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Episode 242

Ask for More with Jennifer Cohen | Win the Day
June 24, 2025
Jen Cohen is the bestselling author of ‘Bigger, Better, Bolder’; a TEDx speaker with 5M+ views; and host of the Habits & Hustle podcast.
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In this episode of Win the Day:

"What we instill in our children will be the foundation upon which they build their future." — Steve Maraboli

What if boldness was the only thing standing between you and achieving your biggest goals? 🧐

Jennifer Cohen has built her life—and career—around that exact idea. She’s a bestselling author, top-ranked podcast host, international speaker, and one of the most influential voices in wellness, personal growth, and business performance.

Her viral TEDx talk, The Secret to Getting Anything You Want in Life, has been viewed over 5 million times, and her latest book Bigger, Better, Bolder is a bold blueprint for anyone ready to stop playing small and start living on their terms.

From selling companies for millions, to advising global brands like Nike, Celsius, and Proctor & Gamble, to interviewing icons like Mark Cuban, Tony Robbins, and Matthew McConaughey on her Habits & Hustle podcast, Jen has built an empire by doing things differently—and showing others how to do the same.

In this episode:
• The #1 habit to transform your life.
• How to rewire your brain for massive action.
• Why most people stay stuck in a rut.
• How to raise healthy, strong, and resilient kids.

Let’s WIN THE DAY with Jennifer Cohen!

Timestamps

00:00 Who is Jen Cohen
1:28 Interview starts
2:15 The gift of being average
3:47 How to be resourceful, resilient, and likeable
7:40 Why kids are losing resilience
9:48 Never put your destiny in someone else’s hands (launching the Habits and Hustle podcast)
12:25 Make 10 attempts at whatever you want most
14:23 When Jen Cohen met Keanu Reeves
17:15 Be more interested than interesting
19:20 Why rejection is better than regret
20:38 How to maintain your friendships
22:56 How to ask for what you want (and get what you want)
25:44 How to become more confident — and remove self-doubt
29:15 Chase what you want, don't take what you get
36:47 If you want something done, give it to a busy mom
39:36 Jen Cohen parenting approach
42:33 Don’t coddle your children
47:16 The #1 skill that parents need to teach children
47:51 The number one skill that parents need to learn
49:00 When children should get access to a smart phone, social media, etc.
52:47 Should parents avoid phone usage around their kids
57:54 Do healthy parents have healthy kids
58:56 How to make your TEDx Talk a success
1:02:58 Affirmation
1:03:39 Rocket Round

Resources / links mentioned:

🎯 Download your FREE Win the Day action plan

⚡ Jennifer Cohen website

📷 Jennifer Cohen Instagram

📚 ‘Bigger, Better, Bolder’ by Jennifer Cohen

🎤 TEDx Talk ‘The Secret to Raising Mentally Strong Kids in a Fragile World’ by Jennifer Cohen

📹 Jennifer Cohen YouTube

🎬 Subscribe to Win the Day YouTube channel

💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts

🙏 Give the Win the Day podcast a 5-star rating on Spotify

💕 Win the Day Facebook group

📝 Win the Day newsletter [weekly LinkedIn exclusive]

Inspiring quotes in this episode:
  • "The precursor of being bold is being likable." — Jen Cohen
  • "Mediocrity forces you to develop other skills. It gives you a chip on your shoulder, where you then want to prove to yourself." — Jen Cohen
  • "I put my destiny in the hands of somebody else, which is a big mistake." — Jen Cohen
  • "Make 10 attempts at whatever you want most." — Jen Cohen
  • "Let naivety be your strength." — Jen Cohen
  • "Rejection is always better than regret." — Jen Cohen
  • "Most people don't go for the job they want. They go for what's available." — Jen Cohen
  • "Most of us count ourselves out before we do anything." — Jen Cohen
  • "Chase what you want. Don't take what you get." — Jen Cohen
  • "The suicide rate at that school was so high because of their inability to fail." — Jen Cohen
  • "The best way to overcome anything is to get better at it." — Jen Cohen
  • "If you want something done, give it to a busy working mum." — Jen Cohen
  • "We've lost the ability to allow our kids to be bored." — Jen Cohen
  • "Competence builds confidence." — Jen Cohen
  • "The job is to be a parent, not a friend." — Jen Cohen
  • "Embody the person that you want your child to be." — Jen Cohen
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