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7 Life Lessons I’d Share with My Younger Self

Hard-won wisdom I wish I had gained in my 20s


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Rob Dobi

During a yoga class recently, I was feeling the aches of too much gardening the previous weekend. I thought, “I wish I had started a regular yoga practice in my 20s.”

My body would be in much better shape had I begun earlier and I would have connected with a like-minded community.

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The thought tugged at my heart like a gentle whisper of hard-won wisdom. What else do I wish I’d known decades earlier? With a bit of self-reflection, I selected these seven lessons:

1. Don’t wait so long to have children

My husband and I didn’t feel ready to have kids when we married in 1988, so we postponed parenthood to build our careers and savor our carefree lifestyle. We waited a decade to start a family.

That meant my boys never got to know my dad or my mother-in-law. I deeply regret waiting so long.

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2. It’s okay to march to your own beat

For most of my life, I have felt like a square peg trying to fit into a round hole. Moments of self-doubt and inadequacy clouded my perception as I measured my worth against the yardsticks of others.

With the grace of aging, I shed the concept of conformity and stopped measuring my worth against others. Guess what? I don’t want to be like everyone else. I’d love to whisper to my younger self, “You’re enough just as you are.”

3. Nurture important friendships

I’m still BFFs with several women I’ve known since my braces-and-glasses-wearing days. And, thanks to social media, I’ve reconnected with many friends I’d lost touch with. But I wonder how much stronger and deeper these reconnected friendships would be today if I’d put in more effort to stay in touch through the years. I’d tell younger me: “Hold these friendships tighter or they’ll slip away as life unfolds.”

4. Keep one toe in the professional world

While I never regret raising and educating my two boys, I wish I hadn’t stopped my career so abruptly. I’d gently advise my younger self to maintain some presence in the business world during those years.

Staying connected with my professional network, keeping abreast of evolving technology and freelancing part-time could have eased my reentry into the workforce at 50. When I rebooted my freelance career in mid-life, it was one of the hardest things I’ve ever done.

5. Think twice about studying for another degree

I could have saved myself a lot of time and money by skipping graduate school. While I did hold a few “real jobs” that might have benefited from an advanced degree, I ended up freelancing for 35 years. That means I alone determined my success. While I enjoyed graduate school and made some wonderful friends, it didn’t benefit my career.

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6. Homeschooling was the right choice

Long before homeschooling emerged as a mainstream educational choice in the pandemic’s wake, I took the plunge with my two boys. I felt like an educational deviant when others questioned my choice. Even strangers would approach us when they ran into us and ask why my boys weren’t in school today.

They didn’t notice the books on the table at Panera as I drank coffee, the boys enjoyed bagels and we tackled schoolwork. And guess what? My sons both turned out fine.

7. Embrace a healthier lifestyle

I admit I indulged in the siren call of junk food, fast food and soda for many years. And, while I worked out sporadically, I never really enjoyed exercise — until I fell in love with yoga during the pandemic.

I don’t know if making healthier choices would have made a difference, but I was diagnosed with two different cancers within six months in my 50s. I know lifestyle contributes to the development of some cancers. I wish I’d adopted a more plant-based lifestyle and found yoga earlier.

The bottom line

Alas, it probably takes a lifetime of learning to know how we would educate our younger selves.

Share your experience: Of course, you wish you knew then what you know now, but what advice do you wish you had known most of all when you were young? Share your wisdom in the comments below.

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