I spent $1,400 on a logo for a business that didn’t exist. It was October 2018, and I was sitting in a cramped Starbucks on LaSalle Street in Chicago, vibrating from too much caffeine and the sheer delusion that a vector file of a stylized mountain would somehow make me a CEO. I had no customers. I had no product. I just had a day job I tolerated and a burning desire to ‘be my own boss’ because some guy on YouTube told me that working a 9-to-5 was a form of modern slavery. What a load of crap.
That business failed within four months. It didn’t fail because the logo was bad—it was actually quite nice—it failed because I was trying to build a cathedral before I’d even figured out how to mix the mortar. I thought I needed to ‘take the leap.’ I didn’t. I needed to stay in my cubicle and build quietly in the dark.
The lie of the ‘Leap of Faith’
We’ve been fed this romanticized garbage that you have to quit your job to be a real entrepreneur. That you need to burn the boats. But if you burn the boats and you can’t swim, you just drown. It’s not brave; it’s stupid. Most of the people telling you to quit your job are selling a course on how to quit your job. It’s a circular economy of desperation.
Building a side hustle while working a full-time gig is exhausting, sure, but it’s also the ultimate safety net. It allows you to be weird. It allows you to fail. When your rent isn’t riding on whether or not someone clicks ‘buy’ on your weird handmade leather coasters, you can actually make something good. You have the luxury of patience. I might be wrong about this, but I think the best businesses are built by people who aren’t terrified of missing their mortgage payment next month.
I used to think you needed a ‘niche.’ I was completely wrong. You just need to be slightly less annoying than the competition and show up consistently. That’s it.
Building in the 5-to-9 is about survival of the most disciplined, not the most talented.
My 5-to-9 is actually 8-to-10 and it’s not a movie montage
The ‘5-to-9’ thing is a bit of a marketing gimmick. Nobody actually finishes work at 5 PM, teleports home, and starts grinding. You’re tired. Your brain is mush from staring at spreadsheets or sitting in meetings that could have been an email. What I mean is—actually, let me put it differently. You don’t need a four-hour block of deep work. You need ninety minutes of not being a loser.
I tracked my productivity for 14 weeks using a physical ledger—yes, a paper one, because looking at another screen felt like physical pain. I found that my output dropped by 62% if I worked more than 90 minutes after my day job. After that point, I was just moving pixels around and pretending to be busy. So I stopped. I do 90 minutes. I ship one thing. I go to bed.
It was pathetic at first. I spent 417 hours over six months on a digital product that made exactly $12. That’s about $0.02 per hour. But those $12 felt better than my entire salary because they were mine. They weren’t filtered through a HR department or a performance review. They were raw.
The math of not starving
If you’re going to do this, you need to be ruthless with your tools. I see people spending $200 a month on ‘tech stacks’ for businesses that make $0. It’s vanity. Here is the only list you actually need:
- A way to take money (Stripe, PayPal, whatever).
- A way to talk to people (Email, a basic site).
- A way to stay organized (A notebook).
That’s it. Everything else is just a distraction. I actively tell my friends to avoid using Mailchimp. I don’t care if it’s the industry standard; the UI makes me want to throw my laptop into a lake. It’s overpriced and the monkey is smug. I use the simplest, cheapest thing I can find until it literally breaks. I’ve stayed with the same $12-a-month hosting plan for four years. I don’t care if something ‘faster’ exists. It works.
Why I hate Trello and other ‘productivity’ traps
Trello is where ideas go to die. I’ve spent more time color-coding labels in Trello than I have actually writing copy or talking to customers. It feels like work, but it’s just ‘procrastivity.’ Real work is uncomfortable. Real work is sending an email to a stranger and asking them to buy your stuff. Moving a card from ‘Doing’ to ‘Done’ feels good, but it doesn’t pay the bills.
I refuse to recommend any productivity app that takes more than five minutes to learn. If you need a tutorial to understand your to-do list, you’ve already lost the battle. A side hustle is like a stray cat that shows up on your porch; it’s cute until it starts demanding you feed it at 3 AM. If you spend all your time building a fancy cat carrier, the cat is just going to die of hunger anyway.
Stop buying courses. Seriously. Every piece of information you need is available for free if you’re willing to dig through some old forums or watch a 14-minute video from a teenager in a bedroom. The only reason to buy a course is if you’re too lazy to search, and if you’re that lazy, your side hustle is going to fail anyway.
Total lie.
The ‘One Small Thing’ rule
I’m writing this on a Tuesday night. I’m tired. My back hurts from my office chair. But I have this rule: I have to do one thing that moves the needle. Not ‘research.’ Not ‘planning.’ An action. Tonight, it was writing this. Tomorrow, it might be fixing a broken link. Trying to scale too early is like putting a jet engine on a tricycle. You don’t need scale. You need a tricycle that actually moves.
I know people will disagree with me. They’ll say you need a brand identity and a five-year plan and a scalable infrastructure. Those people are usually consultants who want to bill you by the hour. I’m just a guy who works a job and makes money on the side. I don’t have a five-year plan. I have a ‘make enough money to buy a nice dinner on Friday’ plan.
The secret to the 5-to-9 is that there is no secret. You just do the work when you’d rather be watching Netflix. It sucks sometimes. Most times, actually. But then you get that notification that someone you don’t know just paid you money for something you created. And suddenly, the 9-to-5 feels a lot less like a cage and a lot more like a benefactor.
Will I ever quit my day job? I honestly don’t know. There’s a certain peace in having a steady paycheck that allows me to be completely reckless with my side projects. Maybe that’s the real goal. Not to escape the 9-to-5, but to make it optional.
Just start. Don’t buy the logo.