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