Good morning,

Over the last couple of weeks, I’ve talked with three people who spent much of their careers as nurses.

You might think that would mean they had roughly the same collection of skills.

Not even close.

One had extensive experience with clinical trials.

Another had worked in a research environment.

Another had spent years around surgery and hospital operations.

Same job title.

Three almost completely different worlds.

And that points to one of the biggest problems I see when experienced professionals start thinking about earning independent income.

They tell me what their job title was.

But the valuable part is usually hiding underneath it.

“I was a nurse.”

“I was an engineer.”

“I worked in HR.”

“I was a CPA.”

“I was an executive.”

Those statements tell me something.

But not nearly enough.

A job title is really just a filing label.

Inside that box may be 20+ years of problems you solved, systems you improved, people you trained, crises you handled, decisions you helped make, processes you created and mistakes you learned how to prevent.

That is where the interesting stuff lives.

And there’s a peculiar problem that comes with being very experienced:

The better you get at something, the less remarkable it may seem to you.

You’ve done it so many times that you think:

“That’s nothing.”

“That was just part of my job.”

“Everybody in my field knows how to do that.”

Very often, they don’t.

And people outside your field almost certainly don’t.

Heidi made a wonderful observation during our Tuesday night session.

Something you did over and over again may feel completely mundane to you.

Meanwhile, there may be somebody out there practically praying to find a person who knows how to do exactly that.

That’s the disconnect.

When I ask people about their accomplishments, they often search their memory for the gigantic career-defining event.

The award.

The huge promotion.

The multimillion-dollar deal.

Those are wonderful if you have them.

But I’m equally interested in what I call the quiet milestones.

Something used to be chaotic.

Then, because of something you did, it ran smoothly.

New employees used to take forever to get up to speed. You developed a better onboarding process.

Management was struggling to make a decision. You researched the alternatives and gave them a recommendation they could act on.

A manufacturing process was producing too much scrap. You helped change the process and cut the waste from 6% to 3%.

Incidentally, don’t describe that last one as:

That sounds like something you would hear shortly before falling asleep in a meeting.

You cut the scrap rate by 50%.

Same facts.

Much clearer picture of the value.

This is part of learning how to translate your career.

You are not inventing accomplishments.

You are learning to see and communicate the significance of accomplishments you may have stopped noticing years ago.

I said something Tuesday night that made me laugh after I said it:

We’re all in show business, whether we like it or not.

I don’t mean sequins, spotlights and tap dancing.

I mean:

Show me.

If you say you can improve a process, show me an example.

If you can train people, show me how you teach.

If you can research a complicated issue and make it understandable, show me.

If you can edit, show me a before-and-after.

If you spent years solving expensive problems, tell me the story of one of them.

This becomes particularly important when you start looking for clients.

A prospective client really has only a few questions:

Can you handle a problem like mine?

Do you understand what I’m dealing with?

Have you successfully done something similar before?

And can I trust you to do it here?

Your experience can answer those questions.

But only if you make the experience visible.

This is where people sometimes get hung up.

They start digging through 20+ years of files trying to find the perfect 130-page report.

Please don’t.

Nobody wants to read 130 pages to decide whether to hire you.

Sometimes five selected pages are better than 130.

Sometimes one page is better than five.

Sometimes the original work is confidential, proprietary or simply ancient-looking. In that case, you may be able to redact it, modernize it or create a demonstration sample that shows the same skill without revealing anything you shouldn’t.

The objective isn’t to build a museum containing everything you’ve ever done.

It is to provide enough proof to make the next decision easier.

That distinction matters.

Set aside the job titles for a moment and finish these four sentences:

Then do the last one.

Not all eight examples.

Not your complete portfolio.

One.

I have watched people spend six months deciding which of three portfolio pieces they should create first.

They could have finished all three.

Sometimes momentum is more valuable than optimization.

And once you create that first piece of evidence, something interesting happens.

You begin looking at your own career differently.

You stop seeing a chronology of jobs.

You start seeing an inventory of problems you know how to solve.

That is a much more valuable way to look at 20+ years of experience.

Best,

Winton

P.S. If you’re looking at a long, complicated career and thinking, “I know there’s value here, but I’m having trouble turning it into something somebody would hire me to do,” that is exactly the kind of problem we work on.

Sometimes you can absolutely figure it out yourself. Sometimes an outside set of eyes can see patterns and possibilities that are almost impossible to see when you’re standing inside your own career.

If you’d like to talk about where you are and whether getting some help would make sense, just reply to this email. We’ll start with a conversation—not a checkout page.