project_log: 030

Yo.

Last week I set up a custom server for the first time in my career. This is something I typically avoid because it falls way outside my comfort zone and carries real risk. One fuck-up and I could take down a client's entire online operation.

But I didn't have the luxury of passing this off to someone else. It needed to be done, and guess whose lap it fell into? Mine.

So I thought fuck it. I'll treat this as an opportunity to learn something new.

What followed was hours of chaos. I tried to SSH into the server and failed (wrong port). I accidentally set up multiple instances of the same site, which tanked performance. It took me 30 minutes to update a single environment variable (something that usually takes 20 seconds).

At one point, I was staring at console logs which might as well have been in Mandarin, wondering if I'd bitten off more than I could chew. Safe to say I was pretty uncomfortable.

But by the end of it, I had a working server and something clicked. I realised I'd been avoiding these types of challenges for months, maybe years. And it got me thinking about why.

We treat learning differently once our livelihood depends on it.

Think about learning to surf. You don't watch 500 YouTube videos. You paddle out, get smoked by waves, and learn through your mistakes. Everyone accepts this is how skills work. The learning process is obvious: you suck, then you suck less, then eventually you don't suck.

But once we start making money from our skills? Everything changes.

Suddenly, we can't afford to look incompetent. We have clients depending on us. We have bills to pay. We have a reputation to maintain. So we stick to what we know and avoid anything that might expose us as beginners.

The thing is, this fear is mostly bullshit. People don't give a shit about you or what you're doing. They're too busy worrying about their own problems. But that fear keeps us trapped in the same patterns, doing the same work, at the same level.

Here's what I've learned: growth requires going backwards before you go forwards.

Every major step in my career has meant becoming a beginner again. Going from in-house developer to freelancer meant learning skills I'd never needed like marketing, sales, client management. It was uncomfortable as hell, but it opened up possibilities I couldn't see from my previous position.

Now that I'm trying to build software, I'm learning even more stuff that makes me feel incompetent: product design, customer research, copywriting. Each time I think "this isn't what I do," but then I remember that's exactly why I should be doing it.

Look at the pattern:

In-house developer at an agency:

• Web development

• Basic client communication

Freelancer:

• Everything above, plus:

• Motion design (to stand out)

• Marketing and sales

• End-to-end service delivery

• Running a business

Software builder:

• Everything above, plus:

• Product design

• Copywriting and landing pages

• Product marketing

• Customer research and validation

Each level requires more skills. Each level has paid more (in my experience). And each level forces you to be a beginner again, which is uncomfortable as hell.

But here's the thing: the discomfort is temporary, but the capability you gain is permanent.

Most people stop at "good enough."

They find something that works and milk it until it stops working. They avoid the discomfort of being bad at something new. Being a beginner sucks when you're used to being competent.

But every skill you avoid learning becomes a ceiling. Every time you say "that's not what I do," you're choosing your current limitations over your potential.

The server setup that sacred me last week? It's just another thing I can handle now. Not because I'm naturally gifted, but because I was willing to look stupid for a few hours.

The more discomfort you can handle as you acquire new skills, the more valuable you become. It's not about being naturally talented. It's about being willing to suck at something long enough to get good at it.

To recap:

• We stop taking learning risks once our income depends on our skills

• People aren't watching you fail.

• Growth requires going backwards (being a beginner) before going forwards

• Every avoided skill becomes a personal ceiling.

Stop avoiding the stuff that makes you feel incompetent. The discomfort is only temporary.

Talk soon.

Will