Kim Perell: Hate Your Job But Don’t Know What to Do Next? Ask Yourself THESE 7 Questions and Build a Step-by-Step Plan for the Career You ACTUALLY Want

Kim Perell: Hate Your Job But Don’t Know What to Do Next? Ask Yourself THESE 7 Questions and Build a Step-by-Step Plan for the Career You ACTUALLY Want

Today, Jay sits down with serial entrepreneur, investor, and powerhouse mom of four, Kim Perell. Known for building her first company from her kitchen table and later selling one for $235 million, Kim shares the raw, behind-the-scenes truth of what it takes to turn failure into fortune. The conversation centers around Kim’s latest book, Mistakes That Made Me a Millionaire, and offers a heartfelt blueprint for anyone feeling stuck, unfulfilled, or uncertain about their next move.

Jay and Kim explore why perfectionism can sabotage progress, how fear often masks itself as procrastination, and why waiting to feel “fully qualified” often leads to missed opportunities. Kim introduces her 70% rule: a concept that encourages action over hesitation and reveals how taking small, imperfect steps helped her overcome self-doubt and build extraordinary businesses. The two also dive into the power of mentorship, the emotional toll of toxic relationships, and why surrounding yourself with the right people is crucial not just for professional growth, but for personal evolution.

In this interview, you'll learn:

How to Start a Business Before You Feel Ready

How to Use the 70% Rule to Make Bold Decisions

How to Find the Right Mentor and Build a Real Relationship

How to Stand Out When Pitching Yourself

How to Know When It’s Time to Pivot Your Business

How to Build a Winning Team Without Doing Everything Yourself

How to Audit Your Inner Circle for Growth and Clarity

Making mistakes doesn’t mean you’ve failed, it means you’re showing up, learning, and trying something new. No success story is smooth or simple, but all of them prove that progress is always possible.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

What We Discuss:

00:00 Intro

02:57 How to Get Unstuck and Move Forward

04:17 When It’s Time to Pivot Your Career

05:50 Is Regret More Powerful Than Fear?

08:06 You Don’t Need To Be 100% Ready To Start

09:52 Are You Ever Really Ready?

11:29 Dream Big, But Start Where You Are

13:09 The Power of Believing in Your Vision

15:24 Be Delusionally Confident

16:29 How Mistakes Help You Iterate and Improve

18:30 How to Silence the People Who Doubt You

22:15 Teaching Kids to Embrace Failure

23:20 Rejection as Redirection

26:02 The Difference Between Innovating and Iterating

29:14 Build a Support System That Elevates You

31:51 How to Find Mentors Who Truly Guide You

33:55 Why Asking for Help Accelerates Growth

34:44 How Books Can Mentor You Too

38:21 The Four People Every Entrepreneur Needs

39:35 Why You Need the Right Peers Around You

41:58 Should You Start a Business with Family?

44:00 How to Audit Your Inner Circle

46:02 How Toxic People Drain Your Energy and Money

47:17 The Power of Taking Initiative

48:56 Don’t Let Your Past Limit Someone Else’s Future

51:19 How to Lead and Manage People Effectively

53:17 What Actually Gets You Hired Today?

57:51 Going the Extra Mile Sets You Apart

01:00:01 The Biggest Mistake Is Not Asking

01:04:03 Why So Many of Us Feel Unqualified

01:07:07 Pivoting Is the Secret to Success

01:10:13 How to Know When It’s Time to Pivot

01:11:53 Kim on Final Five

Episode Resources:

Kim Perell | Website

Kim Perell | Instagram

Kim Perell | Facebook

Kim Perell | YouTube

Kim Perell | LinkedIn

Kim Perell | X

Kim Perell | TikTok

See omnystudio.com/listener for privacy information.

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Lilly Singh: ON Why She Took A Break From YouTube

Lilly Singh: ON Why She Took A Break From YouTube

You can order my new book 8 RULES OF LOVE at 8rulesoflove.com or at a retail store near you. You can also get the chance to see me live on my first ever world tour. This is a 90 minute interactive show where I will take you on a journey of finding, keeping and even letting go of love. Head to jayshettytour.com and find out if I'll be in a city near you. Thank you so much for all your support - I hope to see you soon.Being a YouTube creator can be difficult for anyone, but Lilly Singh really is superwoman. Despite the success, things haven’t always been easy for Lilly. She opens up about everything: how it feels when being called a role model, her relationships both personal and professional, even her struggles with depression and defining what success looks like in her life. Today’s conversation is a deep dive into what drives her to keep creating at such a prolific level and why she’s determined to keep using her influence for positive social change.See omnystudio.com/listener for privacy information.

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3 Reasons I Became a Monk for 3 Years

3 Reasons I Became a Monk for 3 Years

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1 Maalis 201927min

Mike Posner: ON How Fame Ruined His Life

Mike Posner: ON How Fame Ruined His Life

Mike Posner is the musician behind the hit songs I Took A Pill In Ibiza and Cooler Than Me. But behind the flashing lights and sold-out shows lies a very unique mind, one that has learned to deal with fame and fortune and most recently—the loss of his father. On today’s episode, Mike shares his insights on how to deal with loss, why moments of epiphany must be processed, and what the difference between the mind and intelligence is. Mike even turns the table on Jay—and asks him many profound questions about his own experience unpacking mindfulness.  Tune in to this episode to catch a glimpse of the mechanics behind this singer-songwriter’s brain.See omnystudio.com/listener for privacy information.

25 Helmi 20191h 24min

3 Lessons I Learned From My Ex

3 Lessons I Learned From My Ex

Breakups are hard there’s no doubt about that, but sometimes break-ups lead to break-throughs. Don’t worry, it’s normal to have feelings of bitterness, blame, or even have a breakdown. You are not alone.We cover a lot in today’s episode so whether you’re looking to strengthen your current relationship or need a little help getting through a past one you’re not going to want to miss this.See omnystudio.com/listener for privacy information.

22 Helmi 201927min

Novak Djokovic: ON One of the Greatest Comebacks in History

Novak Djokovic: ON One of the Greatest Comebacks in History

Most people, even non-sports fans are inspired by world class athletes like Novak… but why?To be world class at anything it takes more than natural skill, it takes physical, personal, spiritual development and a healthy relationship with one’s own ego to begin a fulfilling journey to greatness - something we are all capable of, given we know how to use the appropriate tools.In today’s conversation, Novak shares everything.He even takes us back to his childhood where he remembers confiding to his tennis coach instead of his own parents about the growing pains of being a young man.See omnystudio.com/listener for privacy information.

18 Helmi 201959min

Russell Brand: ON How He Nearly Ruined His Career

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You may think you know Russell Brand - the actor, the comedian, ect... but that’s only a small part of who he truly is.Prepare yourself, today’s conversation gets intimate.Russell opens up about his struggles with addiction, his experience chasing fame, money, sex, and why that’s not something people should aspire to. He shares what has enlightened and led him to a life of sobriety for over 14 years now and the role mentors and spirituality has played in getting him there.He even shares some surprising wisdom from a mutual friend of Puff Daddy, comparing the challenges of life to levels in a video game.See omnystudio.com/listener for privacy information.

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Jay Shetty Interviews His Wife for the First Time

Jay Shetty Interviews His Wife for the First Time

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