Career Contessa

By Career ContessaBusiness Careers

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Typical duration
35 min
per episode

Based on Podcast App listening data

Career Contessa episodes

November 037 Workplace Conversations That Can Make or Break Your Career
The conversations you avoid at work could be holding your career back. Harvard Business School faculty member and Unspeakable author Christina Wing shares how to navigate seven of the toughest workplace conversations—from asking for more to owning mistakes and talking about money.
You’ll learn:
How to ask for a raise, promotion, or more responsibility with confidence
What to say when discussing mistakes, job security, and personal challenges at work
Simple scripts to make difficult conversations less awkward and more productive

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Book: https://www.christinawing.com/book/
LinkedIn: https://www.linkedin.com/in/christina-r-wing/
Website: https://www.christinawing.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:
Head to vitaclean.co and use code CONTESSA for 20% off your Shower Head Starter Kit. That's code CONTESSA for 20% off at vitaclean.co.
Head to https://cozyearth.com and use my code CONTESSA for 35% off home and sleepwear through December 3rd.
If you’re ready to launch your business before Black Friday, go to shopify.com/careercontessa to start your free trial.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
35 min
October 27Why Simplicity Is Your Biggest Career Advantage in the AI Age
AI was supposed to make work easier—so why are we busier than ever? Lauren talks with Axios co-founder Roy Schwartz about why simplicity is becoming a career advantage and how to cut through the noise to focus on what actually matters.
You’ll learn:
How to identify and eliminate “toxic complexity” at work
How to use AI without creating more work and noise
A simple framework for doing more by doing less

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
LinkedIn: https://www.linkedin.com/in/royschwartz/
Book: https://www.penguinrandomhouse.com/books/813390/simplify-by-jim-vandehei-mike-allen-and-roy-schwartz/
Website: https://smartbrevity.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:
Use code CONTESSA at jonesroadbeauty.com to get a Free Gift with your first purchase! #JonesRoadBeauty #ad
Timeline is offering a 15-day trial of the Mitopure Resurfacing Exfoliator for just $22. Give it 15 days and see how your skin looks and feels. Go to Timeline.com/CONTESSA to try it for $22.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
33 min
October 20Why Discipline Doesn't Work for Most People
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

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Newsletter: https://blog.jiajiang.com/
Website: https://www.jiajiang.com/
Book: https://www.jiajiang.com/easydiscipline

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
Unlock your best hair & skin with @iRestorelaser and HUGE savings on iRESTORE with code CONTESSA at irestore.com/CONTESSA! #irestorepod
Shop now at Fabletics.com/CONTESSA to get 70–80% off everything when you sign up as a new VIP.
Nuuly is a great value at $98 a month, but right now you can get $28 off your first month when you sign up with code CONTESSA.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
33 min
October 13How to Protect Your Career from a Bad Manager
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

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Website: https://cathyalfandre.com/
Book: https://cathyalfandre.com/my-book/
LinkedIn: linkedin.com/in/cathyalfandre

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:
You can try Granola totally free—head to granola.ai/CONTESSA.
Save 20% Off Honeylove by going to honeylove.com/CONTESSA! #honeylovepod
Open a Found account at found.com. Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. Found does not provide legal or tax advice.
If you’re ready to launch your business before Black Friday, go to SHOPIFY.COM/careercontessa to start your free trial.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
42 min
October 06How High-Achieving Women Heal Their "Success Wound"
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.
36 min
September 29What Recruiters Know That Job Seekers Don't
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.

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Instagram: https://www.instagram.com/emily.the.recruiter/?hl=en
TikTok: https://www.tiktok.com/@emily.the.recruiter
Book: https://www.amazon.com/dp/B0FQTM8RQR?lv=shuf&redirect=true&tag=randohouseinc47720-20&channelId=1&plpRedirect=mhFallback
Podcast: https://pod.link/1505520809?fbclid=PAAaaxnLRkpCu19e-HFhhvwjmTjzZkHMXRsFhpw_1zChmw5dM144xiv-_OeXU
Newsletter: https://mailchi.mp/d58604ea1659/newsletter

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:
Granola is an AI-powered notepad that makes your meeting notes useful. You can try it totally free—head to granola.ai/CONTESSA.
Nuuly is a subscription clothing rental service that lets you pick 6 styles for just $98/month. Right now you can get $28 off your first month when you sign up with code CONTESSA.
Shopify handles all facets of business so that you don’t have to use 10 different systems. Start your free trial at shopify.com/careercontessa.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
36 min
September 22The "Fall Crunch": Why High Achievers Feel So Stuck This Time of Year
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.

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
https://uptownpsychologyny.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:
Machine Washable Rugs, Made Better. For a limited time only, our listeners get 10% off + free shipping at tumbleliving.com/CONTESSA #Tumble #ad
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.
Take back control of your business today. Open a Found account for FREE at Found.com Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
31 min
September 15Your Thoughtload Is Sabotaging Your Focus: 3 Ways to Reset
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

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
https://lianedavey.com/books/thoughtload/

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:
Go to granola.ai/CONTESSA and try Granola on your next call.
Ready to make it part of your routine? Go to Timeline.com/CONTESSA20 to shop the full-size Timeline Mitopure Resurfacing Exfoliator and save up to 20%
Thanks to today’s sponsor, Ogee: A higher standard for beauty. Go to ogee.com/CONTESSA and use code CONTESSA to get 20% off certified organic makeup that performs like luxury. Or visit Sephora.com, search Ogee, and shop the Crystal Contour Collection today.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
35 min
September 08The Career Reset No One Talks About After 40
Your 40s are supposed to feel like you’ve “made it.” So why does it often feel like a reset?
In this episode, Lauren talks with Stacey Lindsay, author of Being 40, about why midlife can spark a major career shift—and how to navigate it with clarity and confidence.
You’ll learn:
Why your 40s can trigger a career reset
How to know when it’s time to pivot
What success can look like next

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
https://www.amazon.com/Being-40-Letting-Go-Embracing/dp/0593831195
https://www.staceylindsay.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:
Head to Superpower.com and use code CONTESSA at checkout for $20 off your membership. Get 100+ biomarkers tested every year, plus a personalized health plan and on-demand care team. Detect early signs of 1,000+ conditions. #superpowerpod
Unlock your best hair & skin with @iRestorelaser and HUGE savings on iRESTORE with code CONTESSA at irestore.com/CONTESSA! #irestorepod
Save 20% Off Honeylove by going to honeylove.com/CONTESSA! #honeylovepod
Start your free trial at shopify.com/careercontessa.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
40 min
September 01Why “Just Learn AI” Is Bad Advice (And What to Do Instead)
AI is everywhere right now—and so is the pressure to “figure it out.” If you’ve been feeling overwhelmed or behind, you’re not alone. In this episode, Lauren sits down with Jill Ozovek to unpack what’s really driving AI anxiety—especially for knowledge workers—and why it’s less about technology and more about identity. They break down the biggest misconceptions about “learning AI,” and how to start experimenting in a way that actually feels manageable.
You’ll learn:
Why AI anxiety is really about identity—not just new technology
The difference between using AI vs. building AI (and why it matters)
Simple, realistic ways to start using AI without feeling overwhelmed

Show Notes
Weekly Newsletter Sign-Up: http://bit.ly/37hqtQW

Guest Resources:
Website: www.mvpclub.ai
Join the community: https://mvp-club.mn.co/

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:
Use code CONTESSA at oakessentials.com to get 15% off your first purchase! #OakEssentials #ad
Visit Carawayhome.com/CONTESSA to take an additional 10% off your next purchase
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
33 min

About Career Contessa

From the publisher's feed

Shortcut your path to being more successful at work. This show helps you figure out what you truly want, land a job, make more money, advance your career, and improve your work life with actionable insights from experts that boost work performance.