I Left My Job in Private Equity to Build Things

I’m part of the “Great Resignation”. Here’s my story about why I left my job.

Last Friday was my last day at Plenary Americas, a private equity firm on Bay Street. It is the only professional job I’ve known, having worked there for over 6 years since I graduated university. Although things were going well for me, working from home left me feeling uneasy. When I understood why, I knew it was time to leave.

I joined the company excitedly after graduating from engineering in Toronto. I started as a Project Coordinator, working on existing assets and protecting deployed equity.

I was quickly promoted through the ranks. Within a few years, I was actively managing assets myself and working to secure new assets so that we could deploy even more equity. I acted as if I were the “CEO” of my position: being generally self-directed and ultimately accountable for everything I could influence. This mentality pushed me to take on additional work, train new hires, and take on more responsibilities before I was promoted to do so. Management appreciated this and I was seen as a good employee. I had the respect of my peers and was able (and willing) to take on a wide array of challenges.

Management treated me very well too. To this day, there is nothing but respect between us. They believed in me, gave me more opportunities and I did good work for them.

For my efforts, I was paid very well, more than I anticipated when I was in university. Total compensation was excellent, and I knew that the harder I worked, the better it would become. For the first few years of work, this was my entire motivation.

Besides compensation, culture made up a large chunk of the benefits. Our culture had all the attractions that someone in their early twenty’s would hope for: travel, dinners, events, drinking, etc. When I was interviewing for the job, culture was advertised as a perk, “the cherry on top”, and for a while it was. But as I became disinterested from the work, these perks began to take precedence.

The Misalignment

Things were going well, but something was missing. The more I advanced the more I became distracted by other opportunities. The more responsibility I took on within the company, the more I looked outside for other things to do. Regardless, the perks and the pay kept me content. I chalked up the constant wanting to do more as part of life and moved on. Again, I was treated incredibly well, so what did I have to complain about?

I came across Daniel Vassallo’s Medium article “Only Intrinsic Motivation Lasts”, and it struck a chord (link). I asked myself, “would I really be satisfied if I was paid $20,000 more? How about $50,000? $100,000?” The answered seemed to be no.

Reading his article help me articulate my feelings. I was losing my motivation, and it was only getting worse.

Work-from-home distilled my job into its most basic form: responsibilities and tasks. I didn’t find a lot of joy in fulfilling them. They were previously made enjoyable by the old work environment, until that environment was no longer there. When everything else was stripped away, I realized that my responsibilities were diverging from what I was truly passionate about, which was building.

Work from home held up a mirror and showed me what my job was, and I wasn’t thrilled at what I saw in it.

There’s a lot of talk about The Great Resignation — a mass exodus from the workplace as work-from-home comes to an end. I don’t know about other’s reasons, but in my case, my decision came to be as a realization rather than an ultimatum. I didn’t leave because work-from-home was ending, or because I thought I was treated unfairly, or because I needed something that they could not have given me, I left because work-from-home showed me what work looked like when you’re not distracted by perks.

After I realized this, my biggest stumbling block was deciding what I would do instead. Fundamentally however, I wanted to do something that aligned with my interests.

The ultimate alignment: where demand, your skills, and your interests converge.

The Realignment

With some additional time afforded due work-from-home (no events, no commuting, no pre/post work gym sessions), I dove into a few side hustles. Some friends and I bought a house together. We spent every weekday evening and weekend for 3 months turning it into rental units. Building with my hands after so many years was refreshing. After that project was done, I realized that I had a lot of “gas in the tank”. I learned to develop web applications, ideated an online business with a friend, and spent 2 months developing it. Nothing felt as fun as executing your personal vision and it change my perspective on what work should be.

I wondered why I couldn’t do these side-hustles full time. What could I accomplish in the long term with the best hours of my day? What quality of work could I achieve when I deeply cared about the problem I was trying to solve? I couldn’t come up with a good reason not to, so I took the plunge, but not without a lot of overthinking.

And so last Friday was my last day as an employee, and if all goes well, it will be the last day as an employee for the rest of my life. There are so many ways to make money today, from selling jpegs (seriously) to managing communities, to buying and flipping online businesses. I have faith that with a sober view of my abilities, hard work, and an optimistic mentality, I can go just about anywhere I think is possible.

I’m in search of work that does not require distractions. Ideally, I would be happy doing the work without any perks, satisfied wholly by the fruits of my labour. I want to build with my own hands and be directly responsible for the money that I bring into my pocket.

Next Steps

As for next steps, there are two phases on the horizon. The first will be shoring up my finances by created a diverse portfolio of income-generating businesses and investments. Thankfully, I’ve saved enough runway to afford me some time while I figure this out. The second will be building a technology business in and around the infrastructure space from the ground up, and in public. The first phase is important because I want to go all-in on the second. It will allow me to extend my runway as I invest time and effort into building.

I’m hoping for the best, but ultimately, I’ll either fail or succeed because of me.

I joined Twitter to document my journey. You can follow along there as I continue to write about my next steps. https://twitter.com/_luigilacorte