Tired of being the "reliable one"... but never the one to lead.

I used to work with a guy named D (I call him that here) — a great engineer, the type every startup quietly leans on when things get tough. He was T-shaped - he could work a bunch of different roles outside of their expected core.

He built core infrastructure from day one.
He could hang with the customer team or interview or design product features.

He's a great guy to work with.

But he was tired.
Burned out.
Quietly worn down by a role that no longer fit who he wanted to become.

D dreamed of moving into product management. Or customer team.

Out of engineering.

He knew the product cold. He knew customers. He knew all their problems.
But At the company, he was seen as “the engineer who got shit done".

"If I ever need something done I know D will work 18 hour until its finished".

And what owner would want to give up that addictive drug?

They locked him into the box they needed him in, and even when he asked for more — they handed him some part-time scraps of a customer without backfilling his real work.

Eventually, they never promoted him.
They didn’t invest in him. Even when everyone else was cheering.

D left... and only then did real opportunities start showing up.

And this story?

It’s heartbreakingly common.

The Lie That Keeps You Trapped

If you feel stuck in a role that doesn’t value your full potential, it’s not because you're not good enough.

It’s because companies often only see the version of you they already know.

They reduce risk of putting a known quantity into an unknown role.

The longer you stay, the harder it becomes to reframe their perception.

• You're "the engineer," not the innovator.
• You're "the troubleshooter," not the strategist.
• You're "the workhorse," not the leader.

I lived it too.

Even when I knew more about product and customers than anyone in the company, they still said, "Keep up the great work."

Secret code for: "we like you where you are".

The Frog Boil of Confidence

The longer people tell you “you’re only good at this” (emphasis on only here) - something begins to happen inside you.

You start to doubt yourself.

Your confidence erodes slowly, until one day you realize you’re playing smaller than you should.

And it's not because you aren’t capable, but because you’ve been conditioned to see yourself through their limited lens.

It's boiling the frog. You realize one day you have drifted from your potential.

Over time they have slowly convinced you to hold yourself back.

You look up to people and you trust them to guide you.

Only later do you realize: they weren’t lifting you up. They were keeping you down, one subtle comment at a time.

By the time you recognize it, you've spent years living under someone else’s ceiling.

When You’re Ready to Stop Begging for Permission

There's a truth here you need to see: If you want your next role to reflect who you really are and what you want - and not who you used to be, you have to reposition yourself first.

You can't wait for someone to notice.
You can't hope your current boss “gets it.”
You can’t trust broken systems to fix themselves.

You need a new strategy.
A new way of thinking, positioning, and presenting yourself.
One that makes you the obvious choice for the roles you deserve — without wasting years trying to "prove" yourself in a system that was never designed for you to win.

Become the Obvious Choice

If you are done settling, there’s something I want you to know:

You are closer than you think to your ideal role.

But you won’t get there by doing “more of the same".

You’ll get there by moving smarter, not harder.

And you need to take a step into the unknown.

You might feel weird or uncomfortable. You think people will notice.

What I've found is that most people are too busy to care.

And we all overestimate risk and under-estimate opportunity. (so says Jeff Bezos and when was he ever wrong?)

I'm running a workshop or two in May.

This one is the thirteenth.

We'll talk about the state of the market. I'll show you what I've learned in the last 30 years

Of moving from role to role and company to company and career to career.

You’ll learn how to rethink, reposition, and present yourself so you can step ahead.

faster, easier, and without following the broken traditional norms.

Spots are free but limited, because this workshop isn’t about mass-market advice — it’s for action-takers ready to finally make their move.

If that’s you, claim your spot right here.

​https://www.obviouschoicesystem.com/workshop​