Welcome 2021! In lieu of a New Year’s Resolution I want to spend time to reflect on the course my life has taken and explore how I could’ve handled situations better. Over the next few weeks I’ll go over one mistake I made each of the past five years that hurt my career or other aspects of my life. I’ll describe what led me to the incident, how it affected me in the short term, and how it impacted me in the long run.

Posts in this series:

At the beginning of 2019, Makr went out of business and the entire team was put out of work. This life-changing event caught me off guard, partially because I was working toward a career shift and I wasn’t ready to make the jump yet.

On the flip side I knew that staying in the software industry would also be an uphill battle. Being a founding engineer at a failed company put me in a weird spot. If I hyped myself up as the lead engineer of the startup, interviewers would think I was the one responsible for all of our bad tech decisions. If I said I had no control over the situation, interviewers would view me as someone whose role diminished to the point of insignificance over time. It was a lose-lose situation.

While I was disappointed that my experience at Makr had to end, 2019 opened itself up to a world of possibilities for me. I considered three distinct futures for my career.

Social Media Entrepreneurship

Let’s start by describing the most experimental of my initiatives. Somehow I thought I was savvier with social media than the average user. In past years I managed to get my name mentioned in various podcasts just by chatting with the right people. As I mentioned last time, I was also attracted to the idea of passive income, and would’ve been great if I could monetize my online activity instead of looking for a job.

In retrospect I didn’t produce much content for attracting an audience. With all three of my initiatives kicking off simultaneously I only had Sunday mornings to create what I thought were funny Photoshops or funny videos.

There wasn’t really a coherent plan either. I thought about combining sports and pop culture references, and in April of 2019 we saw both the Mets season and season eight of Game of Thrones begin. I thought about a series of Instagram posts tying the two together, but unfortunately that season of GoT was poorly received and it was also the final season of the show so I was already out of ideas.

Starting an account on platforms like Instagram is deceptively optimistic, since you’ll get likes and follows for the first few weeks. Soon afterwards the platforms wisen up, they either notice people bouncing off your page or see that you’re not as active as they want you to be and all of a sudden you’re not getting attention anymore.

And that’s all before I found a way to make money out of it. Maybe I could’ve ran ads on my site or look for a sponsor. Or I could’ve created a second persona focused on personal finance, which would be more lucrative, and funnel people there. Maybe I could’ve gotten there eventually, but I simply ran out of time as the other two initiatives gained steam.


If I had to remain a software engineer, I could try and do so as a freelancer. Theoretically I could work as much or as little as I needed to, and spend the rest of my time on working on other projects.

I was inspired by Matt Gowie of Masterpoint Consulting, who worked briefly on Makr and lived a nomadic lifestyle. Except in my case I wouldn’t spend my free time rock climbing around the world, I’d instead be building my first indie game.

I decided to try it out when my former teammates from Makr were working on a new social media platform. You’d think being in familiar territory would make the process easier, but I ended up repeating some bad patterns from my previous job like making completely inaccurate estimates for milestones. What looked like a month’s worth of work ended up taking half a year. If I couldn’t timebox this project I couldn’t scale to multiple clients.

Job Search with a Recruiting Agency

This was probably the most straightforward path for me to take, but also the only one that counted since this was how I ended up at my current job.

That being said it was still a difficult process. I went to a recruiting agency to arrange interviews for me but a lot them were mismatches. Clients were looking for a skillset I didn’t have, or they picked apart the work I did at Makr and found something they didn’t like. Other times I just wasn’t prepared to interview. There was a storm of emotions I haven’t unraveled yet, from the all things I could’ve done to keep my previous company alive to all the thoughts of getting out of tech completely, it was hard to describe what I’ve done in a positive light.

It took half a year to run into a team that was willing to pick me up.

Closing Statement

2019 was the year I stretched myself thin. I was overwhelmed exploring three mutually exclusive options, and I felt like was losing control of my life. It wasn’t until the lockdown in 2020 when the burden started to lift up.

I still have thoughts about the headhunting industry, freelancing, and running your own business, but I’ve already opened up old wounds. This process was supposed to be therapeutic but all I’m doing is getting angrier thinking about the past. Maybe I’ll share these thoughts later when I find a productive way of expressing them.