How to Navigate Your Post 40 Pivots, LIVE in Chicago with Pam Sunshine and Jenn Sherman of Sunny and Jenn

Sometimes, the best opportunities come out of nowhere—just ask Pam Sunshine and Jenn Sherman!

Lindsay Pinchuk kicks off a live conversation from a sold-out event in Chicago, where she sits down with Sunny and Jenn to talk about unexpected pivots, reinvention, and rolling with life’s surprises. A chance encounter on the street sent these two best friends viral on TikTok, launching them into a new chapter they never saw coming. With no strategy, no grand plan, and no clue what they were doing at first, they figured it out along the way and built something real.  

Jenn shares how she went from stay-at-home mom to Peloton instructor, proving that taking one small step can change everything. Pam opens up about stepping into the spotlight after decades behind the scenes and why this new venture feels different—it’s just for her. They also talk about balancing careers, navigating midlife shifts, and why embracing what excites you matters at any age.  

The best things often happen when you say yes before you feel ready. This episode is a reminder to embrace change, lean on your support system, and go after what excites you because the right opportunities often show up when you least expect them.

Quotes

• “You have to find something you’re passionate about and that you love that’s going to push you.” (07:49 | Jenn Sherman)
• “You have to dive in and just decide you’re going to figure it out.” (15:36 | Jenn Sherman)
• “We’ve learned that we’re just going with it. And if you don’t feed it, it can’t grow. We definitely have learned that. And sometimes that gets a little tricky.” (16:07 | Pam Sunshine)
• “I’m a big sharer because if I have something good, why wouldn’t I want to share it with people I like? I’m just not a gatekeeper.” (24:12 | Pam Sunshine)
• “When you just can be yourself, it’s very freeing.” (26:17 | Pam Sunshine)
• “You have to first put yourself out there and decide you want to make that change. And don’t wait. You’ve heard it a million times. Just do it.” (34:52 | Jenn Sherman)

Connect with Pam Sunshine and Jenn Sherman:

http://www.instagram.com/sunnyandjenn

Sign up for our newsletter so you know when Dear FoundHer... comes to a city near you:

https://lindsaypinchuk.myflodesk.com/waitlist

Join the Dear FoundHer... Forum: https://www.dearfoundher.com/dear-foundher-forum 

Don't forget to follow Lindsay on Instagram: https://www.instagram.com/lindsaypinchuk

Podcast production and show notes provided by HiveCast.fm

Hosted on Acast. See acast.com/privacy for more information.