Show Notes
Why do so many successful women still feel like they're falling behind—even after achieving the career milestones they once dreamed of? Executive coach and former Google leader Brooke Taylor explains the hidden "Success Wound" that keeps high achievers chasing the next accomplishment without ever feeling like it's enough. Learn how to break free from the cycle of burnout, perfectionism, and self-doubt while pursuing ambition that actually feels fulfilling. You'll learn: Why burnout, perfectionism, and imposter syndrome may be symptoms—not the real problem. The five types of "Unfulfilled Achievers" and how to identify your own patterns. How to cultivate "aligned ambition" so you can pursue big goals without tying your self-worth to your achievements.
Show Notes Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW
Guest Resources: Brooke Taylor LinkedIn: https://www.linkedin.com/in/brooketaylor-coach/ Book: https://www.hachettebookgroup.com/titles/brooke-taylor/healing-the-success-wound/9780306836107/?lens=balance Website: https://brooketaylorcoaching.com/
Career Contessa Resources Book 1:1 career coaching session: https://www.careercontessa.com/hire-a-mentor/ Take an online course: https://www.careercontessa.com/education/ Get your personalized salary report: https://www.careercontessa.com/the-salary-project/
Sponsors Reset your kitchen on a budget. Bundle and save up to $230 on the 12 piece cookware set vs buying the products individually. Explore more set savings on bakeware, food storage, accessories and more. Visit Carawayhome.com/CONTESSA to take an additional 10% off your next purchase. This deal is exclusive for our listeners, so visit Carawayhome.com/CONTESSA or use code CONTESSA at checkout. Download Cash App Today: https://click.cash.app/ui6m/f010o9zo #CashAppPod Cash App is a financial services platform, not a bank. Banking services provided by Cash App's bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card at cash.app/legal/us/en-us/card-agreement, for the Sutton debit flex card at cash.app/legal/us/en-us/debit-flex-card-agreement-sutton and for the Bancorp debit flex card at cash.app/legal/us/en-us/debit-flex-card-agreement-bancorp. Savings and Offers provided by Cash App, a Block Inc. brand. Offers may not be affiliated with third party merchants. Parents and legal guardians can open a managed account for kids 6-12. Cash App will pass through a portion of the interest paid on your savings balance held in an account for the benefit of Cash App customers at Wells Fargo Bank, N.A., Member FDIC. To earn interest on your Cash App savings balance, you need to have sponsor approval. Exceptions may apply. Savings yield rate is subject to change. Visit cash.app/legal/podcast for full disclosures. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
More from Career Contessa
Think you need more discipline to reach your goals? Jia Jiang, bestselling author of Rejection Proof and Easy Discipline, explains why relying on willpower and working harder often backfires—and what to do instead. You’ll learn: Why traditional discipline doesn’t work for most people How enjoyment can make ambitious goals easier to sustain How to redesign your habits so progress requires less willpower
A bad manager can undermine your confidence, hurt your performance, and even derail your career. But what if quitting isn’t an option? Career coach and author Cathy Alfandre shares how to recognize a damaging manager, protect yourself while you stay, and create a strategic exit plan. Plus, learn how to spot red flags during the interview process so you don’t end up with another bad boss. You’ll learn: How to tell the difference between a demanding manager and a damaging one How to protect your confidence and career when you can’t quit How to spot manager red flags before accepting your next job
Landing a job in today's market takes more than submitting applications and hoping for the best. Recruiter, career coach, and content creator Emily Durham ("Emily the Recruiter") shares what hiring managers are actually looking for in 2026, the biggest mistakes candidates make, and the practical strategies that lead to more interviews and better offers. If you're job searching, considering a career pivot, or simply want to stay competitive, this episode is packed with actionable advice. You'll learn: What recruiters actually look for first on your resume, LinkedIn profile, and application. How to network, interview, and negotiate salary with confidence in today's hiring market. The three actions to take this week if you want to land a new job within the next 90 days.
Feeling the pressure to make a big career move before the year ends? You're not alone. In this episode, licensed clinical psychologist Anne Josephson explains why ambitious professionals often mistake burnout for clarity during the "Fall Crunch"—and shares practical, evidence-based strategies to manage anxiety, quiet overthinking, and make career decisions with confidence instead of urgency. You'll learn: How to tell the difference between burnout-driven impulsivity and a genuine desire for career change. Why tying your self-worth to productivity fuels anxiety—and how to break the cycle. Practical CBT and DBT techniques to reduce overwhelm, improve focus, and feel more grounded during high-pressure seasons.
Feel busy all day but still behind? It’s not your time—it’s your mental overload. In this episode, Lauren talks with Liane Davey, author of Thoughtload, about how to reduce overwhelm and work more effectively. You’ll learn: Why being busy doesn’t equal being productive How to protect your focus and reduce distractions One simple shift to get more done this week