303 Corporate Confessions


Read this (+ previous posts) online

Read time: 3 minutes

Hey there,

I’m about to share some worrying trends I’ve seen in 303 conversations this year with corporate executives and senior pros.

PS - Before we start, I'm currently running the best deal we'll ever have on our signature program, Uncaged Life Design.

Grab your Dream Scan call here ASAP before we close for the holidays and prices go up.


The Secret

Fair warning — some of this might sting. But stick with me, because after we face these realities, I’ll share what’s actually working for those people creating wildly better futures.

On to the trends...

The Reality Check: 2024 Trends

After taking stock of all those conversations, here are the alarming trends I'm seeing:

1) Happiness Gap

  • Successful on paper, empty in reality
  • Living for weekends and vacations
  • Knowing you’re meant for more but stuck
  • Building someone else’s dream (neglecting yours)

2) The Hidden Costs

  • Marriage crumbling under career pressure
  • Kids struggling with absent, stressed parents
  • Anxiety, depression becoming normal
  • Relationships dying by a thousand cuts
  • Serious health issues from chronic stress (cancer)

3) Trapped in Provider Mode

  • Chained to the “responsible one” identity
  • Family scared of any career change talk
  • Trading fulfillment for false security
  • Sacrificing everything to maintain status quo

4) Ageism

  • Being told "overqualified" (i.e., too expensive)
  • 30-year-olds get promoted over 20+ year veterans
  • More industries worshipping youth culture
  • Feeling invisible despite decades of experience
  • AI means fewer spots available near the top

5) No One "Gets It"

  • Family dismisses your bigger dreams
  • Spouse stuck in scarcity thinking
  • Zero peers who understand your struggle
  • Alone in a crowd of “successful” people

6) Corporate Walls Closing In

  • Experience is now seen as liability
  • AI replacing senior decision-makers
  • Traditional 9-5 careers vanishing
  • Fewer jobs, more competition

7) Passive Income Dead Ends

  • Real estate requiring impossible capital
  • Franchises & boring businesses "don't math"
  • "Passive" ventures demanding full-time work
  • Returns too small (and slow) to matter

8) Paralysis by Analysis

  • Drowning in books, podcasts, courses
  • Starting LLCs that go nowhere
  • All planning, no real action
  • Stuck in the “getting ready” phase

The Warning: Costs of Inaction

Here’s the hard truth about where this leads if nothing changes:

Your 2025 gets worse, not better.

The stress compounds. The opportunities shrink. The regrets deepen.

And worst of all? You’ll watch others break free while you stay stuck, knowing you could've created forward momentum.

Luckily, chaos breeds opportunity. And I'd like to share how the select few are thriving across all areas of life.

The Path Forward: What's Working Now

Here’s what’s working for people thriving into 2025:

1) Creating Your Own Economy

  • Embracing and packaging your unique genius
  • Choosing to be anti-commodity by design
  • Building a business that thrives through chaos
  • Mastering the full skillset of founder and CEO
  • Creating skills that pay you back for life

2) Building a Portfolio Career

  • Blending W-2, contractor, and founder roles
  • Diversifying income around your unique genius
  • Active/passive streams that reinforce each other
  • Not scattered activities, but genius-centric focus

3) Strategic Corporate Graduation (Not Blind Leaps)

  • Following proven paths, not random experiments
  • Building relationships that open real doors
  • Taking measured steps while keeping stability

4) Leading Family Forward

  • Having honest conversations about the real risks
  • Showing a new way through action, not just talk
  • Creating security through capability, not just salary

5) Designing Your Own Destiny

  • Creating your own opportunities, not waiting for them
  • Building systems that work for you, not vice versa
  • Turning your employer into your investor

Here’s the truth: identifying the exact "how" is unnecessary right now.

What you need is to draw a line in the sand today.

ENOUGH.

Decide that 2025 will be different. Because without that 100% decision — that commitment to a specific future — you’ll stay in reactive mode.

Just thrown about by forces beyond your control.

It all starts with a decision. Then it’s about putting yourself in environments that help you figure out the “how” as you go.

If this resonates, Uncaged Life Design might be the exact environment to help you take control of your destiny and make 2025 the year everything changes.

2024 is winding down. Let’s have a real conversation about your future (book here).

This can't wait.

—Matt

P.S. Click here to book a conversation with us. We’re still in Separation Season, and I have my best deal ever (for the right person).

But we need to talk first — and soon. The investment increases significantly on January 1st.



Mind-Bender



Podcast

138: Separating From the Crowd

It's time. To separate from:

  • The crowd
  • Mediocrity
  • Your past self

All it takes is a decision (not the "how"). I'm not holding back in this episode. Listen closely.


👋 Final Note:

Ready to break those shackles and graduate corporate life?

Transform everything with Uncaged Life Design, rapidly boosting freedom, family, and fulfillment.

For senior professionals who want to:

  • Smartly downshift corporate (protecting lifestyle)
  • Become happy, energized, and self-directed
  • Build your dream online service business

START HERE: Book a Dream Scan chat.​ We'll explore what's right for you.



That’s it for today, my friend! I appreciate you.

—Matt

Corporate Graduation™

Trade corporate success for entrepreneurial ownership. Every Saturday, receive one essay — to help you navigate the complex shift from the default path to an authentic life powered by a premium business, with bold thinking and grounded conviction.

Read more from Corporate Graduation™

#019 | Read Online By Matt Doan · Oct 18, 2025 · 3-min read From Wage Work to Life Leverage “Give me a lever long enough and a place to stand, and I will move the world.” —Archimedes That’s not just ancient wisdom. It’s a modern advantage. Let’s talk about what’s changed... In the Old Economy, leverage was reserved. You needed permission to thrive. A degree. A gatekeeper. A boss. Someone to let you in. Validate you. Promote you. Today? As Naval Ravikant says, we’ve entered the age of...

#018 | Read Online By Matt Doan · Oct 11, 2025 · 3-min read Watch Your Game Film Tom Brady was never the most athletic guy on the field. Not the strongest. Not the fastest. Barely drafted at all. But he went on to become the greatest quarterback of all time. Why? Because he watched the game film. Religiously. Ruthlessly. Relentlessly. He poured over every angle—his throws, his reads, his protection, his failures. But he didn’t stop there. He looked at his body as a system. He noticed how...

#017 | Read Online By Matt Doan · Oct 4, 2025 · 3-min read Skepticism Isn’t Wisdom. It’s Fear. I need to be honest. I have a hard time being around skeptics. Not because I dislike them. But because I just don’t understand them. It’s like we’re living in two different worlds. For years, I’ve trained myself to default to possibility. To seek alignment, not fear. To trust that what’s meant for me will resonate—and what doesn’t, won’t even make it onto my radar. Skepticism rarely crosses my mind....