Feeling Behind in Your 20s? The Pressure to Have It All Figured Out episode artwork

EPISODE · Apr 14, 2026 · 19 MIN

Feeling Behind in Your 20s? The Pressure to Have It All Figured Out

from Doing It Anyway · host Jess Hugo

Ever feel like you’re behind in your 20s… even when you’re actually doing pretty well?In this episode of Doing It Anyway, I’m having a real, unfiltered life update chat about the pressure to have your life figured out, and why it feels like everyone else is moving faster than you. We’re talking societal timelines, hustle culture, social media comparison, and how we’ve gone from one “expected path” to feeling like we need to do everything at once.I also share a recent client story that perfectly highlights how quickly we move the goalpost, going from achieving something huge straight into “okay… but what’s next?” energy. If you’ve ever struggled to actually stay in a good season without feeling like you should be doing more, this one will hit.This episode dives into:why you feel behind in your 20s (even when you’re not)the pressure of having your life figured outhow social media fuels comparison and timeline anxietythe impact of hustle culture on your mindsetlearning to stop rushing your life and actually enjoy where you areIf you’ve been feeling overwhelmed, stuck in comparison, or like you’re constantly chasing the next thing, this is your reminder that you’re allowed to slow down and build a life you actually enjoy living.You’re not behind. You’re just being exposed to everything at once.Connect with me:Instagram: https://www.instagram.com/itsjesshugo/Links

Ever feel like you’re behind in your 20s… even when you’re actually doing pretty well?In this episode of Doing It Anyway, I’m having a real, unfiltered life update chat about the pressure to have your life figured out, and why it feels like everyone else is moving faster than you. We’re talking societal timelines, hustle culture, social media comparison, and how we’ve gone from one “expected path” to feeling like we need to do everything at once.I also share a recent client story that perfectly highlights how quickly we move the goalpost, going from achieving something huge straight into “okay… but what’s next?” energy. If you’ve ever struggled to actually stay in a good season without feeling like you should be doing more, this one will hit.This episode dives into:why you feel behind in your 20s (even when you’re not)the pressure of having your life figured outhow social media fuels comparison and timeline anxietythe impact of hustle culture on your mindsetlearning to stop rushing your life and actually enjoy where you areIf you’ve been feeling overwhelmed, stuck in comparison, or like you’re constantly chasing the next thing, this is your reminder that you’re allowed to slow down and build a life you actually enjoy living.You’re not behind. You’re just being exposed to everything at once.Connect with me:Instagram: https://www.instagram.com/itsjesshugo/Links

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Feeling Behind in Your 20s? The Pressure to Have It All Figured Out

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This episode was published on April 14, 2026.

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Ever feel like you’re behind in your 20s… even when you’re actually doing pretty well?In this episode of Doing It Anyway, I’m having a real, unfiltered life update chat about the pressure to have your life figured out, and why it feels like everyone...

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