"On The Internet, Everyone Looks Rich" with Jenny Blake episode artwork

EPISODE · Jul 21, 2026 · 1H

"On The Internet, Everyone Looks Rich" with Jenny Blake

from The Anxious Achiever · host Morra Aarons-Mele

What happens when the strategies that always worked for you suddenly stop working? How do you keep believing in yourself when success no longer feels certain? In this episode, I sit down with entrepreneur and author Jenny Blake to talk about financial uncertainty, career setbacks, and the emotional toll of building a business. Jenny shares what it was like to lose major clients, question long-held beliefs about success, navigate the "flop era" of entrepreneurship, and find new meaning through creativity instead of certainty. Tune in to discover how to navigate uncertainty with more self-compassion, patience, and purpose. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 Why everyone looks rich on the internet, even when they're not. 04:15 What if your career doesn't go according to plan? 09:15 How Jenny Blake built a successful business after leaving Google. 13:15 What happens when your biggest source of income suddenly disappears? 18:45 How do you recover after a major career setback? 20:45 How to separate your self-worth from your achievements. 24:15 Can your body tell you when you're on the wrong path? 28:45 What Bell's palsy taught Jenny about burnout and self-care. 31:00 How atypical achievers can build careers that work for them. 35:15 How permission slips can help you navigate difficult seasons. 40:45 Would you still do it if it failed? 44:00 Is it okay if your greatest success is already behind you? 47:30 Why letting go of your old identity helps you move forward. 52:00 What permission do you need to give yourself right now? Resources + Links Learn more about Jenny Blake HERE Get your copy of Jenny's book, Pivot HERE Get your copy of Jenny's book, Free Time HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Jenny: on LinkedIn @jennyblake

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