a reputation on twitter for being someone that’s building a transparent “second brain” (h/t Tiago Forte), sharing whatever he finds with his followers.  

He says he does this mostly to keep track of what he’s learning and finding, but it also seems to be something that many people find value from.

• Link To All His Threads: Visa’s Threads

I asked him for his most overrated thread:

…and his most underrated thread:

His tips for getting started on Twitter

Many people worry about attracting attention of influential people. Instead, he suggests you just focus on building genuine connection. Here are the five steps he recommends for anyone that wants to dive in:

1. Don’t follow institutions – if its interesting, people will retweet it
2. Don’t follow people that won’t reply (+3,000 followers): 
3. Follow people with max of 1,000-ish followers
4. Have conversations with people
5. Make friends with their friends

Taking the leap to self-employment

I love his own tips on self-employment. The following tweet summarizes how he’s thought about his own leap (he say’s he us currently on step 4!)

He thinks people should be bolder in creating their own work and using your curiosity as a guide

you can do unpaid work for yourself. I suggest do anything you find interesting

He gives the example of a mean girls essay he wrote that (Power & Social Dynamics In Mean Girls) got a lot of attention from people that were “above his pay grade:

The trap some people fall into is they think they need to do what they think other people will be interested in…that;s like guesswork…and your guesswork is probably off by some degree that you don’t realize.

I love that model. Check out the episode and let me know what you think!

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Visakan Veerasamy On The Curious Humans Of Twitter & Creating His Own Work appeared first on Boundless by Paul Millerd.

Now the handouts are gone and those jobs are off the table. Right? Not according to LinkedIn. In the six months after New York pulled out of the deal, Amazon has hired more than 1,500 people in the greater New York City area:

In other words, they are on pace to meet their target in less than eight years (as opposed to the 15 years they had to do it).

How is it that we are operating in a world in which so many people are unable to find work that matters to them and at the same time, the richest man in the world is getting cities and states to write checks for $1.5 billion for bringing jobs he intended to bring anyway?

This is corporate welfare.

Corporate welfare may have been impactful at some point, but it is no longer serving us now.

In today’s world, corporate welfare often serves the people that need it least, in-demand knowledge workers. The kind of workers Amazon hires are already geographically mobile and actively making the job market work for them.

Why We Glorify The Full-Time Job

In the US, where less than a third of people actually work in full-time jobs, the idea of building economies around large companies and the jobs they offer is an idea from a time when General Motors employ nearly a million people, mostly in a small geographic region. At one point GM employed half of the population of Flint, Michigan.

If you could get GM to relocate to your town, you’d be pretty smart to give them a tax break.

However, over the past 25 years as supply chains and companies have globalized and much of work has become digitized, the kinds of massive companies that operate in one area are a dream of economies past. Now, we have a much more dynamic labor market, which has been great for certain types of geographically mobile and highly-skilled people, but terrible for others.

As the mythical era of steadily increasing salaries, loyalty and pensions is disappearing, we have yet to replace it with a new narrative of how we should think about work.

Many are unemployed or underemployed or even just at jobs where they are resentful and feel trapped. These people don’t just want another “job,” what they want is a shot to reinvent their lives and try something new, without the risk of shame and failure.

Mounds of research shows the health benefits of being employed and show that when people lose their job it is incredibly harmful on their health and mental state.

Have we ever stopped to think a bit deeper here and reflect that there’s something messed up about that?

One one hand almost everyone accepts that companies will lay people off in a second, but on the other hand almost everyone says that staying employed is the more important thing you can do to prove your worth to society.

We need a bit more nuance.

Basic Income As Diagnosis

Andrew Yang is the only current US politician who is speaking honestly about this confusion in the United States. His presidential campaign is founded on a Universal Basic Income of $1,000 a month for every American. When many come across this idea, their gut reaction is something like this:

WE CAN’T JUST GIVE PEOPLE MONEY FOR NOTHING!

Once people work through this outrage, they tend to find the arguments behind Yang’s proposal compelling. He is speaking honestly about jobs disappearing, economic growth stagnating and the fact that modern tech firms don’t need as many people to extract enormous wealth from the world and certainly aren’t hiring any people outside of a few elite cities.

Many people don’t realize this, but when President Obama backed off a single-payer plan for his healthcare overhaul in 2009 one of the biggest drivers was because of jobs:

I don’t think in ideological terms. I never have,” Obama said, continuing on the health care theme. “Everybody who supports single-payer health care says, ‘Look at all this money we would be saving from insurance and paperwork.’ That represents one million, two million, three million jobs [filled by] people who are working at Blue Cross Blue Shield or Kaiser or other places. What are we doing with them? Where are we employing them?

This is a shocking statement and not because of the political maneuvering. It’s shocking because Obama was indirectly accepting that many of these jobs are not even needed…but he wanted to keep them anyway.

The foundation of our economy and our work beliefs depends on there being enough good jobs for people that want them.

This is what makes Yang’s policy radical. He is not proposing to give people something for nothing. He is urging us to update our assumptions and map of reality based on how the labor economy actually works.

Human Capital 2.0

We have a model for thinking about investing in people, but we need to decouple it from the circumstances of its time. 

The idea of “human capital” was born in the 1950s and popularized in 1964 by Gary Becker’s book of the same name. His argument was that similar to financial capital, we need to see people as something we can invest in and that we should do much more of it.

When he put forth this idea, his measured success in wages. If $10 is put towards one’s education and that person is able to increase their earnings by $11, that’s a worthwhile investment.

The problem is that humans are not financial instruments. They are influenced by their family situation, existing resources, mental makeup and their environment. Many can also increase their salaries and earning potential by pursuing credentials detached from any underlying learning. 

Becker reflected on this years later:

This sharp fall in the return to investments in human capital put the concept of human capital itself into some disrepute. Among other things it caused doubt about whether education and training really do raise productivity or simply provide signals (“credentials”) about talents and abilities.

Becker’s “human capital” took off in a time when there was enormous faith in higher education and large corporations as the model for learning and working. 

During periods of rapid growth like the 50’s and 60’s incomes were increasing and people were progressing. Someone born in the 1940’s or 50’s had a 90% chance of doing “better” than their parents. This economic engine made investments in public education a no-brainer.

That era is over. 

We’re operating in a much less optimistic and much more expensive time. Although many acknowledge that education is a good thing, its hard to figure out how to translate money into actual outcomes. Even worse, people like Bryan Caplan argue that the whole system is waste of time. 

In his book The Case Against Education, he says:

The heralded social dividends of education are largely illusory: rising education’s main fruit is not broad-based prosperity, but credential inflation

We need an updated model of “human capital” — one that doesn’t think about humans as something that goes through a factory of learning, but instead people who have fears, hopes, aspirations, creative energy and even desires to be a contributing member of society outside of paid employment.

A Thought Experiment

Let’s imagine that you have worked full-time for five years after college. At that time, you are feeling like you need a break and you decide you will take a couple years off from the working world. 

For the next 24 months, you are going to focus on learning, reflecting on life and figuring out what you want to do next. During that time you also plan to meet people from different cultures, travel around the world, volunteer on different projects that interest you and also take time to spend with your family and loved ones. 

Instead of people giving you a hard time, they praise you. They say you are incredibly smart and what you are doing is very impressive. Many people even suggest to you that you may may a much higher income when you return to the working world.

Sound too good to be true?

What I just described was the full-time MBA. Every year tens of thousands of people leave their jobs around the world and begin a full-time MBA program. 

Everyone in their community praises them for this decision despite the fact that many go into upwards of $200,000 of debt and give up multiple years of salary. 

Yet when I quit my job and decided to start my own business, I was criticized by many people. Why would I take such a risky path and give up my guaranteed salary?

This response has puzzled me. When did the myth of the pull yourself up by the bootstraps American entrepreneur turn into the ideal of the American office worker with a stable salary?

This glorification of the safe full-time job has been great for the kind of high-wage tech workers who skillfully jump from good job to good job and it does wonders for the successful firms like Amazon who are able to make governments beg for them to take free money.

Our system has left behind the average worker. It pretends that there are plentiful good jobs available when there are not.

An example of an alternative approach is Alex Hillman’s 10k independents project, which aims to help 10,000 people build small independent businesses. He believes that by empowering creative individuals, you will inevitably build larger, more successful businesses and also create networks of individuals in local communities that can leverage each other’s skills.

In other words, Alex wants to create jobs, but he wants to do it by investing in people.

Because healthy economies, healthy cities, and healthy business ecosystems are interdependent, fueled by entities who are individually resilient and networked, depending on each other.

Creating 10,000 jobs makes for good PR, but rarely ever leads to the kinds of activities that help dynamic ecosystems emerge. It’s top-down PR politics. These corporate welfare programs help the most successful companies offer 20% pay bumps to the knowledge workers who already have the most opportunities and leverage.

People like Alex want to invest in people and enable them to build the lives they want while also developing new and unexpected skills.

He wants to build the foundations of a new economy. This is the hard, but meaningful work that we need.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Amazon, Corporate Welfare & The Illusion Of Jobs appeared first on Boundless by Paul Millerd.

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Andy Holloway is the founder of Holloway, a company that creates comprehensive, practical Guides researched, written, and refined by experts. He founded the company with the mission of “giving people tools to turn their brains on instead of off.”

We dive into the company, but also dive into Andy’s branding fiasco with his first “startup” as a child, how he started a brewery while still underage, a class and professor that changed his life in college, how he got started writing and how a lake can be a great metaphor for life.

We talk about a number of topics including

• Andy’s writing practice
• Teaching & modern education system
• A college professor that inspired him to think differently
• Unlocking wisdom from books on the internet
• Grappling with success & status in the modern world
• How he stays in touch with the people that matter to him

Here is the full quote we mentioned from Kurt Vonnegut:

When a couple has an argument nowadays they may think it s about money or power or sex or how to raise the kids or whatever. What they’re really saying to each other, though without realizing it, is this: “You are not enough people!

Full Quote Here

You can learn more about Andy and Holloway through his thoughtful Good Work Newsletter or go deeper by buying his guides on Venture Capital and other topics.

Some books we mentioned

• The Artists Way (Cameron)
• Linchpin (Godin)
• Mastery (Greene)
• The Art of Possibility (Zander & Zander)
• 10 Books To Escape The Corporate World (Boundless)

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Andy Sparks on Writing, Entrepreneurship, Success & Life As A Lake appeared first on Boundless by Paul Millerd.

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Passionate About The Ecosystem Behind Good Co-Working

Alex Hillman is passionate about co-working that works. He is the founder of Indy Hall, one of the longest running co-working communities in the world in Philadelphia. When he set out to create the space, he was really just intending to find others like him who were working independently and didn’t want to feel so lonely:

Alex missed the camaraderie he’d found in the companies he’d worked for in the past. He longed to bounce ideas off of creative colleagues, and learn from each others successes and challenges. Anything was better for his creativity and productivity than the isolation of working alone.

What started out as a “clubhouse” for independents ended up turning into a business that he’s still running 13 years later. While he doesn’t love the real estate management aspect of the business, he remains deeply committed to building and cultivating a community that people want to be a part of.

He worries that co-working has come to mean too many things to even be a useful descriptor. He sees many “co-working” spaces being run as real estate occupancy businesses without any deeper meaning:

coworking at its best isn’t an occupancy based business at all. If the only time your members can get value from their membership is when they’re in the room, you’re limiting the potential of your community AND fundamentally you’re limiting the size of your business by tying it to your square footage.

One thing he has found that works in co-working is focusing on the underlying relationships and the people instead of the work. Our natural tendency is to focus first on finding people to help us accomplish something. However, what he has found is that people that cultivate friendships and relationships first end up creating new opportunities and partnerships that last.

From our discussion:

If I look at the best collaborations, the best experiences, the most enduring business partnerships I’ve seen form through the Indy Hall community, its was people that built relationships before they started working together…we want to give people the opportunity to make relationships with people that they might need later, but they don’t need yet…

Alex Wants To Create 10,000 Independent Jobs

After seeing countries across the US lose their mind to woo Amazon and the prospect of tens of thousands of jobs, he thought there had to be a better way. He felt that getting one company to move to your city was not the best strategy (just look at Enron and Houston) for our modern working world.

As he started having conversations, he started brainstorming a more sustainable approach for local communities. This led him to publish a working draft (and in my interpretation, a plea for people to dream bigger!) of what he calls his “10k independents project.” Here is his starting point:

That level of dependence on a single employer is brittle at best and dangerous at worst. And that single source of 50,000 jobs being Amazon, who is notoriously one of the most ruthless businesses in the world, is the WORST worst way to generate those jobs.

We discuss his working plan to use Indy Hall as a basis to create 10,000 sustainable independent jobs. He thinks that through giving people the skills to create their own work, this will inevitably lead to many small (and perhaps a few big) employers that are more sustainable for ecosystems across the country/

More Reading:

• Cargo Cults
• Cubed
• Indy Hall
• Alex’s Writing
• 10K Independents Project

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Alex Hillman on Coworking That Works & The 10K Independents Project appeared first on Boundless by Paul Millerd.

In the months before the trip, I lost several projects and then lost a great project because they weren’t comfortable with me working remotely while I was in Asia.

I was feeling pretty crappy. I had turned down projects for a couple of months prior to focus on some creative projects, but was feeling pretty desperate to land some work so I didn’t feel so worthless in a busy American city.

A couple weeks before my trip, I had a client reach out about a potential project which was right in my wheelhouse. Towards the end of my pitch, I said “sooooo I have this trip planned to Asia. Would you be open to me proposing how I could still do this work remotely?”

They said sure. I was shocked.

The next day I sent them a proposal to spend 25% of my time working on this project from Asia for an hourly rate that would easily support my life over the next couple of months. They accepted it immediately.

A few weeks later in a surf-side cliff town in Uluwatu on the island of Bali, I spent about 5 hour working on the project for the first time from the location pictured below.

As I worked that day, it was one of the first times I was working and didn’t really have any resentment towards that work. How could I with such a view?

It was also the first time where I felt a little silly that I had spent almost a year freelancing and didn’t think about leaving Boston or New York to explore more of the world or visit friends. Especially if I could live here for $20 a night.

Almost a year later, I visited this same place traveling with my partner and realized that this moment, this day of working remotely and abroad at the same time, was a moment that forced me to dream a little bigger and question my own limitations I was putting on my life.

And now I always wonder, am I dreaming enough now?

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Are You Dreaming Big Enough? appeared first on Boundless by Paul Millerd.

The early positive impact of the emergence of two-sided talent platforms on freelancers has started to slowly erode due to three trends:

1. The “atomization” of the talent platform staffing process from one managed by highly skilled ex-consultants to one mostly outsourced directly to the freelancer
2. The proliferation of new talent platforms due to the zero marginal cost economics of a talent platform
3. The incentives of VC-backed talent platforms which prioritizes firm-level growth while ignoring the health of the overall ecosystem

I am going to walk through what I’ve seen as a former employee of a talent platform and now as a freelancer in the strategy consulting space. But first, let us jump back in time to the early 2000s.

Free Agent Nation Emerges

In the early 2000’s Dan Pink, after quitting his job at the White House, explored the trend of workers who left the default path and worked remotely, digitally or nomadically. 

He shared an anecdote from Bo Rinaldi, who was the head of a talent search firm, who shares unbridled optimism that was typical of the time:

“I believe in a talent-driven model,” he says. He has in mind something like the film industry. “In a temp agency, you test ’em and roll ’em out. In my model, everyone is a star.” The new realities of computers and networking make several of the old structures obsolete. “In the new metaphor of work, the loyalty factor is still very high. In the new metaphor of work, you have a smaller-team model and a greater sense of loyalty to the team than to this artifact known as a company. Companies do not exist. Countries do not exist. Boundaries are an illusion. But the team exists,” Rinaldi says. “The loyalty is also to you. This is the summer of love revisited, man!”

While these predictions may have not been fully realized (yet), they did describe an increase in opportunities for people bold enough to leave the default path.

Issue #1: Talent platforms have “atomized” the talent staffing process and outsourced much of the work to an unpaid freelancer labor force

The Talent Platforms 1.0 Companies Emerge

Around the year 2000, the original consulting talent platforms started to emerge. These companies, Talent Platform 1.0 Companies, offered projects to freelancers and in return asked for very little. If you were part of their vetted pool of talent and the right fit, just show up and start working.

These firms — a-connect, BTG, and Eden McCallum — were game changers for the few mavens that were already working independently and while these early consultants typically already had their own client base, were more than happy to trade off some of their earnings (or in some cases not at all because of a higher billing rate through the platform) for the work the firm did in helping source, vet and scope the projects. These firms helped solve a fundamental talent access and matching problem in an age where LinkedIn and Social Media didn’t exist yet.

These early talent platforms were “closed” platforms meaning that clients did not have visibility into the talent pool and the talent pool could not see the projects in progress or in the pipeline.

These firms were very hands-on, spending time building client relationships, sourcing and validating projects and scoping them so they were ready to go when the consultant was staffed. These firms employed highly-skilled ex-consultants and talent executives that understood how to staff projects and execute on complex consulting engagements. Both the clients and consultants were happy to let these firms capture 30–40% margins for all of this value that they offered.

The internal process was labor-intensive and depended on highly customized relationships with each client. These original platforms all explored opportunities for efficiency through having freelancers write their own proposals or debating easier ways for clients to submit projects, but they never really fit with the underlying business model.

After business school, intrigued by the emerging gig economy, I worked for a-connect. Growing up a digital native, I was shocked that they were not more aggressively “opening up” their platform to embrace a two-sided platform approach, enabling clients to submit projects directly and enabling the talent pool to bid for projects directly through a technology platform. 

I realize now, this kind of shift would have undermined the goals of the firms, whose success was dependent on building long-term relationships with clients and offering a world-class talent experience during projects.

Transparency! Talent Platform 2.0 Companies Show Up To The Party

While there had been some platforms that had embraced the two-sided approach from the beginning (freelancer.com, ODesk, Upwork etc..) none had emerged in the strategy consulting space until around 2012 when MBA & Company (now Talmix) and then Hourly Nerd (now Catalant) stepped onto the scene.

This was a big shift and now I realize why the initial talent platforms could not make the shift so easily.

This shift was not simply increasing the visibility of projects and letting freelancers directly compete for projects. It was a shift from the structure of the talent platform as a hands-on talent agency to a hands-off technology company.

It meant a major difference in the types of employees these new talent platforms hired. Instead of experienced ex-strategy consultants who could help scope and manage complex projects, these new firms depended on people that had some understanding of talent and a deeper understanding of how to use technology.

As two-sided talent platforms evolved, the customized talent approach was thrown out the window in favor of building a process that would make it as easy as possible for clients to post projects and for freelancers to bid on those projects.

What this meant most literally, was that freelancers and clients took a much more active role in the matching process, communicating directly on the firm’s talent platform. 

This was a shift from a talent-agency model to a technology company, a shift happening in most industries today. While one of the barriers to entry for a talent platform 1.0 was the availability of high-quality talent within the firm, the barrier to entry for a talent platform 2.0 company is only the technology, which operates on close to zero-marginal-cost economics.

Issue #2: The lack of a “winner take all” platform means every additional platform created more work for the freelancer

In a market with few players, network effects start to take over and result in a winner-take-all zero-to-one dominant player. For example, LinkedIn is the resume for any modern business worker. Instagram is the place for sharing photos. Google is beyond dominant in search, it is the verb used for searching. 

However, no winner has emerged in the consulting talent platform space and this is bad for everyone. As Peter Thiel offers in Zero to One:

“Customers won’t care about any particular technology unless it solves a particular problem in a superior way. And if you can’t monopolize a unique solution for a small market, you’ll be stuck with vicious competition.”

I can’t even keep track of how many talent platforms have e-mailed me a link asking me to sign up for their network. Here are 25 platforms that I have engaged with on some level:

Eden McCallum, GLG Strategic Projects, UpWork, Catalant, TalMix, PeoplePerHour, 10eqs, Business Talent Group, genioo, High Point Associates, a-connect, ex-consultants agency, expert360, mindbench, Consultants 500, localsolo, Sparehire, flexy, PwC talent exchange, comatch, Barton Partnership, LinkedIn ProFinder, Deloitte Open Talent Network, BBEcosystem, expertPowerhouse

Just last week I even received an e-mail from one of the Talent Platform 1.0 companies, Business Talent Group, announcing that they were opening up their platform:

While the emergence of the first few platforms was incredible for the early freelancers 

The high number of platforms leads to a few problems:

1. First, there is no incentive for the freelancer or client to use any platform over another. Harvard professors Feng Zhu and Macro Iansiti call this “multi-homing” which occurs when “users or service providers (network “nodes”) form ties with multiple platforms (or “hubs”) at the same time.”
2. Clients are incentivized to post any project, no matter how likely they are to pursue that project. Clients can access experts and freelancers and get “free” consulting through initial pitches and conversations without the need to start an actual project
3. A large amount of unpaid “busy work” for freelancers who wish to be in good standing and aware of the new projects appearing on the platforms. This work increases with the proliferation of platforms.

As a talent platform 1.0 freelancer, you didn’t have to worry about being a member of multiple platforms. This was due to the fact that the platform only approached consultants when the project was “real” and the fact that we could only ask freelancers to help us pitch to a client so many times without actually enabling them to win a project before losing their trust.

Instead of the recruiters validating projects, I now perform that work, trying to make sense of the 5–10 automated e-mails I received per week notifying me of new projects. Occasionally I receive a personalized e-mail, but most of the time I receive standardized e-mails that rarely vary and in fact, tend to be similar across firms. See if you can tell these apart:

Even if the project seems like a good fit, you realize quickly that many of the projects fail to leave the initial aspirations of the client inputting the project into the system. In other cases, you may “pitch” and never hear back or just be rejected without explanation. Over the past couple of years, I’ve “pitched” about 250 projects for 10+ different talent platforms and have actually worked on 6–7 projects totally less than $20,000 in gross fees.

As the crowd of freelancers increase, the focus of freelancer shifts to figuring out how to “hack” the platform so you can get projects. When I was first started to freelance, another freelance friend encouraged me:

underbid on projects just to get the positive reviews so you get recommended for more projects.

As the number of talent platforms increase, the value to the average freelancer on these platforms decreases. This is shown in the following chart, where I highlight the “Freelancer Value Ratio” which is my rough approximation for the chances of winning any project divided by the amount of work that freelancer does across all platforms.

I spent a couple of hours combing through UpWork’s IPO filing and financial reports to see if I could confirm this hypothesis. Trends on average freelancer earnings or distribution were noticeably missing from all of the reports. The closest I could come was assessing their trailing 12 months data from their filing:

• # of freelancers doing projects: 375,000
• # of projects: 2 million
• Overall Project Fees: $1.56B
• Average freelancer earnings (before UpWork fees): $4,160
• Average project fee: $780 per project

The mature state for a “successful” talent platform is still an overall talent ecosystem which generates more revenue and has many more projects than before but is a worse scenario for the average freelancer due to the amount of increased work due to the increase in platforms and the competition from the increased talent supply.

Issue #3: VC incentives undermine the health of the overall ecosystem

The talent platform ecosystem has been heavily influenced by the venture funding model of the talent platform 2.0 companies. Even Business Talent Group has taken funding to try to reinvent itself as a 2.0 company.

I’ve already shared how the entrance of these new types of firms increased the number of projects available at first and how that benefit tends to disappear with the emergence of more platforms and freelancers. So the benefits to the average freelancer decrease over time. 

If we look at the motivators of the individual freelancer and the incentives of a VC-backed platform, we also see a big difference in what each cares about:

The platform is motivated to grow the firm and develop strong relationships with as many clients as possible. They are aligned with clients over the long term, but not with the individual freelancer. As long as there are enough people that can do the projects, there is no incentive for the platform to care about the success of any individual freelancer.

This alignment is clear if we look at Upwork’s S-1, the filing from the largest talent platform’s IPO last year. It’s first two points in its strategy are “Increase Spend from Existing Clients” and “Attract New Clients Through Marketing Efforts.” 

The only mention of freelancers in the strategy is its goal to “Remain a Preferred Platform for Freelancers” with an action to “continue to invest in new products and features to help freelancers grow their businesses by finding more work and increasing their earnings.”

Thee typical freelancer wants to earn more but is not motivated to make the platform as much money as possible. Most self-employed types are motivated by designing a life that gives them flexibility, the stability of income and community & connection. 

While some people working at the platform may take interest in these motivations, the survival of the platform is dependent on meeting the goals of the client, not the freelancer. If the number of freelancers was fixed, this would be a trade-off worth making.

Based on these incentives, the behavior of people working within the talent platform is always going to shift towards pleasing the client and investor.

It would not be reasonable to expect a VC-backed talent platform to prioritize relationships with freelancers, focus on building a work-class talent experience or sharing in the upside with the freelancers. Nor would the freelancer want this (at least in the short-term).

If they don’t keep growing, keep winning clients and scaling, the platform will die. 

However, given the short-term behavior of the firm and the lack of strong relationships with the firm, the incentive of the freelancer is to explore all possible ways to meet their goals without having to use any platforms.

Feng Zhu and Grace Gu found exactly this behavior, often referred to as “disintermediation,” when they studied a talent platform:

One of us, Feng, and Grace Gu, a doctoral student at Harvard Business School, saw this effect in a study of an online freelance marketplace. As the platform improved its reputation-rating system, trust between clients and freelancers grew stronger, and disintermediation became more frequent, offsetting the revenue gains from better matching.

On several projects I’ve pitched for freelance platforms, I make the initial pitch via the platform, have a call with the client to scope the project and then send a proposal and contract I write myself. 

It is easy to think “I do all the work, so why am I giving 20% of all my fees, for the length of the project, to this platform?”

Part of this neglect may be because the gig economy is not that big compared to the enormous opportunity within companies.

Catalant has already explicitly made this shift towards helping clients leverage their internal talent more efficiently rather than leveraging external experts. Their founder Rob Biederman shares:

Initially, Pat and I saw the opportunity to make external experts available with senior-level experience available to our clientele. The combination of the right experience and a fair price point was attractive to a wide range of companies, particularly smaller companies. But, as the company evolved, we’ve seen the potential to make great talent — both internal and external — more accessible and more efficient through new technologies.

Perhaps the freelancer is the ultimate sucker, hoping that these talent platforms will magically morph to align with their motivations for being self-employed.

As long as full-time employment is the default option for knowledge work and new VC-backed platforms continue to enter this space, it may never be a thriving ecosystem for freelancers.

Three Ideas For The Next Evolution Of Talent Platforms

As a freelancer, I want these talent platforms to succeed. The introduction of firms like Catalant and TalMix have been a net positive in my life. However, as the number of firms has proliferated, I can’t keep track of the number of requests to fill out profiles on new platforms or e-mails sending my projects of doubtful reality.

#1 Focus on Niche Talent Pools & Problems

Gigster and Toptal are two companies that have kept ownership of some of the talent staffing process and been very focused on specific segments of talents and types of projects. Both companies are highly selective for the types of people they allow on their platform. Gigster claims to only accept the “ the top 1% of the software engineering labor pool” and TopTal claims to hire the “Hire the Top 3% of Freelance Talent.”

In addition, they are very focused on the types of projects and talent pools they operate. As seen below, Gigster has mostly focused on technology talent and has grouped its “solutions” across six specific types of problems that companies typically solve:

By limiting the talent pool to a specific type of talent and focusing on a specific number of projects, the company learns what works, helps to scope more complex and higher-priced projects and develops relationships with a very specific talent population. 

TopTal focuses even more explicitly on specific talent archetypes:

These firms are making clear operating decisions. By being highly selective on the types of talent and retaining control over more of the talent process (rather than outsourcing it to the freelancer), they are able to charge premium fixed fees to clients ($100k — $1 million) and pay their freelancers incredibly well, sometimes up to $300 an hour.

Some firms have attempted to copy this, allowing consultants to “advertise” their own services. For example, I have several services listed on my Catalant platform:

In their research of what enables platforms to thrive Professors Marco Iansiti and Feng Zhu find:

“ Lasting competitive advantage hinges more on the interplay between the platform and the network it orchestrates and less on internal, firm-level factors”

Is this is true, how have Gigster and Toptal created enormous value? I believe it is because when you have many individual freelancers making decisions on how to pitch projects, they are likely optimizing around their life principles rather than the overall health of the platform.

By “owning” more of the talent process, Gigster and Toptal are likely reliant on a different internal talent profile than the talent 2.0 companies. Instead of having technology adept salespeople, Gigster and Toptal need people who know how to manage complex projects and scope them with high-value clients.

In the strategy consulting space, only firm that has made an attempt to launch a productized offering is Innosight X, which recently launched.

They have tried to package their services around specific projects with specific timeframes and deliverables.

By focusing on productized offerings, the platform will be able to learn from its projects and continuously improve its current offerings while adding new ones and not compromising on pricing.

The key shift that is enabling a company like Gigster to be valued at close to $1 billion is that they have decided not to outsource all aspects of the consulting process to the freelancer and consultant. They are taking advantage of the innovations of talent platform 2.0 companies with the personal touch of the talent platform 1.0 companies.

These are the types of platforms that freelancers will want to work with.

Note: Some People have mentioned to me that TopTal and Gigster are not as great as I’ve made them out to be. Regardless, I think their business models are worth highlighting as a counter-narrative to the outsource all tasks approach typical of the talent platform 2.0 companies.

#2 Find ways to create a “virtuous cycle” with freelancers

Many freelancers are used to offering help to others without expecting anything in return. However, most are sensitive to organizations which don’t operate from a principle of generosity. 

Given that I’ve written quite a bit about talent platforms, I’ve had several talent platforms reach out to me and have conversations with their leadership team about what they can do better for talent. It seems that many explore the idea, but never really take any action. The ideas I’ve offered include:

• Make it easy for freelancers to refer project and share in the commission
• Open up office space or help solve “life design” problems for the freelancer
• Build customized product offerings around a limited set of freelancers 
• Consider having a paid tier of access for projects for freelancers where the talent platforms are more hands-on in vetting, scoping & staffing projects

An easy “quick win” for talent platforms is to figure out reduce the number of projects that never turn into anything. The talent platform 2.0 companies rely on the unpaid labor of freelance consultants to screen projects and submit pitches. The incentives of the platform are to get clients to post as many projects to the platform as possible, as there is no labor cost to the unpaid freelancers submitting pitch after pitch for projects that may not exist. At a minimum, the platform could show information on what projects actually get staffed. As long as another freelancer gets the work, I’d still be pretty pumped. But how many of my project pitches disappears into the gig economy black hole of never started projects? 

There are many other things the talent platforms could do, but they all fall under the category of things that would help the freelancers lives while also building more brand loyalty and trust with the platform. How do you build a platform that is able to meet its goals while also creating a community freelancers want to be part of.

It is my hypothesis that this virtuous cycle will be foundational for the talent platform 3.0 companies that will win in the space.

#3 Embrace the generosity and human touch of talent-owned platforms

Umbrex is a talent platform for strategy consultants founded by a freelancer himself, Will Bachman, who wanted to build a community of independent professionals where groups of people could share potential projects (and share in the upside) and get together for personal development and community gatherings.

As a member of the network, I have found it to be a dramatically different feel than the technology-based talent platforms. Bachman is transparent about the fees he takes for projects (which are usually negotiable), his willingness to share a cut with freelancers who refer projects and authentic in operating from a position of generosity and compassion in how he constantly thinks about supporting freelancers, finding tools for the community and bringing people together. 

If a technology talent platform wants to succeed, they will have to build in the humanity and generosity that are foundational for talent-owned platforms.

For a vision of what might be possible, we can look to New Zealand, where Enspiral started as a collection of independent freelancers and has emerged into a platform for building companies, social ventures and consulting projects.

New Zealand’s Enspiral Network has also created an inspired model of freelancer collaboration and community. What began as a coworking space among like-minded people in Wellington six years ago has evolved into a new-fangled cooperative linking freelancers and social enterprises in a global network of mutual aid and collective action.

Despite some success in launching companies within this platform such as Loomio and innovating on how to collectively make decisions and run a firm like this, the model isn’t perfect.

“Our freelancer co-op model is still underdeveloped,” cofounder Joshua Vial explains. “We face many unsolved challenges such as recruiting leadership, providing income security, managing quality, securing sufficient working capital, resourcing work ‘on’ the business and supporting people without managing them.”

Paul Millerd writes about the future of work from the self-employed perspective and is fascinated with how our relationship with work will evolve in the future. He works with talent platforms and consulting firms who want to work with the gig economy more effectively and to help them with their positioning and strategy. He also writes a weekly newsletter where he explores the topics in more depth.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Failed Promise Of Freelance Consulting Talent Platforms appeared first on Boundless by Paul Millerd.

#1 Make A Friend Taking A Different Path

People who take a leap often cite a strong influence that gave them proof or the courage that they could do something different. For some, this person is in their own family — a parent or grandparent who lived and worked on their own terms — often an entrepreneur. 

It can also be someone you meet serendipitously. On my podcast, I talked to Lydia Lee, who had a meaningful conversation with someone who was living and working nomadically in Malaysia. It told her that this kind of life was possible, but more importantly, told her that her circumstance in the corporate world was not the only path.

This “friend” can also turn into a partner. Some people find that they want someone else to join them on this journey. This is often the case in entrepreneurial ventures where someone is starting a business. Having a co-founder not only makes your path seem less crazy, it can also be more fun as you learn and grow.

#2 Redefine Money

Everyone who pursues self-employment has to face their emotional relationship with money at some point. 

A paycheck from full-time employment is a rather peculiar arrangement if you frame it in the entire history of humans. In self-employment, you shift away from this arrangement and instead of getting paid a steady income for performing the duties of an employee (showing up, being available, doing good work) you will be getting paid for work you find, things you sell or projects you complete.

There is often an “a-ha” moment when people start a journey of self-employment that has them suddenly look at their expenses instead of their income. People realize any spending means more paid work needs to be done. People will often start taking active steps to lower their cost of living or if they aren’t willing to compromise a certain lifestyle, look for more ways to make money or charge more for their current work. 

The self-employment fear setting exercise I created can help you grapple with some of your money insecurities by explicitly stating the least amount of money you are comfortable making and how long without paid work you are willing to go. This reflection may even tell you that you don’t actually want to make the leap.

#3 Build A “Say No” / “Eff You” Fund

Build up some cash savings. This can build on #2 — you may find that you can dramatically cut your cost of living for several months to build some savings. Having savings for your leap enables you to “pay yourself” when you want to say no to a project that might drain your energy or even take a few months off to work on a creative project that is calling you.

Mohit Satyanand built his own fun by aggressively saving early in his career:

I chose to be different very early. Within a year of joining the ranks of management trainees at a multi-national corporation, I realised that I was not meant to be a corporation man, that I needed to live in nature, to watch the peaches grow. In my spare time, I drew up business plans to run a dairy farm, or drive a tourist taxi. Most importantly, I realised I needed to build up a war-chest from which to fund my freedom. My F*** You Fund, I called it.

Even if you don’t have massive savings, dealing with a dwindling savings account can be a way to stare face to face with your fears and to bet on yourself. Despite my savings, I went through a several month period early in my journey where I didn’t earn any money. I felt terrible, but it also helped me realize how much pressure we put on ourselves to fit into a standard narrative of success.

It might even be helpful to look at your journey as a sort of Master’s education in life. Even if the leap doesn’t work out, many people find that the experience helps them deal with uncertainty, gain confidence in their work and in many cases if people decide to return to work, return in a better and higher-paying role with a bit more wisdom.

#4 Teach Others

We all have so much knowledge than many would die to know. What about your path or journey in life is different? How can you teach that to other people? I recommend creating a list of 25 things you might be able to teach people. This can be as simple as a new way to fold shirts or as complicated as theoretical physics.

One way to put this into action is to write about something you know. An article could be “Here are 5 Things You Should Know About X.” Writing it will have the dual impact of forcing you to learn it at a deeper level and put something out in the world that people might respond to. You may find that others are hungry for the insights you have to offer which gives you a clue to keep following that path.

Another option is to post on social media or e-mail your connections and give them a list of five things you are passionate about sharing with others. I suggest posting something like this:

Hello friends!

I’m doing a fun course online where I’m pushing myself outside of my comfort zone and experimenting with new ways of working. I’m doing a challenge this week where I need your help. I am looking for someone that wants to learn. Here are a few things I know about that I would love to teach you more.

1. XXX

2. XXX

3. XXX

4. XXX

All I ask is that you give me $25 for the “lesson” — this is to keep us both accountable and to raise the stakes on myself so I don’t disappoint you. If I do disappoint you, its $30 back to you so you can enjoy a free coffee on my dime.

Who wants to learn something? Message me

I suggest charging to help you stay accountable and it will help you with #5.

#5 Experiment & Get Paid

You need to have some evidence (for yourself and your confidence) that you can literally go through the process of getting paid for something outside of full-time employment. 

One easy idea that most people can do is to host a topic-related dinner around a certain theme and gather 8–10 people for high-quality food and conversation. People crave these kinds of intimate gatherings and are more than happy to pay $15–20 (or even more depending on the food).

We often underestimate our own networks and the people that may want to work with us. Many people feel bad hitting up their connections and asking them for help with their work, but find that these are exactly the people that want to support them. Plus, people could be waiting to be helped by you but didn’t know there were people in their network that could help.

Here is an example of an e-mail I sent to 100 friends and family that led to two clients hiring me. It was terrifying accepting payment from clients, but it gave me the confidence to experiment further. While still employed I got paid for two speaking gigs, a group coaching event and by several private coaching clients. These were all small fees but gave me confidence that I could make money on my own.

Don’t worry too much about the pay. A pro-bono engagement can be just as rewarding. I did multiple pro-bono coaching and consulting engagements before taking my leap, but treated them as serious commitments. I asked the same of my clients and that they offered generous feedback during and after the experience.

People underestimate the opportunities that are available to them. We are trained to think that we need to find a job before we can start doing something. However, if you are truly passionate about something and willing to offer it for low or no-fee, people are usually more than enthusiastic to be part of your learning journey. For example, if you want to start freelance consulting, you could send this message to an organization you admire:

Hello, I’m a big fan of your organization and have enjoyed how you have focused on X over the last year.

I’m currently in the process of making the transition to freelance consulting and am looking for a couple of initial clients to work with. I wanted to see if you’d be open to a low-fee or pro-bono project where I help you work on Y.

Given this is a path I’m incredibly excited about, I’ll be taking this very seriously. All I ask is that you are generous with feedback and be very direct in helping me determine if companies would be open to paying for this type of work.

Most companies would jump for the chance to work with someone with such initiative and desire to learn.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Five Things You Need Before You Quit Your Job appeared first on Boundless by Paul Millerd.

The benefits and upsides of self-employment are priceless and often overlooked

 

When I took the leap to self-employment, it was an act of desperation. I had lost faith in the leaders I saw around me in the business world, felt disconnected from the work I was doing and had started to question whether I would be able to stay true to my leadership principles that I felt were slipping.

What I found in my journey of self-employment has been a shocking amount of upside and unexpected benefits. If you follow the #futureofwork conversation in the media, you read mostly about people being exploited and underpaid, people without benefits and financial insecurity.

These are major issues that need to be solved but if you dig deeper into the research you find that despite all of the downsides, people are choosing self-employment over traditional alternatives.

When people ask me about working on my own, they say things like “I could never do that, I need to get paid every month.” While financial insecurity is real, most miss are the enormous upsides, many of which I could not have anticipated until I had the courage to take my leap.

---

#1 Doing things that matter with an “opportunity mindset”

To be a successful full-time employee, you must navigate a complicated system of “hoop-jumping” as William Deresiewicz noted in his famous commencement speech. You focus all your energy presenting yourself as someone that meets a standard.

I was an accomplished, if not excellent, hoop jumper. I even created a 45+ page “Career Transition Playbook” that I give away for free since it never really felt right to monetize my knowledge of a system so focused on the wrong things. The problem with this system was that it is impossible to get through the hoop-jumping without telling some sort of marginal lie about who you are and what you hope to achieve.

Being self-employed, an “opportunity mindset” flips this broken paradigm:

1. Put myself out there in the world as I am

2. Look for opportunities that look interesting or people that inspire me

3. Connect with those people or groups and share my story fully

4. If there is a connection, find ways to work together and see what happens

Earlier this year, I was at a memorial service for the founder and director of the grad school program I attended. During the service, several people spoke of this man’s commitment to the community.  I admired this and I felt pulled to find a way to offer myself to the program.

I e-mailed one of the professors asking if I could help and he proposed that I be a teaching assistant for the summer leadership seminar. Taking this position made no sense from a financial perspective, but made complete sense in my new self-employed universe.  It was the point of becoming self-employed: having space to say “yes” to things that mattered to me.

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#2 Being forced to define my own success

In the corporate world, I always received the most praise when I started a new job or got a promotion. Combine this with the ability of anyone to take your title from LinkedIn and plug it into Glassdoor to see how much money you make and your definition of success (even if you have one) is undermined by our collective obsession with money and status (and our ability to figure out where you stand).

A feature and a bug of self-employment is that you have no idea what people are making and you have no way to judge them. This forces some to ask you about what you are working on. While people do still ask about extrinsic factors (“how big do you want to get?” “how many people do you want to hire”), it is more natural to shift the conversation to the definition of success I have defined.

While many people still think my goals may have to do with money, self-employment forces a shift to think about how to live a life you are proud of rather than thinking about your job or career above all else. In his book Skin In the Game, Nassim Taleb echoes this sentiment which closely aligns with how I now think about success:

“I will keep mentioning that I have no other definition of success than leading an honorable life.”

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#3 Not Being In A Rush

In the corporate world, there is always a sense that you could be moving faster. The two years I spent in New York were the most extreme version of this. Someone once said to me, “you’re doing well for your age” which must have meant I was headed in the right direction. Personally, I was already plotting my escape.

A career is an artificial path which you must always manage, have a story for and be networking so that you can take the next step. The next step being up, of course.

Being self-employed, there are no promotions or paths to judge yourself against. Other people’s confusion with this fact comes out when people invariably ask “what’s your plan?” or “how’s business doing?”

While this question has no answer, I respond with what I know to be true: “I am following my creative energy and seeing where it takes me.” This tends to drive a lot of people who are deep into career thinking a bit mad.

The poet David Whyte offers the idea of the “pathless path” which I take to mean that there may be a general feeling that you are headed in the right direction, but that you may not know which direction that is.

Staying true to my inner creative drive and trusting that things will work out forced me to put faith in other people, see myself as part of a bigger community and world and think deeply about how I can be a more generous member of this world and my communities.

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#4 An escape from the inevitable insanity of corporate cultures

While the corporate world embraces teams, careers are an individual sport. While I may have been praised for helping others in my jobs, I would not be promoted, given a raise or good bonus without shameless self-promotion.

Managing your reputation and any gaps between perception and reality are perhaps the core work of a full-time job and career. Lacking strong cultures to transcend this, most organizations end up rewarding people who are good at acquiring power, which poisons the culture, destroys trust and makes most people within those organizations a bit nauseous.

Working on my own, those dynamics are non-existent. The energy wasted on that drama can be re purposed to all sorts of positive activities in my life, including ironically helping people recover their sanity from within those toxic cultures.

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#5 Detaching from the self-importance of career and embracing vulnerability

For the longest time, I identified as a successful professional who worked for good companies and went to good schools. That was the problem.

Today’s knowledge economy, once you’ve gained access, has almost no downside. You can go from job to job and even if you “fail” you’ll probably still get a higher salary in a new job. Facing vulnerability or uncertainty is to be feared, but rarely experienced.

Working on my own means an almost constant sense of fear, uncertainty and vulnerability. If I ran from vulnerability, I could not make this work. Within that vulnerability, I have had to dance with my fears and take action regardless. Doing so has made me feel much more alive than at any moment in any previous jobs.

Brene Brown shares her wisdom on vulnerability with us by pointing out, “Vulnerability is the birthplace of innovation, creativity and change.”

While creating and sharing in public is scary, it has had the counterintuitive outcome of making me realize that I am in fact, not that special and that perhaps I have tapped into a courage I did not know I had before.

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#6 Instant connection & camaraderie

Without a team or office to go to every day, I’ve had to purposefully start cultivating relationships and connections. The best way I’ve found to connect with people is to share my story, both through writing and in-person connections.

When I share my story and what I’m passionate about, I often here an offer “you have to meet X!”

At a conference in New York, someone I had met connected me to another self-employed soul working on many of the same things as me. That connection started with an enthusiastic video call, but quickly moved into a real-life friendship and hopefully future collaboration. This process has happened over and over again. Many people underestimate how many people are out there in the world who may be on a similar journey.

When you combine mission with the shared experience and vulnerability of being self-employed, I’ve found it often turns connections into meaningful friendships in no time.

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#7 Being able to “ramp down” my paid work

Being self-employed, the money shows up after you complete work or projects. This can be much less consistent or predictable than full-time employment. Here is what my income looks like over the past fifteen months:

 

Some of this inconsistency is by design. Over the past year, I took two one-month trips to test out extended travel. One trip was completely without any work and one I was able to take while doing some remote work.

In months 10 and 11, I said no to all incoming work because I wanted to work on my podcast and launch the future of work mindset assessment that I had been building. Neither were projects designed to make money, but burning ideas that I needed to create to feed my passion.

Being able to “ramp down” your work is a huge feature of being self-employed not available to many full-time workers. To take a leave of absence or unpaid leave is a sign of failure. This is why so many people often “burn out.”

Working on my own, I can take time to recharge, spend time with family or focus on projects that I’m excited by to make the journey a lot more sustainable. My goal for this summer is to spend 50 days working or not working remotely hanging with my grandmother and family at the family lake house. This would be almost impossible if I were working in a traditional full-time job, but quite easy with the ability to ramp down my work and push for more remote opportunities.

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#8 Re-framing money

Photo by NeONBRAND 

A steady job meant my income on autopilot. Paychecks showed up in my bank account no matter what. Since I was lucky to have jobs that paid me much more than I needed, it led to a certain recklessness and willingness to pay for convenience because much of my time was spent at said full-time job. $300 for an Acela train to Boston to save 45 minute? Done. $75 dinners? Why not?

My relationship to money has flipped. Periods of unpaid work are not a failure, but valuable space to let my creative energy run wild. After all, this journey is a long-term committment.

I’ve also lost a lot of interest in expensive things and experiences. The more I spend, the less creative space I’ll have in my life. There are some things I still splurge on, but I’m much more intentional about what I really need and have embraced a minimalism and “don’t buy it” mentality with most things.

This led me to create a tool for other self-employed people to understand the relationship between how much work they need to do and the cost of their lifestyle (freelance target income calculator).

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#9 Unlocking creative energy

It took about six months after leaving the corporate world for my creative spirit to awaken. While I had worked in an industry which does encourage some creativity, large organizations always have at least one person around who will spend more time poking holes in your creations than sitting with you to dream. Risk-management will always win over new ideas in most companies.

Combining responsibility for my own life (in terms of making money to meet my basic needs), no one to question my ideas and intentional downtime or space to let my mind wander, I’ve found my mind flooded with half-baked ideas to experiment with and put into the world.

My rule of thumb has been to take action once two un-related people push me in a certain direction. This framework led me to launching a podcast, attending a conference of unconventional thinkers in Portland and launching my own digital learning experiment/academy despite my fear and uncertainty.

A strong current of creative energy can easily overcome fear to help turn half-baked ideas into things that make a difference. Some people will never give themselves permission to have space in their time to ever let that creative energy appear.

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#10 Healing & becoming a nicer person

I wouldn’t claim I am Mother Teresa, but relative to the person I was in the corporate world, I find myself being more patient, kind and generous to the people around me. The marginal blows of insanity and negativity in the corporate world slowly eat away at you in a way that is hard to put a finger on, but easy to spot once you get a bit of distance.

Having ownership of my own time, creations, and work enables me to take responsibility for the person I am being in the world at all time, without the opportunity to place blame on anyone else. In addition, it also gives me the freedom to say no to any projects or situations where I would be working with or spending time with people who are good at draining my energy (I like to call these people energy vampires).

Deep down I always had a fear that a long corporate career would be a death by a thousand blows, slowly destroying the person I wanted to be without me realizing it.

It took me almost eleven years to gain the courage to carve my own path, but I now see a path in the world where I have some confidence that I can be who I want to be in the world.

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41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

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In March, I launched a 27-question assessment that asked people various questions across three main categories:

 

Respondents were given 27 statements (full report here) and noted how strongly they agreed on a scale from 1 to 5 with 1 being completely disagree to 5 being completely agree. With almost 100 responses, the data has been somewhat surprising and also has confirmed some other hypothesis I have had about the shift towards the future of work.

Alternative workers finding more satisfaction in work and life

I asked people to categorize themselves in four categories and found that “alternative workers” — solopreneurs and entrepreneurs — are finding the most satisfaction in life and work. Full-time workers averaged a score slightly over 5 out of 10 in this question.

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Alternative workers place more importance on questioning the norm and autonomy

Both full-time workers and alternative workers consider themselves open to new ideas and experiences and also think about their career in terms of a set of skills and projects, rather than specific roles or a path.

However, three things stood out relative to full-time workers. Alternative workers:

• Have more autonomy
• Are actively designing the life they want
• Are looking to build skills from areas outside traditional academia

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What makes alternative workers different than full-time workers?

When comparing the answers with the gaps between full-time workers and alternative workers, the biggest gaps were from the following five questions:

Alternative workers have more freedom and autonomy

• “I have the freedom and autonomy to work on things that matter to me” (+37%)

Alternative workers do more “deep work”

• “I get into a flow state to do deep, meaningful work at least once per week” (+32%)

Alternative workers are more energized

• “I am highly energized through my work and how I spend my time” (+29%)

Alternative workers design the lives they want

• “I make decisions to design the life I want, even if it goes against the norm” (+28%)

Alternative workers do more remote work

• “I am experienced working in global, remote teams” (+25%)

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Full-time workers that have side gigs tend to prioritize skill building and mastery

One surprising finding was the differing priorities of full-time workers and full-time workers with side gigs. Within the top five mindsets, full-time workers with side gigs focus deeply on skill building, looking for ways to improve and evolve and looking for projects that will push them beyond their current capabilities.

Pushing yourself beyond your current capabilities is another way of defining “mastery” and element that has been proved to drive human motivation. So it is no surprise that full-time workers with side gigs are finding more satisfaction in both their life and work.

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What are the biggest differences between full-time workers with side gigs and full-time workers?

 

Compared to their gig-less peers, full-time workers with a side gig are more active in creating their own future, building skills and cultivating meaningful connections. In addition, the biggest difference was the answer to the question:

“I am okay not knowing what work I will be doing in two years”

Side-giggers rated the question very close to alternative workers, acknowledging that there is not a well-known or established path they may be pursuing. In addition, the biggest difference between their gig-less colleagues:

• Okay with uncertainty: “I make decisions to design the life I want, even if it goes against the norm” (+17%)
• Focused on skill-building: “I am increasingly looking for alternative ways to develop skills outside of traditional educational institutions” (+15%)
• Mastery-minded: “I seek out projects that are slightly beyond my current capabilities” (+13%)
• Building relationships: “I cultivate deep, meaningful connections where we help each other grow” (+13%)

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Bottom 5 Mindsets: The Challenges In The Future Of Work

 

The lowest scores among alternative workers were focused on action, experimentation and focus, finding community and purpose — challenges for most people. The nature of being “on your own” often forces attention on these deeper and more fundamental questions.

Data from the survey shows that people are struggling with these five areas:

• Testing Ideas: I test ideas or take an 80/20 approach to projects to quickly assess whether or not to invest more time in something
• Defining Success: I have a personal definition of success that I regularly reflect on
• Taking Breaks: I know how to balance deep work and breaks (e.g. health, fun, mindfulness)
• Community: I feel part of in-person or virtual communities that have shared values
• Purpose: I have a long-term mission or sense of purpose that I am committed to

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Interested in taking the survey?

Take Survey: You can access it here.

Partner? If you are an organization interested in experimenting within your organization, more information on the approach is here.

Why it matters: My essay on why the “future of work mindset” matters

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

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The post Future of work mindsets: comparing full-timers, side-giggers and alternative workers appeared first on Boundless by Paul Millerd.