Middle age is about making tough decisions — but do you know how to make bold decisions? The art of boldness is a desired trait but often misunderstood. On this episode, we’re joined by Jen Cohen, the entrepreneur and bestselling author of Bigger, Better, Bolder: Live the Life You Want, Not the Life You Get. Together, we dive deep into the concept of boldness, dissecting the misconceptions that often blur the lines between boldness, narcissism, and genuine confidence. Jennifer shares practical strategies for building confidence, stepping into boldness, and cultivating self-awareness. Plus, we tackle the pervasive issue of Instagram coaches peddling bullshit advice, offering savvy tips on how to sift through the noise and find mentors who truly walk the talk.

Brought to you by:

Plunge—The best home ice baths. Save with code MidlifeMale https://plunge.com/

Sisu Sauna—My go-to barrel sauna. Save with code MidlifeMale https://sisulifestyle.com/

—

In this episode, we cover:

(03:46) How middle-aged men struggle with being bold

(07:04) Why boldness is a skill that can be learned

(10:04) The importance of self-awareness and emotional intelligence

(13:15) How we can all improve self-awareness, boldness, and confidence

(17:30) Tips for building confidence

(20:54) How choices impact our lives

(25:00) The importance of doing hard things

(26:45) Why consistency is key

(27:10) The differences between men and women when it comes to achieving goals

(31:02) The 10% target

(33:01) The problem with most coaches and men’s groups

(40:20) Advice on finding a coach or mentor

(45:20) Reframing middle age

(48:22) The problem with chasing youth

(52:25) Dating differences with men and women and why loneliness is an epidemic

(57:30) The lies we tell ourselves about success

(1:02:34) Why guys who are confident and secure don’t want to date women decades younger

—

Where to find Jen Cohen:

Website: https://www.jennifercohen.com/

Instagram: https://www.instagram.com/therealjencohen

X: https://twitter.com/therealjencohen

TikTok: https://www.tiktok.com/@therealjencohen

Where To Find Greg Scheinman:

Website: https://midlifemale.com/

Instagram: https://www.instagram.com/gregscheinman

LinkedIn: https://www.linkedin.com/in/greg-scheinman-b442004/

—

Production and marketing by https://penname.co/