A Reflection on One Year of Solopreneurship

In May 2018, I left my job at an F100 financial services firm to pursue an independent life-work path in the digital product research, design, and development world. I wrote this article to tell my story, share my learnings, and call out the many things I’ve yet to figure out.

Intense, seated gesturing during a Paper Ventures future-casting design workshop | 2019

My most recent departure from traditional employment is, perhaps, an uninspiring corporate-job-departure story.

When I left, I didn’t have any grand startup visions. I had no exciting plans to globetrot around the world. I hadn’t gotten a dream job in a dream city, nor was I making a heroic, storybook move to leave a toxic work environment to — at last — prioritize my wellbeing.

What makes my departure even more anticlimactic is that it was the second time in my career that I had left this particular large company.

After college, I spent a couple of years within its corporate strategy division before leaving to dive into the Boston startup world, first as an early-stage employee and then as a founder myself. After perhaps one of the #fastest #fails in #fintech history, I boomeranged back to the more comfortable W2 Life of Big Corporate.

I had stimulating and challenging roles that I am very grateful for. After some time working on a new product innovation team, I accepted a role in the organization’s core business operation. As a Senior Product Manager, I managed a team of Product Managers focused on building and optimizing the digital purchasing journeys for our online customers.

In short, my job was to:

1. Ensure that the Product Managers on my team built and executed on roadmaps that helped the organization achieve its objectives
2. Make it as easy as possible for the Product Managers on my team to execute by removing blockers and lobbying for resources
3. Invest in my team’s professional development and help prepare for roles ahead

The role was challenging and allowed me to tackle difficult technology and people management questions, such as:

• How do you balance technology stack modernization and new feature development with finite resources and short-term sales goals?
• How do you incentivize and inspire product, engineering, and design talent to do their best work?
• How do you help a Product Manager motivate a squad towards a sprint goal when group tensions are high?
• How do you scale agile methodologies within a 20+ squad department while ensuring that leadership is embodying those principles in its decision making, too?

While grateful for the opportunity to further my leadership, managerial, and technical skillset in a healthy work environment, I eventually arrived at a point of self-reflection in my job where I knew the following to be true:

1. I missed being close to a product, its users, and building something.
2. I lost energy and began to develop a dangerous apathy towards my work when I encountered large company politics and lag.
3. I did not want the jobs of my leadership, whom I still admire greatly. For me, if I took those jobs, it would be mean more of feeling like #1 and #2 on this list.
4. To stay in the role with my waning excitement and budding resentments would be unfair to my team, my peers, and my management. I believed there were others out there who could offer more to the organization in that role than I could.

So, I decided to leave.

When hearing that someone is leaving a job, most folks expect to hear a fairly concrete description of what’s next.

They want an answer; usually something justifiable within their mental models of career growth and values: a better compensation package for the high-performer; a more flexible work schedule for the new parent; a shorter commute for the new homeowner.

I continually wondered: why do we crave such discrete logic?

Perhaps it’s just a need for efficiency in our cognitive processing that we’ve evolved towards to save space. Perhaps it’s our selfish selves that would prefer to cut these conversations short to return to checking typos before that 1 PM presentation. Or perhaps it’s because those answers that don’t fit into the career logic structure that we operate within could force us to question that structure, generating an uncomfortable cognitive dissonance that we’d just rather avoid.

Whatever the reason, I didn’t have much of a discrete, logical answer to share at the time. I had more of a “Work in Progress” update than a “Next Step” one:

“I’m going to spend more time focusing on Product and UX freelance projects for now. I’m not sure officially what’s next, but I’m hoping that those projects will help me explore a bit. And, well, I also want the flexibility to enjoy my summer.”

You hear some interesting responses when you tell your colleagues, family, and friends that you’re making a career move that involves less money, less stability, less prestige, and worse (read: no) benefits.

Admittedly, some people are amped for you. Others, however, are confused. They respond — with a type of sympathy — in a way that justifies the career move for you or that tags your decision with a recognizable piece of logic that allows them to digest it themselves.

It’s oddly similar to the funeral home rationalization chatter you might hear when a grandparent, well into old age, passes. She was 92, right?

These responses aren’t wrong or harmful; they’re just abbreviated reactions that allow us to quickly make sense of something that might otherwise be confusing, illogical, or uncomfortable to steep in for any longer than necessary.

People frequently asked if I was nervous or afraid to go out on my own.

While there certainly were some mind-racing, stressful moments, I largely felt at ease with my decision. Choosing to leave my corporate job this time was perhaps one of the easier career decisions I have made. I attribute this largely to:

1. Validating & Encouraging Data Points I Previously Gathered: I had left secure, stable jobs before and, well, things worked out. The world didn’t come crashing in on me. Those departures introduced me to some of the most rewarding career opportunities I have experienced. I had also been freelancing for 9 months already on the side, and people were paying me in real dollars to help them. While this volume was small, it was a good, early test of assumptions that built my confidence that leaving could still be financially viable.
2. My Support Network & Privilege: I had family and friends nearby that had couches and homes should I ever need them. I had savings from well-paying jobs and a network happy to provide emotional and career support if I needed it. And, perhaps I was overly optimistic, but I told myself that my worst-case scenario would be to just apply for another job.

Where I’ve Been

The past year has been one full of experimentation, and I am grateful for the diverse client set that has trusted me to work with them.

I’ve worked with early-stage and high-growth startups in addition to venture and innovation teams of some of the largest companies in the world.

I’ve performed ethnographic design research in homes and workplaces, facilitated prototyping and experimentation workshops, managed new MVP builds, co-designed provocative visions of our future, collaborated with a fantastic community of creators, and picked up some new design and software development frameworks along the way.

It’s also been a hard year. There’s been a semi-permanent feeling of anxiety that questions if my work is good enough and if I’m making silly decisions for the long-term. Working alone can also be lonely, and there have been times when self-doubt makes a biweekly paycheck appear very, very attractive.

Overall, however, it’s been fruitful in so many ways, and I’m grateful to so many for their help, support, feedback, and opportunity.

One thing I’ve struggled with throughout the year is my title and career label. What do I call myself? Admittedly, this struggle is likely driven by the tension between my ego (“I want people to think I’m impressive!”) and fear of how others perceive me (“What if I sound pretentious?”).

Am I a freelancer? A contractor? A consultant? An entrepreneur? A founder? A business owner? Am I giving myself enough credit in my title? Not giving myself enough credit? How does that title translate to my LinkedIn headline? Does my email signature sound annoying? Principal? Partner? Managing Director? Ooh, that one sounds impressive! I’ll call myself that. Wait, what does Managing Director even mean?

I’ve come to a point where I now accept all of those titles as correct. To me, my title should matter only in how it communicates the work that I do and how that work gets done.

With this framing, and for summary purposes, over the past year I have gone to market as a:

1. Freelancer: when I work on fairly discrete pieces of project work that can be handed over to a client team (eg. MVP happy path UX mock-ups)
2. Contractor: when I join a team for a certain amount of time to bring a certain skill set or perspective (eg. join a design agency’s team as a business designer on a client project)
3. Product & Design Consultancy: when I build teams and partner with start-up and corporate clients on new product research, design, and development efforts (eg. help new venture lab develop empathy for its customers, identify opportunity areas, build prototypes, launch software MVP & experiments)

I am lucky to have experienced all of these engagement models and to have gained project experience across the domains of insurance, personal finance, health and wellness, pharma, energy, and construction along the way.

What I’ve Learned

I’m hesitant to share a well-packaged advice column and, instead, am sharing a compilation of learnings and observations from my own story. Hopefully, this allows readers the freedom to identify with whatever they’d like and not feel any pressure that they’re doing anything wrong.

While not categorized, the items in the list below tend to touch one or two of the following labels:

1. Things I’ve learned and am amped about
2. Things I’ve learned that I’m less amped about and need to work on
3. Things I’m observing and still figuring out exactly what they mean

With that, here we go:

I strongly value autonomy in my work and my day. It is wonderful to build the day in a way that works for me and what I need to get done. I can prioritize my own physical and mental well-being, I am now present for my friends and family in new ways, and I have explored dramatically different projects, conversations, and commitments.

To me, there are two pieces to this:

1. My 9AM-5PM commitments going away and the opportunity to build a schedule up from zero instead of assuming a full plate as a given and jockeying to squeeze in new things.
2. A slow shift in my own work identity. I can meet new people over coffee just to meet them and not feel this employee guilt or pressure to run back to the office.

Good clients are great. You hear this across channels, but it is true. To me, good clients evolve from transactions into partners as trust develops. Ideally, this trust enables a candor and transparency that paves the way for everyone’s best work. I don’t have this ideal state with every client all the time, but I am now much more aware of ensuring that my client’s values align with my own before kicking off work.

I work more hours, but when it works for me (and oftentimes when it doesn’t). My previous mental model of how Monday, Friday, Saturday, and Sunday all differed is gone. Day of the week and time of day mean much less to me than building chunks of deep work time into my schedule and delivering on commitments to others. I can, however, overcommit or madly procrastinate. This usually means my weekends and evenings are spent in front of the computer. I’m still working on that.

My composite career background has been an absolute superpower. My varied background in corporate strategy and operations, start-up sales, start-up accelerators, traditional product management, design ethnography, and corporate innovation has been invaluable. I can bring many skillsets to the table that span the role verticals we often latch ourselves to.

I believe that this world is missing out on so much creativity, brilliance, impact, and meaning by valuing role predictability over role exploration in our careers.

There is a truly wonderful world of solopreneurs out there who also seek lives of flexibility, autonomy, and meaningful work. I am not the first one to go out on my own, I won’t be the last, and I am constantly in awe of the individuals I have met on this journey. That said, it’s not always easy to find other solopreneurs to work with. Nomenclature varies and many of us weave in and out of this world due to financial pressures and other interests.

My own business model continues to be an evolving experiment. Early on, I read several articles that warned me of the pitfalls of “Project Type X” and “Pricing Approach Y”. And I legitimately let many of them get into my head.

My reality has been one of experimentation and evolution. Depending on the project type or the client, some engagements work better as fixed projects and others work better on an hourly or retainer basis.

That said, the advice I would tell myself if I were to start again would be:

1. Have an answer to how you work, even if that answer is new to you and going to change for the next project. Presenting options can work too — just make it easy and digestible for someone to envision how working with you might look.
2. Be confident in that answer.
3. You are probably (read: definitely) underpricing yourself.
4. Lose any guilt, shame, or embarrassment talking about money and pricing with clients or other partners.
5. Honesty and transparency in a pricing conversation should always be priorities. If you need to, show your math and stand by it.

I often feel compelled to give a positive update when friends and family ask how things are going. Usually, I share some proxy of healthy financials that I think people want to hear.

While I sometimes convince myself that my untraditional career path is evidence that I don’t care about what others think about me, I find that I still care a whole heck of a lot. I feel compelled to have a positive, stock answer ready for others that also assumes they are implicitly questioning my financial health and career-choice viability with their simple “How is business?” inquiry.

This one is a work in progress.

Confidently understanding the basics of being a compliant, legal business owner is not easy.

I’m surprised and humbled about this one. On many occasions, I have thrown my hands up in frustration and confusion over LLC compliance, taxes, and contract law. I confidently (and falsely) assumed that a degree in Economics & Good Googling would mean smooth, compliant, legal, and easy sailing. It hasn’t.

The individuals I’ve brought onto my project teams look a lot like me.

I’m grateful for the opportunity to have built teams of researchers, designers, and engineers to do some stellar work together. So many individuals have introduced me to new ways of approaching projects, taught me new tools, and brought irreplaceable energy to the work.

Over the past year, I have brought more than a handful of contractors on board for various projects and, well, they all look, talk, and act pretty much like me. I’ll save space by avoiding excuses or explanations and just share that it’s a priority for me to disrupt this pattern in the next year.

Things I’m Thinking About

If you’ve gotten this far, you may have ascertained that there’s a lot on my mind. That’s true; however, there are four larger themes that I am pondering as I enter into this next year of work:

• Continued Learning & Upskilling: How do I continue to expose myself to new industries, experiences, and skillsets when there is a strong incentive to market and leverage what I already know to generate value?
• Celebrating the Composite Career: Why is there such a reputational stigma around the composite career when the benefits, both for the individual and the world around her, can be so large? How might I help others better celebrate career exploration?
• The Solopreneur Community: How do we foster a community around the solopreneur that helps create sustainable, lasting career choices?
• Different Perspectives: How do I proactively bring in new, diverse perspectives onto my work that are different from my own?

Thank You

I’ll end this with a thank you to the family, friends, mentors, teammates, clients, and partners that contributed to this experience so far. Looking forward to what’s ahead.

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Luke is the Managing Director and Founder of Paper Ventures (www.paperventures.com), an ethnographic research and futures design firm. You can connect with him via luke@paperventures.com.