Dear Midlife...

Reflections from the Dating Pool with Cindy Drummond


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Our guest today, Cindy Drummond, found herself in a unique situation. She woke up one day to find her, then, significant other was being arrested for some serious crimes.  In the blink of an eye, Cindy's world had been turned upside down. She fled the situation with her two daughters in tow and had to start again from the basement of her parent's house. She'd lost trust in others and faith in herself.

But, these moments are what define our character.  Perhaps, some of you in our audience  have similarly find yourselves feeling a bit lost amidst significant life shifts and wonder what to do next. Cindy learned quickly that action creates momentum and  self-imposed goals are the catalyst to action. In a short period of time, Cindy founded a network of women by forming the Women Only Weekend and found a new tribe.  She also boldly went on 50 dates in 52 weeks and, well…you'll have to listen to the podcast to find out how that experiment went! You can also read about it in her book "Reflections from the Dating Pool. A Story About Resilience, the Importance of Finding your Tribe and the Power of Falling in Love with Yourself." Cindy could have easily portrayed the victim in this situation. But she, instead, chose to uncover her own  personal interests and desires through journaling and meditation and, then, pursued these daily fueled by courage and determination to face and triumph over the things that made her most uncomfortable. To many, this path may sounds difficult…the reward, however, is a renewed trust and love for herself. By having the strength to face her own fears and discomforts, she saved her own life.

In this episode Cindy teaches us to:

  1. Find your "tribe" and spend time with people who lift you up and empower you.
  2. Do what terrifies you.
  3. Put as much into the experience as somebody else is putting into the experience when building relationships with others.
  4. Practice gratitude, listen to your own instincts and learn to trust yourself.
  5. Sometimes you have to go through some "yucky stuff" in order to find what brings you joy.
  6. Use self-imposed challenges as a catalyst for action.

Find more of Cindy at:

Facebook | Cindy-Drummond

Ready to ditch midlife mediocrity and level up your life? We've got your back with a no-nonsense blueprint and a supportive tribe. Visit dearmidlife.com for:

Accelerated Education: Tap into our toolkits that contain expert interviews, curated resources, and actionable steps that demand growth.

Supportive Problem Solvers: Navigate midlife challenges with the fierce friendships of our community, helping you solve any problem, find your purpose and redefine yourself.

Unapologetic Friendship Fuel: Build a strong inner circle that supports, cheers, and holds you accountable every step of the way.

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Dear Midlife...By Shelby Bybee and Trinity Greenfield

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