I don't usually show up in your inbox on Sunday, but I saw something this weekend that I couldn't wait until Friday to share with you.

I don’t play a musical instrument.

I tried when I was a kid. I was miserable at it.

But music has been part of my life for a very long time.

In fact, my first real experience with freelancing came when I was 19 years old, working as a rock-and-roll photographer.

Over the next several years, I photographed bands and people including the Rolling Stones, The Who, Tina Turner, Arthur Fiedler and a number of other musicians and then on to news personalities like Bill Moyers, Sander Vanocur, David Susskind, and Robert McNeil.

I loved photography.

And I absolutely loved the freedom of freelancing.

What I didn’t understand yet was the business of freelancing.

I was an artist. I knew how to make photographs. I didn’t know nearly enough about marketing myself, finding clients, pricing my work, managing money, or building a sustainable business around something I loved doing.

Eventually, I moved into corporate America, where I spent about 20+ years learning an entirely different side of business.

Then, in 2000, I punched out.

And I became a freelancer again.

More than 20+ years later, I’m still at it.

Which brings me, strangely enough, back to rock and roll.

One of my favorite content creators on YouTube is Rick Beato.

If you’re not familiar with Rick, his channel is about music.

He’s a musician, producer, educator and interviewer who has a wonderful ability to take apart a song, a guitar riff, a recording or a musician’s career and help you understand what’s really going on.

Most of what he talks about is way over my musical head.

Remember, I don’t play an instrument.

But I love listening to someone who has spent decades mastering something explain what he sees and hears.

Rick teaches people to notice things.

And rather than spending 20 minutes doom scrolling, I sometimes go through Rick’s YouTube Shorts.

I almost always come away having learned something.

This week, one of them stopped me in my tracks.

Did you catch what just happened?

Billy Joel was talking about “Just the Way You Are.”

Today, we know it as one of his classic songs.

But Billy Joel didn’t think it was particularly special.

In fact, he was considering leaving it off The Stranger because he thought it was too soft. Too mushy.

Then Linda Ronstadt and Phoebe Snow heard it.

Linda Ronstadt’s reaction was essentially:

Are you out of your mind? That’s a hit record. You have to put that on the album.

Fortunately, Billy Joel listened.

“Just the Way You Are” became his first Top 10 hit and later won Grammys for both Record of the Year and Song of the Year.

Think about that for a moment.

Billy Joel had written the song.

He had performed it.

He had lived with it.

And he was prepared to leave it off the album.

Someone else had to hear what he couldn’t hear himself.

As soon as I watched that clip, I thought about something I see all the time with people who are trying to figure out what they want the next chapter of their lives to look like.

After 50, we’re often encouraged to think in terms of winding things down.

I tend to look at it very differently.

You may have 20+ years of experience behind you, but that doesn’t mean the most interesting part is behind you.

In fact, those decades may contain the raw material for an extraordinary third act — more freedom, more interesting work, more travel, more learning, more contribution, more control over your time, and perhaps some additional income along the way.

But first you have to recognize what you’ve accumulated.

And that’s where something interesting happens.

People routinely discount the very experiences that could help them craft what comes next.

Someone will casually mention something they did 10, 20 or even more years ago.

Maybe they managed a difficult project.

Created a training program.

Solved a problem nobody else could solve.

Built a team.

Developed a presentation that helped win a major contract.

Turned around a struggling department.

Helped people through a complicated transition.

Or became the person everyone came to when something really needed to get done.

Then they’ll shrug and say:

“I was just doing my job.”

Or:

“That was a long time ago.”

Or:

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

Or:

“Nobody would really be interested in that.”

And sometimes I’m sitting there thinking exactly what Linda Ronstadt must have been thinking:

Are you kidding me?

That’s going on the album.

Sometimes it literally becomes something that belongs in a bio, a LinkedIn profile or an Upwork portfolio.

But it might also become the foundation of a consulting practice.

A coaching service.

A course.

A workshop.

A book.

A completely different kind of freelance work.

Or simply the realization that you have far more possibilities available to you than you thought you did.

There’s a reason for that.

You lived your career.

You were there every day.

The things that once required enormous effort eventually became normal to you.

If you managed major projects for 20+ years, managing projects doesn’t seem particularly remarkable.

If you’ve spent decades calming down unhappy customers, building teams, solving technical problems, writing, negotiating, teaching or making complicated things understandable, you may think:

“Well, that’s just what I do.”

Exactly.

And that may be precisely where the next chapter starts.

Creating an interesting life after 50 isn’t necessarily about throwing away everything you’ve done and reinventing yourself from scratch.

Quite often, it’s about looking back at the person you’ve already spent decades becoming — with new eyes — and asking:

That’s a much more interesting question.

After you do something long enough, you develop an eye — or an ear — for things other people miss.

Rick Beato hears things in music that I would never hear.

Linda Ronstadt heard something in Billy Joel’s song that Billy himself was apparently too close to recognize.

And after decades of freelancing, working online, creating content, teaching, coaching and talking with tens of thousands of people about their careers, I’ve developed a pretty good ear for another kind of thing:

The accomplishment someone mentions almost in passing that actually belongs front and center.

Sometimes I’ll stop someone in the middle of a conversation and say:

“Wait a minute. Go back. Tell me more about that.”

Because they may think they’ve just told me something ordinary.

I may be hearing a portfolio item.

A case study.

A consulting service.

A story for their profile.

An idea for a workshop or course.

Or even the beginning of an entirely new source of portable income.

In other words:

That’s going on the album.

Take another look at your career.

Not through your own eyes for a moment.

Pretend you’re Linda Ronstadt sitting in the recording studio.

Look at the projects you completed.

The people you managed.

The problems you solved.

The things people repeatedly came to you for help with.

The unusual assignments.

The difficult situations you navigated.

The knowledge you accumulated that younger people in your profession simply haven’t had enough years to acquire yet.

And ask yourself:

Maybe you dismissed it because it happened 20 years ago.

Maybe you assumed everyone could do it.

Maybe you grew up believing you shouldn’t talk too much about your accomplishments.

Maybe you simply never thought anyone would care.

Take another look.

Because sometimes the very thing you’re prepared to leave off the album is the thing someone else needs to hear.

And occasionally, all it takes is another set of experienced eyes to say:

That one.

Don’t leave that one out.

Best,

Winton