Losing The War?

Recent Updates

As I write this, I'm sitting in a lawnchair in my driveway. Eyes swelled with tears, staring at the concrete.

I recently wrote a post about a week from hell. That was a week from hell, between my day job, my startups, and tornados threatening to destroy my house. Thankfully, the house is fine, and I made it through that week. Barely.

This week, only a few days of tornado warnings (I am petrified of them) that are over for the moment, and I'm feeling quite optimistic about Didact, as I recently wrote a blog post on its site telling my early adopters that I'll be doing more frequent updates with them going forward. Last week, I also made a landing page for an open source digital signage platform that I'm thinking about making called Litescreen; I already have three years of experience from Displagent, and I've been extremely burned out from that market, but lately I've been considering reattacking it from a different angle.

So weather? Still scaring me half to death every other day, but the house is thankfully still fine.

So startups? Still overwhelmed, recently crossed my three-year anniversary of solopreneurship, still nowhere close to making $10K/month. So... same ole, same ole I suppose. Still walking into the meat grinder week after week, torturing myself with this bootstrapper crap, though I am optimistic about Didact (and maybe Litescreen sometime soon).

But work? Ah... work...

Work is running me straight into the ground. I am so unhappy right now dealing with work.

The Predicament

I have been in a difficult predicament with work for quite a while now. These days, I am utterly miserable. Work is very, very unpleasant for me right now. It's gotten to the point that it's exhausted me every week, I'm barely able to function on the weekends, and I'm having a lot of emotional issues caused directly by it.

We are in the middle of the most painful, most overwhelming project in the company's history, and I am right dead center at the core of it. I was the hero dev that saved the company's software and data infrastructure five years ago after the entire previous dev team abandoned it, back in the days when I was working alone, putting out fires every day for eight hours, gaining weight, and suffering from severe stress and loneliness. Those were very dark days for me, they left me with some major scars that I carry to this day. I will never subject myself to that ever again. Ever.

Things are different now, I have a team and so on. But since I was there five years ago, single-handedly fixing the production databases, enhancing core reporting infrastructure, and maintaining all existing software, I have unintentionally become the expert on the company's data models, databases, and so on. That's not a brag, it's just a fact: I am the expert on the company's data. I am very, very strong in SQL and relational databases, among the ten thousand other skills I've acquired since becoming a fullstack software dev and solopreneur.

And this major project we are in the middle of right now - that I am in the middle of right now - requires this exact set of skills, expertise, and domain knowledge (emphasis on the third one).

So guess what's been happening?

Yep, you probably guessed it. They are piling it on me. Again. And again. And again.

Week after week. Racing exhaustedly towards a major deadline I had no say whatsoever in agreeing to or sharing input on.

They are running me straight into the ground. And I am losing it, man.

I'm in a really, really tough spot right now. I want to nurture my startups and go full time, but I can't - I'm not making enough money from them yet, even after three years of sacrifice. And my wife is an elementary school teacher which means she is unfairly underpaid by the state that we live in. She should be making at least quintuple what she makes now, but the imbeciles in our government don't seem to care about paying teachers enough money (subject for another time).

So I can't just quit my job willy nilly. I can't up and move to Bali and live off of a thousand USD a month. I'm not rich, and I don't know any angel investors, so that's out. VC will probably ruin my startups, and I don't want what they want, so that's out.

So... I am stuck... for the moment. I am holding on for dear life to the last part of that phrase: "for the moment."

Pick Your Poison

So what do I do? How do I fix this situation?

My predicament is that I've been trying to stay put these past few years since I started my solopreneurship journey, just staying put, doing my day job, and grinding out nights and weekends on my startups. It has really sucked some days, and it's a soul-crushing grind, but I've stuck it out nonetheless.

And many will tell you to just simply "not care" about your day job. Just do whatever, get through the day. But "not caring" is not in my DNA. I am Type A, and I take great pride in my work. I don't know that I've ever really been able to take that advice.

Considering that and the fact that they are crushing me right now, considering how upsetting it is not being full time on my startups after three years, and with everything else, well... I'm sure you can see why I've been struggling lately.

I hate the irony of it because I'm naturally an extroverted and very happy person. This stupid freaking startup journey has taken a lot from me.

Work is taking a lot from me.

And I don't know what the next step is.

What's worse? Staying put while work crushes me week after week, stressing me out and putting me into tears, running me into the ground? Do I throw myself into the leetcode grind and torture myself with job interviews? Should I even consider a fulltime job at this point? Should I look into contract work? How much money would I make, how do I get work? How I balance this with my startups?

I survey my potential options to fix this situation, and it's all poison cups. And I don't know which one to drink.

Stabbing At The Dark

So I'm afraid I have no uplifting or happy resolution to share with you this time. I am miserable right now, I am losing it, and I don't know how to fix my situation. I don't even know if I can fix my situation - not without giving up on my startups entirely? Yuck, even typing that makes me cringe.

This journey is so hard. Lately, it feels like I've been losing battles, but when work sent me over the edge today worse than it ever has in all five years, I have to wonder: am I losing the war, too?

I think of Ben Chestnutt at MicroConf 2024, when he said that entrepreneurship is "stabbing at the dark", waiting for something to land. That's where I'm at right now.

Am I losing the war?