But she’s at a transition point now. She decided not to pursue clinical practice as a physician—again turning away from the default path right in front of her. She’s been a full-time stay-at-home mother since then to her two children, raising them bilingually after becoming bilingual in Spanish herself during her time in Cuba.

She’s a self-described early AND late bloomer, having sped through milestones early on but now slowly figuring out what’s next for her work and family. She understands many of the challenges of going off the default path—like the paradox of choice—and how decision-making and prototyping are skills to be learned and practiced while building a pathless path.

She is from San Francisco originally but now lives in New York with her husband and kids.

Podcasts Links: Choose Your Player

Conversation Topics:

1. Finishing High School at 15 and going to Med School In Cuba: Her early life, her decision to test out of high school at 15, and her journey through college and medical school. She completed her medical education in Cuba, which was entirely funded by the Cuban government.
2. Medical Practice and Transition: Her experiences practicing medicine in Cuba and her eventual realization that she didn’t enjoy the job as much as she thought she would. Despite the privilege of having her education funded, she decided to veer away from clinical practice.
3. Life Transitions and Mental Health: She underwent significant life transitions after returning from Cuba, including becoming a stay-at-home mother. She talks about the psychological weight of leaving a prestigious profession and the impact of these transitions on her mental health.
4. Exploring New Paths: Her journey of self-discovery and exploration of new paths. She discusses the importance of small experiments in life and work and the value of reflection. She also talks about her experiences with writing and other creative pursuits.
5. Late Bloomers: The concept of “late bloomers” and the societal obsession with early achievement. She references the book “Late Bloomers” by Rich Karlgaard, which highlights the value of those who find their path later in life.
6. Sharing Her Story: The importance of sharing her story to normalize the struggles and transitions people go through. She discussed the positive response she received when she started sharing her journey on Twitter.

Quotes:

Freedom In Childhood:

I grew up with a lot of freedom around following whatever we thought was interesting. It was like from the very beginning, like if you want to do this activity, oh now you’re done with this activity you want to do this other thing, you want to do violin great, you’re done with that, you want to do gymnastics great, you’re done with that. We had a lot of freedom.

On Graduating High Schol Early

I was very determined about what classes do I need to take to make sure that I can get out and I can transfer because I don’t want to kind of extend it in three or four years at city college. I knew I just wanted to be able to graduate so that I could continue to dance.

The Good Parts of Medicine

I loved studying medicine so I loved learning the why, I liked reading the textbooks, I liked learning the physiology. So it was like I liked all that background knowledge around medicine but there were clearly people like my husband who was in the program with me, he was ahead a year ahead of me, but we met down there, he clearly loved medicine. I was like oh yeah I can kind of see the difference, I’m not quite that one.

On Ordinary Excellence

it’s okay to not be exceptional. Like there’s so much exceptionality in being regular like having my family and having the kids and teaching them all of these things and having my family come to visit like the kind of ordinary regular things are things to still be celebrated.”

👉 Follow Aida on Twitter and Read Her Writing

Links Mentioned:

• Life Is in The Transitions
• Late Bloomers
• Lost Connections
• The Hilarious World of Depression

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 Aida Alston: College at 16, Med School in Cuba & Starting Over After Kids | The Pathless Path Podcast appeared first on Boundless by Paul Millerd.

As I started my career, I began my own sort of philosophical and liberal arts education.  But given my limited background, I had to lay the groundwork to get to some of the deeper questions and mental models that helped me eventually take a leap to carve my own path beyond the corporate world.

I often see people suggesting deep philosophical books that question the meaning of life but realize given my own past mental models, that this approach doesn’t make sense for many people.

It is easy to dismiss books such as Dale Carnegie’s “How To Win Friends And Influence People” or David Schwartz’s “The Magic Of Thinking Big” but to someone indoctrinated in business, those may be the most reasonable books to start with.  Alas, it was these kind of books that made me hungry to go deeper.

What follows are ten types of books that you can use as a roadmap to dream of a life beyond the corporate world.  I’ve offered a “starting point” for each category which is probably the most accessible of the options:

1. Thinking About What Matters
2. Building “Human Skills” In The Workplace
3. Know Thyself…In The Business World
4. Questioning The Modern State Of The Business World
5. Finding Some Hope In The Business World
6. Mindfulness & New Emotional Mental Models
7. Carving New Paths & Wandering Into The Unknown
8. New Models For Seeing The World
9. Grappling With The Role OF Work In Our Lives
10. Going Deep – The Hard Questions

I. Thinking About What Matters

Start Here  Tuesday’s With Morrie (Mitch Albom)

Helped me to think about life from the perspective of the end of one’s life. In this story, Morrie has lived a full life and has deep relationships as evidenced by the number of people who are constantly visiting him.

So many people walk around with a meaningless life. They seem half-asleep, even when they’re busy doing things they think are important. This is because they’re chasing the wrong things. The way you get meaning into your life is to devote yourself to loving others, devote yourself to your community around you, and devote yourself to creating something that gives you purpose and meaning.

Last Lecture (Randy Pausch)

Randy Pausch is a dying professor who decides to devote his energy into a literal last lecture.  What transpires is a talk focused on never ignoring your inner child and a story that will likely deeply resonate with many.

Survival In Auschwitz (Primo Levi)

This book is a deep contemplation into what is means to live and survive in the darkest of places.

Sooner or later in life everyone discovers that perfect happiness is unrealizable, but there are few who pause to consider the antithesis: that perfect unhappiness is equally unattainable. The obstacles preventing the realization of both these extreme states are of the same nature: they derive from our human condition which is opposed to everything infinite.

II. Building “Human Skills” In The Workplace

Start Here  How To Win Friends And Influence People (Dale Carnegie)

I know, I know!  Cliche.  So What? The simplicity of the book makes it powerful.  It doesn’t need the latest and greatest psychology studies.  It just offers principles about how to treat people and is a reminder that the norms and assumptions about behavior in the modern business world lead people astray.  For example, if you want to change someone’s mind, focus more on getting that person to like you instead of attacking them with facts and to focus on simple things like listening:

Talk to someone about themselves and they’ll listen for hours.

Influence (Robert Cialdini)

This book was a bit mind-blowing, making me realize we are more susceptible to influence than we realize.  Cialdini has written extensively about how things such as social proof, reciprocity, commitment, authority, liking and scarcity drive our behavior.  Becoming aware of our behavioral biases will help you identify the decisions you really want to make as opposed to the ones you are just falling into

The Art Of Learning (Joshua Waitzkin)

This book is terrific. Waitzkin walks through how he became a chess champion at age 8 and brought Gary Kasparov to a draw at 11 years old. After quitting chess, he applied the same approach to Taiwanese push hands and became world champion. He introduces the concepts of “beginner’s mind” as well as his own framing of “numbers to leave numbers” which is a great way to show that to go fast, you first need to go slow.

III. Know Thyself…In The Business World

Start Here  How Will You Measure Your Life (Clayton Christensen)

This book is a fascinating perspective on how to define success from within the corporate world.  Christensen made me gain hope about leading with principles in the corporate world, positioning “management” as a way to have a positive impact on other people:

“If you want to help people, be a manager”

Quiet: The Power of Introverts in a World That Can’t Stop Talking (Susan Cain)

I thought I had a good understanding of introversion and extroversion until I read this book. This book also made me realize I was a lot more introverted than I realized. This is where I first heard of the term “ambivert” and realized I am energized by a mix of alone time and activity with others. I was fascinated by the history of how extroversion became such an ideal in modern society and the mistakes that can lead us to make.

Mastery (Robert Greene)

Mastery is an incredible book for anyone with a creative bone in their body.  Greene talks about the different phases one must undertake if they want to become a master at their craft or develop a wide range of skills.  He helps people understand the hard decisions that need to be made, such as leaving a teacher (see: manager, leader) once you have learned enough so that you can go out on your own.

IV. Questioning The Modern State Of The Business World

Start Here The Halo Effect . . . and the Eight Other Business Delusions That Deceive Managers (Phil Rosenzweig)

A clear and convincing case that most explanation of who is “successful” and a failure in the business world is highly subject to market dynamics and the firms that happen to have the most profitable business model of the time.  This book will make you highly skeptical of modern business “research” and stories praising or criticizing leaders.

Shareholder Value Myth (Lynn Stout)

This book is a must-read for anyone who has a suspicion that there may be other and better ways to measure success in the world than money and especially, “shareholder value.”  This book helps show that our current state of affairs is a recent innovation.

Reinventing Organizations (Fredrik Laloux)

This book highlights organizations that are typically led by truly transformational leaders that have questioned the status quo and built organizations (sometimes very large ones) that start with deep trust in people and their ability to solve problems.  This book shows that self-organization can work and that it is likely the only path forward if we want to build a better business world.

Skin In The Game (Nassim Taleb)

Taleb looks at the concept of “skin in the game” in terms of people, employees, and organizations.  His perspective on the modern state of the employee/employer relationship:

So employees exist because they have significant skin in the game –and the risk is shared with them, enough risk for it to be a deterrent and a penalty for acts of undependability, such as failing to show up on time. You are buying dependability.

He argues that the modern employee is no longer a “company man” but rather a “companies man”:

A companies person is someone who feels that he has something huge to lose if he loses his employ-ability

V. Finding Some Hope In The Business World

A big part of my career in the business world was an obsession with trying to understand first why organizations seemed to drive so much stress and anxiety in people and then second, what we could do about it if anything.  This led me to discover a number of books that not only helped me discover new ideas for business, organizations, and leadership but also develop my own perspective on what’s happening in the modern workplace.

Start Here Drive (Dan Pink)

Pink’s introduction of the concepts of autonomy, mastery, and purpose through research and company examples is a great way to discover self-determination theory, which is a foundational theory of what motivates people.  If you look at modern organizations through the lens of motivation, you would assume that everyone had lost their mind.

Work Rules! (Laszlo Bock)

The key takeaway from this book was the fact that many things you can do to improve the employee experience are free.  Too many organizations think that transformation comes at a major cost.  But as Bock shows in many examples in his experience at Chief People Officer, the hardest things to do are to trust people and give them freedom to make mistakes.

VI. Mindfulness & New Emotional Mental Models

Start Here The Heart Aroused (David Whyte)

I wish I read this book at the beginning of my business life, but I wonder if it would have been too soon.  Whyte speaks poetically about the experience of the business world in a way that well, arouses your heart. Whyte’s summary of the book:

(it) will look at the link between soul and belonging, creativity and failure, success and stasis, efficiency and malaise at work, but it sets as its benchmark not the fiscal success of the work or the corporation (though this certainly can be good for the soul) but the journey and experience of the human spirit and its repressed but unflagging desire to find a home in the world.

Nothing Special (Charlotte Joko Beck)

This was the first book I read about Zen Buddhism and mindfulness. The story is a conversation between Beck and her students and will resonate with anyone who is curious about mindfulness, meditation, and spirituality.

VII. Embracing The “Pathless Path”

Start Here: My Book! The Pathless Path (Paul Millerd)

My book, The Pathless Path, was published five years after quitting my job and carving my own path. It’s sold over 25k+ copies with minimal marketing so people seem to like it. It’s not a how-to guide but an inspirational account of my journey combined with “recipes” on how to embrace an unconventional path.

Anything You Want: 40 Lessons For a New Kind Of Entrepreneur (Derek Sivers)

Sivers build a company selling CDs of independent artists in the early internet era.  He ignored most of the advice about how to build a company.  He also ignored the advice on how to write a book.  This short book shows that “best practice” doesn’t always lead to happiness.

Field Guide To Getting Lost (Rebecca Solnit)

Rebecca Solnit puts words to the journey of “getting lost” and wandering into the unknown. If this quote resonates with you, you are ready for this book:

That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.

Linchpin (Seth Godin)

Godin has been a self-employed solopreneur and freelancer for decades.  He helps people re-frame their thinking away from needing to be “chosen” for a job towards a world where the world depends on you expressing your creativity and daring to “make a ruckus.”

Designing Your Life (Burnett & Evans)

This book by two Stanford professors was designed to help undergraduate students figure out what they want to do with their lives.  Based on design thinking, they have a number of useful question prompts and exercises that push you to expand the number of ideas and options you can come up with, rather than picking from default options.  If you want to imagine new possibilities, this is the book for you.

Crossing The Unknown Sea (David Whyte)

Whyte is my favorite writer and this book is a beautiful reflection of his own journey from naturalist to non-profit worker to poet. He talks about the inner game of doing the thing which is scary (people thought he was crazy to quit his day-job) and living full out.

The Good Life & Sustaining Life (Andrew Taggart)

A practical philosophical reflection on what it means to live the “good life” in the modern world and the many approaches one might take to sustain such a life.

There may be no greater vexation in our time than the question of how to make a living in a way that accords with leading a good life. Yet if nearly every thinking person has faced this vexation at one time or another and doubtless throughout most of his adult life, virtually no one has ventured to think it through in a well-considered, systematic fashion.

VIII. New Models For Seeing The World

Start Here A Lesson On Worldly Wisdom (Charlie Munger)

This fantastic graduation speech from Munger highlights the need for many different “mental models” for seeing the world and how to move between them.  Worth reading in full.

The Righteous Mind, Why Good People Disagree On Politics & Religion (Jonathan Haidt)

This book made me rethink how people arrive at their beliefs.  Haidt shows that morality is something that is highly influenced by your environment and biology.  This book made me much more understanding of a wider range of ideas beyond politics and religion.

Wanting (Luke Burgis)

The self-employed path is filled with hustle traps and the most powerful one is “mimetic desire.” Luke walks through his own personal journey of awakening and helps steer people toward finding their “thick desires” – things they can sustain over the long term.

Sacred Economics (Charles Eisenstein)

A bold re-imagination of our world to one based on generosity, connection, and embrace of the environment.  This book is a beautiful mix of technical economic analysis with a spiritual questioning of the status quo:

I think ultimately what is happening is that our deep ideologies and belief systems, and their unconscious shadows, generate a matrix of synchronicities that looks very much like a conspiracy. It is in fact a conspiracy with no conspirators. Everyone is a puppet, but there are no puppet-masters.

IX. Grappling With The Role Of Work In Our Lives

Start Here Bullshit Jobs (David Graeber)

Graeber looks at the modern workplace through his definition of a “bullshit job” which is when employees define their job as pointless and without meaning.  He looks at the history of work and shows that our current relationship with employment, time and money was not always the way it was and challenges readers to think beyond the status quo.

Rest (Alex Pang)

Pang’s incredible book on rest covers sabbaticals, unplanned breaks, naps, and sleep while challenging our modern understanding and definition of things like time, leisure, idleness and rest.  He boldly challIf your work is your self, when you cease to work, you cease to exist,” shares counterintuitive results from people who worked 2-5 hours a day and shows the benefits of not following the conventional wisdom that more = better.

As a result, service workers and professionals are rewarded not just for performing work but also for “performing” busyness at work.

Reclaiming Work (Andre Gorz)

Gorz argues that “real work is no longer what we do when at work” and that a lot of what we are doing in the workplace is performing a social ritual we have decided is necessary to “earn a living.”  This book imagines a world “beyond the wage-based society.”

The Normal Chaos Of Love (Beck & Beck-Gernsheim)

While this book is very much about love and relationship, it also frames those relationships and our modern ideal of a family in contrast to the workplace.  The authors (a married couple) argue that the modern reality of having everyone be workers is great for the workplace and freedom, but creates chaos and complexity at home – complexity that we have yet to fully grapple with:

Everybody – including parts of the women’s movement – has the right to expect that offers once made to men should now be extended to women, and assert that women are as useful as members of the job world as men are. They should however realize that this road does not lead to a happy world of co-operative equals but to separateness and diverging interests.

Leisure: The Basis Of Culture (Josep Pieper)

In the late 1940s, Pieper wrote of a crisis of “overwork” and a disconnect from the classical sense of leisure.  He wrote that we “mistake leisure for idleness, and work for creativity” and was skeptical of Max Weber’s assertion that “One does not only work in order to live, but one lives for the sake of one’s work.”  In today’s world, “leisure” often just means a break from work.  Pieper argued instead that leisure was:

the disposition of receptive understanding, of contemplative, beholding, and immersion – in the real. In leisure, there is, furthermore, something of the serenity of ”not-being–able–to–grasp,” of the recognition of the mysterious character of the world, and the confidence of blind faith, which can let things go as they will; there is in it something of the ”trust in the fragmentary, that forms the very life and essence of history.

X. Going Deep – The Hard Questions

Start Here: Not a book, but perhaps better than a book? Brain Pickings is perhaps the best source for wisdom on the web.  A voracious reader and learner, Maria Popova pulls the most powerful parts of great writers in history on topics such as love, creativity, art, poetry, philosophy, life and work into compelling synthesized posts.  Start with one post and you’ll end up opening up a ton of tabs in no time.

• Recommended posts: 10 lessons from 10 years of BrainPickings, Ursula K. Le Guin on Busyness, Reclaiming Our Human Dignity in a Culture of Workaholism, or David Whyte on Work/Life Balance

The Great Work Of Your Life (Stephen Cope)

Stephen Cope’s The Great Work of Your Life is a spiritual guide to finding your life’s purpose. The book uses the ancient text of the Bhagavad Gita to frame stories of famous people who have followed their dharma, including Tubman, Whiteman, Frost, Keats, and Susan B. Anthony.

Zen And The Art Of Motorcycle Maintenance (Robert Pirsig)

This book has been around since the 1970s and its central argument still rings true (perhaps more so?) that in our continued acceleration towards the future, we are losing touch with a deeper, spiritual side of ourselves.  Pirsig contemplates what got us to this point:

The range of human knowledge today is so great that We’re all specialists. And the distance between specialization has become so great that anyone who seeks to wander freely among them almost has to forgo closeness with the people around him.

At the Existentialist Café: Freedom, Being, and Apricot Cocktails (Sarah Bakewell)

What does it mean to be free?  How should one act in accordance with that belief.  Bakewell tackles these tough questions through the lens of the existentialist philosophers that emerged in the early and mid 1900’s featuring the philosophies of Kierkegaard, Sartre, de Beauvoir, Heidegger and more.

The Wisdom Of Insecurity (Alan Watts)

Watts contemplates our desire to continue to put life into neat little boxes:

The more one studies attempted solutions to problems in politics and economics, in art, philosophy,and religion, the more one has the impression of extremely gifted people wearing out their ingenuity at the impossible and futile task of trying to get the water of life into neat and permanent packages.

and on following the default path:

To keep up this “standard” most of us are willing to put up with lives that consist largely in doing jobs that are a bore, earning the means to seek relief from the tedium by intervals of hectic and expensive pleasure. These intervals are supposed to be the real living, the real purpose served by the necessary evil of work. Or we imagine that the justification of such work is the rearing of a family to go on doing the same kind of thing, in order to rear another family . . . and so ad infinitum.

Meditations (Marcus Aurelius)

While it was written over 2,000 years ago, we get a peek into the Empreror of Rome’s private journal and his meditations on life:

When you arise in the morning think of what a privilege it is to be alive, to think, to enjoy, to love …

and

Leisure lives on affirmation. It is not the same as the absence of activity; it is not the same thing as quiet, or even as an inner quiet. It is rather like the stillness in the conversation of lovers, which is fed by their oneness.

Essays (Ralph Waldo Emerson)

Emerson’s collection of essays are a great read and accessible for being written in the 1800’s.  Emerson on self-reliance:

There is a time in every man’s education when he arrives at the conviction that envy is ignorance; that imitation is suicide; that he must take himself for better, for worse, as his portion; that though the wide universe is full of good, no kernel of nourishing corn can come to him but through his toil bestowed on that plot of ground which is given to him to till. (Self-Reliance)

Nature:

The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles.

…and Education:

The book, the college, the school of art, the institution of any kind, stop with some past utterance of genius. This is good, say they,—let us hold by this. They pin me down. They look backward and not forward. But genius always looks forward. The eyes of man are set in his forehead, not in his hindhead

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 35+ Books Recommendations To Help You Quit Your Job appeared first on Boundless by Paul Millerd.

She was probably right. I quit my first job at the gas station because I kept missing Patriots games. This was 2001. Looking back, it looks like a great decision — it was the start of the Brady-Belichick dynasty. But I was just being selfish.

However, that word — ambition — stuck with me. I knew deep down how much I was capable of and wanted to prove her wrong.

But I now realize the kind of ambition that drove me was not what my mother was talking about. She was talking about responsibility and ownership.

I was more worried about the kind of ambition that is seen as the path to success in today’s world — climbing the ladder, working at good companies, getting paid well.

In college, I spent a lot of time crafting myself to fit the mold of what I thought these companies wanted. At first, I wasn’t great at it, but I got better and better.

I was able to land jobs at top companies and then use those positions to land even better jobs. I was then accepted to one of the top grad schools in the country.

My resume made it look like I was crushing it, I was winning a game I like to call prestige bingo. But winning prestige bingo has nothing to do with doing what matters to you and deep down, I couldn’t shake that fact.

Losing It All

When I finished grad school I was on top of the world. I had earned two masters degrees from one of the top universities in the world.

Several months later I was waking up every day after 10 hours of sleep completely exhausted — I was muddling through each day. I spend my time trying to make it through work and the rest trying to figure out what was wrong with me. This was not how I envisioned my post business school career!

I eventually was diagnosed with a bad case of Lyme disease and began the road to recovery. As anyone who has dealt with health issues knows — there is a constant sense of uncertainty and I struggled to process it all. A supportive boss at work encouraged me to take a leave of absence just to get my head straight.

Without work I sat home for hours a day, focusing on my recovery. But I also experienced an overwhelming sense of loss. Not only the loss of my health but the loss of my career. I came to realize that my identity was tied up in my job, my career and my resume. Not only that, I realized that as my savings dwindled and my grad school loans still loomed, I was pretty much broke.

Yet, I had started to realize I had been deluding myself about what really matters. I didn’t have much money, but I had family that cared about me and cared more that I showed up rather than where I worked. I had achieved some modicum of career success but really hadn’t done much on my own. I was still scared to put my ideas into the world.

Deep down, I knew that the default formula of success was not going to work for me, but also started to realize that failure as we conceive it in the business world is mostly an illusion. Failure is impossible if you have your health, relationships and freedom to do things that matter.

The default path comes with certain assumptions — These are the jobs you should strive for, the promotions you should get, this is the salary you should expect, you should always try to do more!

The reality is, you can carve your own path. It just takes a bit of work. Over the next few years, I started to test out this belief, not without learning a few lessons along the way.

Crafting a new story

I continued to gain strength over several months and felt a renewed sense of energy. I may have had less energy than everyone else but my brain was moving a mile a minute.

I started to look around at some of my high-performing colleagues and ask are they truly happy? Is everyone just pretending? I asked myself — is there a better way? Is there a way to build a life instead of a career?

I started simple. I made a list of my priorities.

Number one was health. I had known what it felt like to lose my health and didn’t want to compromise on it ever again. My next inclination was to list career but then had the crazy idea that maybe my career should be last. I finished my list: second was relationships, third was fun & creativity and fourth was career. I still have a calendar alert that pops on my phone each morning with these priorities.

I use this simple list to make decisions. For example, I have said no to any type of job or opportunity that is going to force me to compromise my health. No amount of money is worth it. Second, I will never let work interfere with my relationships. I don’t cancel on the important people in my life.

This list makes people uncomfortable.

Shouldn’t you work as hard as possible early in your career? Isn’t that the path to success?

What if we already know a better way to define success?

In the 1970s, Edward Deci and Richard Ryan came up with what they called self-determination theory. They found three elements that helped maximize intrinsic motivation or doing work for its own sake. Those three elements are competence, relatedness, and autonomy.

The theory also helped explain why I felt so lost when I became sick. I was basing my success on a number of extrinsic rewards — the jobs, schools, degrees, prestige, and pay associated with my early career and when I had to leave my job — I had nothing deep down driving me. Deci and Ryan found that these types of rewards often backfire and undermine intrinsic motivation.

While recovering, I spent a lot of time reflecting on what was energizing me. I realized that I spent a lot of time mentoring people to make career changes and helping them make sense of the working world. I love helping people. I also would get so frustrated when people felt “stuck” in companies that treated them poorly. I realized a second big motivator for me was making the working world a better place. I started sharing this with people, saying yes to any opportunities that would enable me to learn more and taking some risks through a couple of side hustles.

Over the next three years, I pursued a number of experiments. Many freelancers tell me it often starts like this — years before they make a formal “leap.” My first side hustle was a career coaching business, after a career coach I met challenged me to put my dream into the world.

Taking this first step was terrifying, but it also taught me a vital lesson about the future of work. By stepping into uncertainty, creating new challenges and taking responsibility, you will naturally push yourself to learn and develop new skills at a rapid pace.

My second experiment was a group coaching event to help people tell their stories and try to find more meaning in their careers. The big lesson for me was realizing how much fun I had creating the content and tools and doing deep research on the topics I was most passionate about.

Over the next couple of years, I kept sharing my passion and looking for opportunities to build my skills. I volunteered to give a 45-minute talk on careers at my alma mater, I gave my first paid speech about careers in consulting and gave another speech at PwC as part of their coaching program for young professionals.

All of these experiments scared the crap out of me, but they were also exhilarating. It was the challenge and rapid skill-building that I wasn’t finding in the corporate world. Pieces of all these experiments have informed what I am currently focused on now — helping people navigate the future of work. Luckily as a freelancer, my life is now one experiment after another.

As I put my energy into the world — reading, writing and taking action (competence) I became more confident. As I connected with others with a shared mission, I felt part of something bigger (relatedness). As I started working on work I was excited by, I came alive (autonomy).

Deci and Ryan were geniuses.

Popping The Delusion

My eyes were on the verge of tears. I felt ashamed. I was sitting in my manager’s office and I knew what was coming. I had reflected on my own performance over the last six months and knew that while my work was great, I wasn’t being my best self at work. I was frustrated and wasn’t even close to being the positive influence on my peers I aspired to be.

Although I had started to tap into something deeper — something more aligned with my intrinsic motivation, that was happening mostly outside the confines of my day-to-day job.

My re-assessment of values and priorities was helping me figure out what mattered, but they left me an increasingly bad fit for the corporate world. When I talked about things that excited me — I found very few others that shared the same interests. When I came up with new ideas or experiments, I was told I was naive or that I needed to learn how things worked.

It wasn’t anyone’s fault…I was still trying to fit a square peg into a round hole.

Around the same time, I had also been trying to position myself for a raise or promotion. I kept getting the responses “you need to be patient” or “you should be happy with what you have.” I was pissed. I was doing great work.

I’m also thankful that I didn’t get that raise or promotion. 

If I had gotten either, I would have been in a worse position. Deeper into a system that did not align with my values of how I wanted to live, create, or work. There was no one to blame. The onus was on me to carve my own path and create the conditions where I could thrive.

If you don’t get out now, you may end up like the frog that is placed in a pot of fresh water on the stove. As the temperature is gradually increased, the frog feels restless and uncomfortable, but not uncomfortable enough to jump out. Without being aware that a change is taking place, he is gradually lulled into unconsciousness.

(William Reilly, from Brain Pickings)

“What does a good life cost?”

There is no right way to leave full-time employment. While some people have ways to earn money before becoming a freelancer, it is mostly a leap of faith. After talking to my employer about my plan, I was able to negotiate a three month transition period.

During this time, I did all of the technical things required to start a company (detailed here). In talking to several people who were full-time freelancers, the most important thing seemed to be commitment. This part was easy for me. I had no intention of returning to the corporate world if I could help it.

…but what about rent?

The most popular question I got when I told people about my plan was “what about rent?” or “aren’t you worried you won’t make money?”

My conclusion: people worry about money a lot.

My second conclusion — A full-time paycheck warps our thinking. It makes us think that money is supposed to come in at regular periods. For most of history, this was not the norm.

There are many good things people get from employers. However, it is often at the cost of doing the work we want to do. We look at someone with a job that they hate and say “good job.” But at what cost?

What I realized was that happiness really has nothing to do with the stuff we have. We buy things because that is what everyone else is doing. We stop buying “two buck chuck” from Trader Joe’s not because we dislike it but because that’s not what you are supposed to do past a certain age. When we make decisions like this for more expensive things like our apartment, clothes, and other possessions, it means we become trapped in a job we hate.

So as I started looking at my finances as a freelancer, I realized I wanted to question everything. I started with the question “what does a good life cost?”

I reflected back to early in my career when I was barely saving a couple of thousand dollars a year. I loved my life! I still loved my life, but the lifestyle creep was real! It was the same happiness for a higher cost.

So I sat down with a spreadsheet challenged myself to answer that question. I was able to lower my cost of living $20,000 a year by making some simple changes and moving cities. All that meant was more time to commit to freelancing, more time to make mistakes and more time to learn.

Stumbling into a future of work mindset

The second chapter of my career started five years before I quit my job and had nothing to do with work. It started with me becoming progressively sick over six months and then a year-long battle to regain my health.

In that time I was forced to question everything I believed and was forced to look at the world, my life, and my career with a different lens.

This was the start of a personal “awakening” that pushed me into high gear to discover a different path. It took four years from the health crisis I faced until I took the leap to become self-employed, but what I learned along the way was priceless.

In the near future, I believe many of us will face this type of transformation — forced into the “future of work” without a path to follow. It is up to you whether you want to start planning for it today or have it take you by surprise. The quicker you face that challenge, the better you will be prepared for the future

I was lucky that my health crisis forced me to discover a mindset shift that has enabled me to better navigate the massive shifts happening in today’s economy. While I am excited, most people I talk to are stressed, anxious and are terrified at the idea of making a change.

We blame companies, bad managers, and even ourselves for our misery. At the macro level, we distract ourselves with stories of how robots will replace our jobs or how politicians limit our ability to succeed. This tells us more about how scared and unprepared we are for the future than the reality that there is more opportunity than ever.

I was never a great fit for the corporate world. The corporate world still defaults to rewarding people who prioritize money, status and power — to the benefit of few and increasing disillusionment of many. Going through the process of identifying my priorities and questioning what success meant helped me make decisions and focus my time on building towards a more sustainable future for my career and life.

Ten years into my career, I had no choice but to take the leap.

The future we are shifting to will be closer to what the firm Vega Factor has uncovered — that when people are at their best work feels like play, it has purpose, and helps you realize your potential. It will likely also lead to an awakening about how we are meant to live, spend our time and support each other.

I am excited about the future. By many lucky coincidences, I ended up working at the types of companies and having the types of experiences that gave me both the confidence and skills to be able to compete in this new economy.

My mission now is to put those skills to use to help others unlock their creativity and curiosity to do things that matter to them.

I aspire to help build the world that Ralph Waldo Emerson talks about when he said:

The purpose of life is not to be happy. It is to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.

So instead of asking someone “what do you do?” let’s ask each other “what are you meant to be doing?”

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 My awakening: How I learned to harness my creativity, build the courage to quit my job, and start a new chapter of my life appeared first on Boundless by Paul Millerd.

The Career Transition Playbook is a collection of exercises, lessons and personal stories I’ve collected from over 10 years of helping people make transitions in their careers and lives.

I’ve always been fascinated with the impossible and am a fan of the underdogs. Whenever people told me I couldn’t do something, that made me want to prove them wrong. When people tell me, “I can’t do this because of Y,” I want to help them change their mind.

I’ve seen amazing things happen. I’ve helped people land jobs at GE, McKinsey and The White House as well as make transitions from being a nurse to an IT consultant, a teacher to a researcher and a social worker to a technology recruiter.  In addition, I’ve helped people later in their career shift to the next chapter in their life, figuring out the next step after being CEO’s, business owners and executives.

This e-book is based on the belief that deep reflection, getting out of your comfort zone and embracing vulnerability are the only options for building a life we find worth living.  If you’re reading to be open and take some chances, let’s get started…

The e-book covers ten “chapters” each with lessons, exercises, and takeaways to help you make progress:

#1 What Matters (Values)
#2 Check Your Beliefs At The Door
#3 Research Potential Roles
#4 Track and Share
#5 Assess Your Strengths
#6 Upgrade Your Resume
#7 Share Your Story
#8 Tailor Your Story
#9 Activate Your Fans
#10 Hang In There (Apply, get rejected & stay resilient)

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 Career Transition Playbook appeared first on Boundless by Paul Millerd.

common question I hear is, “Should I go to Business School?” My answer is always the same, half cynical and half serious:

“You should go to business school if you want to go to business school”

Simple, but I really do believe this. Advice from other people can be valuable, but most people tend to tell you to do what they did. If you’re confident that business school is the next step for you, you will always have that thought lingering in the back of your mind. Go do it!

There are two questions I ask everyone who solicits my advice:

1. “What do you want to do after business school?”

2. “Why don’t you do that now?”

Even if you know what you want to do, there are still a number of benefits of going to business school (which I will get to). I was always impressed by my classmates who knew exactly what they wanted to do — they were able to take advantage of every resource, connection, class, and project to help them build their skills.

For people that are less sure, like I was, business school can be a confusing place. Many prestigious jobs instantly become more attainable. For those that have been crushing it in their life, it is incredibly hard to not pursue those paths, whether it is working at Google, McKinsey, Goldman, or the hottest startup.

I’ve been having a lot of conversations with classmates three years after graduation who are all facing the same issue: they are in a great job, but something is missing. I have a friend at Google who loved his job, but when a few things changed — a new manager and position, he realized he didn’t care where he worked — he just wanted to work on a great team.

That same friend recognizes now that business school may have delayed him coming to this realization. All the things that made the two year experience exceptional (exposure to diverse perspective and time to reflect) also made career planning more confusing.

Business school is an option multiplying machine. Of course, this is one thing I found attractive — it expands your pool of opportunities. Since I didn’t have a clear understanding of what I wanted to do when entering business school, expanding my options seemed like the best idea.

But expanding my options did not solve the age old question of “What do I want to do?”

My one caveat about business school is always:

Business school will not help you decide what you want to be when you grow up

You may figure it out during the two years of conversations, classes, and projects but I don’t think business school is well suited to answer this question — and it shouldn’t be! The burden is on you.

Like me, a lot of people go to business school because they want to go to business school — and I think that is fine! So for these people, I offer what I consider the six best things about going to business school:

1. The life-long friends: A lot of people talk about “the network.” This is definitely real. My classmates are doing incredible things in their career and every one of them will pick up the phone to have a conversation or help me in my career. That support system is invaluable. However, the real power comes from the friends you make from spending 12 hours a day together, struggling through the same assignments or choreographing a dance for an upcoming cultural event. I will guarantee that you leave school with at least one or two life-long friends. These are people that will be in your wedding party, take vacations with you or offer a place to crash when you visit a new city. This paid off for me when I faced some health challenges after graduation. The unexpected love and support of my classmates was amazing. I had life-long friends, not a network

2. Shrinking the world: It is very easy to expose yourself to different industries and perspectives during the two years you spend at business school. Whether through clubs, classes, speakers or just conversations with classmates, you will likely learn about industries you never knew anything about and jobs you never heard of. At MIT Sloan, almost half of my class was international. Beyond the obvious benefits of travel recommendations for life and inside food knowledge, working with diverse groups broadened my perspective. One of my groups composed peolpe from the US, Mexico, Israel, and Korea — which made the world seem a lot smaller and the world’s challenges a lot more solvable

3. The ability to take a step out from the “hustle”: Business school is certainly fast paced, but it’s also a step out of the increasingly complex and competitive working world. I am a big fan of taking breaks or walks during the day to increase my productivity and creativity: the benefits of this are well known. I haven’t found any research on the impact of a two year break during your career, but my hypothesis is the benefits are profound. I like to think of business school as a two year walk, where I had time to reflect, think, learn, dream and wonder

4. Eliminating stories of why you can’t do something: Being surrounded by such successful people can be a double edged sword. If you start comparing yourself to your classmates, you will always find someone more accomplished or impressive. However, the fact that you share a beer or lunch with them makes you realize they don’t have superpowers, they just don’t spend any time creating excuses. It made me realize that the only thing that will hold me back from what I want to accomplish is my own beliefs. Everyone, including me, is capable of greatness

5. Thinking like a leader: Being accepted into an amazing business school gave me a lot of pride. It also gave me the self-imposed pressure that I need to embrace this opportunity and do something with it. Prior to business school, my definition of a “leader” was something defined by a title or number of direct reports. During a leadership class I took, this idea was destroyed, as I realized these people haven’t cornered the market on leadership. I was filled with the anxiety and excitement that anyone could be a leader. I embraced this mindset and try to ask myself “How should I act in this situation, as a leader?” For me this comes out by having integrity and being authentic to who I am. I’m passionate about building positive and meaningful work environments where people can flourish — so I try to embrace this spirit in every interaction I have in and out of work. I’m grateful that I literally had a class to think about leadership and what it means to me

6. An experimental lab: I looked at everything as a new learning opportunity. The improvisational leadership class that made me dance around in front of my classmates taught me how to be more fearless. The healthcare project I did made me realize I didn’t want to go work in healthcare. The choreographed dances I did with my classmates for the New England Cultural Function (yes, really) made me realize I love making a fool of myself for the sake of having a good time. Finally, the many hours I spent helping others with their job searches and interviews made me realize I love helping others achieve their dreams

Going to business school was not a rational decision for me. I didn’t calculate two years of lost salary and factor in the ROI of tuition payments and future salaries. It was just something I had always wanted to do, a dream that I had.

I went to business school because I wanted to go to business school

Why do you want to go?

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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I was recently asked this by a mentee and I did not know how to respond.

Everyone has had that period at work when things are incredibly frustrating. The feeling overpowers you on Sunday night as you dread returning to work or paralyzes you in bed as you avoid starting your day.

These moments suck, but they also give us valuable insight: if you focus on what’s driving that feeling you can determine what is “off” in your own career or life and then take action to address it. Is it the lack of support from your manager? Is it the type of work you are doing? Is it the speed of work? Is it the people? Do you not have enough stress-free time out of work? Or is everything off?

As I think back to leaving my first job after college, I didn’t ask myself these questions. I just knew I wanted out. That first job was in Cincinnati, where I joined an entry-level management rotational program. The program was prestigious and well-run by all accounts, but I felt like a fish out of water. I was desperate to be in a role I was more passionate about.

I always promised myself I would not stay in a job that I did not enjoy, so I decided to take action. With or without a new job, I was going to leave and move to Boston.

I committed to this 100% and started telling friends and family. For some reason, people have always had faith that things will work out for me. I’ve always been relatively confident, but at this moment I had a lot of anxiety and worry. I was terrified of moving without a job. A month before my self-designated “quit date,” I got lucky: I landed a job in consulting, an industry I had been trying to break into for over two years.

To the outside world, this has always been seen as a good move for me. I moved from one good job to an arguably better one. I don’t have to spend much time selling people on why I left. Does that mean I knew what I was doing?

Of course not.

I could have spent more time asking myself questions around why I was frustrated, but I was not thinking with a clear head. I was an emotional wreck — driven by a lack of interest in the work and uncertainty about where I would be living as well as a big dose of homesickness. My drive to take action was mostly to quell that feeling.

If you are feeling something similar, I’m not saying to quit tomorrow. Just because I landed a role I loved after leaving my first job doesn’t mean it was the right approach. I didn’t know how to enjoy the journey as much as I do now. Reading Robert Greene’s book Mastery I was stunned to find that some of the world’s greatest minds in history took years and decades to reach a level of mastery and find their “dream jobs.” I wanted my dream job at 22.

A good question to ask when deciding to leave is, “Can I get what I want in my current company?” A lot of people are surprised when the company desperately tries to keep them upon quitting. Just because you are incredibly frustrated and know you are not maximizing your potential does not mean you are seen as a low performer.

A friend recently quit his law job and was surprised when they offered him a month’s paid leave and the opportunity to switch to a different practice area. He left anyway, but he was prepared for that counter offer. A good exercise is to put yourself in that situation. If the company would give you a counter-offer to retain you upon quitting, what would you be willing to accept? Why not ask for that now?

We often think that things are out of our control in the workplace, that things are what they are. However, I’ve found that people in the workplace are usually much more empathetic than you would expect. Due to some outdated beliefs about how we are supposed to act in the workplace, we are scared to be vulnerable. However, when you have the courage to say to someone you trust, “I am struggling, this is not working for me” it often ends with an ally in your corner and a brainstorming session on what to do next. Early in my career, I was scared to share with others how I was feeling. It was much easier to go pursue something else.

The true challenge is being true to yourself. Most people will give you conservative advice when talking about your career: how to ruffle the least feathers and pursue paths that are seen as successful or safe by others. This makes sense. Nobody wants to see anyone else suffer or fail.

But that’s crap.

You have to realize that if you listen to what everyone else is saying, you will be miserable. Everyone has that friend that has been complaining about their job for years. Those people drain your energy. You don’t want to be that person.

The great thing about life is you make the rules. You don’t have to do what others expect for you. Have you ever seen someone’s eyes light up when they describe something they are working on? Something they would gladly do for free? Everyone deserves that — and I know everyone can find some form of it.

So is it time to leave your job?

Unfortunately, I don’t have that answer for you.

There is always going to be a rational approach for figuring these things out, but emotions are always going to claim a seat at the table. One of my recent clients was in a good job — but the endless hours and work culture were crushing his spirit. He decided he needed a job change to get some breathing room to figure out what he really wanted long-term. Sure, he could have tried to negotiate for a different role at work, but he had reached a point where he was done. He had to move on. This was the right decision for him, but every situation is unique.

There is no perfect career. In today’s world, there will be missteps, side steps and steps forward. The important thing is that you are learning and reflecting along your journey. The closer you get to something that you are passionate about and aligns with who you are, the better off you will be.

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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