I couldn't leave my job to start a company
Forces at play when weighing entrepreneurship and stable employment
Work is a big part of my identity. I often conflate it with self-worth, which I know is unhealthy. It’s a bad habit that’s hard to shake, even after years of enduring mood swings directly linked to how well I do at work on any given day.
So when I meet new people and the question of “what do you do” comes up, I secretly like it. I like it because it allows me to share a mini-version of my founding story and its core to who I am.
“I couldn’t leave my job to start a company.”
This is the most common response I hear. It’s a knee-jerk reaction to something people perceive as a large, uncertain, and unpleasant undertaking. I usually take it as a compliment, but in this post, I wanted to explore some of the considerations that made me take the plunge.
For context, in 2017, I left my job as a Product Manager to pursue a startup called Prodsight as a solo founder. In 2022, I successfully sold it, which now, six years later, validates that decision, but at the time I obviously had no clue how it would pan out.
This post is not meant to convince anyone to do what I did, but instead to offer a perspective on the factors that might lead one down the path of entrepreneurship.
Forces at work
Changing from stable employment to entrepreneurship is a significant change for the individual. It was certainly something I had to think through myself before leaping.
When considering a significant change, I like to use the Forces Diagram to break down the various factors involved. The Forces Diagram shows the energy involved in the transition from the current approach to a new solution. It includes two forces promoting the switch (push/pull) and two hindering it (anxieties/inertia). Push represents struggles in the current situation that drive the search for a better solution. Pull is the attraction to the new solution. Anxieties involve concerns and uncertainties about the new solution. Inertia refers to factors that make changing from the current situation difficult.
Push: Risk and Reward
Shortly after graduation, I got a Product Management role in a small boutique mobile development agency. I watched the founder work with awe and tried to absorb as many lessons as I could from him.
Less than a year in, he sold the company, and I witnessed years of his work pay off instantly. It planted a seed in my head as an example I could follow someday.
I was fortunate to continue learning from him when he and his co-founder invited me to join their new startup as a Product Manager. I could watch them build the company from scratch and play a significant role in the process. And I could do all of this with no downside risk of actually being a founder.
Jobs are low-risk, low-reward. This means that as long as you show up every day and do a reasonable job, you are guaranteed to receive a paycheck. There is not much volatility in that contract. Entrepreneurship has a very different risk profile and tends to be high-risk, high-reward. There is a very high likelihood that your startup will fail (in fact, 90% of them do), but for some that end up being successful, it can mean outsized returns in the event of a company sale or an IPO.
Once I internalised the lessons and my personal growth slowed, the reality of “risk vs reward” caught up with me. I wasn’t the founder of this startup. I wasn’t taking any risks, so I won’t share the rewards even if it succeeds.
It became clear that I had to take more risks.
Pull: Wearing multiple hats.
I greatly respect people who go deep into a subject and become experts. I love working with these people.
But that’s not me. Whenever I try to go deeper into something, I get bored and find it limiting. I immediately want to pick up something new.
At university, I deliberately picked the broadest degree I could - Business & Management. It was a perfect mish-mash of disciplines that were cool to learn about but didn’t prepare me to do anything specific.
However, the startup I worked at as a Product Manager was the perfect boot camp for starting my own company someday. Because the startup was so small, I could get involved in many of the activities that go into founding a company. Customer research, prototyping and building the first product, figuring out branding and growth, and implementing metrics.
This type of “skillset” is precisely what you need in an early-stage venture, so going down that path made a lot of sense. I loved wearing many hats, which was a big attraction to starting my own company.
Inertia: Sense of stability
Despite all the push-and-pull forces, I wasn’t ready to jump immediately. I loved the founders and my team. It gave me a social circle and an environment where I could try different things and create alongside intelligent people.
The regular, stable paycheck was something I relied on heavily. We have just taken out a mortgage to buy our first home and just got married. For most people, this would be the time to hunker down, and the idea of giving my 30 days’ notice was certainly weighing down on me.
Anxieties: Fear of failure
The most significant anxiety about leaping into entrepreneurship was the very likely event of failure, with the aftermath of burned-out savings, disappointment, shame, and finding a new job with the tail between my legs.
At the same time, that outcome didn’t seem that disastrous because I would have ended up pretty much where I started, albeit a bit bruised.
In case you are wondering, I didn’t have a fallback cushion. I come from a single-parent household in Lithuania. While my mom is a superwoman for raising my sister and me on a single teacher’s income, she gave us all with nothing to spare. My wife had a decent full-time job, but her income wasn’t enough to support both of us.
I might publish a separate post about all the steps I took to prepare to quit my job. In short, to make this work, I made a detailed financial plan and made a stop-loss agreement with my incredibly supportive wife. If I don’t start generating income before we run out of savings, I will shut down the startup and find a job.
We accumulated six months’ savings. We cut our expenses to the bare minimum. We Airbnb'd our spare bedroom for extra income. I leapt.
The leap
I have considered many factors when jumping, but I didn’t have the clarity of thought I have today, six years on.
It would have been wise to do the Forces Diagram exercise then. I’m also happy I didn’t, as I might not have ended up where I am today.
In summary, it didn’t come down to what I would lose by leaving my job. It was all about what I could gain by starting a company.
Special thanks to Renata Labude for reviewing a draft of this post.