From Trapped to Uncaged: How to Leave Your Job Without Losing Everything

Dear Legend,

Have you ever wondered what it’d be like to have your own business? Whether you’re cut out for it, whether you’ll be able to weather the ups and downs, whether you’ll be able to make the same amount of money you’re making now? Or more? (I did.)

I had those questions for many years, and I never took the leap. Until the choice was made for me. It was emotionally painful and I had to go through quite a roller coaster. It wasn’t entirely bad, I grew a lot.

But if I had to do it over, I might have done it differently. And this last interview was exactly what I would have needed—how to escape the corporate cage and graduate.

A few weeks ago, I was chatting with Matt Doan, former C-suite consultant turned entrepreneur and founder of Uncaged Life Design. He said something that stuck in my head like a lightning bolt (more on that later 🧠) :

“People don’t buy from companies. They buy from people they trust.”

That was exactly my experience and yet, when I was an employee, I didn’t see it that way. I downplayed my value. Why?

Because in that world? You learn to be a good soldier. You defer to the company name, the brand, the logo, the system. You learn to say “we” when it was really you who closed the deal, saved the account, or pulled off the impossible on a Tuesday at 9PM.

Matt’s own transformation led him to help others do the same

He was traveling every other week across the world, when one day he found himself in a bathroom of this “gold-plated” hotel in Munich. At first he was thinking “this is great!” then he realized he was missing his baby son’s birthday for a meeting he didn’t need to be at, with people he didn’t really care about. He laid on the floor sobbing. “What is going on? This has got to change”

There he planned his way out.

I don’t think this is unique to Matt. I’ve chased titles and corner offices for almost 20 years until I was forced out and then my identity vanished. Only to realize that I was chasing what society was telling me to chase, what my peers were chasing… listen to your heart ❤️, that tiny voice that’s been conditioned to stay quiet. What does it say?

If you feel the same way, trapped, caged, living a life that’s NOT what you actually want, you must read on! If you don’t, remember the following mindset shift and strategy for when the time comes (if the time comes.)

Ok, onward.

Before you do anything, the most important thing is to shift your mindset “You can’t build a new life with the mindset of the old one”. Following what I mentioned earlier, understand that 🧠 YOU ARE THE BRAND.

You need to OWN the fact that you are valuable on your own

Matt said something during the interview that hit home: “It’s crazy. Companies paid me six figures for my skills. But somehow, I still didn’t believe people would pay me directly for the same thing.”

If you’re in that place right now, let me tell you something:

That hesitation? That “who am I to do this?” voice?

It’s lying to you.

You’re not a fraud. You’re just new at seeing yourself as the product.

Are you ready for the corporate graduation strategy? This is something “gurus” don’t ever talk about, because they haven’t actually gone through the transformation, or they went through it by burning all the boats when they were young. But what if you have a family to support? Kids to take care of? Just quitting or grinding from 5pm to 9am is just nonsense.

Here it is, the three step 🧰 corporate graduation strategy (most people start with #3 and that’s why they fail):

1. Create Space

“You can’t build a new chapter if your plate is full.”​

• Reduce meetings, obligations, and noise

• Get time, energy, and mental clarity back

• Eliminate distractions like weekend Slack/Teams time

2. Activate Your Future Self

“You need to install the version of you that’s already 3 years into their business… and live as that person now.”​

• Reprogram your identity: corporate employee to business owner

• New beliefs, language, and behaviors

• Embody the energy of the version of you who already made it

3. Launch Your Genius Business (watch a short IG clip on this)

“The intersection between your zone of genius and who you are compelled to serve.”​

• Look inward, acknowledge and package your genius

• Find the massive problem for the people you feel compelled to serve

• Build a brand around your story + transformation

• Launch small offers with a warm audience

• Validate before scaling

Create space, adopt a new identity, and then launch a side business. This is what makes Matt’s method so smart and sustainable. He’s not selling the fantasy of quitting in a blaze of glory. He’s offering a realistic path for people who want freedom without burning down their life. (Let’s continue the conversation on a post I shared on Linkedin)

(If you want to hear Matt tell his story, how we dive deeper into more mindset shifts and what it means to graduate internally and then externally, listen to the podcast episode on Apple, Spotify or on the web.)

This week, for our influence psychology lesson:

The Pygmalion Effect

Expect more, and people rise. Expect less, and they shrink.

This is the Pygmalion Effect—a phenomenon where higher expectations lead to higher performance.

Why does this happen you ask? (Boy am I excited to tell you!)

The foundation of this is that humans subconsciously respond to belief and social cues. When someone expects you to succeed, they act differently—giving more attention, encouragement, and opportunities.

That belief changes how you show up.

A classic study proved it (a more recent study also had the similar conclusions)

In 1968, researchers told teachers a few students were “academic bloomers.” The students were randomly selected.

By the end of the year, those students had significantly higher IQ scores.

They weren’t smarter. The teachers just believed they were—and treated them accordingly.

Belief changed behavior. Behavior changed results.

Here’s how you can use this effect:

• Set high—but achievable—expectations for your team, and communicate them clearly. "I know you’re the right person for this."

• Onboard new clients with a belief-infused message. “You’re here because you’re the type of person who finishes what they start.”

• Frame your messaging around who your audience is becoming:
  “If you’re reading this, you’re someone who leads.”

• BONUS: Use it to nurture as a parent, a partner, or friend. “You always figure it out,” or “I love how you keep showing up.”

Because people live up to the story you place them in. Choose it wisely.

This week I want to shout out to Tia Smith 🙏🏽 for this wonderful message she left on the poll: “Thank you for sharing such great words of wisdom each week!  I was just laid off from my corporate job - 25 years in HR, most recently as the VP, Global Talent.  I knew the layoff was coming due to a recent acquisition, so I’ve been slowly preparing to leave the corporate world and start my own consultancy. It’s terrifying and exciting all at the same time. I look forward to reading your posts for little bits of insight and inspiration that I can apply in my own journey.  Here we goooooo!”

Legends, if you are looking for help to build extraordinary cultures and exceptional employee experiences, don’t hesitate to reach out to Tia!

See you next Sunday.

Make your mark, live your legend 🤘🏽,

Howie Chan

Creator of Legend Letters

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