I used to despise managers. Seniors. Leaders. Domain experts.
Anyone who got a title because they’d been around longer.
Having found relative success in my career early on, my mindset was simple: why can’t a 28 year old be a director? If you work hard enough, gather enough knowledge, and have strong passion, then why shouldn’t companies line up to hire you as their next VP?
I absolutely hated the idea that you need “insert number of years of experience” for certain positions.
Does it even matter?
Well. Yes and no.
Having been exposed to 10+ companies and their inner workings over the past few years, my mindset has evolved. Hopefully for the better.
Yes, there are roles where a number of years should not be the concern. Technical roles especially. If you can code, you can code. If you can design, you can design. The work speaks.
But leadership is different.
If you are going to lead people, you need to have been in the trenches.
See, people problems are the biggest kind of challenges. For enterprises. For products. For startups. For communities.
Books can only take you so far. You need action.
I run office hours every week for The Wandering Pro. Early career devs, freelancers, people stuck in the middle of career transitions. And the pattern I see over and over again is this: the problems that hold people back are rarely technical.
It’s not “how do I set up a database.” It’s “how do I tell a client they’re wrong without losing the project.” It’s not “which framework should I learn.” It’s “how do I negotiate a raise without sounding desperate.”
These are people problems dressed up as career problems.
And you can’t learn people problems from a tutorial.
I’ve watched junior freelancers struggle not because their code was bad, but because they didn’t know how to handle a difficult client. They didn’t know when to push back on scope. They didn’t know how to price their work without feeling ashamed. They didn’t know when to walk away.
These things take reps. They take exposure. They take time.
A few weeks ago, I had to send a message to someone I was hoping to bring on full time. The plan had shifted. Structurally, things on my end weren’t where I expected them to be. I had to offer project-based work instead, at a lower rate than originally discussed.
That conversation was uncomfortable. But I’ve had versions of it before. I knew how to frame it honestly. I knew how to leave the door open without making promises I couldn’t keep. I knew how to be direct without being cold.
That’s not something you learn from a course. That’s something you learn from being on both sides of those conversations. From being the one who got the uncomfortable news. From being the one who had to deliver it.
You can’t speed up the process of gathering this kind of knowledge. You can’t read two books in parallel and expect to absorb them both. There are only 24 hours in a day. If you spend them wisely, you just do better.
But “wisely” doesn’t mean “faster.” Sometimes wisely means letting time do its work.
Here’s what changed for me.
I stopped resenting people with more experience. I started sitting with them instead.
When I see a domain expert now, a leader, a director, or just someone who is doing well, I don’t compare. I extract.
I sit with them. I ask questions. I listen to their experiences. I try to understand what they learned that I haven’t yet.
Then I build my own path.
The irony is that the more I mentored others, the more I understood this. When you’re on the other side, watching someone struggle with something you’ve already been through, you see it clearly. You see how much of what you know is just the residue of time and exposure.
You can’t skip that.
And the uncomfortable truth is, most of what holds people back isn’t a lack of information. It’s a lack of reps.
Freelancers without corporate experience often suffer from weak soft skills. They can ship work. But they struggle to have the harder conversations. They don’t know how to read a room, how to navigate politics, how to manage up.
This is why I still tell people: put in your time. Serve your sentence. Then worry about going solo.
Not because the corporate world is great. But because it teaches you things that freelancing alone never will.
As time goes by, you realize the biggest asset you have over someone younger is not knowledge alone. It’s wisdom. It’s pattern recognition. It’s knowing when something is about to go wrong before it does.
And that only comes from being wrong enough times to recognize the signs.
Now, when I look at where I am versus where I was, the difference isn’t how much I know. It’s how much less wrong I am.
As you grow older, you don’t become right. You just become less wrong.
And that’s worth more than any title.
Originally posted on: <a href="https://thewanderingpro.com/why-experience-matters/" target="_blank" rel="noopener nofollow">https://thewanderingpro.com/why-experience-matters/</a>

A space for wanderers who want to turn ideas into execution. We bring together developers, designers, freelancers, and founders who believe execution matters more than talk. https://thewanderingpro.com/

The Wandering Pro

A reflection on why years of experience genuinely matter for leadership and people-facing roles, even if not for purely technical ones. The author, who once resented experience-based hiring, now argues that soft skills like navigating difficult client conversations, negotiating, and reading interpersonal dynamics can only be built through repeated real-world exposure. Freelancers without corporate experience often struggle not with code but with the harder human conversations. The core insight: most career blockers are people problems, not technical ones, and those require reps, not just information.

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