Build your life now, not after you’ve "made it"

A friend of mine recently finished his studies, dabbled in a few different things, and is now looking at the next career step. 

So now, he’s weighing joining a startup or going into the corporate world. 

I asked him: “what’s the lifestyle you wanna live?” And his answer surprised me: 

“I’ve always dreamed about becoming an actor and going to acting school; I wanna design furniture, and spend more time playing music.” 

Hm. That’s very far away from a corporate career. 

And yet, that’s the life he actually wants. 

Most people treat those things as something for later. After they’ve “made it”. After they’re retired. 

I believe that’s a mistake. ⬇️

There’s this implicit assumption that you work first, and live later. I think that’s dangerous. 

First, you might not get there. I just attended the funeral of a former teammate. He was 27. 

Second: even if you do – will you still have the energy? The curiosity? The willingness to start something new after doing the same thing for 20+ years? 

I wouldn’t wanna find out.

So instead, layer in the things you’ve always wanted to do into your current life. 

A simple way to think about it: the “regret minimization framework”. 

1. Project yourself forward to 80. 
2. Then, ask yourself: “which decision will I regret not taking?” 

Not what’s safest, looks best on paper, or what your peers are doing. 

What you’d regret not trying. 

Now – what does this actually look like? A few examples: 

1. You could take a mini-retirement: take 6-12 months off to take on a big project. I did this in 2024, and it yielded an online course (an idea I’d been toying with since 2018) and the first draft to a book (yet to be published). Both things I’d always wanted to do. 
2. You could de-prioritize other things in life to just do the thing right now: for instance, I’m consciously not pursuing other hobbies right now because I want to double down on playing Lacrosse at a high level. I’m 32 now, most players retire at 34. I literally can’t do this later. 
3. The same is true for my friend: acting schools (as I learned recently) don’t take in new students after they turn 29, so this has an expiration date. Hard to overcome that later on. 

The first step is to realize that most people (possibly including you) can just do those things right now. 

But you need to design your life accordingly. 

Part of the reason why I founded Generalyst was … Lacrosse. I knew that in most settings that I’d be interested in working in, I wouldn’t have the flexibility to play the sport as I’d like to. Playing Lacrosse at a high level involves a lot of time input and commitment – and sometimes, that happens during the week: 

• 2 hour lifts at lunchtime. 
• Practices that begin at 7pm. 
• Tournaments that go from Wednesday through Saturday. 

In most jobs, that just wouldn’t work. Being self-employed in a lean company, with a high-performing team, mostly remote, you get to make your own rules.

But it comes with trade-offs: 

• I miss being in the office with colleagues. 
• I won’t build the next unicorn. 
• Most founders and candidates I work with will make more money than I will. 

And that’s okay. Because right now, I wanna be on the field. 

You don’t have to found a business to have that kind of flexibility. But you do have to be willing to do things differently. 

If you want to live an extraordinary life, you have to do extraordinary things. 

My grandfather always talked about the “direttissima”: the most direct route from A to B. He was obsessed with finding the direct way. 

Most people take a detour. They optimize for safety, status, money first. Hoping that one day that’ll translate into the life they actually want. 

Reminds me of the fable of the fisherman and the businessman. Here’s the TL;DR: 

• A fisherman goes out to fish for a few hours daily, then spends most of his day on the beach, with his family, and sipping crisp cold beers (ok that’s my addition)
• One day, he meets a business who asks him why he doesn’t work more to invest in a second boat
• With that, he could hire additional people, add more boats, catch more fish and build an empire
• The fisherman asks: “and then what?”
• “Well”, the business man replies, “then could you lie on the beach, spend time with your family, sip crisp cold beers, and maybe go out to fish here and there.” 

A lot of career development talks I have feel similar to this. 

So, let me ask you this:

If you already know what your dream lifestyle looks like – why not start building towards it now? 

Most people build a life first, and try to live it later. 

You can do it the other way around. 

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[1] Reclaim up to 4 hours per day and find time to do the things you've always wanted to do by enrolling into Personal Productivity OS.

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