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Podcast Episode

The Millennial Career Crisis: We Were Promised a Very Different Life

Two Girls, One Haircut··17 August 2026·43 min

About this episode

Have you ever looked at your career, your bank account, your student loans, and the price of a house and thought, “Wait… wasn’t this supposed to get easier?” Yeah... us too. This week, Jessie and Kiki are diving into the Millennial Career Crisis—and quickly realizing it might actually just be the Great Millennial Everything Crisis. We were told there was a formula: go to college, work hard, climb the corporate ladder, stay loyal to your employer, buy a house, build a career, and eventually you’d arrive at this magical place called “success.”Except somewhere between 9/11, the Great Recession, crushing student loan debt, a global pandemic, skyrocketing housing costs, stagnant wages, burnout, and now AI threatening to completely reshape the job market... somebody apparently changed the formula. Jessie and Kiki come at the conversation from two completely different sides: Jessie has spent her career climbing the traditional professional ladder, while Kiki has spent years running her own creative business. And somehow, they’ve both ended up asking versions of the exact same question: Is this really what work is supposed to feel like? In this episode:The Millennial Career Crisis and career burnoutWhy the career roadmap we were given stopped workingCorporate careers vs. owning your own businessStudent loans, housing costs, and financial insecurityWhy hard work and company loyalty don't guarantee successWork-life boundaries and actually taking your days offGoing back to school in your 30s and 40sAI, automation, and the future of workUniversal basic incomeSeparating your identity from your jobWhat “success” actually looks like as you get olderAnd, somehow... robot gynecologistsWhether you’re burned out, underpaid, questioning your career, fantasizing about quitting your job, trying to turn your side hustle into something bigger, or simply wondering why adulthood looks absolutely nothing like what we were promised—this episode is for you. Maybe the crisis isn’t that we failed at the plan. Maybe the plan stopped making sense. New episodes every Wednesday with Behind the Pod every Friday!The conversation doesn’t stop here! Head over to our website for show notes, bonus content, recommendations, and all the links from today’s episode. Then join our growing community on social media @TwoGirlsOneHaircut for even more laughs, hot takes, and behind-the-scenes chaos.