Career Change at 50: The Price of Doing Your Own Thing (And the Cost of Not)

Making a career change at 50 and starting again isn’t just brave.

It's strategic, and for some people today, not optional.

I know because I’ve been there.

Twelve years ago, I was escorted out of my day job and into self-employment.

It wasn’t always as glamorous as the gurus say. There were no angel investors or Shark Tank moments.

Just a guy with some Google Adwords experience, a fantasy football blog, and a gnawing sense he could do more.

Oh, and some latch key stubbornness to figure this shit out.

What I’m Seeing

There’s a price for doing your own thing… and a cost for not.

If you want more freedom, you’re gonna have to trade comfort.
If you want to work on your own terms, you’ll have to walk away from a few perks.
If you want to get closer to the value you create, you’ll probably have to fire your boss.

It takes time.
It takes energy.
And yeah, it takes courage.

You need to bet on yourself.

What I’ve Learned

A few things I had to figure out the hard way:

• Clarity beats confidence. You don’t need to know everything. You just need to know what you want more than you fear what you don’t.

• Curiosity is a flywheel. It’ll pull you through the discomfort. It’s the best defense against burnout.

• Energy is a resource. And at 52, I’m managing it like a hawk. No more 18-hour days unless they compound.

So much of this reinvention game isn’t about working harder,
it’s about working on things that compound.

Email lists.
Content flywheels.
Personal brand trust.
Systems that run even when you don’t.

And…

Betting on yourself.

For A Deeper Dive (Podcast Highlights)

On an episode of Gen X Unplugged a few weeks ago, Mike and I dove deeper into this and:

• The moment I knew I had to leave the cubicle forever

• What it really means to “own your value” (and why most of us downplay it)

• Why energy management > time management at this stage

• The myth of the overnight success (and why your messy backstory is your biggest asset)

• And more…

If you missed it, you can listen to it here…

Did you listen already?

Keeping reading, here’s why I’m sharing again…

Building in Public (So You Can Copy Me)

Just a heads-up…

If some of the subject matter above sounds familiar, its because it is.

Here’s why.

Over the next few weeks, I’ll be testing a more streamlined way to create these mixtapes.

The idea? Repurpose lessons from my YouTube videos right here in the newsletter.
Same voice. Same depth. Just fewer hours staring at a blank screen.

Why?

Because I’m working on a system that:

• Works even on the weeks where life gets busy or I just don’t want to work

• Compounds across platforms (without creating double the work)

• Helps me show up consistently without burning out

But don’t worry, this isn’t turning into a video transcript dump.

You’ll still get music.
Still get AI tips.
Still get tools, real stories, and behind the scenes insights.

I’m just pulling back the curtain a little so you can see how I’m building in public. And maybe dub a few moves for your own personal content flywheel.

Kinda like you’re using the two cassette boombox back in the day.

AI Tip of the Week

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