The Learn-It-All Podcast 166: 12 Brutal Truths I Wish I Knew In My 20s | Damon Lembi
In this solo episode, Learnit CEO and bestselling author Damon Lembi shares 12 powerful truths he’s learned over the years that he wishes someone had told him in his 20s.
From managing money and making bold career moves, to saying no, navigating failure, and redefining your identity, Damon gets real about the missteps and wake-up calls that shaped who he is today.
In this episode, you’ll learn:
- Why time—not money—is your most valuable asset
- How to stop making decisions you’ll regret
- A 5-part plan to take control of your finances (without needing to be a CPA)
- What most people get wrong about failure
- How to know when it’s time to quit the job, relationship, or habit
- Why your job title isn’t your identity—and what matters more
- A mindset shift that makes confidence inevitable
- The secret to avoiding burnout (especially if you're a top performer)
- How living abroad can completely change the way you lead
Timestamps:
00:35 – #1: Time is the only asset you can’t get back
02:00 – Why you need to be intentional about your relationships
03:00 – Are you overworking or failing to delegate?
04:00 – #2: Money management tips Damon wishes he learned earlier
06:00 – #3: Stop making emotional decisions—use “purposeful awfulizing”
07:30 – #4: Get comfortable with failure (and why not trying is the real risk)
08:10 – #5: Don’t stay stuck—recognize the sunk cost fallacy
09:00 – #6: Life isn’t linear—adaptability is the superpower
10:30 – #7: Take action—confidence comes from reps, not perfection
11:45 – #8: Learn to say no—and avoid the “VIP curse”
13:00 – #9: Don’t avoid tough conversations (especially as a leader)
14:30 – #10: Your identity isn’t what you do—it’s who you are
15:40 – #11: You’ll regret the chances you didn’t take
16:50 – #12: Travel, live abroad, and widen your worldview
17:55 – Damon’s challenge to listeners: Pick one, apply it this week
About Damon Lembi:
Damon Lembi is a 2x bestselling author, the host of The Learn-It-All Podcast, and CEO of Learnit – a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.
Resources & Mentions:
Damon’s book: The Learn-It-All Leader: https://www.amazon.com/dp/B0BZXKR784?ref_=cm_sw_r_ffobk_cp_ud_dp_4NRSE6WY9TWPASVJZ2H2
Gary Ridge’s book: Any Dumb Ass Can Do It: https://a.co/d/hTV9gD0
Erin Lewellen and Tilting Futures: https://www.tiltingfutures.org: https://tiltingfutures.org
Connect With Us:
Uplevel yourself and your team with our trainings: www.learnit.com
Email us: podcast@learnit.com
Follow Damon on LinkedIn: https://www.linkedin.com/in/damonlembi/
Follow Damon on Instagram: https://www.instagram.com/damonlembi/