By Matt Doan · June 14, 2025 · 3 min read

The Forgotten Phase of Leaving Corporate

Most people assume that leaving corporate is a moment.

A decision. A resignation letter. A dramatic pivot.

A number in their bank account.

But the truth?

It’s rarely a clean break.

It’s a phase. A process. A slow unwinding of one identity… and a gradual construction of another.

I call it the Gray Space.

You’re not fully in, not fully out.

You still show up to meetings. You still collect the paycheck.

But deep down, a part of you has already walked out.

I remember this season vividly.

I had stopped caring about the next big cybersecurity conference.

I didn’t want to read the latest threat reports or memorize new tools.

I found myself opting out—emotionally first, then intellectually.

I was still “doing the job,” but it felt like I was playing a role someone else had written for me years ago.

What took its place wasn’t clear—but it felt more real than anything before.

I began coaching people inside the company. Quietly. Organically.

I turned my role into a lab.

Tested ideas. Mentored colleagues. Paid attention to what lit me up.

I still remember the moment I joined my first entrepreneurial mastermind.

It was a room full of business owners—and I was the only corporate guy.

They spoke a different language. Moved with a different energy.

I felt wildly out of place… and completely at home at the same time.

I didn’t know how I would ever get there.

But I knew I had to stay close to that world.

Somehow, in some way, I knew I had to become one of them.

That was my Gray Space.

And it was deeply uncomfortable.

This is the stage no one talks about.

You’ve mentally resigned—but haven’t left.

You dream about freedom—but still rely on the system.

You crave meaning—but spend your days moving decks and dialing into calls.

It can feel endless.

And if you don’t have language for it, you’ll mistake it for failure.

Like you’re lazy. Or lost. Or ungrateful.

But it’s not failure.

It’s the start of something real.

It’s the early chapters of building a life you actually want.

One where your time is yours.

Where you do meaningful work.

Where your family sees the best of you—not the exhausted version that corporate gets first dibs on.

And maybe most importantly—this is the season where you bring your spouse into the vision.

Not as an afterthought. As a partner.

This isn’t talked about enough.

Because the person you love most needs to feel safe—and also invited.

They don’t just need a spreadsheet or a vague “I’ll figure it out.”

They need to hear you say:

“I know it feels far off, but I’m serious about this. I’m building something real. I’m doing the work.”

I’ve seen marriages deepen in this phase.

Not because everything’s figured out… but because truth is finally being spoken.

Dreams are being shared again.

The energy in the household starts to shift—because you’re no longer silently suffering or hiding the desire for change.

This is what navigating the Gray Space can look like:

• That quiet moment with your spouse where you finally say it out loud: “I can’t keep doing this.”
• The strange freedom of an empty calendar block—and the urge to fill it with meetings just to feel useful.
• The first time you post under your own name (not the company’s) and feel your future self stir awake.
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It’s messy. It’s uncertain. But it’s not meaningless.

Here’s the part most people miss:

The Gray Space isn’t what you avoid—it’s where the real work happens.

Everyone wants to skip straight to the sexy part: the new business, the income stream, the external win.

But this is where the real foundations get built.

You confront fears you’ve buried for years.

You wrestle with time, identity, and value in a way your old life never demanded.

You create space—for your body, your brain, your creativity, your family.

You learn to tell the truth—to yourself and to others.

You reframe your past not as something to escape… but as material for what’s next.

Yes, it’s slower than you want.

Yes, it’s harder than you expect.

But this is where your next life is shaped.

And it’s worth every second.

You need to stay connected to what’s on the other side.

Because this isn’t just about work.

It’s about a harmonized life.

Presence. Purpose. Real freedom.

Where you feel like the fullest version of yourself—not just professionally, but personally.

And here’s the thing: you grow in the process.

You grow skills, beliefs, and perspectives that you’d never touch if you stayed stuck.

You stretch. You stumble. You find your voice.

And one day, you wake up and realize—you’re no longer in the gray.

You’ve crossed. You’ve built traction.

You’ve graduated.

This is the work we guide people through in Corporate Graduation™.

Not just leaving—but becoming.

The Gray Space is murky.

But for those willing to walk through it deliberately?

It becomes the birthplace of everything you’ve been chasing.

One aligned life.

One clear identity.

One powerful new path forward.

And it all starts… in the Gray.

—Matt

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PS - If you're ready to navigate the Gray Space and want a taste of how this works, apply for our next Corporate Graduation™ Lab, happening June 30th. It’s free to join, but built for those serious about real change. We’ll help you see possibilities and find traction fast.

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