Redefining Retirement Planning: My Career Change Story

How my midlife career change evolved into an early retirement

When people find out that I’m self-employed, one question comes up now and then.

How are you planning for retirement?

The short answer is… I’m not.

At least not in the traditional sense. You know, where you turn 65, stop everything to golf all day, OR jump in a Winnebago and hit the road.

Nope, not my style.

And, by the time you finish reading this post, you’ll see that it may not be your style either.


Why I’m Never Going To Retire

When I realized I needed to pursue self-employment, I knew I needed to find something that was long-term and flexible enough to be future-proof.

At that point in my life, I had already held 19 different jobs and reinvented myself a couple of times, and as exciting as it can be, it’s also not easy.

I also knew I didn’t want to do something to tide me over until retirement because I didn’t want to retire.

There are way too many stories of people who get to retirement, lose their sense of purpose, and then die.

I want to be as productive as possible until the day of my funeral.

I don’t want to be forced to “work” either.

I want to love what I’m doing.

If you love what you do, you’ll never work a day in your life.

Confucius (I think)

Which is precisely what I’ve been doing for the past ten years.

I’ve been helping business owners and entrepreneurs.

I love learning new things.

And I love the challenge of making money at it.

I love what I’m doing so much that it doesn’t even feel like I’m working.

And if it doesn’t feel like working and I love doing it, why the hell would I retire?

I already feel like I’m retired.

NEW HERE? Tap here to subscribe, and I’ll send you the Gen eXit Playbook. You’ll discover my new offensive approach to retirement.

Let’s Redefine Retirement

Instead of viewing retirement as a one-way ticket to leisure town, let's redefine it.

I see retirement as living each day by my rules, doing what I love most.

So, am I retired? In a traditional sense, no.

But in a redefined version, I’ve been living my retirement for ten years now.

It's an empowering journey where the destination is the journey itself.

Who’s with me?

Join me in this version of retirement, one that is filled with Gen X-style fun, purpose, and discovery.


Speaking of never retiring, last week we talked about Metallica still bringing it in their 60s. But how about Willie Nelson?

Check out this performance from just a few months ago. It was his 90th birthday party, and he was joined by Snoop Dogg.

A lot of forgotten lyrics. Not sure it’s the weed or the age, but he’s still givin’ er’.

If we play our cards right, we’ll all be doing what we love with a bunch of cool people at our 90th birthday party.

And, we will be less of a drag on society because we’ll still be useful like my old dusty cassette in this story.

There you have it. As always, thanks for reading.

Until next time,


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