4: Side hustles rarely work. Here’s why.

Happy Monday,

I’ve spent the last week in Dubai. It’s been a suprisingly productive week. Probably because I’ve been waking up at 4am every morning and not being able to fall back asleep.

Fortunately, there’s a 24/7 Starbucks down the road (coffee snobs, don’t @ me). So I’ve been getting a few hours work in before everyone else wakes up—which is nice.

Who said jetlag was a bad thing?


Let’s talk side hustles, and why they usually fail (in my observation—which should be taken with a massive grain of salt because I do talk a lot of shit).

The problem with side hustles

The very nature of a side hustle is that you do it on the side.

You have a job. Probably one that pays okay.

Maybe you’re happy in your job, maybe you’re not. Doesn’t matter. You want to build something—likely a business—on the side.

It’s a rational approach to building a business. You reduce your downside risk. It’s not stressful. You can make decisions from a place of abundance rather than extreme scarcity because you have income from your job.

But this is also why they rarely work.

There’s no urgency.

There’s no pressure.

There’s no deadline.

You have no skin in the game unless you’ve already invested $$$ in building your side hustle (most people do not).

It’s hard to artificially create pressure

It’s difficult to artificially create urgency, pressure and real deadlines. And this is why it’s hard to actually succeed with a side hustle.

It’s why you see people who “build their brand” for years on end without ever building a product or shipping something—simply because they don’t need to ship and make money, even if they want to.

It’s why you see people work on their “revolutionary SaaS tool” for years on end while the market has already evolved past the point where the only thing revolutionary about said SaaS tool is… well… nothing.

Side hustles give you the freedom to do silly stuff like this.

Doesn’t mean you should. Who wants to spend 5 years building a brand without making any money? Not me. 

So what’s the solution?

How do you actually succeed with a side hustle?

I don’t have the answer. I’m not going to pretend I do either.

I built my first business because I had to. 

It was either that or get a job. I didn’t want to get a job. 

In other words: I had pressure, urgency, and drive.

So I’ve never really done the “side hustle” thing the way most people define it. 

But I do know people who have done it—to great success. Here’s why I think it worked for them:

  1. They build something that the market actually wants. They are systematic about what they’re building and who it’s for, instead of just making something they’re “passionate” about. Passion helps, but you can be passionate about something that has zero market viability (aka no one will pay for it).
  2. They give themselves deadlines. I remember a friend saying to me “If I can’t make enough from this business to quit my job by the end of the year, I need to pivot to something else because it’s clearly not working.”
  3. They are paradoxically extremely patient but have a violent sense of urgency. They want to build, market, sell and make money as fast as humanly possible. But they’re also in it for the long haul and know that it takes time.
  4. They ship. They reject the idea of building in silence for months or years on end. They put things out into the market and usually fail at first, but then they iterate and start getting results.
  5. They are incredibly consistent. They usually work every day (even weekends—at least for an hour or so). They embrace the more mundane, repetitive actions required to build something great.

Figure out how you can embed a sense of urgency, drive, and pressure. Expect it to be uncomfortable. Do it anyway.

Interesting things

🎙 Video/podcast – I really enjoyed this interview with Robert Greene. Gained more of an insight into his rise as an author. There are a few useful mental tools hidden in this interview. Recommend.

🐦 Tweet – Great thread from Dakota Robertson on how to become a full-time writer. He‘s written for 407 days straight. Inspiring. 

☀️ Dubai – I’ve enjoyed my time here, but I understand the criticisms of the place. It’s flex-city. It lacks depth. It’s not walkable. That said, I could see myself doing a longer stint here (6-12 months). There’s an energy to the place which I like. I’m spending another week here then I’m off to Romania. 

Thanks for reading this newsletter! See you next week.


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