The Paradise Paradox

“If I had that kind of money, I’d just retire.”

“Well, that’s why you don’t have that kind of money.”


When I see this classic debate, I always fail to choose a side.

On one hand, I would certainly take some sort of break if given a life-changing amount of money. On the other, willingness to lay back and relax isn’t common among the wealthy. Herein lies the paradox – paradise can be achieved through endless work, but then you’ll have no time left to enjoy it.

The original argument is paradoxical because it’s framed as “pick one.” It suggests that you can’t have a balanced lifestyle and be wealthy.

This is a false pretense, though.

In fact, putting in just slightly more work than average can create outsized returns. It’s not hard to find these stories. Browsing Indie Hackers or Starter Story will prove my point. Of course some of the stories highlight the hustle, but plenty others focus on the daily discipline that led to their success.

For specific examples, start by looking into @jdnoc or @dvassallo on Twitter.

Since I know you probably won’t click either of those links, here’s the summary.

Jordan (@jdnoc) built his company Closet Tools by getting up every morning before his family and putting in a couple hours of focused work. As of the time of writing, it appears to be around $35k MRR.

Daniel kicked off his entrepreneurial journey by launching a technical guide on Gumroad. Although it takes a while to build an audience and write in-depth content, it’s not something he’s sacrificed his lifestyle over. He’s since released another guide about thriving on Twitter. He currently hovers around $25k MRR from these two products on average.

So there you go. Contrary to popular belief, you can maintain the rest of your life while still building something of value. It takes hard work and discipline, but it’s entirely possible.

Winemaking and Indie-hacking

This weekend, my wife and I headed out of the city for a relaxing trip. Between short excursions at a couple state parks, we dropped by a local winery for a tour.

When we arrived and checked in, we were in for two big surprises. The first – we were the only ones who booked a tour. And second – the head winemaker himself would be hosting our tour.

Now, we’ve done wine tours before… this one was nothing like those.

For over two hours, their friendly winemaker told us everything about their growing, picking, and fermentation process – from the unique soil qualities of their plot, to the painstaking year-round attention they give their youngest vines.

It wasn’t just good things he told us, either. He was up-front about the winery’s failures.

We can’t grow Cabernet for the life of us. Trust me, we really wanted to make it happen.

He said this frustrates him, especially since other nearby wineries can grow Cabernet just fine.

Before I could ask why nearby vineyards can grow something he can’t, he explained:

Each and every plot of land has its own micro-climate. These “micro” qualities are the difference between a thriving vine and a dying one.

So how does this winery narrow down which vines will thrive on their land? Well, it’s just an educated guess. He knows what’s likely to work, but a test batch is the real tell. They plant a row or two of vines, nurture them for a couple years, and see how they perform.

What does this have to do with indie-hacking? Jordan’s tweet sums it up better than I can.

When the next step is unclear, asking for advice is often our first instinct. But you’ve got a unique set of skills and qualities. Nobody – even the successful – know what you should do next.

So learn something from this winemaker. Take an educated guess, get started, and nurture what grows.