Reflection · Why I decided to go freelance June 2026
Betting on yourself is the best investment you can make
Just having faith that things will work out isn't a strategy.
Plenty of people flee self-employment because they're afraid of the risk. And that's fair. But it can also be one of the best investments you make — especially if your work is purely intellectual.
It depends on what you do with your day. If you spend your hours repeating mechanical processes, betting on yourself really is dangerous: your value is tied to a task a machine, or anyone can replicate. But if you create value with your head, the outcome changes, because you learn at the same time as you produce.
I see it as compound interest: something that grows a little each day and rests on what you built yesterday. I mean, an exponential function.
And not all knowledge is worth the same. Learning the depths of the "trendy tool" expires fast... that gets discarded in a few years. I feel the real return is in transversal knowledge: learning to learn and solving complex problems strategically, in how that tool shaped the way you think.
Our intelligence abstracts that knowledge and builds our mental model. Today I'm running the juanpablocastro X.1 model; tomorrow it'll be X.2. Our training is the result of other people's reflections, and of our own, which is why it's so interesting to surround yourself with peers who push you to update your model of the truth. In this case it was us who inspired the AI to think in models... But we, we'd like to believe that, unlike the AI, we don't accept categorical truths about any subject, that judgment that makes us human. An AI doesn't understand... But anyway, I don't want to ramble. The point is that we keep shipping updates to the way we solve problems, incrementally, through patterns our mental model detects.
Hard as it is to admit, that's what university really gives you. I remember a certain professor who turned my face red in front of the whole class because I didn't know how many bytes a long double takes up in C. She even told me I was in the wrong degree. It was a trivial fact, the kind you look up on Google and that I can't even remember anymore. The ironic part is that she judged me by the knowledge that expires, ignoring what I actually took from those years: the mental framework for solving software problems.
I've spent weeks obsessed, building tools for myself and learning on my own. Some will see the light of day and others will stay for my own use. And it's an obsession I choose. As the days go by, there's a certain inertia that makes you think about time.
When something grips you, the hours fly and you stop watching the clock. Though, let's be honest, that also happens in a good job, when you feel ownership of the project.
The real difference with being freelance or self-employed is where you put your energy. At a company your talent can explode, no doubt. But often a huge part of your time drains into processes, endless meetings, and bureaucracy that, many times, is strictly necessary to operate inside a company... and other times is just waste. By dedicating yourself 100% to you, you remove that friction. You trade "security" for speed and control over your time.
It's not that one path is better than the other. They simply prioritize different things: a job gives you structure and a certain illusion of security; when you're self-employed, the time is yours to manage.
But careful: being freelance, on its own, guarantees you nothing. You have to be willing for things to go wrong, and it's often felt as a more solitary kind of work. That's why it's normal for it to be seen as risk. That said, staying stuck for years as an employee, learning the bare minimum, is just as risky... it's only that there the risk is better disguised. If you don't grow intellectually because of the shelter of a permanent contract, you're taking on a debt with yourself; every day you didn't progress will be paid by your future self.
Jumping into self-employment just to "feel free" is a mistake. Believing in yourself is fine, it's necessary, but it's not enough. Having faith that it'll all work out isn't a plan. Hope is not a strategy.
Real control is born from evidence: from seeing that your actions change the results. Without a plan, you're a boat adrift.
So what's the plan? Start by answering three hard questions:
- What am I going to produce?
- For whom?
- How much time do I have before the financial cushion runs out?
The way to know whether you're on track is the results:
- Is anyone using what you built?
- Is anyone paying you for it?
Sometimes they'll come in that order, sometimes not. You're always doing something for someone. We don't write software to type for the sake of typing; our human nature drives us to solve problems, to create something that didn't exist before and now does.
Give yourself a reasonable deadline based on your cushion... If time passes and you don't have that evidence, it's snowballing on you. It's dead easy to confuse being busy with making progress.
That's why being self-employed is the strategy, not the goal in itself. The goal is to produce something real.
Your inner voice: —It's not that simple. You can do everything right and still not land clients or a financially sustainable living over time.
Which is completely true; there's always a luck factor. Faced with that, think about two things:
- If you managed to bring REAL value to another person with your tool or in the process, it was already worth it.
- If you managed to gain transversal knowledge applicable to your future self, it was already worth it.
- If you managed to inspire other peers to improve through your blogs or your talks, it was already worth it.
- Luck doesn't always come... but you have to be ready.
This is my strategy to make this investment pay off, so I don't fall into a loop of self-deception — this is my plan:
- Put an expiry date on the cushion, and make it public. Say it out loud and you force yourself to deliver — nobody likes breaking promises. Keep it to yourself... It's just a wish, a nice to have.
- Decide what to build and for whom, and force myself to ship something into the world soon so reality tells me whether I'm on track.
- Define a success metric: someone uses it and/or someone pays for it.
- Write down the worst that can happen, and have a plan B. Once it's on paper, the worst-case scenario almost always scares you less than it did in your head.
- Not learning for the sake of learning, but learning in order to produce.
- Surround yourself with people who support you and push you to level up — we're not alone: someone who's already been through this, something that helped you can help them too, sharing reflections both ways that update our model of the truth. Stay on your own and it snowballs on you; they're your reality check.
Careers aren't straight lines, they're cycles. I don't rule out going back to being an employee, it'll probably happen at some point. But right now, I decided to bet my time on myself.