You Are Your Own Boss

Time to Build Your Portfolio Life

Everyone needs to boss themselves around—especially in mid-career. Because if you don’t design your life, someone else’s agenda will.

In The Permission Paradox, we talked about giving yourself the green light. Permission matters. But permission alone is passive.

It’s the ignition, not the engine.

So let’s talk about what comes after permission.

The Premise You Need to Reject

The traditional career arc is a trap:

Work 40+ years → Hit a finish line → Retire.

It’s outdated. It never served most people. And it definitely doesn’t serve high-achievers who still have a ton of drive, purpose, and energy left.

That’s why this Wall Street Journal piece landed so hard. It featured a woman in her 50s who hoped her employer would keep her until her early 60s.

Hope isn’t a strategy.

And waiting for a corporation to “let you” stay is the opposite of aliveness.

But then the article profiled someone who got it right.

Meet the Anti-Retirement Case Study

When Bank of America offered early retirement in 2023, Kevin Crain—then head of retirement research—didn’t quietly exit.

He designed a second act with intention.

Now 64, he consults part-time, directs a retirement association, advises nonprofits and startups, and works about five hours a day.

Not because he “slowed down.”Because he optimized.

“Had I known there were ways to transition into retirement and still work and be engaged, I would have thought about doing it earlier.”

Kevin didn’t plan for retirement.

He planned for aliveness.

He watched his father go from 100 mph to zero—retiring overnight and losing his sense of purpose and energy. Kevin refused that script.

He chose something better:

A Portfolio Life.

Your Turn

Where are you?

• Thriving?

• High-functioning but flat?

• Successful but secretly bored?

• Energetic or just… fine?

That feeling you can’t name?It’s the gap between what you’re doing and what’s actually alive for you.

Some of you are coming out of a season where everyone else came first. Now you get to decide what comes next for you.

And if you’re in your 20s or 30s, this matters now. Don’t wait for mid-life to start thinking like the CEO of your life.

The earlier you build a portfolio mindset, the more freedom you’ll have later.

Whether you’re 35 or 55, employed or launching, here’s the truth:

You are already your own boss.The question is whether you’re acting like it.

A portfolio life isn’t a luxury.

It’s the natural next step once you stop living on autopilot.

Designing Your Portfolio Life

A portfolio life is built on what Dan Sullivan calls the Four Freedoms:

1. Freedom of Time

You choose how, and with whom, you spend it. You reclaim space for what fuels you: exercise, travel, creative projects, and the hobbies you abandoned years ago.

2. Freedom of Money

You know what you earn, what you need, and what’s enough. You design your finances around sustainability, not stress.

3. Freedom of Relationships

You prioritize depth, not default. Meaningful relationships over casual acquaintances win every day. Who you surround yourself with determines your energy.

4. Freedom of Purpose

You pursue what actually matters: purpose-work, service, contribution. The things that give you back to yourself.

Kevin built all four.

That’s why he’s not just stable—

He thrives.

Why This Matters

Every freedom influences your energy:

• When your time isn’t yours, you burn out.

• When your money dictates your choices, you contract.

• When your relationships lack depth, you detach.

• When your work lacks meaning, you perform.

  
  

Designing for aliveness—not obligation—is the real unlock.

Start Exactly Where You Are

You don’t need a lay-off or a dramatic exit.

If you’re in a corporate role:

• Act like your own boss.

• Decide where your energy goes.

• Know your value.

• Negotiate what matters.

• Start designing.

• Build the side project.

If you’re in transition:

• Say yes to what lights you up.

• Say no to what drains you.

• Think like the CEO of your life—even if someone else signs your paycheck.

• Build the side project.

And Here’s the Part Most People Miss

A portfolio life isn’t built on vibes.

It’s built on structure.

Here’s how Kevin actually did it:

Kevin earns ~$110K through consulting and supplements the rest with retirement income—replacing about 80% of his former salary.He didn’t optimize for more; he optimized for enough.

He kept his rhythm by working from home, split time between city apartment and coastal home, stayed visible on LinkedIn, and never slipped into “retired.”

This is the structure of a portfolio life:

Enough income. Flexible work. Purposeful engagement.

A life shaped around energy — not status.

The Freedom Gap

Your next chapter isn’t blocked by complexity.It’s blocked by one gap.

Look at the Four Freedoms:

Time • Money • Relationships • Purpose

Ask yourself:

Which one feels off right now?

That’s the gap.

Not a flaw.

A signal.

This week, close the gap by 1%:

• Say no.

• Name what you need.

• Redirect money toward what matters.

• Choose the people who choose you.

• Do one small purposeful act.
  

A portfolio life isn’t built in big leaps.

It’s built in the quiet, simple Vital Shifts you choose to make now.

Your Portfolio Life Awaits

You don’t need to leap from 100 mph to zero.You don’t need a life-quake to validate the shift.

You just need to start designing like you’re in charge.

Because you are.

Your portfolio life isn’t a someday project.

It’s a now project.

And it’s waiting for you.

— Carolyn

I’m Carolyn Regan, leadership coach for successful people who feel alive and in charge of their lives. If this resonated and you’re ready to design instead of drift, let’s talk. 👉🏼 Reach out to book a discovery call—we’ll map your portfolio life.