The Mindset Mentor with Rob Dial

Episode: 3 Pieces of Advice I’d Give My 20 Year Old Self

Date: October 31, 2025

Overview

In this episode, Rob Dial candidly shares the three pieces of advice he wishes he could give his 20-year-old self—insights that apply to anyone, regardless of age. Drawing from personal experience, years of coaching, and the wisdom of thought leaders, Rob urges listeners to examine what they’re chasing, intentionally design a life they love, and build unshakable confidence through action, not just mindset.

With his trademark directness and empathy, Rob explains why so many people wake up one day successful on the outside but feeling empty within, and delivers practical tools to break that cycle. This episode is a call to create a deeply satisfying, authentic life—starting now.

Key Discussion Points & Insights

1. Stop Chasing the Wrong Finish Line

• Timestamp: 03:25

• Rob reflects on his younger self’s obsession with making money, believing that financial achievement would fix all his problems.

  • Quote: “The only problems that money solves are money problems. Achievements of any kind...will not fix what's going on inside of you.” (04:10)

• Achievement-focused people tend to:

  • Move the goalpost as soon as they reach a goal (06:10)
  • Delay their peace, always thinking they’ll be happy “when they get there” (06:50)
  • Never celebrate wins, but quickly look to the next target (07:40)

• Personal example: Rob wrote his first book—a three-year effort—then barely acknowledged the accomplishment. His VP asked if he had celebrated himself:

  • Quote: “Have you ever celebrated yourself that you wrote your book? ...A lot of my friends have, like, two or three books. So I’m comparing myself to everybody else.” (08:10)

• Big Reframe:

  • “Real success is NOT about what you achieve. It’s about who you are and how you feel as you’re achieving those things.” (09:00)
  • Achieving is important, but only if you enjoy the journey and become a better person in the process.
  • Many people realize too late that they built lives to impress others, not themselves, leading to hollow success.

• Actionable takeaway:

  • Build a life that feels good on the inside, not just a life that looks good on Instagram. (12:20)

2. Design a Life You Don’t Want to Escape From

• Timestamp: 12:25

• Most of Rob’s successful clients are exhausted—not from overwork, but from striving toward a version of “success” they don’t want.

  • Many built lives to meet someone else’s expectations (parents, society, childhood dreams), ending up “stuck at the top of a ladder that was leaning against the wrong wall.” (13:45)

• Guidance:

  • “If I’m building this ladder, is this the wall that I want to find myself on the top of in 20 years?” (14:20)
  • Start with the end in mind—not income, not job title, not parental pride.

• Self-reflection prompts:

  • What kind of life do I want to wake up in?
  • What would I do for free? What energizes me without caffeine? (18:55)

• Rob’s story: He realized early in his entrepreneurial journey he didn’t want to be “the guy who makes money on Amazon,” but felt deeply pulled to coaching and helping people.

  • Quote: “If I fast forward five years, do I want to be known as the person who’s coaching and helping people in their lives? ...It was immediate—hell yes.” (20:10)

• Principle:

  • Do work that feels like play to you—even if it looks like work to everyone else.
  • “The man who loves to walk will go further over the course of his lifetime than the man who’s running toward a goal.” (21:35)
  • Design your days for a life you don’t need a vacation from; don’t just hustle for the weekend.

• Shortcuts to fulfillment:

  • Money follows passion—not the other way around. “Money should always come second. Passion should always come first.” (Attributed to Oprah, referenced at 19:55)
  • If you love it, you’ll work harder and longer than anyone else can.

3. Confidence Comes From Proof, Not Pep Talks

• Timestamp: 22:35

• Confidence isn’t gifted from reading motivational quotes or giving yourself pep talks—it comes from evidence stacked through actions.

  • Quote: “Confidence that you are looking for comes from proof, not from pep talks.” (22:40)
  • Example: Rob was a shy introvert, terrified of public speaking at 19. Repeated exposure (15,000 hours over five years) built his confidence through experience rather than willpower or belief alone. (26:10)

• Rob’s ‘Jenga block’ analogy:

  • Every time you do what you say you’ll do, you add a “confidence block.”
  • Every time you flake out or break your promise, you remove a block. (23:40)
  • “I must win more than I lose. If I do that, I will start to build more confidence in myself.” (24:20)
  • Confidence is not a feeling; it’s a pattern reinforced by daily action.

• Practical strategy:

  • Shrink big goals into tiny tasks you can finish today.
  • Celebrate showing up and doing the work, not just the outcomes.
  • “Proof of you doing what needs to be done is what builds trust within yourself, and trust builds courage. Then your courage is what builds your confidence.” (27:10)
  • “Stop trying to think your way into confidence and start acting your way into confidence.” (28:30)

Memorable Quotes & Moments

• “Your goals are like the horizon—every time you get closer to them, they get further away.” (06:10)
• “Are we just going to keep going for the next thing and the next thing...Is the reason we were put on this planet just to chase some random goals until we die? What a hollow existence if you really think about it.” (10:30)
• “Design your days like someone who wants to stay in them.” (21:25)
• “Most people wait to feel ready, but readiness is a byproduct of putting in the reps, not the requirement for them.” (25:55)

Action Prompts and Takeaways

• The Big Question: “What do you want?” Rob finds most people can’t answer this, which is why they chase the wrong goals.

  • Figure this out and it gets easier to:
    • Not chase the wrong things (Lesson 1)
    • Design a life you love (Lesson 2)
    • Take action and build confidence (Lesson 3) (29:10)

• Celebrate process and self-trust, not just end results.

Structured Overview by Section with Timestamps

• [03:25] – Stop Chasing the Wrong Finish Line: Money and achievement don’t solve internal dissatisfaction; real success is internal.
• [12:25] – Design a Life You Don’t Want to Escape From: Choose your “wall” and start with the end in mind; success is most sustainable when built on authentic passion.
• [22:35] – Confidence Comes From Proof: Build confidence by doing, by stacking small wins, not by waiting to “feel ready.”
• [28:30] – Final Wrap-Up: The importance of asking “What do I want?” and building your daily practices to align with that vision.

Episode Tone

Rob's tone is relatable, candid, and motivating—often using blunt language and storytelling to drive home his points. He mixes personal anecdotes, simple analogies, and actionable advice to ensure listeners feel both challenged and supported.

For Listeners Who Missed the Episode

This episode isn’t just for twenty-somethings. Rob’s distilled wisdom is for anyone who feels they’re chasing the wrong finish line or feels success should feel better than it does. His actionable advice will help you redefine what you’re pursuing, intentionally craft your days, and build real confidence—one action at a time.

Listen to more at: rob’s Instagram or coachwithrob.com