The portfolio life experiment.

A friend of mine has spent thirty years becoming one of the best tax attorneys you can find.

But he recently told me he fantasizes about burning his business to the ground.

"I'm great at doing something I hate. How's that for success?”

Meanwhile, another friend is on her third wildly different career in 13 years. She ran a marketing agency, started a food brand, and now she’s using AI to code software. Each new business was built on lessons from the previous one. And not surprisingly, each new era gets more profitable than the last.

I wouldn’t call her a master of anything specific, and neither would she. But she's having the time of her life building, learning, networking and just growing in general.

This all makes me think we've got “careers” backward.

The 40-year myth

We're taught to find our thing and stick with it. Build deep expertise and become irreplaceable.

But in following that advice, many people become prisoners of their own expertise.

The lawyer who can't leave because the money's too good. The consultant who's given the same presentation 500 times and can deliver it in her sleep. The agency owner who dreams of doing literally anything else besides servicing another client.

Sure, they built “successful” careers. But now they’re comfortably trapped.

The portfolio alternative

What if instead of one 40-year career, you planned for four 10-year adventures?

Adventure #1 (age 20-30): Learn the fundamentals of how business works. How to sell. How to deliver. Make all of your mistakes when the stakes are much lower.

Adventure #2 (age 30-40): Apply what you learned to build something completely different. Go faster because you’ve learned the patterns. Build something bigger because you've seen what works.

Adventure #3 (age 40-50): Combine everything, or pivot entirely. You've got money, connections, and credibility. The world is literally your playground at this age if you’ve played your cards right.

Adventure #4 (age 50-60): The victory lap. Build for joy, not just profit. Teach. Invest. Create. Do whatever the heck lights you up.

Four different phases, different businesses, and new opportunities to feel the rush of going from 0 to 1. Of course, the time horizons for each era aren’t going to line up exactly like this. Feel free to ignore the ages or think it has to be exactly 10 years. Maybe your first adventure lasts for 6 years, and the next one is 11 years. But you get the idea.

Why this actually works

The reason a portfolio career works is that you’re never truly starting over. You’re simply transferring what you learn to a new application.

Sales. Marketing. Systems. Customer Service, Leadership. Finance. Customer psychology.

When you stay in one business for 40 years, you stop learning around year 10. The rest is just muscle memory on repeat.

But when you start fresh, you're forced to try new things, question old assumptions, and stay curious. Everything compounds, just in a totally different way than you expected.

The hidden benefit

The biggest benefit of a portfolio career is that starting over is energizing.

That first customer in a new business hits different than customer #985 in the old one. Building version 1.0 feels electric. Maintaining version 12.4 can be soul-crushing.

So, portfolio builders get to experience that startup energy over and over. They're always learning something new. Always three years from a big breakthrough or 10 years from their next beginning.

The fear factor

"But what if I fail at the next thing?"

If you’re asking that question, you might be missing the point. Because when you've got four 10-year shots (or some variation of this), your failure is just data. But when you've got one 40-year shot, failure is literally catastrophic.

See the difference?

Portfolio builders can afford to experiment, take risks, and try things that may not work.

But traditional “careerists” can't do that. They've got too much invested in one path.

Now, to be clear, I’m not saying to abandon everything every 10 years like clockwork. That's overly rigid thinking.

I'm suggesting you give yourself permission to evolve, close chapters, and start fresh, applying everything you've learned to something new.

Maybe your 10-year business becomes a 15-year business. Cool. Maybe you keep one business running while starting another. That’s great, too. Maybe you sell, delegate, or automate. All are completely valid!

My point here is to get away from the “single career” thinking and to navigate your work with the possibility of reinvention in mind.

This way of thinking feels refreshing to me, and my tax attorney buddy really appreciated this new perspective. He has a ton of career skills and knowledge, and he loves craft beer. Now, he’s exploring how he might use his experience to break into the beer industry. I’m super excited to see what his next chapter looks like (without a suit and tie).

The bottom line

By 65, you can be one of two people:

Person A: World-class expert in one thing. Deep knowledge. Narrow experience. Maybe really bored.

Person B: A dangerous amateur across several things. You’ve got broad knowledge. Cross-domain info. Definitely not bored.

Person A might make more money in year 40, but I’d argue that person B will have more fun in years 1-39.

I’ve had the benefit of having multiple careers:

• Pharma rep to operating room rep
• Tech salesman, to manager, to VP
• Chief Revenue Officer
• Creator
• Writer

And who knows what’s next…I’ve loved having the opportunity to pivot, try new things, and bring the skills I learned from each role to the next.

Maybe you have another career in you?

Today might be a good day to mess around and find out.

That’s all for this week.

See you next Saturday

P.S. If you don't know how to start a new career (or start dabbling in one), consider watching my flagship course, The Creator MBA. There's even a bonus mini-course called "How to Start from Scratch" that will show you the 12-step framework for standing up a new business in any industry.