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"On The Internet, Everyone Looks Rich" with Jenny Blake
21 July 2026

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

The Anxious Achiever

About
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.



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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