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

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