If It Needs a Second Person, It Is Not a Side Hustle

My brother-in-law called me on a Wednesday around nine-thirty, which is his tell. He doesn't call at nine-thirty to catch up. He calls at nine-thirty because he's done the math on something and needs a second opinion before the excitement wears off.

"Okay so hear me out," he said. "It's a vending machine route. But the twist is—" and I already knew I was going to listen to the whole thing, because I always do. The twist was that he needed someone to handle the restock side while he handled the "relationship management," which I was pretty sure meant he wanted to drive around and talk to people while I loaded Cheez-Its into a machine in a break room off I-85. We'd split it down the middle. Equal partners.

I said I'd think about it. I did think about it — for about four minutes, while my coffee was reheating. Then I wrote a rule on the whiteboard above my desk that has stayed there ever since: If it needs a second person, it is not a side hustle. It is a job you don't have yet.

The Whiteboard Has Been Wrong Before, But Not About This

I have a whiteboard above my desk that is supposed to be for business ideas. In practice it is a graveyard of half-finished thoughts and one very aggressive sticky note that says "SHIP IT" that I put there in 2023 and have not shipped the thing yet. The vending machine rule went up there in red marker and is still legible, which is how I know I believed it.

The rule didn't come from nowhere. It came from a specific pattern I'd watched play out a few times — including once with myself, a guy named Darnell from a Facebook group, and a dropshipping arrangement that lasted eleven days before we both quietly stopped responding to each other's messages. I had been the "technical side." He had been the "marketing side." Neither of us had been the money side, which turned out to be the only side that mattered.

The thing about a side hustle is that it has to run on the energy left over after everything else. The day job, the kids, the dishes that are somehow always there. The day job doesn't flex — it doesn't care that I had a thing going on Tuesday night. So whatever I do on the side has to be mine to start, mine to pause, mine to kill on a random Thursday without a conversation. The moment there's a second person, there's a calendar. There's an expectation. There's a group chat.

What Actually Happened When I Ignored My Own Rule

I ignored the rule once after I wrote it. I want to be clear about that, because the rule sounds like something a person who learned their lesson would say, and I had not fully learned mine.

A guy I know — Marcus, works in logistics, good dude — had an idea for a small local delivery thing. Not a platform, just a private arrangement with a couple of restaurants that didn't want to pay the app fees. He needed someone who could write a dead-simple order-tracking page. I could do that in a weekend. We talked about it over wings at a place on Atlanta Highway, and it sounded easy, and I said yes before I got to the parking lot.

I built the page. It worked fine. Marcus handled the restaurants. For about three weeks, it was a thing. Then one of the restaurants backed out, and Marcus got busy, and I had a build that kept breaking on iOS that I was embarrassed about, and we both just sort of let it dissolve. I had put in maybe nine hours of actual work. We made, combined, somewhere in the range of sixty dollars before the restaurant pulled out — I saw thirty of it. Marcus was apologetic about it. I told him it was fine. It was fine.

But here's the specific part that sticks: I couldn't quit when I wanted to. Around week two, I was tired. The day job had been loud that week, my oldest had a thing at school, and I just wanted to sit on the couch and watch something dumb. I couldn't drop the tracking page because Marcus had told the restaurant it was live. So I fixed the iOS bug at eleven-fifteen on a Friday, sitting in my car in the driveway, because the wifi is better out there for some reason. You should be able to quit on a Tuesday. I could not quit on a Tuesday. That's the whole thing.

"I feel bad, man. You put in real work on that." — Marcus, when it fell apart. Which was kind of him to say and also the saddest possible sentence about thirty dollars.

I don't blame Marcus. He's a good guy and the idea wasn't stupid. But the shape of the thing was wrong from the start, and I knew it when I said yes, and I said yes anyway because the wings were good and I was optimistic.

Thirty Dollars and a Friday Night in My Own Driveway

The money part is almost not worth discussing, which is its own kind of discussion. Thirty dollars for somewhere between eight and ten hours of actual work, if I count the back-and-forth messages and the iOS fix and the initial setup. I don't count them usually because counting makes me feel like an idiot, and I already know I'm an idiot without the math confirming it.

The real cost was the Tuesday problem. For three weeks, I had something I couldn't put down. Every hustle has an exit cost — the time to wind it down, the conversation you have to have, the thing you let lapse instead of officially killing. With a solo hustle, that cost is small. With a partner, even a casual one, even a good guy like Marcus, the exit cost involves another person's expectations. It involves a text that starts with "hey so I think I'm going to step back" and then waiting for a response and feeling vaguely guilty for two days.

I am not good at that conversation. I will do almost anything to avoid it, including fixing an iOS bug at eleven-fifteen on a Friday in my driveway. That's the honest version of what this cost.

The Rule Is Still on the Whiteboard and I Still Break It in My Head

The rule stayed. The vending machine thing with my brother-in-law never happened — he moved on to a different scheme within about two weeks, something involving a trailer and a pressure washer, which I also did not join. I heard him out, though. I always hear him out.

What changed is that I got more honest with myself about the difference between a collaboration and a side hustle. A collaboration can be great. Marcus and I could probably build something real if we both had more hours and fewer obligations. But a side hustle, the kind I actually run, has to fit in the margins. DoorDash fits in the margins — I open the app, I take a run, I close the app. The little tools I build fit in the margins — I work on them when something's compiling, I ship them or I don't, nobody is waiting on me. The Roblox thing with the kids fits in the margins because the kids are already there and the whole point is the time with them, not the revenue.

My brother-in-law texted me last month about a new thing. He said it would be "basically hands-off" and that he just needed someone to "handle the back end." I sent him a thumbs up. I'm still thinking about it, which means I'm probably going to hear the pitch over wings sometime in the next few weeks, and I'm probably going to say it sounds interesting, and then I'm going to come home and look at the whiteboard and remember that I already know how this goes.

Note: Everyday Hustle Jeff is the written side of a digital series. These accounts are composite and dramatized. Any figures are what they were on the day, for one person, and are not a projection, a track record, or advice.