When we’re young, adults seem to have everything sorted.
They know what they want. They know how to get it. Life seems to follow a logical order when you’re watching from the outside, innocent and naive.
Then we grow up... and the illusion starts to crack.
We realize we don’t have it all figured out. We have doubts. We have uncertainty. We have those quiet moments where we wonder what the hell we’re doing.
But nobody talks about it.
We’re so obsessed with keeping up appearances, with projecting the image that everything is fine and under control, that we all silently agree to pretend. And because everyone pretends, we each end up feeling like we’re the odd one. The only one who doesn’t have it together. The only one still figuring it out.
There are few things worse than feeling like the odd one out.
I’ll give you a personal example.
From the outside, my situation looks pretty good. Since leaving my job in 2021, I’ve been working for myself - while traveling for the majority of that time. I’ve made enough money to sustain my lifestyle. What I do gives me a lot of freedom and agency over how I work and live. Plenty of good things.
But there’s an invisible side to it. An internal feeling that comes back regularly, asking: “WTF am I doing with my life?”
Financial uncertainty is the default setting. When you say yes to entrepreneurship, you also say yes to uncertainty - it’s part of the deal. Some quarters are great financially, some are not. It has a real impact on how you live, on what you can plan, on how you see the year ahead. Overall I’ve always been fine, and I’m decent at managing money and cashflow... but there’s always a sliver of doubt lingering in the background.
Saving for the future is genuinely hard. A consequence of working for yourself is that retirement isn’t handed to you. A few years here, a few years there... there’s no pension system to fall back on. We have to build our own nest. Some days I think that’s smart - at least I have control over it. Some days I think it’s nuts, and wonder if going back to a regular job would be more sensible - for current stability, but also for the future.
I don’t belong in the traditional professional world anymore. I know this. I’d struggle to fit in and feel fulfilled. Once you’ve tasted the freedom of working for yourself, it’s hard to go back to being told what to do, when to do it, how to do it. But that awareness comes with its own weight.
I’m a generalist in a world that rewards specialists. Most companies want experts. People who stick to one domain. My brain doesn’t work that way. I get bored in the cruising phase. I need challenges. I love the dopamine of learning something new, building something from scratch. I know a good amount about a lot of different things, and I’m not afraid to pick up new skills - but in most traditional settings, that’s “jack of all trades, master of none.”
This is also a double-edged sword as an entrepreneur. I’m great at going from 0 to 1. Once everything is built though, I struggle to stay motivated doing the same thing on repeat: acquire clients, deliver, repeat. My brain starts looking for the next thing.
There’s a term for this now: building a portfolio career. Multiple income streams from sometimes completely different things. It fits my personality well. The downside is that spreading your focus across many things makes it much harder to build solid, reliable sources of income.
I’ve been doing coaching and web design for a year now. And as much as I genuinely love coaching people - through personal challenges or business ones - I’m bored of the constant client acquisition grind. My brain keeps getting pulled toward AI-related stuff those days. I know that itch won’t go away until I scratch it.
That’s where I’m at right now. From the outside, it’s all good. I work, I make money, I have freedom. But internally, I have those constant conversations with myself. Questioning. Doubting. Wondering.
And I’ll bet you do too.
I’d be willing to bet that the majority of you reading this have some version of these conversations going on in your head. Questioning your current situation - professionally, personally, in relationships... wherever you are in life. Looking around and wondering how everyone else seems to have it all figured out.
When I was a young adult, I thought being in your 30s or 40s meant having cracked the code. I thought if you followed the right rules and principles, life would be a smooth ride. Easy peasy.
I don’t believe that anymore.
I think we’re all acting like we know what we’re doing... but to some extent, it’s all BS, it’s all a performance. We’re just riding the waves as they come, doing our best not to lose balance.
Maybe that’s the “curse” of stepping outside the traditional path. Of becoming aware of certain things. I didn’t have these thoughts much in my 20s when I had a normal job and treated it like a job - not worrying too much about whether I enjoyed it or not. But once you’ve been on the other side, you can’t unsee what you’ve seen.
The good news? I’ve stopped letting this tension bother me too much.
Those conversations in my head don’t stress me out the way they used to. Over the years, I’ve come to understand that this is just part of the human experience. I’m actually glad I question things. I’m glad to have the awareness to even have these thoughts. The tension is there, present... but it’s not holding me back. It’s something I sit with, knowing the answer will eventually come.
Now I’m curious about you.
What are the things that, from the outside, look like you have it all figured out... when in reality you’re still working through it?
Hit reply, I’d love to hear.
J
I also have a portfolio career. Didn't know there was a name for it! I've always called it my spiderweb - if one strand breaks, the web won't fail because the others keep it together.
But you're right that none of my strands are as profitable as they could be, because my attention is spread thin. Good food for thought while I consider my next pivot, thanks!