That Time I Told My Wife I Wanted to Quit My Job

Tuesday, September 21st 2021

It was around midnight on May 22nd, 2016 that I pushed my first commit to GitHub for a new idea. I had just celebrated 3 happy years of marriage with my wife. A few hours earlier, I had been working on a desktop app with a business partner and we were weeks away from launching. So let's start there —

I had spent the last couple weeks setting up our billing and licensing system. Billing was easy since Stripe was the new kid on the block, and devs love shiny new things (well, Stripe was "new" to me at the time). But I wasn't thrilled about setting up licensing, and I thought it was weird that I couldn't find any services that offered a licensing API like Stripe's billing API. I paused, logged a note to mentally explore the idea later, and continued writing the in-house licensing server.

Before the first commit, I had gotten home from $WORK some odd hours earlier, ate dinner, spent time with my wife. I was now relaxing on the couch, probably watching TV or reading a sci-fi book, which I loved to do. The usual. But that idea I jotted down earlier was nagging at me. During dinner, in the shower, while watching TV. I just couldn't get it out of my head. So, I did what all hackermans do…

I grabbed my laptop and started sketching the service using Ruby on Rails. Hours turned into days turned into months. I had written side projects before, but nothing like this.

The desktop app I mentioned earlier flopped for various reasons, but this new project… I really thought I had something special. (We all do, probably.)

I kept working nights and weekends, for 3 whole years I did this. "Stripe for software licensing", I told myself. I ultimately launched around October, 2016. My 5 year "launch" anniversary is coming up. It's been a hard journey, through late nights, through burnout, through impostor syndrome, but it's been good.

But I'm getting ahead out myself here —

I've always been kind of anti-authority, I guess. I don't like being told what to do, especially when I don't agree with what I'm being told to do. I don't like strict rules, and I definitely don't like micro-managers, or managers in general, really; I kind of just want to be left alone to do what I do.

As you could imagine, this doesn't really jive well with life as an employee. So I went through a few jobs, some of my own accord and some due to layoffs, but never fired. Some I liked, some I didn't, but regardless I always clashed with managers and micro-managing employers. (Don't get me wrong — I was always a good, productive employee or at least tried to be.)

I enjoyed being a part of new startups, those that were still "scrappy." But each time, once that growth-stage hit and managers started coming in to make things "more efficient", that's when I knew that those types of places weren't for me. I would get through my day job, and then spend the rest of my brainpower on side projects. I did this for a long time, and I struggled with burnout. It was on and off.

In 2019, I had had enough of the cycle. I was utterly burned out, thrice over. I was agitated all the time and I could literally see the stress on my own face. My wife referred to me as "Grumpy" for months on end. That was my new name. It was as hard on her as it was for me, perhaps moreso. I hadn't read a sci-fi book in probably a good 12 months. I felt like I was losing myself, and losing the moments I had with my family because my mind was so overloaded and preoccupied with things that ultimately didn't f****** matter.

I couldn't focus on the present. But I so wanted to, but my brain was fried.

At the time, my side project, now a side business, was making about half of what my senior software engineer position at $CRYPTO_EXCHANGE was netting me, before ~~theft~~ taxes. After many, many internal discussions, I was going to do it —

I was going to tell my wife that I wanted to quit my job.

I was scared to death that she would say that it was a bad idea. We had just had our first baby, so this seemed like ~~bad~~ abysmal timing (if there was ever such a thing as good timing). We would be sacrificing a lot finacially, and losing any stability we had.

I thought to myself, I'd preface it with the fact that I'm at my breaking point — that I can't do 2 jobs anymore. I was going to say that I either need to quit my job and go full-time on my side ~~project~~ business, or sell it. I can't do both jobs.

One thing to note about me is that it's incredibly hard for me to "open up." Sometimes I don't even know how to put into words the way that I feel, sometimes I don't want to hear an obvious answer. Either way, it's hard for me. (Even now, I'm ~~uncovering~~ discovering some of these feelings as I'm writing this post.)

My heart was pounding. I literally put years of my life into this and I'm sitting here ready to give it up if that's what she thinks is best for us.

I couldn't tell her. I didn't tell her.

This happened a few times. My heart pounding, I couldn't tell her, I didn't tell her. It was a bad idea, I thought. Maybe I'm just going through another rough patch and the burnout will lessen given time. (It didn't.) So, I kept going. Until one day, after venting about a manager and having to work late at the day job, and being on overload because I was up late the night before dealing with an outage for my own business, she asked me what I wanted to do. She prefaced it by saying she supported me.

My heart was pounding out of my chest. And I told her. I told her exactly how I felt, what our options were, and what I wanted to do. I told her that we had savings, and that if it didn't grow like I thought it would, that I would sell it.

Without hesitating, she told me to do it. "Do what you need to do", "I'm here for you", "we can make it work", "you don't need to sell it", "quit your job."

The next day, I put in my letter of resignation.

A weight was lifted off my shoulders.

The years leading up to that moment were challenging. The years after, challenging. The years are still challenging, but a challenge is good.

There were times, and still are times, that I felt like an impostor. I've been working on the business for 5 years and I still don't have a go-to growth channel. I can't tell you what my customer acquisition costs are. I'm still trying new marketing strategies like I was years back, albeit with a more conservative budget since the stakes are higher now. I still have little idea as to what I'm doing. But I make my customers happy, and I provide for my family, and so I think I'm doing a pretty good job.

My goal was to be self-sustainable. This year, I think I've met my goal of being self-sustaining. I mean, I look forward to more growth so that we can rebuild our savings, but we've survived for almost 2 years now, and that's all I asked for back in 2019.

The business is doing well, growth is pretty good, customers are happy. I just recently closed our first deal with an F500, helping them replace their legacy licensing system with us. (I've seen that same scenario a few times this year, very recently with an F1000, probably because enterprise contracts are coming up for renewal.)

Savings are a little less than they were, but I'm happy and my family is happy.

I just finished reading 1984.