Leading With Meaning

I told a client to take two weeks off.

She was a talented journalist, mid job search, completely fried. The scattered, high-speed version of her wasn’t helping anyone, least of all her.

So I said: stop. Rest. Two weeks.

When she came back, she apologized for taking the time off.

I had assigned it. She apologized for doing it.

That’s when I started thinking about what I now call the inner scorekeeper.

It’s the part of you that doesn’t care what your manager said, what your coach said, or what your out-of-office message says. It has its own standard of what’s acceptable, and it runs quietly in the background keeping score.

That’s why you send the “I’ll be back Monday” note from the beach. Why you do the apology tour when you return from holiday. Why you feel the need to perform busyness even when someone has explicitly told you to stop.

External permission can’t quiet it. It doesn’t accept that currency.

The note from your boss saying “enjoy the break” doesn’t reach it.

The thing worth asking is whether your inner scorekeeper is actually serving you — or just keeping you tired.

Confidence is not the fuel.

It’s the exhaust.

I’ve had a few hundred coaching conversations at this point, and this pattern is remarkably consistent.

Someone wants the promotion. The raise. The career change. They’ve apparently owned the domain for their future business since around 2012.

I ask why they haven’t done it.

The answer is usually some version of: “I’m not ready yet.”

Then they show me the person they’re comparing themselves to. Someone with the title. Someone who made the jump two years ago. Someone on LinkedIn who apparently wakes up every morning radiating executive certainty.

Here’s the thing.

I’ve coached those people too. They’re improvising. They just started improvising sooner.

And somewhere between the things that worked, the things that didn’t, and the things they somehow survived — confidence showed up.

That’s the whole stupid thing.

You don’t need it to start the trip. It’s what you bring home from taking it.

And then everybody looking at you assumes you had it before you left.

Part 2 of 3.

Tomorrow: what actually happens when you keep waiting.

Confidence is not the fuel.

It’s the exhaust.

I’ve had a few hundred coaching conversations at this point, and this pattern is remarkably consistent.

Someone wants the promotion. The raise. The career change. They’ve apparently owned the domain for their future business since around 2012.

I ask why they haven’t done it.

The answer is usually some version of: “I’m not ready yet.”

Then they show me the person they’re comparing themselves to. Someone with the title. Someone who made the jump two years ago. Someone on LinkedIn who apparently wakes up every morning radiating executive certainty.

Here’s the thing.

I’ve coached those people too. They’re improvising. They just started improvising sooner.

And somewhere between the things that worked, the things that didn’t, and the things they somehow survived — confidence showed up.

That’s the whole stupid thing.

You don’t need it to start the trip. It’s what you bring home from taking it.

And then everybody looking at you assumes you had it before you left.

Part 2 of 3.

Next up: what actually happens when you keep waiting.

Gen Z has got it all figured out - see why 👆

There’s an interview mistake I’ve seen really, really smart people make.

Mid-interview, they find themselves rambling for minutes in response to a question that should have taken 30 seconds to answer.

Smart people especially fall into this trap because they know they have the experience and knowledge to impress the interviewer, and want to be sure it shows up in their answer. They want to be sure they come across as the most qualified candidate.

But the truth is that interviewer is typically not looking for proof of your experience.

They got that from your resume. It's how you got the interview in the first place.

What they want to see is how you answer questions under pressure and how you think on the clock.

That means it matters how succinctly you can answer the question and then move on to the next part of the interview.

You want to answer that question in the first 15 to 20 seconds.

Only add color if they ask a follow-up or ask for more detail.

It lets you take control back over the interview instead of just suddenly finding yourself in the midst of a long explanation that you probably didn't need to give in the first place.

For more tips like this, or to have a conversation ahead of your next interview and see where your stories stand, go ahead and click the link in my bio and set up a time to call, or just drop me a note.

I look forward to working with you on the next phase of your career.

I spent about forty years misunderstanding one of the biggest decisions my dad ever made.

Which feels like a very efficient use of four decades.

My dad left a very good job at a big accounting firm to start his own business. And I always admired it — not the accounting part, but the confidence it seemed to take.

He was an Air Force pilot. A CPA. A college instructor. Grown-up stuff. So I assumed he had figured something out before he made the leap. That he had certainty the rest of us didn’t have.

I think I got that completely wrong.

He hadn’t arrived at certainty. He just went first. And then he figured out the next part because now there was a next part to figure out.

We do this constantly. We look at someone who made the move and assume the confidence came before it.

Usually, it didn’t.

Part 1 of 3.

Tomorrow: where confidence actually comes from, and why waiting for it is the one thing almost guaranteed to keep you stuck.

Comment CONFIDENCE below and I’ll send you the full piece on Substack.

Obvious waste announces itself. You can resent it in real time.

The expensive kind is polite.

The standing meeting you attend to stay in the loop, where nothing in four sessions has changed a single decision you made. And you know that. And you’re going again Thursday.

The escalation you fixed yourself in eleven minutes - which would have shown your VP exactly how broken that process is — that you’re now going to have to explain in six months with less evidence and more at stake.

The deck you rebuilt at ten at night because the alignment was bothering you.

Every one of those felt like leadership while it was happening.

Some were pacifiers. Some were stalls — a convenient place to stand while not making a decision you didn’t want to make.

Your attention is a resource. It spent itself on things that paid you just enough in the moment that you didn’t notice it was gone.

The question isn’t whether you were busy.

The question is what your attention was actually buying.

That’s the series. Five videos. One through-line: the job isn’t broken because of the people doing it.

Obvious waste announces itself. You can resent it in real time.

The expensive kind is polite.

The standing meeting you attend to stay in the loop, where nothing in four sessions has changed a single decision you made. And you know that. And you’re going again Thursday.

The escalation you fixed yourself in eleven minutes - which would have shown your VP exactly how broken that process is - that you’re now going to have to explain in six months with less evidence and more at stake.

The deck you rebuilt at ten at night because the alignment was bothering you.

Every one of those felt like leadership while it was happening.

Some were pacifiers. Some were stalls, a convenient place to stand while not making a decision you didn’t want to make.

Your attention is a resource. It spent itself on things that paid you just enough in the moment that you didn’t notice it was gone.

The question isn’t whether you were busy.

The question is what your attention was actually buying.

That’s the series. Five videos. One through-line: the job isn’t broken because of the people doing it.