My Awakening: Quitting The Default Path, Becoming a Freelancer and Why I Want To Help You Navigate The Future of Work

Chasing prestige

My mother said I lacked ambition.

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 looked. 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 asking 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 what they called self-determination theory. They found three elements 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 type 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 things 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 were 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 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 you become more trapped in a job you 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 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 had nothing to do with a job. 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 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. However, while I am excited, many 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 too 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?” lets ask each other “what are you meant to be doing?” Here’s to enabling more people to do what matters to them…

I created Boundless, which is based on the idea that we are capable of more than we believe. I host a podcast, write and create tools to help people and organizations like you unleash your potential and navigate the future of work.