13 Ways I Challenged Myself

I preach the importance of getting out of our comfort zones, of challenging ourselves, at any age. But let’s face it, as we hit midlife and beyond, it’s tempting to stick to our familiar routines, surroundings, and people. And Covid may have made our worlds and possibilities seem smaller.

Sometimes I too slide into the tried and true, but eventually I feel restless and I resolve to fight my growing complacency. There’s something inside me that tells me it’s time to get out there and explore, and in so doing honor my values of courage and growth.

Truth is, I never feel prouder than when I try something new, even if it ends up being ho-hum. I learn something regardless of the outcome. And I remind myself that I can show up bravely and authentically, and I will be ok no matter how it goes.

I’ve been in a bit of a rut lately, and that realization is what convinced me it was time to change things up. Newly back in Chicago, I am pushing myself to say yes to new activities and connections. I am re-engaging with the world in a deliberate manner, with a focus on exploring my interests and meeting new women.

In the last few weeks, here’s a sampling of ways I pushed myself…

1. I attended a language café Meetup at a brewery in Chicago—with some trepidation, as I did not know a soul there and don’t particularly like beer—and enjoyed connecting with the mostly twenty-something participants as we practiced speaking French.

2. I pushed past the guilt and set boundaries on two separate occasions, with two family members—unpleasant business but necessary for my wellbeing.

3. I “cold emailed” two women to invite them to speak in my THRIVE personal growth community and held fruitful Zoom sessions with each—they both agreed to present!

4. I shared a post inside my Facebook group, knowing that my assertion would lead to some members leaving the group. While I don’t allow political or religious discussions inside this group, I wanted to make it crystal clear that “women’s rights are human rights,” that “science is real,” that “love is love,” and more.

5. I joined and attended several online support groups focused on parenting adult children and navigating grief—and shared my struggles with vulnerability.

6. When a friend wanted to strategize with me how we could convince her adult daughter to relocate to Chicago, I gently suggested it might be time for her to “drop the rope” and stop telling her grown child how to live her life (and I recommended the book I’m currently reading, Walking On Eggshells: Navigating the Delicate Relationship Between Adult Children and Parents by Jane Isay).

7. I organized and attended a dinner with other local women members of a favorite organization, none of whom I’d met before, and we enjoyed getting to know each other over wine and a charcuterie board.

8. I stopped “thinking about it” and joined two memberships, one related to parenting and another to wellness (as a membership leader myself, I am a big believer in the power of this format).

9. I agreed to give an in-person staff training at a local nonprofit supporting disabled teens and young adults and, pushing past my inner impostor, I asked to be paid (at a discount, given their nonprofit status, but still!).

10. I said yes to an afternoon of fly fishing while visiting Cashiers, NC, despite my having no interest in fishing and never having done any fishing before. As is often the case, I was surprised to actually enjoy it! I found it to be a meditative experience in a beautiful setting, and I caught a few trout! (And promptly released them).

11. I researched ways to become involved in the fight for women’s reproductive rights (beyond donating) and messaged the leader of a women’s organization about putting on a program focused on activism in a post-Roe world.

12. I reached out to three women I’ve only had online contact with to meet up in real life and so far two lunches have been scheduled.

13. I took the first step in planning a 60th birthday celebration—for me! (I NEVER celebrate myself.)

Now some of these actions may feel easy to you—or they may feel scary. We each have our own thresholds for what challenges us. But the point is to find that sweet spot where you are pushing yourself just the right amount for you.

YOUR TURN: What actions are YOU taking to get out of your comfort zone? Tell us in the comments!