Knowing your worth is easy to say but can be hard to live.

In this episode of Leading Ain’t Easy, Ryan and Erny unpack what it really means to understand your value as a leader; beyond titles, money, or years of service. From imposter syndrome and loyalty traps to quitting without a backup plan, they explore how self-worth quietly erodes when effort isn’t recognized and support disappears at the top.

This is an honest conversation about:

• When loyalty turns into self-sacrifice
• Why “prove yourself first” can cost you years of progress
• The difference between confidence, entitlement, and arrogance
• How leaders can objectively evaluate their worth using feedback, results, and integrity
• Why settling eventually leads to burnout (even when you don’t see it coming)

If you’ve ever stayed too long, taken less than you deserved, or waited for permission to be valued… this episode is for you.

Episode Chapters / Timestamps

00:50 — Intro: Know Your Worth (not titles or money)
01:33 — Erny’s story: stuck in a broken system + glass ceiling
02:10 — When effort isn’t valued at the top
04:54 — “They were chanting my name” 
06:55 — The “donuts” moment: realizing support isn’t coming
08:51 — Walking away without another job lined up
10:22 — Worth vs perception: when others define your value
12:10 — Ryan: undervaluing yourself and the loyalty trap
14:59 — “You’re not the only idiot”: taking less pay to prove yourself
18:21 — Guilt, loyalty, and why companies won’t match it
19:54 — Negotiating up front vs earning your place
21:00 — A brutal interview failure and learning to sell yourself
24:18 — Turning failure into a long-term strength
25:29 — Advocating for yourself while staying team-oriented
28:13 — The hidden cost of settling
29:22 — Overvaluing yourself: arrogance vs entitlement
30:33 — Confidence vs arrogance (where it crosses the line)
32:23 — Slowing down and leading with data
34:30 — Measuring worth: metrics + intangibles
40:29 — How to actually gauge self-worth
41:00 — Ryan’s reflection framework
44:43 — Erny’s feedback-driven approach
49:21 — Key takeaway: Worth is earned through integrity
49:42 — Standing up for yourself without burning bridges
50:46 — Listener reflection question
51:16 — Closing

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

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