Readjusting to Routine: Life After Entrepreneurship

Over the past decade I’ve been fortunate to pursue work that I was passionate about as an entrepreneur. Today I find myself adjusting to a work routine driven by necessity. The transition process has me questioning questions. I imagine I’m not the first, nor the last, former entrepreneur to experience this adjustment, but that doesn’t make it any easier.

Now you might immediately assume that this is a journal of some budding mid-life crisis, but I don’t think that’s the case. To date, I believe my personal and professional efforts have produced good for the world. I’ve had opportunities to help build communities, teach people new skills, and create long-lasting friendships. Now I’m exploring the process of coming to terms with the road forward.

Up to Now

My personal and professional successes have been efforts of narrow but intense focus. I discovered the process of mastery through Brazilian Jiu-Jitsu. College and the work that followed immediately afterward were just things to do in between training. I was obsessed with the sport, an active competitor, and have been part of two teams that had become a second family. The most important thing Jiu-Jitsu taught me is that it was within my capacity to excel significantly. It was the first thing I could claim I was really good at.

In my mid-twenties, I realized that while I would always love jiu-jitsu, there wasn’t a pathway to permanency I was interested in pursuing. Attempting to become a mixed martial artist wasn’t in the cards as I didn’t like getting punched in the face, and opening an academy didn’t contain the exponential growth potential that I was looking for in building a business. I set to work on evaluating industries and understanding possibilities for a new focus.

In 2011 I co-founded what would ultimately become a moderately successful e-commerce business that I sold in early 2019. The process established an 80 to 100-hour workweek as the standard mode of operation, including consistent seven day work weeks for the two years of service. Every productive moment was spent thinking, planning, and executing new strategies to grow and expand. It was an obsession that I happily fell into.

As the business matured, I found myself with more free time that I dedicated to expanding my knowledge in areas unrelated to my niche. Political philosophy and government had sparked my interest, and I began the process of consuming knowledge about our institutions and circumstances. Like many others, 2016 was a paradigm-shifting year for me. It was the year I decided I had to be a part of the transformation. It also meant that whatever free time I had earned was going to be refocused.

In 2017 I founded a 501c3 civic-tech non-profit dedicated to opening up access to local elections. I self-funded the project and was able to assemble an excellent volunteer team to help manifest our shared vision.

We built the first-ever free election campaign platform for local candidates. Our 2018 beta test in New Jersey was a success, with our research revealing that local election information was inaccessible for most people in the state. The efforts concluded with an impact report and suggestions for state legislators on how to deepen democracy in our state.

In January of 2019 we received and accepted an offer which finalized the sale of my for-profit business. Selling a company, even a relatively small organization like ours was, is a lot of work. The long-grind restarted itself and lasted until the beginning of April 2019 when I officially exited the business.

As my eight-year grind finally had a light at the end of the tunnel, I found myself at a candidate training seminar facilitated by the Working Families Party. With peaked interest, I consulted with friends I had connected with through activism and my non-profit work about a potential run. Words of encouragement and commitments to action led me to embark on a campaign challenging entrenched corporate democrats as a progressive.

Our chances were slim from the start, but I am hesitant to waste an excellent learning opportunity, especially one so relevant to opening up citizen access to democracy. Fortunately I was able to assemble a great team and we moved forward.

Campaigning was an incredible experience that I would recommend to everyone. I loved connecting with community members, door knocking, and developing new ideas for how we could improve our state. I was genuine with my intentions and had I won I believe I would have made an excellent State Assembly person.

In some respects the campaign may have been a subconscious extension of a lifestyle I was hesitant to let go of. It required immense focus and effort. Winning meant being able to channel my existing intensity structures into a public service. To say I was excited about the prospect would be an understatement.

But I didn’t win. Then came the lull.


The underlying theme of my efforts in jiu-jitsu, e-commerce, and non-profit is the enforcement of self-imposed milestones. Tournaments to train and lose weight for, quarterly sales goals to meet, and election cycles that determine your platform viability were my motivators. Every habit builds upon itself, getting stronger as long as it is practiced. For a decade I’ve been a person of rapid habit.

Now there was no direction to reinforce. It wasn’t that I was unwilling or unable, just that I have no professional focus I’m committed to. No negativity entered the space, I was happy to enjoy nothingness for a few weeks.

Progressive activism had ignited a new passion, one that intertwined my independent research, my experience building organizations, and a passion for connecting with people. It was an opportunity to combine creative work and social good, something I strongly desired. Keeping myself open to opportunities that were a good fit. Not working was not an option.

If you’ve ever struggled with motivation to apply for jobs I’ll share what got me through it. Put it in your weekly task list for 20 hours a week. Four hours a day, usually beginning the day’s productivity with it to ensure it gets done. After that you’re free. I would spend time volunteering for activist organizations, writing, and researching.

How do you enter a new vocation untested, unproven, and unaligned with the experiences so often required? I was unqualified for many of the positions I was applying for, but it never deterred me from applying.

I was willing to work at entry or mid-level positions that would be below self established pay-grade but was also constrained by the economic requirements of my family. The feedback was clear, I was either unqualified or “overqualified” for many of the activist and non-profit positions I was seeking.

That hurt, because ultimately the failure was mine. I was unable to convince others of what I knew to be true. As a successful founder, I would add a uniquely advantageous perspective for any organization. Again I needed to readjust my expectations, opening myself up to positions that didn’t ignite passions.

In retrospect I am still very happy with my professional accomplishments, but they are generalist in nature. Positions within established organizations are often specialist. They are two very different types of work. Entrepreneurs returning to the workforce should be prepared to exhaust all options.

Slightly defeated, I began to churn out applications for any companies looking for my hard skill sets. I dreaded the idea of being stuck in some nine to five office routine. Micromanagers, co-worker politics, and the corporate ladder was… a personal prison that embodied everything I imagined would lead to psychic and spiritual death.

Even here, I struggled.

Three months and 97 job applications later nothing had materialized. Changing careers is never easy, the entrepreneur is no exception.

The experience of consistent and persistent rejection began to take its toll. Usually high-optimism, I began questioning the worth of my experience. As if the word worth could ever accurately describe experience.

Imposter syndrome creeped in. Were the last eight years irrelevant? Was I going to be pigeonholed into starting another business and restarting the cycle of grinding from day one? Did I have the skills that I believed I did? I’ll admit that I spent more time in this space than I would have liked.

Today, I embrace the imposter. In many respects, it is true. Everything I have ever done in my life successfully started with committing to a mission that I was woefully unqualified to do. No entrepreneurs course is determined before the venture is taken. That’s the fun of it, you learn as you go.

My transitioning to routine work forced me to grapple with some of our society’s inherited frameworks of success. The greatest strength of the entrepreneur is an adaptation. But a wide array of skills doesn’t translate well in a world of corporate specialization. It’s one of the reasons I am so passionate about political reformation, our system stifles creative experimentalism by design.

Then there is the financial stress. It felt terrible to see money consistently draining out of my account without any realistic prospect of stemming the bleeding on the horizon. School loans, rent, food, family, etc. I was and remain incredibly fortunate, I can only imagine the despair of many in cyclic poverty. .

Money made me question my self-worth. The institutions of our society today determine that economics is our primary means of survival. What good is someone who’s last eight years of experience can’t land a job that they don’t even want? I never did, and presently do not, tie my or anyone else’s self-worth to capital. My fears were irrational, given my circumstances, but real in those moments.

Through these moments of negativity I persisted. Under duress, discipline is freedom. Being at home all day and not feeling exceptionally positive about my circumstances was a procrastination gateway. I’ve always found that in times of overwhelming stress, the best solution is action. Action frees the mind from the infinite possibilities that dwell within it and focuses your attention on individual tasks.

Hourly blocks of time mapped out weekly. The discipline was freedom. Monday through Friday was the same schedule. Get up, exercise, meditate, read, apply for jobs (about five hours a day), write, and then free time. Forcing myself into a standard routine was vital to my mental health while in transition.

Center represents total applications, displaying two different data comparisons. Graph made with


At the end of month three, I found a new profession. While it wasn’t the intended path, it provides a great opportunity to help people. It’s one of the many changes happening now that has me thinking about the space I inhabit. For so long, my life has been a project of deep passion, high engagement, and singular focus. Now I am a part of someone else’s project.

Readjusting now becomes shifting expectations from extensive and creative work to a more routine occupation. I’ve always felt an aversion to routine work. It can erode the soul if you don’t want to be there. After accepting my new position, I questioned my ability to adapt.

But every entrepreneur should have faith in their ability to change when needed. I’ve found that despite my fears, my skills are very useful. I can work with people I enjoy and have been granted a wide array of creative decision making. If you’re an ex-entrepreneur in the transition phase right now, take hope that there are employers out there who recognize the value of non-unicorn founders.

Another adjustment was how I would continue staying active in the local political space. For the past four years, I’ve had complete freedom with my schedule. That’s gone, but my ability to be active is not. Now, it’s about doing what I can, when I can.

There are also the important things like family and friends. I first started planning my e-commerce business at the age of 25. Things are fairly different at 35. It’s like you come up for air and you can’t help but admire the surroundings.

Thinking temporarily, I believe that the universal experience of time is a wave-state: a vibration. It moves up, it moves down, there could not be one without the other. Readjusting to routine is a new opportunity to learn more and explore. Recognize that here you are, and that’s ok.

Readjusting to routine after a life of entrepreneurship hasn’t been an easy process, but it is getting easier. It’s about giving your existing strengths a new form, knowing that your primary advantage is adaptability. Today it’s about focusing on the task at hand, knowing that each day is a step forward in your new direction.

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