Ep 59: What to Do When You've Done Everything Right But Still Feel Off with Malaika Smyth

About this episode

You did everything right. The school, the job, the hustle. You followed the path, and you're good at it! So why does it still feel like something's missing?

This week, Tess sits down with Malaika Smyth, a coach for high achievers who have checked every box and still find themselves asking a surprisingly hard question: what do I actually want for myself?

Malaika brings a rare combination of experience as a Division I athlete background, nearly eight years scaling coaching operations at BetterUp from 50 to over 3,500 coaches, and her own winding path through quarter-life crisis, identity shifts, and a gift box business detour. She helps people build success that actually feels like theirs.

This conversation goes deep on the psychology of high achievement, what Silicon Valley's performance culture does to young people, and why so many accomplished professionals have never once stopped to ask what they actually want.

In this episode:

• Why high achievers often tie their entire self-worth to how hard they work
• The Silicon Valley "duck effect" — calm on the surface, paddling furiously underneath
• What a Gen Z employee taught Malaika about a kind of career maturity she'd never seen before
• Why age doesn't automatically equal wisdom — and what actually does
• The sunk cost trap that keeps high achievers stuck on the wrong path
• What every client ultimately wants at their core (it's always the same thing)
• The 75-year-old exercise that cuts through all the noise and gets to what actually matters
• Where AI fits in the future of coaching — and where it absolutely doesn't

To connect with Malaika Smyth, visit malaikasmyth.com or find her on LinkedIn.

CHAPTER TIMESTAMPS

00:00 — Welcome & Malaika Smyth introduction

01:20 — When Malaika first questioned whether being a high achiever was actually working for her

02:43 — Where the drive came from — internal wiring or outside pressure?

04:10 — Growing up in Silicon Valley: the unspoken assumption that you had to do something "big"

07:00 — The duck metaphor: calm on the surface, paddling furiously underneath

08:40 — College as non-negotiable — and how environment sets a path without anyone saying a word

09:50 — Graduating in 2014: a Bay Area overflowing with opportunity and equity dreams

11:00 — Following her brother into product management — and realizing it wasn't right

11:40 — Quarter-life crisis at year two: the moment she knew something had to change

12:40 — Designing Your Life — the book that opened a new door

13:50 — Joining BetterUp and discovering what coaching actually was

14:55 — The question Malaika asks clients who are rewarded for hustle

16:00 — "My only value is that I work hard" — and why coaching helped her see beyond it

17:00 — The decision to leave BetterUp and what came next

18:30 — The gift box business detour — and the important lesson it taught

20:25 — The sunk cost trap: why people stay on the wrong path long after they know better

23:40 — Selling yourself vs. selling a product: the vulnerability of a coaching business

24:35 — "I don't really care if you work with me. I care that you work on yourself."

28:45 — The power of silence — and celebration — in a coaching session

32:00 — Learning to trust your instincts and why being wrong can still be useful

37:30 — What every client ultimately wants at their core

39:50 — Managing both younger and older employees at BetterUp

41:10 — The Gen Z employee who floored Malaika with an unexpected kind of maturity

43:00 — Age does not equal wisdom — a lesson that changed how Malaika leads

46:45 — "I've been talking to ChatGPT all morning and I need to talk to a human"

48:00 — Tess on AI: the real hope, the real fear, and what's actually at stake

54:15 — The first question to ask when you've done everything right and it still feels off

55:00 — The 75-year-old exercise: what do you want your life to have been about?

57:00 — How to connect with Malaika + closing thoughts

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