Starting your own business is a secret dream of many and with the emergence of more clear paths to make money online, many knowledge workers are deciding to test the waters of self-employment and entrepreneurship.  In making such a leap many people hope to increase the amount of freedom and fulfilment they have with their work.  However, because of how little we think about the way we work, many find themselves caught in one of many hustle traps.

A hustle trap is something that we fall into without asking “why?”  Many of the traps exist because of outdated work beliefs or behaviors we have carried forward from full-time employment.  Many people only realize they have fallen into a trap when they find themselves burned out and noticing that they have created another job for themselves.

Wasn’t the point of becoming self-employed to avoid such a fate?

Let’s dive into ten of the most common traps I’ve seen in my conversations with people on the self-employment journey from around the world.

Hustle Trap (noun): A mental model built on legacy ideas of how one should work and live that leads to burnout, anxiety or the sense of being trapped. Often obvious in retrospect.

#1 The dopamine bomb of internet fame

Creating content on the web is still a relatively new thing and because of this, If you are able to consistently create content, explore topics you are genuinely interested in and develop some way to improve as you go, you will inevitably get some version of 15 minutes of fame. This could come from a famous person promoting your content, getting published in a mainstream publication, economic success or or some piece of content going semi-viral for a few days.

To the self-employed creator that dances in daily uncertainty and self-doubt, this can unleash a satisfying dopamine bomb of approval. It can be so exciting that it can reshape everything you claim to care about.  This effect is so powerful that even some of the most successful media organizations have gone the way of chasing clicks rather than focusing on the content they claim to care about.

I got a dose of this when I posted a Twitter thread exploring the “40% of Americans can’t afford a $400 emergency bill” meme. If you read the report and the data, you’d be doing some serious mental gymnastics to land on such a takeaway. However, I was looking at it from the perspective of a former consultant who is skeptical of how data is represented and didn’t realize I was walking into a political talking point. This exploration earned me the applause of right wing trolls and a twitter follow from Ann Coulter.

That wasn’t a path I wanted to keep exploring.

#2 Copying the tactics of a guru who isn’t you

It has become a norm for successful entrepreneurs and creators to share their approaches for how they got to where they are.  This includes things like writing and audience building strategies, pricing tactics, content creation approaches and so on. The depth of information available to people who want to follow certain paths is more honest and useful than before.

However, many people mistake the tactics for the journey and overlook the unique psychology, motivations, and financial situation of the person they are following, not to mention the role of luck and timing. Eleanor Roosevelt highlights the risks of this path:

When you adopt the standards and the values of someone else or a community or a pressure group, you surrender your own integrity. You become, to the extent of your surrender, less of a human being.

The only sustainable path over the long-term is to find your own way. Robert Greene spent years exploring how some of the most successful people in history did this, resulting in his book Mastery.  He found that people progress through three stages – the passive, practice and active modes:

  1. Passive Mode: Learning the rules of the game (often working for someone else over a series of years)
  2. Practice Mode: When someone start taking action on their own, taking ownership of what they are creating and actively building a set of skills
  3. Active mode: The person goes out on their own, creating under their own name, or starting their own venture.

As Greene says, shifting from the practice to the active mode is often the hardest thing:

most people wait too long to take this step, generally out of fear…you must force yourself to initiate such actions or experiments before you think you are ready

Similarly, people often follow gurus and take courses from others much longer than they should.  Most people would be better off by hitting publish on their own creations despite them not feeling like they are perfect.

#3 The productivity trap / Streak trap

Growing up in the US and many other countries these days is to be convinced that your purpose in life is to continuously be doing things. To rest is to be lazy.

It can be useful when you first start creating to commit to some type of rhythm, such as posting once a week, because this can help you overcome a lot of the self-doubt and friction that emerges when you first start sharing online.  However, this can quickly become a trap as you mistake the streak for the thing that you want to be doing.  

Anne-Laure Le Cunff, who has written a lot about the traps of productivity, argues this is a way to avoid the questions that matter:

We are scared of idleness because stopping would mean having to really consider what we want out of life and what we currently have. Sometimes, the gap feels so wide, we’d rather stay on the hamster wheel.

To build a sustainable path, work has to be downstream from life and at least some of what you work on needs to be something you actually want to create. When you are self-employed you definitely need to find some way to motivate yourself, but often people mistake the insecurity of not feeling productive for the thing that keeps them going.

When you create deadlines that stress you out, remember that you are the one tuning self-employment into a job and isn’t the whole point of self-employment to avoid having a boss telling us what to do?

So I give you permission to take a week off. If anyone gets mad, blame it on me.

#4 The desire to prove yourself, especially to your parents

In my conversations with people around the globe, the secret anxiety that many share in a  deeper conversation is that they fear what others think of them, especially their parents.  

The fear of parental disapproval can keep a lot self-employed working on things they hate or keep them from taking bolder risks.  Being self-employed in the digital world is a life that is illegible to many people over the age of 40 and I’ve seen many people not ever give working for themselves a fair shake before returning to full-time employment.  

It’s easier to default into socially accepted roles than to try to carve your own path and for that reason there needs to be something deeper driving you than winning approval from others. 

Stephen Warley, who has become a friend and mentor, has been self-employed for almost the last twenty years, but says it took years before his mother accepted his path. Once he came to terms with the fact that the approval may not come, he was able to move forward.

4 years in, I was struggling and I was talking to my mom one day and she asked if I would ever consider getting a job.

I told her absolutely not and I haven’t struggled since!

The hard truth is that acceptance may never come.  As someone taking a path that is outside the norm, people are always going to be a bit uncomfortable with what you are doing.  The only way 

#5 Chasing “audience” over people you actually want to engage with

At some point someone will say to you, “you need to be on ______ to be taken seriously.”  Insert the medium of the moment:  a blog, a personal website, a medium, instagram, snapchat, patron, tinyletter, podcast, substack, twitter, YouTube.  You get the point.  

Engaging with other people online is one of the biggest challenges modern creators and entrepreneurs face.  The insecurity and FOMO of not being on a certain platform plus the algorithmic nudges towards engaging in ways that get the most attention are a double whammy of anxiety.

My approach has been to pay attention to what platforms result in meaningful conversations, both online and in-person.  In choosing where I engage, I ask myself the question “How do I build an audience in a way that might align with the life I want to live?”  

For me, more connection = happier Paul.

Through experimentation, my answer has been writing weekly on substack, posting longer pieces on my blog, recording podcasts when I find people I’m excited to interview, posting the random video to YouTube with no set schedule, and light twitter engagement.  I don’t really spend any time on any other platforms except for personal reasons.

I know many people that have built sizeable audiences, but have done so through sharing things they aren’t all that excited by.  They let the algorithm decide.  

Spend a month in Bali and you’ll inevitably meet an instagrammer with a massive following but feels trapped by what they are doing.  They’ve created a job for themselves, decoding what an algorithm wants rather than figuring out what smaller group of people might make their life better.

#6 Chasing status to calm your insecurities

Khe Hy left his job as an investment banker in 2015.  His initial plan was to take 18 months for some time off with his family and then to start a venture-backed tech company.  Where did he come up with this idea?  

As he details on the ZigZag podcast:

My plan was initially…to become a venture-backed entrepreneur.  I wanted to go and raise money and do the thing that Fast Company writes about….it sounds so lame but to me a big portion of success was other people thinking I was successful and what better way to do that is to do the thing that was actually even harder than what I was doing on Wall Street.

However, a few months into his break from his job.

I had had just enough separation from my old life that was like I don’t think I really want to do this.

He had realized that his desire of others to see him as successful was driving him to create trade one identity for another, which would have just delayed his inevitable leap into a more unknown, but more rewarding path.  Instead of trying to quiet that insecurity of not being seen as “successful,” he took the path towards more freedom and uncertainty while also grappling with it in public through his writing, which is a treasure trove for other self-employed creators trying to avoid hustle traps.

One of the most common insecurities is one’s relationship with money.  After years of a steady paycheck, a couple months without an income is the ultimate test for your ego.

Similar to Khe’s initial plan, the easiest way to calm this insecurity would be to make a ton of money.  While practically this can make sense immediately after your leap, over time you’ll just end up creating another full-time job for yourself instead of creating the space for new opportunities and your creative energy to emerge.

#7 Not Changing Your Environment Or Making New Friends

There’s a saying that goes “if you want to change yourself, change your environment.”  

I would offer a similar but slightly different claim: if you are making a big change in your life, your current environment may feel a bit lacking on the other side.

The number one recommendation I make to anyone making a major work change in their life is to make at least one new friend who is on the path ahead of you.

When I became self-employed, I was living in New York City and the majority of my friends and family operated their lives around full-time employment.  While those people are fantastic, I didn’t have many people in my life that understood what it felt like to go months without an income or try to design a life around working independently.

This led me to put myself in circumstances where I could meet more people who were working and living outside of the default path.  Joining a coworking space, attending conferences like the World Domination Summit, and living abroad and meeting people in global nomad communities helped me make new friends who I could lean on when the question “what the hell am I doing?” emerged,

I’ve had a number of weekly, biweekly, or monthly virtual or in-person conversations with these friends.  Beyond sharing our experiments and catching up, they are often deep contemplations on the deeper questions of life.

This kind of friendship, or what William Deresewiecz called “the deep friendship of intimate conversation” is a way of helping me feel at home when I am feeling lost and feeling connected when I am living in a new place around the world.

#8 Not Taking Time Off

Spend long enough in full-time employment and your sense of reality shifts to think about life as mostly work interrupted by two to four weeks of vacation per year (or more if you are lucky enough to live in Europe!).  

When you first graduate college this seems terrible but over time as all of your friends start to march to the same schedule, it just seems like what is.  At first many who become self-employed gravitate towards a similar schedule, working Monday through Friday, but find themselves burned out much quicker than they might in a full-time job.

This is because the amount of motivation needed to do work on your own is much higher than it might be in a full-time job.  When you are working for someone else, it may be painful to do something you don’t want to, but you find a way.  I tell people that when they are working on their own, if you aren’t at least “8 out of 10” excited about doing something, it’s going to feel like pushing a boulder through quicksand,

Even when you find work that you are motivated to do, it can be hard to step back and figure out a broader strategy for your life and work.  In full-time employment, job changes and promotions help you shift your focus, but in self-employment, the best way is usually to take an extended break.   This can be scary for many of the above reasons, but is often pivotal in figuring out what kind of work you are truly drawn to.

#9 An income goal as the metric of success

Nothing will force you to compromise quicker than lofty income goals for your self-employed life. In my first year of self-employment I used my freelance target income calculator and figured out that if I’m living in the US, I could pay for a life I really liked for about $35,000-40,000 in earnings per year.

This required a year of testing my limits after living in a high-end apartment in New York City, but it also helped me to be able to say no to many paid projects in that first year. Instead of those paid projects I developed things like Boundless, the Reimagine Work podcast and my future of work mindset assessment.

While these things haven’t led to any financial success, they help bring me alive.  If I only optimized around reaching an income goal of something like $100,000 a year, I would not have pursued any of these experiments.

Money is important but most people tend to overvalue the importance of money as they start their self-employed journey and undervalue the unexpected upsides of more flexibility, space for creativity and leaving time for unknown opportunities to emerge.

#10 The “I am a x” identity trap

You used to have an easy answer to the “what do you do?” question. Now you find yourself mumbling random lines about making friends on the internet and writing 25 blog posts about an obscure topic you’re fascinated by and you get hit with blank stares.

This can make a lot of people desperate to have an easier to understand label.

There’s a subtle difference between adopting labels to increase legibility to potential clients and seeing that label as who you are. It makes sense to tell potential clients you are a freelance consultant, but if you start seeing the world through the eyes of what a freelance consultant might do and looking at others freelance consultants for what kind of work to do, this might be a trap.

You are a human playing the role of a freelance consultant. Always remember that and your game will be a little more fun.

The anti-hustle path forward doesn’t come with a how-to guide

When I started sharing publicly online a few years ago, the dominant narrative for online creators was a hustle narrative. Do as much as possible, as productively as possible. This works for some people but is a trap for most and in some cases, people start to mistake the productivity hacks for the work itself.

I tend to agree with Anne-Laure that a lot of this comes from fear:

…Consuming too much productivity porn can sometimes be a symptom of lack of confidence. The process of learning from supposedly more productive people is akin to asking for permission to start working on an ambitious project

The only way to gain confidence in self-employment is through the discomfort, finding things you want to create and people you want to engage with. It doesn’t make sense to create 100 podcast episodes if you hate podcasting.  Find a better medium or take a break and see where your energy goes.

When you first become self-employed, it’s easy to let legacy work beliefs dominate how we think about our time:

“I need to make a lot of money”

“I need to have a lot of followers”

“I need to work all the time”

“I must scale”

“I need to prove to others I am successful”

It’s great to have some direction and despite trying to do so, I’ve failed to find a good map that gives people a lot of confidence about what comes next.  When successful individuals recount their stories, there are often more surprises and moments of inspiration than well-thought out plans.

At the beginning of my journey I felt a huge relief when I read this line from David Whyte.

…it can be a release then, to think, that when we first come across the idea of a pathless path, by definition, we are not meant to understand what it means”

I’m still on a journey and where I’m headed? I’m not sure.

I’m just trying to take it a bit slow and avoid falling into the many hustle traps along the way.  Hopefully I can help you navigate the path with a little more care as well…



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