The Pursuit of Happiness

Why I quit a lucrative job as Director of Engineering to bet on myself

Two weeks ago, I left my job as a Director of Engineering for a medium-sized Saas company with no other position lined up to replace it.

I joined this company as a junior front-end developer when it was relatively tiny. There were maybe 35 employees, and the development team was the CTO and five devs, including myself.

Over the next few years, I moved from front end to back end and had been promoted twice to a senior engineer. Then, the company started to grow, and I began taking on a lead role on the backend team. I had a lot of freedom, responsibility and got interested in Functional Programming during this time.

My esteem within the company grew over the years, and I was an expert in many technologies central to the company’s vision. As the company and specifically the Development team grew, I was promoted to Director of Engineering, overseeing a team of approx 75 developers of all specialties across two offices.

Also, the people I worked with were fantastic. The CTO was generous and full of empathy and trust for his team. I’m very grateful for everyone I worked with there.

My career was going well, and if I had stayed, the promotions and salary bumps likely would have kept coming. However, the motivation to go to work each morning and do a great job was decreasing. Like Daniel Vassallo noted in his blog post ‘Only Intrinsic Motivation Lasts’ it was happening in an almost inverse trend to my career and income growth.

Decent is not good enough

The first few years on the job, I was highly motivated. I reported directly to the CTO. We could choose what we wanted to work on and had much independence. If we felt that something needed doing, we got to do it.

The culture began to change when the company founders decided it was time to move on and sold to a Private Equity firm. The change was slow but unrelenting.

The company encountered rapid success and scaled accordingly, requiring new roles to be created and filled. Suddenly, there were two, three, or more people you needed to involve before taking action on something. Naturally enough, every new stakeholder had opinions on what needed doing and how to do it. As a result, objectives became somehow less clearly defined and more ambitious at the same time.

A top-down leadership style became the norm, and management did not seem empowered to change this new culture. As a result, I found myself increasingly doing things I didn’t want to.

It had gone from a great fun job to just a decent one.

Having followed Daniels’s journey from afar, I knew that this trend was not likely to reverse course regardless of what happened in the company. Like Daniel, it felt like my freedom and happiness were declining along with my motivation.

Make a bet

Stanley Druckenmiller once explained that if you look at the careers of the most successful investors, you will see that most of their returns came from a small number of concentrated bets. This approach is contradictory to the conventional wisdom about diversification.

I started thinking about where the most significant returns in my life have come. Sure enough, I think I can nail it down to between 2 and 4 decisions I made that I had high conviction about but were nonobvious to most at the time.

Working for a company you have no stake in could be seen as a form of diversification. Being an employee is a relatively safe bet. There are multiple people or even teams who are thinking about how the company should make money. If any single person doesn’t do their job right, your job and salary are likely still safe. Even if the company goes through bankruptcy, employee salaries are among the first debts the courts will ensure are paid. The price for this security is to get shut out from the company’s profits.

So what is the opposite to that? Well, it’s probably starting a company and trying to turn it into the next Amazon or Google. Doing so would be a very concentrated bet with a potentially high upside. Unfortunately, it’s also extremely risky and likely to fail.

As Naval Ravikant said, venture-funded startups are the Olympics of business. Most people never make it to the Olympics. I likely don’t have what it takes to win the Olympics.

So is there something in the middle? Ideally, something on the opposite end of the risk spectrum from trying out for the Olympics but still with high potential upside. I think so.

I am lucky enough to enjoy continuously learning new things and building things. I have been doing these things since I was a kid, long before anyone paid me to. If I was doing it for free, there must be something about it I find intrinsically motivating.

With these interests, it is possible to solve problems. Moreover, if you can solve the correct problems for the right people, they will likely reward you for it.

What’s Next

If the goal is not to create something worth a billion dollars but to create something that brings in $100K/year, it doesn’t sound too ambitious.

If I can do that, with a bit of extra effort, maybe it could bring in $200k/year or build a second thing that’s just as successful.

So that’s what I will try and do, bootstrap a series of B2B software products and see if I can sell them.

Ensuring that this adventure doesn’t have to stop requires generating income. By myself. With my ideas. Two things will dictate success or failure:

- The merit of my ideas

- The quality of my execution


Here’s my plan for the rest of 2021:

-> I’m going to launch one product every month.

-> I’ll measure everything and share it on Twitter.

-> By the end of the year, I’ll know what to double down on in 2022.

Follow me @rbmdotdev on Twitter to follow along as I build + ship.

Along the way, I’ll be sharing things like:

  • The financial stats, no matter what.
  • My biggest wins + fails.
  • What tactics did and didn’t work.
  • Any valuable content and tools I find along the way.

The aim is to be covering my monthly expenses by Jan 1st, 2022.

I will explore the strategy and tactics I will employ to achieve this in detail in subsequent blog posts.

This bet is not guaranteed to pay off, but the downside is minimal, the upside worth the risk, and I will learn a lot regardless. It won’t be easy, but I think it will be fun.

This article was originally published on on 7/01/2021

I have been a software engineer & technical leader for 7 years.Follow me to hear more about Development,Product Creation,Marketing & Success & Failure!