Listen " 36: My Journey in Leaving Corporate"
Episode Synopsis
This is a personal and emotional episode. In the months leading up to quitting corporate in March 2022, I recorded my thoughts and feelings. This episode is a compilation of those recordings — a personal journal, if you will.
I discuss why I needed to make the leap, including the strategy and mindset that made it possible. I hope it helps you identify the “leaps” worth making in your life.
Ready to take ownership of your career and life? I’ve got something next-level for you: the Uncaged Academy.
***
TIMESTAMPS
01:35 90 DAYS out from resignation
05:58 60 DAYS out from resignation
09:14 People stuck in their Matrix
11:20 Leaving corporate as a forcing function for growth
13:55 Anticipation (visualization) of Freedom Day
14:38 30 DAYS out from resignation
15:48 Readying to lose my “guaranteed” paycheck
19:01 Feeling “alive” as I’ve cultivated my passion
21:20 7 DAYS out from resignation
24:16 Default Path vs. Pathless Path (Paul Millerd)
26:33 Resignation (Freedom) day
28:02 I resigned from corporate!
***
TAKEAWAYS
1. After life fell apart for me, I took control of my corporate situation over recent years and found ways to operate on my own terms.
2. Soon, I was helping others do the same, and I discovered the seeds of a new entrepreneurial business.
3. COVID allowed me to experiment and lay the groundwork for a post-corporate life.
4. Personally, I eventually felt it wasn’t risky to leave corporate. It was riskier to stay — living a “small” life, being undiversified, denying my burning inner purpose.
5. I realized I could model out my net worth, free time, etc. in corporate for decades ahead. That “cap” scared me. I’d rather have uncapped potential.
6. Imposterism (imposter syndrome) took hold early on as I contemplated entrepreneurial life. I had to train my mind to welcome the shift as a worthy fear.
7. Leaving the corporate “safety net” became a forcing function for me to become who I’m capable of being.
8. I had to get comfortable with not having a rigid plan or “ideal results” before taking the leap.
9. I worked with my coach to execute a strategic, well-planned exit from corporate. I wasn’t going to leave my family (including wife and 4 kids) in a tough situation.
10. With massive moves in life (e.g., buying a house, having a kid, starting a business), the timing just has to be “good enough.” It’ll never be perfect. Trust yourself.
***
RESOURCES
Join the Uncaged Academy (cohort-based course)
Subscribe to the Wednesday Wisdom newsletter
Connect w/ Matt on LinkedIn
Follow on Twitter @MatthewRDoan
Check the show on YouTube
Related episodes: Self-Reliance (#17), Imposter Syndrome (#30)
I discuss why I needed to make the leap, including the strategy and mindset that made it possible. I hope it helps you identify the “leaps” worth making in your life.
Ready to take ownership of your career and life? I’ve got something next-level for you: the Uncaged Academy.
***
TIMESTAMPS
01:35 90 DAYS out from resignation
05:58 60 DAYS out from resignation
09:14 People stuck in their Matrix
11:20 Leaving corporate as a forcing function for growth
13:55 Anticipation (visualization) of Freedom Day
14:38 30 DAYS out from resignation
15:48 Readying to lose my “guaranteed” paycheck
19:01 Feeling “alive” as I’ve cultivated my passion
21:20 7 DAYS out from resignation
24:16 Default Path vs. Pathless Path (Paul Millerd)
26:33 Resignation (Freedom) day
28:02 I resigned from corporate!
***
TAKEAWAYS
1. After life fell apart for me, I took control of my corporate situation over recent years and found ways to operate on my own terms.
2. Soon, I was helping others do the same, and I discovered the seeds of a new entrepreneurial business.
3. COVID allowed me to experiment and lay the groundwork for a post-corporate life.
4. Personally, I eventually felt it wasn’t risky to leave corporate. It was riskier to stay — living a “small” life, being undiversified, denying my burning inner purpose.
5. I realized I could model out my net worth, free time, etc. in corporate for decades ahead. That “cap” scared me. I’d rather have uncapped potential.
6. Imposterism (imposter syndrome) took hold early on as I contemplated entrepreneurial life. I had to train my mind to welcome the shift as a worthy fear.
7. Leaving the corporate “safety net” became a forcing function for me to become who I’m capable of being.
8. I had to get comfortable with not having a rigid plan or “ideal results” before taking the leap.
9. I worked with my coach to execute a strategic, well-planned exit from corporate. I wasn’t going to leave my family (including wife and 4 kids) in a tough situation.
10. With massive moves in life (e.g., buying a house, having a kid, starting a business), the timing just has to be “good enough.” It’ll never be perfect. Trust yourself.
***
RESOURCES
Join the Uncaged Academy (cohort-based course)
Subscribe to the Wednesday Wisdom newsletter
Connect w/ Matt on LinkedIn
Follow on Twitter @MatthewRDoan
Check the show on YouTube
Related episodes: Self-Reliance (#17), Imposter Syndrome (#30)
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169: “Founders” Don’t Wait for Permission
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168: Watch Your Game Film
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167: Skepticism Isn’t Wisdom. It’s Fear.
04/11/2025
164: Futureproof Yourself
30/09/2025
163: Love Your Work. Or Pay the Price.
16/09/2025
162: It Gets Late Fast
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