Skip to main content
Spotify for Podcasters
Uncage Yourself

Uncage Yourself

By Matt Doan

Uncage Yourself explores how to build a career and life on your terms.

Many people are trapped in the Corporate Cage — a dangerous position where work dominates their days and personal lives. But it doesn’t have to be this way. You can direct your corporate experience and unlock a life of freedom, right where you are.

This show is about your transformation: from Caged to Uncaged. Your host, Matt Doan, brings forward the guests, stories, strategies, and tactics to make it happen.
Available on
Apple Podcasts Logo
Castbox Logo
Google Podcasts Logo
Pocket Casts Logo
RadioPublic Logo
Spotify Logo
Currently playing episode

97: What Everyone Misses in Creating Personal Freedom

Uncage YourselfSep 26, 2023

00:00
16:60
97: What Everyone Misses in Creating Personal Freedom
Sep 26, 202316:60
96: Delusional Minds Chase Passive Income
Sep 19, 202321:55
 95: How to Put Corporate on Autopilot
Aug 29, 202322:15
94: [HITS] The "Employee" Is Dead
Aug 22, 202317:55
93: Bravely Stepping Out of Your Cage
Aug 15, 202317:20
92: [HITS] You Need Skin in the Game
Aug 08, 202314:02
91: [HITS] Should I Choose Safety or Passion?
Aug 01, 202313:46
 90: Using Corporate as Rocket Fuel
Jul 25, 202314:21
89: Building Your Corporate Offramp
Jul 18, 202327:24
88: [HITS] Mike Gardon - Investment In Loss

88: [HITS] Mike Gardon - Investment In Loss

The trading life nearly destroyed ⁠Mike Gardon⁠. Since stepping away, he’s obsessed with creating “life options.” At the core is the idea of “investment in loss”: to make significant changes, we often need to step backward. Today, his mission is to “break our mental constructs for what it means to make a living.” Enjoy!

***

👉 ⁠⁠⁠⁠⁠⁠⁠⁠Training: escape the Corporate Cage⁠⁠⁠⁠

🌐 Show website: ⁠⁠⁠⁠⁠⁠⁠⁠UncageYourself.FM⁠⁠⁠⁠⁠⁠⁠⁠

***

TIMESTAMPS

(00:00) Intro02:17 Ironman mentality

(06:37) Compounding personal gains

(09:48) Stratify your goals

(12:31) Mike’s childhood → career start

(17:56) Rebelling against the default path

(20:06) Investment in loss

(23:31) Portfolio mindset

(25:34) Passion for career coaching

(27:50) Mike helping his former self

(33:47) Involving your family in major change

(34:52) Risk mindset for personal growth

(37:00) “Is what you’re pursuing big enough?”

(40:02) Life options

(41:50) Skin in the game

(47:03) Money, time, & energy

(52:30) Uncaged = ownership

***

TAKEAWAYS

1. Pushing yourself with a new venture is not just about the accomplishment. It’s the person you become in the process.


2. “What’s your Ironman race?” Find the near-term thing in your life that forces your growth.


3. The entrepreneurial journey starts with a flicker inside you (an inclination) before you take tangible action.


4. The ultimate safety isn’t choosing the “right” path; it’s creating life options.


5. Portfolio mindset: make multiple concurrent bets and see what sticks. Even with the “failures,” you’ll grow tremendously.


6. Slow down (even step back) to speed up.


7. In managing the risk of major life decisions, too many remain stuck protecting what they have instead of pursuing what’s possible.


8. “Don’t tell me what you think, [show me] your portfolio.” —Nassim Nicholas Taleb


9. “Every decision is an investment decision.” You must devote appropriate money, time, and energy to the transformation you seek.


10. Choose yourself.

***

RESOURCES

Connect w/ Mike on LinkedIn⁠

The Break Podcast⁠

The Break Newsletter

⁠⁠⁠Connect w/ Matt on LinkedIn⁠⁠⁠

⁠⁠⁠Follow on Twitter @Uncaged_Matt⁠⁠⁠

⁠⁠⁠Check the show on YouTube⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠"Badass Corporate" Private Facebook Group⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠Newsletter: Uncaged Secrets⁠⁠⁠⁠⁠⁠

Jul 11, 202356:43
 87: Corporate Sellouts - Post-COVID Corporate Life

87: Corporate Sellouts - Post-COVID Corporate Life

Taylor and Tori, the dynamic hosts of the Corporate Sellouts podcast, join Matt to share an enlightening view of how Millennial females experience the post-COVID corporate world.

They discuss what it means to be a corporate sellout, how to get the most gain for the least pain in corporate life, and how ambitious individuals can pursue their entrepreneurial dreams while navigating a day job. 

Prepare for a candid and empowering exploration of the corporate landscape, where we uncover hidden opportunities to find freedom and fulfillment in your professional journey.

***

👉 ⁠⁠⁠⁠⁠⁠⁠Training: escape the Corporate Cage⁠⁠⁠

🌐 Show website: ⁠⁠⁠⁠⁠⁠⁠UncageYourself.FM⁠⁠⁠⁠⁠⁠⁠

***

TIMESTAMPS

(00:00) Intro

(03:08) What is a “Corporate Sellout”?

(06:05) “Transactional” is not a dirty word

(11:35) Post-COVID corporate life challenges

(16:52) Configuring work to your life needs

(18:40) How Gen Z is shaking up work norms

(21:10) Industrial-era mentality is disintegrating

(23:46) Female perspective on work-life balance

(28:15) Clarify expected outcomes at work

(32:22) Challenge: buy back your time

(35:47) Kickstarting entrepreneurship with a 9-5

(40:47) Corporate: venture capitalist for your life

(44:18) Entrepreneurship transforms us as people

(45:06) What it means to live Uncaged

***

TAKEAWAYS

  1. Maintaining a transactional mindset in the workplace is a massive unlock for winning back time and energy from corporate to live a fuller life

  2. Return-to-office efforts are an opportunity to evaluate your employer and assert your life preferences (set your business case)

  3. Gen Z is challenging traditional workplace norms and advocating for a life-first approach.

  4. We need to consider gender dynamics at home when seeking “balance” (outsourcing tasks can help regain mental peace and capacity)

  5. If you’re stressed and burned out, can you afford NOT to buy back your time and energy?

  6. View your corporate job as an investor in your future self (and business) 

  7. Small, concentrated entrepreneurial efforts can transform your entire career trajectory (and life)

***

RESOURCES

Corporate Sellouts Podcast

Corporate Sellouts Instagram

Taylor's TikTok

Tori's TikTok

⁠⁠Connect w/ Matt on LinkedIn⁠⁠

⁠⁠Follow on Twitter @MatthewRDoan⁠⁠

⁠⁠Check the show on YouTube⁠

⁠⁠⁠⁠⁠⁠⁠"Badass Corporate" Private Facebook Group⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Newsletter: Uncaged Secrets⁠⁠⁠⁠⁠⁠

Jun 27, 202349:39
 86: The Real Costs of Burnout
Jun 20, 202319:11
 85: 15 Reasons You’re Stuck in the Rat Race
Jun 13, 202324:30
 84: What Are You Still Tolerating?
Jun 06, 202313:39
 83: Corporate Countermeasures
May 30, 202325:54
82: Goal Activation (Your Missing Ingredient)
May 23, 202312:58
81: [HITS] Paul Millerd - Awakening From the Default Path

81: [HITS] Paul Millerd - Awakening From the Default Path

Paul Millerd⁠, author of The Pathless Path, joins me to talk about "default path" addiction and what it's like to awaken. As former management consultants, we dig hard into this arena too. Enjoy!

***

👉 ⁠⁠⁠⁠⁠⁠Masterclass: escape the Corporate Cage⁠⁠

🌐 Show website: ⁠⁠⁠⁠⁠⁠UncageYourself.FM⁠⁠⁠⁠⁠⁠

***

TIMESTAMPS

03:12 The Great Contemplation

06:21 How Paul's book affected Matt

08:25 The process of Awakening

09:51 Pre-awakening (most people trapped here)

15:58 Addiction to Default Paths

19:03 Value of an early-career foothold

21:56 "There's a pebble in my shoe"

23:51 Higher stakes if you're a parent

27:10 Understanding life tradeoffs

28:28 The Pathless Path

31:21 Uncertainty as a feature

33:10 Testing boundaries at work

38:31 The great work of your life

41:15 Minimal risk in betting on yourself

44:21 Thoughtful re-entry into corporate life

51:20 Rapid-fire

57:53 What's your "work" story?

***

TAKEAWAYS

1. Great Resignation might actually be the Great Contemplation: a rejection of scripted life, healthier conversation about our identification as "workers," and a desire to take control of your life.  


2. Rule of thumb: most people you'll meet are asleep (80%), some are groggy (15%), and a few are truly awake (5%).


3. The Protestant Reformation triggered an "obsession" with work, which has taken global hold. 


4. Aim of life for people came to find work and then hold on tight to that path.


5. The Default Path feels addictive because the start is so thrilling. Eventually, we stop growing and become sleepy.


6. Instead of doing the work, you eventually find yourself doing performative work (pretending to be valuable).


7. Tough for parents to fake it at work while simultaneously encouraging your kids to blaze their own path.


8. We can't let sunk costs weigh us down. Your life season hugely impacts what you should say "yes" to next.


9. Not knowing what comes next might actually be a feature, not a bug.


10. "If there are clear boundaries [at work], there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges." —David Whyte


11. Great work of your life: continually find the great work of your life (Stephen Cope).


12. Know yourself: deliver targeted value inside your 9-5; push yourself for exponential growth in the outside world. 

***

RESOURCES

⁠The Pathless Path (book)⁠

⁠Paul's newsletter, site, & podcast⁠

⁠Follow Paul on Twitter⁠

⁠Connect w/ Paul on LinkedIn⁠ 

⁠Connect w/ Matt on LinkedIn⁠

⁠Follow on Twitter @MatthewRDoan⁠

⁠Check the show on YouTube

⁠⁠⁠⁠⁠⁠"Badass Corporate" Private Facebook Group⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠Newsletter: Uncaged Secrets⁠⁠⁠⁠⁠⁠

May 16, 202358:57
 80: Invisible Progress
May 09, 202315:25
 79: Play the Game (So You No Longer Have To)
Apr 25, 202321:21
 78: Doing Corporate Detached
Apr 11, 202315:36
 77: Hybrid Entrepreneurship
Apr 04, 202318:31
 76: Mastering the Game of Incentives
Mar 21, 202314:17
 75: Escape Velocity
Mar 07, 202313:19
74: Don't "401k" Your Life Away
Feb 28, 202314:09
73: Amp It Up
Feb 21, 202315:19
72: Getting Out of Your Own Way
Feb 14, 202310:50
71: Be Grateful in Advance
Feb 07, 202309:46
70: Strategic Ignorance
Jan 31, 202315:12
69: Engineer Your 9-5 for Freedom
Jan 24, 202318:21
68: Invisible Scripts That Run Your Life
Jan 17, 202319:18
 67: Addition by Subtraction
Jan 10, 202317:14
66: Entrepreneurship Is the Most Brutal (And Effective) Way to Discover Yourself
Jan 03, 202312:56
65: Reflections from 2022
Dec 27, 202221:47
64: Convert Your Job Into a Utility
Dec 13, 202208:46
 63: Billy Keels - Leveraging Corporate for Your Dream Life

63: Billy Keels - Leveraging Corporate for Your Dream Life

Billy Keels is one of the “awakened” ones. After years of undeniable success in the corporate world, he intentionally started leveraging those gains to fuel his bigger, more badass life. Now, as an entrepreneur, Billy helps highly-paid professionals take control of their lives and create wealth through cash-flowing, tax-efficient investments. He’s a fountain of actionable wisdom!

***

👉 Complimentary Uncaged Masterclass

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

02:48 Comparing U.S. & Europe

06:06 Importance of environment

09:18 The allure of default paths

11:23 Awakening

16:05 A fresh view on corporate life

19:55 Doing corporate on your terms

24:02 Outcomes over hours

27:20 Scratching that entrepreneurial itch

34:26 Failing forward

37:32 Rapid fire questions

***

TAKEAWAYS

1. Default paths can quickly become your identity. Therefore, we must consciously decouple from them.


2. What we’re surrounded by, we adopt.


3. Corporate life can be a great accelerator to your career, but we must control that ascent.


4. Don’t just plug into the corporate machine like everyone else. You can deliver results (more efficiently) on your terms.


5. No one really cares about your work hours, only the value you produce. So use that to your advantage.


6. Too many people are “theoretical ninjas” — passively consuming good information without implementing it.


7. Healthy person = healthy worker. Focus primarily on being the former; the latter is a byproduct.


8. “The next logical step” is often the most illogical thing to do.


9. “It’s not about the money. It’s about how you’re investing your time in the moments that matter the most.”

***

RESOURCES

How Highly-Paid Pros Can Pay Less Tax

Connect w/ Billy on LinkedIn

Going Long Podcast

First Generation Capital Partners

"Badass Corporate" Private Facebook Group

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Dec 06, 202247:40
 62: You Need Skin in the Game
Nov 29, 202214:02
 61: Don’t Take Your Gifts to the Grave
Nov 22, 202214:44
 60: Mike Gardon - Investment In Loss

60: Mike Gardon - Investment In Loss

The trading life nearly destroyed Mike Gardon. Since stepping away, he’s obsessed with creating “life options.” At the core is the idea of “investment in loss”: to make significant changes, we often need to step backward. Today, his mission is to “break our mental constructs for what it means to make a living.” Enjoy!

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

02:17 Ironman mentality

06:37 Compounding personal gains

09:48 Stratify your goals

12:31 Mike’s childhood → career start

17:56 Rebelling against the default path

20:06 Investment in loss

23:31 Portfolio mindset

25:34 Passion for career coaching

27:50 Mike helping his former self

33:47 Involving your family in major change

34:52 Risk mindset for personal growth

37:00 “Is what you’re pursuing big enough?”

40:02 Life options

41:50 Skin in the game

47:03 Money, time, & energy

52:30 Uncaged = ownership

***

TAKEAWAYS

1. Pushing yourself with a new venture is not just about the accomplishment. It’s the person you become in the process.


2. “What’s your Ironman race?” Find the near-term thing in your life that forces your growth.


3. The entrepreneurial journey starts with a flicker inside you (an inclination) before you take tangible action.


4. The ultimate safety isn’t choosing the “right” path; it’s creating life options.


5. Portfolio mindset: make multiple concurrent bets and see what sticks. Even with the “failures,” you’ll grow tremendously.


6. Slow down (even step back) to speed up.


7. In managing the risk of major life decisions, too many remain stuck protecting what they have instead of pursuing what’s possible.


8. “Don’t tell me what you think, [show me] your portfolio.” —Nassim Nicholas Taleb


9. “Every decision is an investment decision.” You must devote appropriate money, time, and energy to the transformation you seek.


10. Choose yourself.

***

RESOURCES

Connect w/ Mike on LinkedIn

Career Cloud Podcast

The Break Newsletter

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Nov 08, 202256:43
59: Tara Horstmeyer - Ghostwrite Your Life

59: Tara Horstmeyer - Ghostwrite Your Life

Today’s thoughts become tomorrow’s reality. And when you write down those thoughts, it’s a lightspeed jump into your better future. The lovely and super authentic Tara Horstmeyer joins me to talk about life-career seasons, LinkedIn mastery, and the power of “ghostwriting your own life.” Enjoy!

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

03:00 Words that penetrate the soul

05:20 Writing when the emotion is hot

09:18 Tara’s childhood influences

14:02 Empathetic languaging

16:06 Doing what lights you up

20:06 Words are the catalyst for change

22:36 “Everyone is a ghostwriter”

25:20 Shifting your focus: outward to inward

29:01 Personal brand = personal advantage

34:02 Embracing “life seasons”

40:38 Rapid-fire questions

***

TAKEAWAYS

1. Create a simple system for capturing your ideas when inspiration strikes.


2. Develop a method for fleshing out those idea “seedlings.”


3. When inspired, write with “editor” mode turned off (revisit with that lens later).


4. “Make sure you have something to say before you say it.”


5. Ghostwriting your own life is a process by which you find and build yourself.


6. You already have a personal brand (it’s your reputation). “Make it your business.”


7. You’re always juggling glass and rubber balls. If you drop the glass ones (e.g., family), they shatter.


8. If you’re speaking to everyone, you’re speaking to no one.

***

RESOURCES

Connect w/ Tara on LinkedIn

Happy Words Sell (Tara's business)

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Nov 01, 202247:54
 58: Tony Albrecht - In The Creative Arena

58: Tony Albrecht - In The Creative Arena

Tony Albrecht is one of my favorites. He’s a writer, podcaster, social entrepreneur, and student of the creative process. As the author of In The Creative Arena and co-founder of The Rowdy Creative, he works with people old enough to know they want a different trajectory and young and crazy enough to believe that big change is possible. His work is informed by his recovery from two afflictions, alcoholism and becoming a lawyer.

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

03:03 Powered by espresso

06:18 Chapters of Tony’s life

08:32 Creative awakening

12:07 Offscripting

13:41 How to be a “creative”

19:08 Gen Z is freeing older generations

23:49 Dying to feel alive

29:00 Plugging “back in” on your terms

32:02 Surrounding yourself with non-conformists

34:34 Battling Resistance

37:50 Spartan way: extreme discipline

40:56 Examples of discipline

44:20 “Creativity is life or death”

46:34 How our children grapple with the scripted life

48:17 Rapid-fire questions

53:49 Choices today raise your trajectory for tomorrow

***

TAKEAWAYS

1. The idea of creativity “isn’t just for the arts department…it’s how we make new stuff happen.”


2. View your engagement on social media as a forcing function for personal growth.


3. Oh, you’re scared? Evaluate the risks of doing versus not doing.


4. We must retool education: for leading and solving interesting problems (see Seth Godin’s “Stop Stealing Dreams”)


5. Make work happen: create the conditions to increase the likelihood that you’ll put your butt in the seat.


6. “Creativity is dirty work…It demands discipline.”


7. Relying on inspiration alone will not get you anywhere.


8. The scripted life we grew up with is quickly withering away.


9. Worst advice Tony received: “Law degrees are great because you can do so many things with them.”


10. “The small man builds cages for everyone he knows, while the sage, who has to duck his head when the moon is low, keeps dropping keys all night long for the beautiful, rowdy prisoners.” —Hafez

***

RESOURCES

Connect w/ Tony on LinkedIn

In The Creative Arena (Tony's book)

Tony's entrepreneurial efforts

The War of Art (book mentioned)

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Oct 25, 202255:30
 57: The "Employee" Is Dead

57: The "Employee" Is Dead

“Employee” is an outdated concept. (Literally, a relic of the Industrial Age.) Learn how power is shifting from employer to employee, and how this completely changes your work and life options.

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

02:12 The old employment agreement

04:04 No one wants a job, they want a life

04:39 RIP employee, welcome Uncaged Pro

06:14 Keeping your job — on your terms

07:37 Stability of the 9-5 + Prosperity of entrepreneurship

09:48 Your 9-5 can just be a utility

10:07 Validate that you’re in a healthy workplace

10:53 Clarify the life you want

11:54 Define what “work” means to you

12:49 Shape your corporate role

14:11 Build your external brand & side hustle

16:38 Framework summary

17:01 Working for great companies? Alive. Employee? Dead.

***

RESOURCES

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Oct 18, 202217:55
56: Paige West - Millennial & Gen Z Workforces Collide

56: Paige West - Millennial & Gen Z Workforces Collide

Paige West went “national” in sharing her Quiet Quitting story on CNN, Good Morning America, and elsewhere. Here, we go behind the scenes on what fueled her decisions while also comparing and contrasting Millennial and Gen Z worldviews in the workplace. So good — enjoy!

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

03:51 Doing the “inner” work

08:05 Paige’s formative years

12:16 Friction when weighing professional paths

16:47 Indicators that corporate wasn’t a fit

19:03 Keeping life options open

21:47 Hitting a breaking point

23:38 Applying the Quiet Quitting strategy

26:34 Did anything bad happen?

29:40 Fake “pressures” at work

30:51 Millennial vs. Gen Z values at work

36:45 Power of vulnerability on the job

39:01 Benefits of the corporate journey

42:57 Rapid-fire questions

48:44 Identity is a choice, reinforced by tiny actions

51:24 Keys to uncaging yourself

***

TAKEAWAYS

1. Inner work is meant to get your inner and outer worlds to align.


2. Externalizing your thoughts sharpens and clarifies your thinking.


3. Learn from PAST regrets, ANTICIPATE future regrets, use that information NOW.


4. Be careful when corporate systems have rigid growth models — hard to be authentic.


5. Irony of Quiet Quitting for Paige: her reputation improved at work.


6. Ruthlessly protecting your time and being selective at work is good for you and your company.


7. Gen Z grew up in an era of publishing your emotions, and that’s showing up in corporate environments now.


8. Invest (in yourself) before you’re ready — time and money.

***

RESOURCES

Subscribe to Paige's YouTube channel

Follow Paige on Instagram

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Oct 11, 202253:33
55: Andy Storch - The Ownership Mindset

55: Andy Storch - The Ownership Mindset

When you take extreme ownership of your career and life, magical things happen. Remember, you care more about your life and career than anyone else. Author and speaker Andy Storch joins us for a masterclass on listening to your inner voice and taking full ownership of your career and life.

📬 Get the newsletter: Uncaged Secrets

🌐 Show website: UncageYourself.FM

***

TIMESTAMPS

02:35 Andy’s evolving definition of success

04:50 Dependency on external circumstances

08:10 Andy’s childhood & backstory

12:27 Entering the corporate world

16:29 Accelerators for self-transformation

20:08 Ownership mindset (being entrepreneurial)

21:27 Drifting

26:42 Modern view on professional development

31:18 “I don’t have time”

32:31 Personal brand = reputation

39:26 Andy’s cancer battle

45:05 It happened for me, not to me

49:40 Rapid fire questions

54:49 It’s on you: extreme ownership

***

TAKEAWAYS

  1. Minimize the “I’ll be happy when” mentality; cultivate inner joy.
  2. Take a lesson from Stoicism: focus on what you can control.
  3. On paper, your life might look good. But you might actually feel dead inside. Signal for radical self-transformation.
  4. Find coaches, mentors, and resources that help you see new possibilities and co-design a better future (tailored for you).
  5. Many people are drifting through life — being reactive and adopting external definitions of success. Better way: live an intentional life.
  6. Substantive change is atomic: it’s both small and highly targeted for long-term impact.
  7. Your personal brand is “what people think and say about you when you’re not in the room.”
  8. Clarify what you want your brand to stand for (e.g., kindness, generosity)
  9. Attitude when hitting a major roadblock: “This is what I get to deal with.”
  10. We go through our life challenges so we’re qualified to help others.

***

RESOURCES

Own Your Career Own Your Life (Andy’s book)

Andy’s Site

Connect w/ Andy on LinkedIn

Owning Your Journey with Cancer (free guide)

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Sep 27, 202257:19
54: Dennis Geelen - The Accidental Solopreneur

54: Dennis Geelen - The Accidental Solopreneur

You have gifts. But chances are, they're locked up inside of you. A 9-5 job only lets you unleash a fraction of those gifts. Dennis Geelen joins us to tell the story of The Accidental Solopreneur (his recent book). It's a fascinating look at unleashing your gifts and maximizing your potential.

Access the newsletter: Uncaged Secrets

Cohort course: Uncaged Academy

Show website: UncageYourself.FM

***

TIMESTAMPS

03:12 What Dennis misses about corporate

06:28 Re-thinking the scripted life

10:50 Investing in your highest-leverage asset

13:31 Dennis's entrepreneurial experiments

18:52 Going from non-fiction to fiction author

21:30 The Accidental Solopreneur

23:31 Emotions of the entrepreneurial rollercoaster

26:12 Importance of niching down

32:18 Advice for starting a career today

35:06 Closing Message

***

TAKEAWAYS

1. "The amount of learning I had to do to get that company off the ground is more than I learned in my 20 years of corporate." — Dennis Geelen


2. In solopreneurship, you must first master the inner game to then win the outer game. 


3. Nearly high-performer in corporate should try entrepreneurship (on the side at least). If you don't, you'll likely regret it. 


4. Don't expect instant success. Embrace the journey — it's amazing if you allow it to be.


5. Make your main goal about helping others. Goodness will flow your way if you do that.

***

RESOURCES

The Accidental Solopreneur (book)

Connect w/ Dennis on LinkedIn

Dennis's website

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Sep 20, 202237:46
53: Paul Millerd - Awakening From the Default Path

53: Paul Millerd - Awakening From the Default Path

Paul Millerd, author of The Pathless Path, joins me to talk about "default path" addiction and what it's like to awaken. As former management consultants, we dig hard into this arena too. Enjoy!


Access the newsletter: Uncaged Secrets

Cohort course: Uncaged Academy

Show website: UncageYourself.FM

***

TIMESTAMPS

03:12 The Great Contemplation

06:21 How Paul's book affected Matt

08:25 The process of Awakening

09:51 Pre-awakening (most people trapped here)

15:58 Addiction to Default Paths

19:03 Value of an early-career foothold

21:56 "There's a pebble in my shoe"

23:51 Higher stakes if you're a parent

27:10 Understanding life tradeoffs

28:28 The Pathless Path

31:21 Uncertainty as a feature

33:10 Testing boundaries at work

38:31 The great work of your life

41:15 Minimal risk in betting on yourself

44:21 Thoughtful re-entry into corporate life

51:20 Rapid-fire

57:53 What's your "work" story?

***

TAKEAWAYS

1. Great Resignation might actually be the Great Contemplation: a rejection of scripted life, healthier conversation about our identification as "workers," and a desire to take control of your life.  


2. Rule of thumb: most people you'll meet are asleep (80%), some are groggy (15%), and a few are truly awake (5%).


3. The Protestant Reformation triggered an "obsession" with work, which has taken global hold. 


4. Aim of life for people came to find work and then hold on tight to that path.


5. The Default Path feels addictive because the start is so thrilling. Eventually, we stop growing and become sleepy.


6. Instead of doing the work, you eventually find yourself doing performative work (pretending to be valuable).


7. Tough for parents to fake it at work while simultaneously encouraging your kids to blaze their own path.


8. We can't let sunk costs weigh us down. Your life season hugely impacts what you should say "yes" to next.


9. Not knowing what comes next might actually be a feature, not a bug.


10. "If there are clear boundaries [at work], there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges." —David Whyte


11. Great work of your life: continually find the great work of your life (Stephen Cope).


12. Know yourself: deliver targeted value inside your 9-5; push yourself for exponential growth in the outside world. 

***

RESOURCES

The Pathless Path (book)

Paul's newsletter, site, & podcast

Follow Paul on Twitter

Connect w/ Paul on LinkedIn 

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Sep 06, 202258:57
 52: The Impact of Quiet Quitting

52: The Impact of Quiet Quitting

"Quiet quitting" may same new and shocking, but it's an age-old concept. It's about setting your terms at work and prioritizing your desired lifestyle. In this episode, we cut through the noise and discuss practical scenarios for implementing this strategy.

Develop advanced-level "quiet quitting" skills in our cohort course: Uncaged Academy.

Access the newsletter: learn Uncaged Secrets

Show website: UncageYourself.FM

***

TIMESTAMPS

02:14 Framing

02:29 What Quiet Quitting is

03:41 The argument for it

06:59 The argument against it

09:46 Real-world scenarios

16:10 Healthy person → healthy worker

***

TAKEAWAYS

1. Quiet Quitting isn't about actually quitting or being lazy. We're not glamorizing mediocrity here.


2. At the core, it's about establishing boundaries at work, but you need a more comprehensive approach if you're going to create the life you want.


3. Not everyone wants to be an "elite athlete" at work, so we don't need to expect everyone to operate in an elite way. In contrast, choosing to be "average" at work can create capacity for spending time and energy on what excites you.


4. It generally makes sense to "go hard" early in your career to establish a foothold (resume, financial security, etc.). Once you're 10+ years in, you have much more leeway to back off and prioritize lifestyle.


5. Quiet Quitting (or whatever term you use) is another tool in your toolbox. Deploy it wisely as you methodically create more freedom in your life.

***

RESOURCES

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Aug 30, 202219:30
51: The Power of Regret

51: The Power of Regret

"No regrets." You've seen it tattooed on arms and in song lyrics. Enough — let's stop trying to suppress this natural human emotion. Instead, let's learn to harness it for our advantage in work and life. 

Apply the power of regret. See our cohort course: Uncaged Academy.

Show website: UncageYourself.FM

***

TIMESTAMPS

02:15 Framing

02:36 How we view regret

04:47 Types of regret

09:33 A strategy for using regret

12:24 How Matt uses regret to his advantage

***

TAKEAWAYS

1. Per the American Regret Study, 82% of adults experience regret — spanning a wide range of domains of life (family, career, education, finances, health, etc.).


2. Four types of regrets: Foundation, Boldness, Moral, and Connection.


3. Why regret matters: stability, growth, goodness, love.


4. Regret is a valuable emotion — it's telling you something. Learn to harness it.


5. Strategy for harnessing it: (1) Learn from PAST regrets, (2) anticipate FUTURE regrets, (3) apply that knowledge in the PRESENT.

***

RESOURCES

Book: The Power of Regret (Daniel Pink)

Top 5 Regrets of the Dying (Bronnie Ware)

Go deep: try the Uncaged Secrets newsletter

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Aug 23, 202214:54
 50: Introducing Uncaged Academy (Cohort-Based Course)

50: Introducing Uncaged Academy (Cohort-Based Course)

Think back to those one-way college lectures or those on-demand courses you've taken. Did you really transform as a person? No.

That's why I'm proud to introduce Uncaged Academy to you. It's an immersive, cohort-style approach to learning that focuses on community (friends), accountability, and rapid transformation. With our first cohort in the books, I'm excited to discuss the future of this unique program with you.

Make corporate work for YOU. Apply for our cohort course: Uncaged Academy.

Show website: UncageYourself.FM

***

TAKEAWAYS

1. The Education Technology (EdTech) realm is rapidly changing the modern learning experience.

2. You no longer need to give years of your life (or extreme amounts of money) to improve your mindset, skillset, or career trajectory.

3. Uncaged Academy helps you (a) design your 9-5 experience in a way that (b) unlocks the life you really want.

4. While still in corporate, you can create more freedom: Financial, Time, Purpose, Relationships, Health.

5. This course is for high-performing mid-career professionals who feel "stuck" and want something more out of their lives.

***

RESOURCES

Go deep: try the Uncaged Secrets newsletter

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Aug 16, 202210:20
49: [REPLAY] Should You Side Hustle?

49: [REPLAY] Should You Side Hustle?

The universe is speaking: start your side hustle. Everyone's doing it, right? Actually, let's pause and rethink that.

Not everyone should ignite this "parallel path" outside of their corporate career. Listen to this episode to help you understand if side-hustling is right for you.

Make corporate work for YOU. Apply for our cohort course: Uncaged Academy.

Show website: UncageYourself.FM

***

TAKEAWAYS

1. Know the difference between "investments" and "side hustles."

2. Side-hustling requires you to adopt a business owner mindset.

3. Following your passion isn't what makes a side hustle effective.

4. You'd better make sure it gives you energy.

5. Shifts in the global economy make side-hustling a "high upside, low downside" bet if you play the long game.

***

RESOURCES

Go deep: try the Uncaged Secrets newsletter

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Aug 09, 202215:17
 48: Timely vs. Timeless Skills

48: Timely vs. Timeless Skills

Look around and you'll see people chasing "in-demand" skills and credentials. It's like they're on a hamster wheel. But others seem calmer, in possession of enduring skills that always keep them ahead. This is the difference between Timely and Timeless skills. Which are you fixated on?

Make corporate work for YOU. Apply for our cohort course: Uncaged Academy.

Show website: UncageYourself.FM

***

TAKEAWAYS

1. Are you choosing to build skills that legitimately interest you? This matters if you want to maintain energy for decades.


2. Be clear on where the "crowd" is going. Go the opposite way.


3. Timely skills have a short shelf life (usually 2-4 years).


4. Timeless skills (e.g., psychology, persuasion, copywriting) endure no matter the time or context.


5. Build Timeless skills to ensure you're always ahead and relevant, even as our digital world rapidly changes.  

***

RESOURCES

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Live Uncaged: try the Wednesday Wisdom newsletter

Aug 02, 202208:33