In August 2021, I resigned from my role as COO at ConvertKit. I sold most of my stock and set aside funds for a sabbatical of undetermined length. In the 18 months following my departure, I transitioned industries; pursued three six-month career experiments; experienced deep anxiety and depression; and came out the other side, more aligned to myself than I’ve felt in years.
A career transition can be an opportunity for a step change in personal and professional growth. I know this is true, and yet the more senior I’ve grown in my career, those transitions have actually felt riskier. We need more people to talk publicly and openly about how they go about making big mid-career changes.
This essay is the real version of what it’s like to try to find a new thing.
After telling myself a story about being an “extremely important person” at a “highly successful company,” this is about the work I had to do to find my way through.
This is about the stories we tell ourselves in order to work and serve and be a part of something authentic and rewarding.
Elements of this will resonate for some folks and not others. Wherever you are—in a career transition now or not—I hope you’ll be able to translate my experience into your own context to find your way through.
A framework for experimentation
There were two questions I asked myself when thinking about what to do next in my career.
- What role do I want to play? Setting aside what a resume says and what my past experience dictates, I wanted to explore what I wanted to spend my time doing.
- What career adjustments do I want to make? Regardless of what career path I would choose, it was important to decide what elements of a new role were negotiables and what weren’t.
As I considered these questions as frameworks for my decision making, the following floated as possible choices to, “What role do I want to play.”
1. I can return to my roots as a creator.
Working as a creator would give me control over what problem I worked on and would put me in charge of my own growth. It would also mean continuing to work from home and in relative isolation as compared to joining another company. The biggest obstacle was determining a business model for my writing and podcasting, which often do not directly translate to revenue. Short-term earning potential would be low, but long-term it would be driven by my own commitment and execution.
2. I can lean into my experience and leadership perspective to found a startup.
Founding a company could allow me to check all of the other boxes. I could work on an important problem, build an in-person team, hire for leadership and culture, and grow immensely. The two key challenges here were to 1) come up with an idea that would solve an important problem better than other companies I could join and 2) find a cofounder with compatible values, experience, and skills. Income would be low for a couple of years and chances of failure would be high. But once the company hit a growth trajectory, it could unlock earning potential unlike any other career outlet.
3. I can accelerate a startup already working on an important mission
Joining another company felt safe and secure. I could filter for companies working on important problems, look first for companies in Portland, and apply to roles that would stretch me. If I filtered for startups in the Series A range, they’d be able to pay me what I’m worth while still being at a stage where I could make a massive impact. The biggest challenge would be putting myself out there for a job search process that can often be discouraging and humiliating, even for the most talented of people. I was also doubtful whether I could find a company that met my criteria here in Portland.
Regardless of which path I chose, there were a list of career adjustments I wanted to make with this opportunity to start fresh. I wanted:
- To work on solving an important societal problem (ie climate change, food systems, education)
- To work in person with a team after more than a decade working remotely
- To work alongside people at least as committed as me to building wholesome organizational culture and pursuing the inner work of leadership
- In a field, role, and company stage that would challenge me to grow both personally and professionally
Admittedly, there was no obvious way to pick a path without 1) specific options for each path and 2) experiencing what each path might be like in reality compared to the idealized version in my mind.
I decided to treat the path forward as a series of experiments. Rather than holding tightly to any one thing, I would follow my intuition and remain open to doors that opened that I couldn’t have predicted. Thanks to the freedom of financial planning for a year or more of sabbatical, I wouldn’t need to remain tied to any path that turned out not to be what I imagined or that was a dead end for my goals.
Picking a lane: Creator economy or something else?
Even with a mindset of experimentation, the most important and challenging question in the entire transition was, “What problem do I want to work on next?”
I am a creator economy veteran and have the deep expertise to prove it. I had been in and around the creator economy since starting my first business in 2011. First as a founder. Then as a growth marketer and teacher. Then as a software exec.
But if you work in an industry long enough, you get to see every side of it—and that’s not always a good thing. The massive infusion of cash into the creator economy as the early pandemic raged on, the growing toxicity of social media, the egos in the industry, and the sometimes pyramid-scheme-like nature of creators teaching creators how to be creators had worn on me.
The negative aspects started to outweigh the hope and optimism I once felt as I saw people taking control of their careers to build something they believed in. Despite working to tell stories of creators building important and meaningful businesses, I continuously felt a certain emptiness in the work. For every inspiring and impactful business a creator started it felt like there were ten more “make money online” entrepreneurs.
While it would’ve been comfortable and straightforward to join another creator economy company, I knew I had lost passion for it. At least for now.
Meanwhile, I felt a growing sense of urgency around climate change. With major corporations and governments ignoring the problem, I was worried. My typical response to worry is to try to do something about it.
Before going all in on climate, I wanted to make sure I wasn’t missing something important that I could be working on. Education, food systems, biodiversity, sustainable fashion and home goods, sustainable housing and building materials, small/local business, wellness and preventive healthcare, and a host of other topics were all of interest to me as well.
After sitting with myself, I knew there were a few issues I felt most drawn to:
- Human flourishing and wellbeing
- Preserving Earth’s natural environment and biodiversity
- Food systems that promote human, animal, and ecosystem wellbeing
- Physical goods made from circular materials that promote human and environmental health
My interests are at the intersection of using business as a force for good, promoting human wellbeing, and preserving natural ecosystems. Climate change is one of the biggest threats to human, animal, and ecosystem health. Business is the tool I most know how to use to do good.
That settled it. I’d pursue career opportunities that contribute to solving climate change while promoting human wellbeing and preserving ecosystems and their inherent biodiversity.
Establishing Practical Criteria: Finances and Flexibility dictated the options I was willing to consider
While there were clear criteria I wanted from my work, there were also constraints. The two biggest were financial and family-related.
ConvertKit created an incredible financial win for our family, but mostly in the sense that we now have a nest egg that we can ignore as we continue to build our careers and plan for retirement in the future. I still need to earn a healthy income to cover our family’s bills.
We looked at our household budget over the past couple of years to arrive at a target gross income for our family based on typical monthly expenses and savings and investment goals.
To support the lifestyle we want for our household of six (my wife and I, our two sons, and my in-laws) I’d be looking for a role or to build a business with substantial earning power. This added an important element to my search for the right next thing — I needed to be able to earn enough money to do my part to support our family..
On the flip side, we also had a two year old son and a second child on the way. It was important to me that I was able to be home for dinner and bed time, have the flexibility to travel as a family a few times a year, and maintain sufficient mental health to be present and joyful with my wife and kids.
I was looking for a damn near perfect job and I felt threatened by the possibility that I might not be able to find something to meet all of my criteria.
Nonetheless, I turned my attention to finding the opportunities I felt most drawn to. With everything a possibility, it would take a combination of following my intuition and a lot of research to find the right thing.
My First Priority Was to Increase My Exposure to Climate Tech
Now that I knew what direction I wanted to go in, I needed a plan. Making a jump between industries without taking a step back in role and comp is a hard move to pull off.
I needed to build credibility, reputation, proof of work, and connections that would open up job opportunities or connect me to potential cofounders.
The best way I knew how to do this was to start learning in public and create a track record of essays and projects related to climate change. I made three decisions to:
- Start writing a newsletter about ongoing news in climate tech, as well as long-form essays on promising climate tech companies
- Sign up for the next available On Deck Climate Tech program to get to know other folks interested in transitioning into the industry
- Look for projects to contribute to that would help me build knowledge, connections, and proof of work
I planned to spend 6-12 months following this path. I figured I would grow a large enough audience that the creator path would become viable, I’d meet someone to start a company with, come up with an idea I couldn’t ignore, or research companies until I found one working on a solution I cared about enough to go to work there.
The next 18 months from September 2021 to March 2023 were spent exploring different avenues for making an impact on climate change with my career.
Three six month career experiments allowed me to explore multiple possible futures
Looking backwards, I spent the past 18 months doing three distinct career experiments with a couple of side experiments along the way.
While I wish I could say I set out to do three six month career experiments, in reality I was just following my intuition and trying to make the right next move given what was in front of me. Throughout the process I stayed true to two things:
- This might be one of, if not the only opportunity I have to try different paths in the middle of my career; I should take advantage of the exploratory opportunity
- Nothing *had* to work long-term; I had the financial freedom to move on when and if something wasn’t the right fit
Knowing these truths and acting on them are two different things. From where I sit today, I’m proud of myself for both investing fully in each experience and also being willing to move on to a new experiment when I knew something wasn’t right.
I’ll try to break down my thought process on why I pursued each experiment, what I learned, and how it led me to my next step.
Building My Foundational Knowledge On Climate Change: Managing Editor of The Carbon Almanac
Before I could start on my master plan, I had a stroke of luck. Three days after my last day at ConvertKit, I found out Seth Godin was thinking about a project related to climate change and was putting together a team to make it happen. Seth and I initially worked together in 2013, almost worked together again in 2018, and we reconnected to chat about the new project on climate.
I spent the next six months (September 2021 -> March 2022) volunteering full-time as the managing editor of The Carbon Almanac, a bestselling book of facts about climate change. In just 11 months, 300 volunteers collaborated to write, design, and publish the anthology in partnership with Penguin Random House. We sold out the first print run in less than a year.
The project did so much for me:
- I gained confidence that all of the leadership skills I had built in one particular context at Convertkit were broadly applicable in many settings
- I was inspired by the heart and goodwill put forth by so many generous, thoughtful people on the project
- I built a broad-base of knowledge on hundreds of topics related to and tangential to climate change
- I had a concrete project I could point to as a bridge between my creator economy work and the climate work I hoped to continue to do
Because the project was an all-volunteer effort, I knew it wasn’t going to be my next career move. It was a project and a bridge to something unknown in the future. I wrapped up my involvement on the project in March 2022 after we sent the final proofs to the publisher and the project moved into the promotion phase.
Testing Different Paths at the Intersection of Entrepreneurship and Climate Change: The Build for Climate Accelerator and The Carbon Economy Newsletter
While I was working on the Carbon Almanac, I also wrote a newsletter on climate tech and joined the On Deck Build for Climate program. Both were opportunities to continue building a track record and connections in climate tech.
I started writing my newsletter, The Carbon Economy, in September 2022. The name was an ode to the creator economy + my interest in climate change. My goal was to write weekly about important news at the intersection of climate change and startups. This was also a chance for me to flirt with a dream I had let go of when my first business failed — earning a living as a creator.
While I was learning a lot writing the newsletter, I knew there wasn’t enough personality and voice in what I was writing and it wasn’t the kind of newsletter I would subscribe to. The writing I love on the web comes from the unique perspective of the creator and is often distinct from anything else. I decided to shift my creator efforts to writing long-form essays on companies combating climate change.
The first essay I published was on Carbon Direct. It spread quickly, gained attention from the company’s founders, and gave a small proof point that there is an audience for this style of writing within climate tech. It seemed like there might be a path forward as a creator writing deep dives on climate tech companies if that’s what I wanted.
While I was testing the creator route, I also wanted to explore founding a company. I signed up for On Deck’s Build for Climate program, which was designed to bring people together to explore the climate tech landscape and potentially found new companies.
I joined a team of four talented people to explore applying AI and big data to increasing adoption and effectiveness of regenerative farming practices.
We researched the problems farmers face that prevent them from employing regenerative practices. While data will certainly play a role in improving farming, it was nowhere near the top of the list of barriers farmers face. We were a solution in search of a problem, which isn’t a good reason to start a company. Although we enjoyed working together, the team split up after the program.
The combination of leading The Carbon Almanac, writing The Carbon Economy, and exploring startup ideas in Build for Climate showed me that there were a nearly infinite number of interesting problems to solve at the intersection of climate change and startups. Yet I still didn’t feel strong conviction towards any one direction.
To make it more challenging, I didn’t feel like I had found an idea and founding team to start a company around. And I hadn’t yet found an existing startup that met my criteria beyond being in climate tech. I was still facing the eternal problem of confronting the fear of doing my own thing as a creator, and wasn’t ready to commit to that path either.
The exploration continued. Just as the Build for Climate program was getting started, a friend in Portland threw me a career curveball.
A Detour Into Specialty Coffee: COO at Good Coffee
Sam Purvis is a long-time friend and mentor who I admire deeply. He’s the co-founder and managing director of one of the many storied Portland coffee companies, Good Coffee. One day he gave me a call and asked if I’d be interested in joining them as COO.
Throughout my career transition, I had an alternative career path in mind that focused on:
- Making a physical product or in-person experience
- Working in an office with real life human beings
- Being a part of the social and cultural fabric here in Portland
The romantic in me wanted to give it a shot. Not to mention my infatuation with the craft of coffee in particular. We agreed to a two-day-a-week trial run at the same time I was participating in the Build for Climate program. Almost immediately, I felt an excitement and energy that had been missing from my work at ConvertKit. I loved showing up to an office and seeing the product being made, packaged, and shipped from our headquarters.
Outside of the office, I got to meet the owners, chefs, and craftspeople at some of my favorite food, coffee, and cocktail spots around town (the core of the culture of the city). The Good Coffee name carried respect and a reputation of thoughtful hospitality in those circles. I felt like a part of the cultural fabric of the city.
When I didn’t have a clear direction coming out of Build for Climate, I decided to turn the trial run at Good Coffee into a commitment to join the company full-time. I spent six glorious and highly caffeinated months immersing myself in the world of specialty coffee.
The two biggest drawbacks were:
- Infinite access to coffee, which meant my caffeine consumption, and therefore anxiety, were way too high
- After growing used to startup exec pay scales, I was only making about 35% of my former salary (even aside from the value of profit sharing and equity)
After I got back from a month of parental leave with our second son, the CEO and I sat down to map out my future with the company and talk about compensation. He had done generous and helpful research on comp for COOs in food and beverage companies at our scale. Unfortunately, I wouldn’t be able to earn a sufficient salary to meet our financial goals as a family.
My heart sank. There wasn’t a path forward. I was bummed, even a little heartbroken, because I had so enjoyed my time at the company in particular and in the industry in general.
I decided to start looking for jobs in climate tech. It was more comfortable than declaring myself a full-time creator or founding a startup, which I still didn’t have a compelling idea for. The same day as our conversation about compensation, I started browsing open climate tech jobs. I couldn’t believe what I found on the Lower Carbon job board…
“Director of Operations, Stealth Renewable Energy Startup, Portland, OR.”
Jumping Back Into Startups to See If Fighting Climate Change Would Feel Different: VP of Communications at Stealth Renewable Energy Startup
I had long ago written off renewable energy companies on the assumption that most wind, solar, and nuclear companies would be too large for me to have the impact and scope of role I wanted.
This opportunity was the only one I found that was:
- In climate tech
- Building a solution that would make a substantial dent in emissions if it worked
- Located in Portland and working in person
- With a role open that fit my skill set (albeit a narrower role than I preferred)
I immediately applied and then dropped a follow up note to the listed point of contact. After a long interview and deliberation process, they offered to create a role of VP of Communications to lead investor communications, their public launch plan, and marketing.
I knew there were no other companies in Portland that met my ideal criteria, so I decided to take the leap back into startups.
Due to my NDA and the company still being in stealth, I can’t share much about the work I did, so instead I’ll jump ahead.
By December 2022 (4 months in), I had a feeling the culture and role weren’t the right fit for me. I wasn’t having the impact I was hoping for and I didn’t feel at home within the organization. I chatted openly with the CEO and EVP (their operations leader) about my concerns and we committed to working hard to find me a larger set of responsibilities to make more of an impact.
By February 2023 (6 months in), I was experiencing a set of feelings I had grown to recognize as signs it’s time to make a change.
My stress and anxiety levels were rising despite the workload being low compared to what I’m used to and capable of handling. I started drinking more coffee, sleeping less, and wearing myself out worrying about how to solve the problem. This is my classic burnout pattern and it’s typically a sign that I’m out of alignment with myself.
As I got curious about the experience I was having, I had a realization: I’d been running from what I truly wanted and it was finally becoming clear. I am the leader I had been looking for. My vision for strong leadership and good culture is clear. I’m fully committed to accelerating business solutions to climate change and other important societal problems. I have everything I need to build my own company.
Being out of alignment with what I truly wanted was at the root of my stress and anxiety. Sure, I could blame it on the startup, but taking one more role in a startup was the final push I needed to realize what I truly wanted. I had to rule out every other possibility before I could be honest with myself.
I wanted to return to being an entrepreneur. Still, something was holding me back.
Telling Myself a New Story About Past Failure
Throughout this 18 month journey, I worked with my executive coach to be sure I was seeing things clearly, doing my own inner work, and thinking through all of my career options. As I prepared to leave the startup he helped me see why I had been deceiving myself: I was scared.
Logically, that makes no sense. I’m 35. I have 13 years of experience as an entrepreneur, operator, and executive. I was part of the team that built ConvertKit into a $30M ARR creator economy juggernaut with no outside funding. Selling a portion of our ConvertKit stock allowed my wife and I to put more money into retirement accounts than the average American 65 year old. I’ve proven over and over that I’m employable in high paying jobs in startups and elsewhere. I have everything going for me that should give me a high level of risk tolerance for taking control of my own career.
No amount of logic was breaking through the fear. Why?
Because in my mind I’m still the 26 year old guy who had to shut down his first business. The guy who spent two and a half years trying to make his naively altruistic idea work. I’m the altruist and optimist that had been hit in the gut by reality. I’m a failed entrepreneur.
The two realities could not be farther apart. But deep inside of me, my brain was battling my heart to protect me from becoming that guy from 2014 again. I was willing to do almost anything not to make myself vulnerable to ending up in the same spot — a failure.
Once my coach called this out, I could finally see behind the curtain of my own career decision making. I was looking for any way NOT to take the risk of failing again.
After reflecting on this, I remembered the truth about my experience as an entrepreneur at the beginning of my career: it was the most transformational experience of my professional life that opened the doors to every opportunity that came after it.
Was it hard? Yes. Did it strain my relationship with my wife? Yes. Did I shut the business down? Yes. But did I fail? No.
The business failed. I did not.
I knew there was only one possible answer: try again. Everything I had been looking for was on the other side of that decision. I just needed to make the call and get started.
The number one issue to address was the same as it was as I left ConvertKit: I knew I wanted to write and podcast at the intersection of climate change and using business as a force for good. But I needed a business model.
Then it hit me: Coaching is the perfect business model for the kind of writing I wanted to do. Although I have been coaching for ten years on and off, I’ve never taken it seriously as a career option… until now.
Confronting My Fear of Once Again Becoming an Entrepreneur
When I raised the possibility of coaching as the most viable business model for my work as a creator, my own coach (Andy Crissinger at Reboot) became all the more valuable because of his personal and professional path to coaching.
I shared with Andy my deepest fear about claiming coaching as my profession. I know what I think when I hear someone else say they are a coach. Something like, “What have they done to be a coach? Have they done their own work to make a real difference with their clients? Was coaching the thing that was left after they couldn’t find another role or company to start?”
What if people I respect think about me as a fraud or a huckster?
I’m scared of being seen as the kind of person who couldn’t build startups, so instead I coach people who can. I’m scared of being discounted, left out, and disrespected. I’m scared of being seen as a huckster.
I’m scared of being criticized for owning who I am and what I’m great at.
That fear is rooted in experiences from long ago, but just as present today as ever. It’s a fear rooted in high school. A fear rooted in being rejected for being me and having to transform myself into something unrecognizable to be accepted. It’s a fear of going backwards to a painful time of life.
Me today… the strong, capable, experienced leader who has built substantive companies knows that the people who would shun me for who I am are not worth listening to. I know that coaching has transformed my life and that I have the component skills and experiences to do the same for others.
While I have a negative perception of some coaches, I also have immense respect for many other coaches (including my own!). The thing that sets the exceptional coaches apart is how committed they are to improving at their craft.
I decided I would set out to be that kind of coach, knowing that the people worth listening to will see the same in me.
Establishing the Kind of Coach I Want to Be
Andy’s first recommendation for rethinking my relationship to coaching as a profession was to go back to the beginning of the Reboot podcast, where Jerry Colonna does live, recorded coaching for entrepreneurs.
I listened to 30 episodes in three weeks.
In it, Jerry said something that stood out: “there aren’t enough elders, mentors, therapists and coaches in the world to meet the collective need.”
This rings true to me.
My years as a founder and startup executive have left me with three core convictions:
- Startups grow at the rate their founders grow
- Organizational cultures centered on belonging and accountability allow people to reach their full potential at work
- A company can be one of the most powerful forces for social good under the right leadership
In service of those beliefs, I’ve set out to become an executive coach for courageous founders, execs, and creators using business as a force for good.
I want to work with the kind of people who care about serving others and solving the most important problems of our time. Leaders who want to build organizational cultures that allow people to flourish. Leaders committed to integrating the hardships from their past to break the cycle of pain for their families and teams.
Selfishly, coaching also gives me something I want. It’s the business model that will allow me to finally claim the career I’ve always dreamed of but never been able to fund: that of a writer and podcaster.
The people I most admire for their body of work are all writers. These people have changed my life through words on a page. I hope one day my words will do the same for others.
But before I could make the latest leap, I needed to gain alignment with the most important person in my life. Did I mention my wife was also in the middle of a career transition and we have two small children at home?
Gaining Alignment With My Wife to Move Forward Together
My wife is a talented exec and communications professional. She also has been in a career transition after leading her prior agency for four years as managing director. With her transition starting first, we agreed that I would stay at the startup and maintain one stable income while she made her move.
Now I had reached the point of knowing that it was time to move on. I felt energy towards becoming an entrepreneur again and wanted to capitalize on it.
Not only was I going to ask her to go back on my word, but also to take a leap back to entrepreneurship. I was scared about my career goals and our family goals being in conflict with one another.
A huge part of my work in therapy over these past few years has been learning to acknowledge and ask for my own needs and wants. I decided to have the conversation from a place of vulnerability — not just so that I could make the career leap, but as a way to practice showing up more fully in our relationship.
Before I did, I learned from our experience in my first business and wrote out my plan and back up plan for building my business as a writer and coach.
I sent the plan to her ahead of time and scheduled time to sit down and chat. As anyone would be, she was at first concerned by the idea of our family having no income for a period of time while still having all of our normal expenses.
She needed time to think. That made sense to me. Conveniently, we had a joint therapy session scheduled later that week to work through it together.
In that session, we talked about each of our fears. Our joint fears of having no income and the doom spiral that sparks in our minds. My fears of returning to entrepreneurship. Her resentment that I had made a promise I was now asking to break. My worry that staying in my job would lead me to a tough mental and emotional place that would slow my entrepreneurial momentum if I waited.
We arrived at a joint perspective of abundance: we are privileged to be in the position we’re in at this stage of our lives. Let’s take advantage of it and each go after what we want.
Reclaiming My Seat as an Entrepreneur, Writer, and Coach
On March 6th, 2023 I reclaimed my seat as entrepreneur. I declared my profession as a writer and executive coach, in that order. I found my way back to being a creator, with the full support of my wife, my coach, our therapists, and my extended family.
I’m an altruist. Sometimes naively so. I’m an optimist. I’m a solutionist. So much about the world worries me. Some days it overwhelms me with fear and anxiety. But most days I see problems and suffering as an opportunity to do good. To serve. To build solutions.
And companies are the best way I know how to create positive change. So I’m going to tell stories, teach, and coach my way into helping as many people as possible use companies to do the most good possible.
If you think less of me as a result, that’s ok. But this is my work to do. It took me 18 months to find my way back here. You could argue it took me nine years since the day I shut down my first company.
I’m right where I belong.
And if this story of career transition resonates with you because you’re going through a career transition of your own, it would be an honor to work through the process together.
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Featured image by James Zwadlo on Unsplash