You’ve worked hard, checked the boxes, and built a life that looks good on paper. But you still find yourself thinking, “Is this really it?” How do you figure out what’s missing—and what to do next?
In this episode, executive coach Rachel Barbaro joins us to unpack why achievement doesn’t always translate into fulfillment and how to get clearer on what you actually want. Rachel works with founders, CEOs, and senior leaders across banking, law, healthcare, and tech, helping them navigate burnout, career pivots, and the pressures of high achievement.
We explore how to distinguish a difficult season at work from a sign you want something different, why familiar unhappiness can feel safer than change, and how to recognize when you’re pursuing someone else’s definition of success.
We also talk about building a personal board of directors, creating more room for joy, and taking a next step when you have too many interests—or no idea where to begin.
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Follow Rachel here:
Linkedin: https://www.linkedin.com/in/rachelbarbaro/
Instagram: https://www.instagram.com/rachelbarbaro/
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Sponsors:
Thank you to Strawberry.me for sponsoring this episode. Visit strawberry.me/thefiveyearplan to get 50% off your first coaching session.
Want to partner with us? anna@thefiveyearplanpodcast.com
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The Five Year Plan
Instagram: https://www.instagram.com/thefiveyearplanpodcast/TikTok: https://www.tiktok.com/@thefiveyearplanpodcastNewsletter: https://substack.com/@thefiveyearplanEmail: anna@thefiveyearplanpodcast.com
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Timestamps:
00:00 Meet Rachel Barbaro
00:49 The Sunday Scaries
02:26 Ego Versus Intuition
03:37 Redefining Success
04:15 From Corner Office
07:11 Kids And True Self
09:56 When Goals Disappoint
11:54 Dip Or Sign
14:48 Six Month Check
17:46 Control In Toxic Jobs
22:24 Find Your Purpose
24:16 Purpose When Lost
27:13 Interview Them Too
28:36 Asking About Culture
29:15 Interview Recon Tips
30:38 Unhappiness vs Existential
32:43 Setting Conditions for Joy
34:59 Phone Boundaries Focus
38:22 Fear of Change Loop
42:32 Burnout Body Signals
47:11 Highest Leverage Priorities
49:09 Coach Me Rapid Fire
52:59 TFYP Question
