The Dip, The Messy Middle, and Why Most People Quit Too Soon

In this episode of The Bold Biz Podcast, Jenny dives into one of the most important, and least talked about, phases of building a side business, the dip.

That uncomfortable, confusing middle stage where the initial excitement has worn off, results feel slow, and self doubt starts creeping in. The part where so many people quietly quit, not because they’re incapable, but because they don’t realize this phase is normal.

Inspired by The Dip by Seth Godin, Jenny breaks down what the dip actually is, why it’s inevitable for side business owners, and how to tell the difference between a temporary dip and a true dead end.

She also talks openly about the messy middle, how it shows up in real life, especially for women in midlife juggling work, family, and limited time, and why this phase can feel even harder when you’re building something later in life.

In this episode, Jenny shares:
 • What “the dip” really is, and why most people aren’t warned about it
 • Why the messy middle is not a sign you’re failing, but often a sign you’re growing
 • How shiny object syndrome can pull you out of the dip too soon
 • How to tell the difference between a dip and a dead end
 • Real examples from Jenny’s own journey, including Knit & Knot Co., The Bold Biz, and ideas she quit too early
 • How to mentally prepare for the dip instead of fearing it
 • Why staying a little longer can be the difference between quitting and breakthrough

If you’re feeling stalled, discouraged, or questioning whether your side business is “working,” this episode will help you reframe what you’re experiencing and decide your next step with clarity instead of panic.

✨ Sometimes the dip isn’t a sign to quit. It’s a test of how much you want it.

⭐ LINKS AND RESOURCES:

• Join the membership, The Bold Biz Collective:
https://www.skool.com/the-bold-biz-collective-5477/about?ref=452be9165f334da2943a1959010dd81c

• Follow The Bold Biz on Instagram:
 https://www.instagram.com/theboldbiz/

• Website:
https://www.theboldbiz.com

• Email:
 hello@theboldbiz.com

Chapters

• 0:02 Main Intro
• 0:39 Episode Intro
• 2:19 What the Dip Actually Is (And Why Nobody Warns You)
• 4:41 The Messy Middle in Real Life (AKA How This Actually Shows Up)
• 7:09 Why the Dip Feels Extra Hard in Midlife
• 9:04 The Dip Versus a Dead End (And How to Know the Difference)
• 11:22 Shiny Object Syndrome and the Dip (The Thing Nobody Tells You)
• 12:45 My Own Experiences with the Dip (The Honest Version)
• 14:36 What the Dip Actually Needs from You (Spoiler: Not What You Think)
• 16:05 Reframing the Dip as a Commitment Test (Not a Failure)
• 17:11 Preparing for the Dip Instead of Fearing It
• 18:49 Gentle Closing Reflection
• 19:42 Main Outro