Dear Midlife...

Breaking Free and Leaving the Grind Behind to Design a Life You Love


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Ever Felt Stuck, Burned Out, and Wondering WTF is Next? Yep, me too. Trapped in a job that sucked the life out of me, clinging to what felt “safe” even though it made me miserable. Stuck in the muck, as today's guest, Michael Gardon, calls it. Sound familiar? 

Mike knows a thing or two about breaking free. He walked away from corporate burnout, turned a side hustle into a million-dollar business, and built a framework called Advantage Mapping to help others do the same. He’s a 3x entrepreneur, career pivot pro, and founder of The Break Community, where he helps 14,000+ people ditch unfulfilling work and design lives they actually love. 

Here’s the kicker—your identity isn’t set in stone. You have way more agency over who you are and where you’re headed than you think. Mike will show you how to **stop asking “What do I want to DO?” and start asking “How do I want to FEEL?”** Because real transformation starts with knowing yourself and then mapping out multiple paths to get where you actually want to be. If you’ve ever thought, "Is this really IT?"—you’re gonna want to tune in. 🚀

In this episode, Mike teaches us

  1. our brain values certain over uncertainty. That is often why we stay "stuck" in the muck...the thing that is making us unhappy...the work or the relationships.
  2. Our Identity isn’t permanent and we have a lot of agency over what it is and what we want our identity to be. Once we realize we have agency over identity we can start to look into the future to determine who do I want to be and what are the steps I’m taking to get there.
  3. When visioning your future, don’t start with what do you want to DO, start with what do you want to feel like.
  4. In order to know where you want to go, you have to have a solid understanding of who you are today and what are your strengths. Use an advantage map (from Warren Buffets Circle of Competence) to explore 8 different dimensions to explore how you can create advantage in your life.
  5. Don’t look at your “next step” as a singular path. Develop and work 2-3 different options at once with the expectation that you learn from the experience and that one of the paths will work, allowing you to then focus your time and energy on that.

For more of Michael:

Website | michaelgardon.com

LinkedIn | Michaelgardon

And if you find yourself feeling stuck and wondering who you are and what do you want to become-join us. We are a tribe of like-minded, women in midlife who are trying to build connection with one another. You see, the more connections and friendships you have, the happier you will be as well. We will be launching a membership in 2Q 2025 and we want you to be a part of it. Our goal is to connect women from around the world for friendship and fun...virtually and face-to-face (where possible). If you're interested in being a founding member, email me at [email protected] to get in on the action. Find us on Facebook and follow us on Instagram to stay tuned for more fun info!

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Dear Midlife...By Shelby Bybee and Trinity Greenfield

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