Indie Hacker Diaries #24: The Upside of Pain

Twelve years ago, I had a near-death accident.

I was living in Michigan in a loft apartment. It wasn’t “big” (just a one bedroom), but it had brick walls, wood floors, and 20 ft. ceilings. I loved it.

It also had the best office space I’ve ever had. Accessed via ladder, there was a small loft space that looked down to the kitchen and living room. There was just enough room for my desk, chair, record shelf, and turntable.

It was perfect. Until it wasn’t.

At the time, I was working on a SaaS you’ve never heard me mention before: Conduit. It was something I came up with while interning at a local TV station in college: a tool for helping TV stations plan and “run” their broadcasts. Back then, my front-end skill set was limited to HTML, CSS, and some jQuery. My back-end experience was...WordPress.

I knew the idea I had was worth a shot, so I decided to hunt around for a developer who could help me on the back-end. Starting in late 2011, we teamed up and would meet over a Campfire (!) chat every few days. I handled the UI design and front-end, he would handle the back-end (if I recall, it was a Rails app).

One night, having finished the stack of freelance work on my plate, I decided to put a few hours into Conduit. I made a cup of coffee and started to ascend the ladder up to the loft.

Then, the ladder started to slip. I will never forget staring at the coffee cup I had just placed on the ledge of the loft, my hands desperately raking at the landing trying to grip the ledge before I fell.

In a matter of seconds, I’d fallen 10 or so feet, straight on to my tailbone. Fortunately, I didn’t break my back or hit my head on the ground.

I was in shock. For a few seconds, my left hand was paralyzed. I was in an utter state of panic, but incredibly, able to get up and move around.

Fast forward a few days and I was covered in bruises, could barely move, and realized: “I don’t have insurance.”

In what was easily one of my most hardcore moments, I decided to skip going to the hospital or a doctor and just ride it out. Fortunately, that worked out. In about a month’s time, I healed up. I was able to walk fine. There was no discernible damage to speak of.

Fuck. That was a close one.

After that initial healing phase, I didn’t notice any issues. No back pain or anything that was a cause for concern.

Fast forward to 2018 and that all changed.

I decided to take up strength training to help me improve my strength and help with my weight. The menu? Squats, deadlifts, and bench press (with the occasional split squat set thrown in by my trainer to push my limits).

Everything was peachy until one night when I came in for a normal workout, excited as I was finally starting to make progress with my lifts. My normal trainer wasn’t there so one of his teammates stepped in to guide me. He had me do barbell rows instead of the usual deadlift I was used to.

The first few sets went fine. Then, as I started to approach my max, I pulled the bar up and felt an immediate, sharp pain shoot from my tailbone down to my foot.

I dropped the bar and tried to stand up but struggled. I eventually recovered after a few minutes of walking around. In the days that followed, I noticed a sharp pain in my lower back. I later found out it was sciatica. I put together that the initial injury from the fall in 2012 had weakened my tailbone area and that one fateful lift undid any healing that had taken place like that.

Since that night, every few months, I’ll wake up with sciatic pain. Sometimes it lasts for an hour, sometimes it lasts for days.

About two weeks ago, after a prolonged time off from lifting, I decided to start lifting again. Nothing crazy, just a few small sets. But, it was enough to trigger the sciatica. During the lift I was more-or-less fine (perhaps a little stiff), but the next morning? My back was fried.

This put me into a little bit of a spiral. I’ve been trying to get as much as I can shipped this year and the pain was so bad this time it essentially shut off my brain.

Instead of making progress on stuff like Parrot, the CheatCode rebrand, and Mod: I was fighting with my nerves to stop hurting long enough for me to think. It also worked out that I was only a few days away from my first real vacation in lord knows how long. I was, to put it lightly, pissed.

Something I learned a long time ago was that in the face of adversity, to avoid slipping into despair, you absolutely must find the silver lining. No matter how difficult or frustrating, try to find the good in the situation. The thing you might not have seen had you not been in that place.

Over the past week, dealing with the pain, I made a connection.

In the weeks prior, I had grown incredibly frustrated with the state of my accounting and bookkeeping.

I’d been paying a service $300/mo for the past few years to help me manage my books and help me keep an eye on taxes. Over the past year or so, they’ve started to struggle.

I’d get notifications that everything was being handled properly, only to get another message months later that I needed to re-upload bank statements (their API integration with Plaid never really worked and so they fell back to importing transaction data manually).

Anybody who’s run a business knows: one of the most stressful things you have to deal with is keeping track of finances. If you’re in the early stages of a venture, unless you want to fail, you have to be an absolute hawk about where your money is going and how that will impact your tax liability.

The only real solution I’d found until now to help with this—and avoid distracting me from my real work—was to hire someone. Having now worked with a lot of different services, ranging from clever-but-expensive startups to old school bookkeepers, I finally had had it.

I knew I had to make the October 15th deadline for tax filing (I did an extension this year) and I knew that the service I was using was dragging their feet. I also knew that some corner-cutting they’d done in the years prior had cost me far more in taxes than I should have been paying. To put it bluntly: it was a mess.

So, frustrated and feeling the pain, I decided to lean in and ask “can you just solve this problem, once and for all?”

I downloaded my transaction history from my bank and got to work. 24 hours after I started, I had what I needed: a dirt-simple way to categorize transactions and total up revenue, expenses, and estimate taxes due. It was rough, but it worked well enough to help me get my taxes done.

That’s when the lightbulb came on. “I can’t be the only one frustrated by this. I could turn this into a business.”

I’m aware that there are already a ton of different tools for bookkeeping, but compared to the simple tool I built to help with my taxes, they’re bloated.

As a solopreneur, the needs list is limited:

• The ability to track and categorize expenses.
• The ability to track revenue.
• A way to calculate estimated taxes (in the U.S., taxes are due quarterly).
• A way to create simple reports to track revenue growth and monitor where you can trim expenses.
• Bonus: send and receive payments on invoices.

Simple. But shockingly, a lot of what exists today makes the above list a chore to complete. Features you don’t need. Clunky UIs. Half-working integrations to pull your data. You name it.

Instead of staying in this trap and putting aside time for my annual rage fest come tax season next year, I’ve decided to work on this problem.

I’m calling the app Fin. The app will be 100% focused on serving solopreneurs. People like me who are running their own thing—either as their main source of income or as a side gig. I’ll use the initial prototype I built for this year’s taxes to guide my thinking as I build out a product others can use.

If you’re interested, you can sign up for the mailing list here.

This isn’t one I’m looking to rush. My goal is to ship something in 2025, hopefully by Spring so others can use it to help with their own 2024 taxes. It will be U.S. only to start so I don’t fry my brain keeping up with regulatory requirements.

As you know, my plate is already full with other stuff so official work on this (aside from dabbling here and there) won’t start in earnest until next year.

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So, pain. It sucks. It’s not fun. It can really drive you insane.

But it can also help you. I see a lot of indie hackers asking “what should I build” quite often. My answer? Look for the pain. Get good at paying attention to the things that are making your life more difficult. Sure, try existing solutions and see if they help, but if they don’t: consider that thing as your target.

It’s way too easy these days to think it’s not worth trying an idea because a similar product or service already exists. Personally, my approach has always been “try it and see what happens.” You don’t know and you really can’t know. All you can do is try, learn, and keep moving forward.

You have a choice: let the pain dominate you, or, take control and do something about it.

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P.S. If you’re dealing with any sort of chronic pain (specifically, nerve or muscle related), I highly recommend getting a TENS unit (I got one for $25 at Wal-Mart). I’ve been using that on my back over the past few days and it’s gotten the pain down to a dull roar now to where I can actually function. All without the need for ingesting pain killers.