Lesslee Dort

To help celebrate my recent birthday, a small group of friends asked me what I’d like to do to mark the milestone. There are a couple of quietly beautiful things about that question. First, they wanted to take time out of their lives to celebrate me. That alone feels overwhelming and humbling. Second, they didn’t simply plan a party and tell me where to show up. They wanted to know what I would enjoy. They were offering me the gift of my own desires.

I answered quickly. I imagined a snowshoe hike through the woods, ending at a secluded spot where we could build a fire, stand around warming our hands, and enjoy one another’s company. Nothing fancy. Just movement, nature, and conversation. All we needed was snow.

We kept the group small and the day simple. We gathered on the chosen day with a beautiful, fresh blanket of white on the ground. The kind that softens the world and quiets your thoughts. The men dropped us off at the beginning of the trail and headed ahead to the end location. By the time we finished our hike, they had stamped out a clearing and built a roaring fire that felt like a welcome hug.

As we stood around the flames laughing, someone asked me what advice I might give now that I was “older and wiser.” I chuckled a little at the phrasing, but the question stopped me cold. I can’t remember being asked that question so directly. Come to think of it, I can’t remember being asked it indirectly either.

I paused. I gave an answer. But the question didn’t stay behind at the fire when we packed up and went home. It followed me. It continues to pop up in my mind, as though I’m meant to keep going – meant to continue examining what I’ve learned over these six decades.

It’s been a surprisingly enjoyable exercise. We all accumulate lessons simply by living. We make easy decisions and difficult ones. Some play out beautifully, others… not so much. Every day, we learn something new or something that shifts what we once believed to be true. We take what we’ve learned, apply it, adjust it, and sometimes abandon it altogether as we move through different seasons of life.

So, I decided to make a list – one piece of advice for each decade I’ve lived. I’m sharing my list, not because I think I’ve figured anything out, but because I hope it prompts you to pause and consider what you have learned. No matter where you are along your life span, you’ve gathered wisdom. You may as well acknowledge it.

Here’s what surfaced for me:

First, we cannot choose another’s path for them. It’s not up to us to tell other adults what do or how they should behave. We only have control over ourselves, and even that is limited. We can influence, encourage, and love people. But we cannot determine the path they take. Nor should we. Learning to loosen our grip is both humbling and liberating.

Second, we have nothing to prove to anyone. So many of us quietly shape our lives around others’ expectations, chasing approval that was never required in the first place. We are already valuable. Already enough.

Third, stop doing things that make you deeply uncomfortable or push you farther than you want to go. Stretching yourself, trying new things, and saying yes to adventure can be amazing if it’s truly your choice. There’s a difference between growth and self-betrayal.

Fourth, boundaries are healthy and loving. They are not walls; they are guidelines that teach others how to treat us and remind us how to care for ourselves. Standing up for yourself isn’t selfish; it’s necessary.

Fifth, when communicating, always lead with respect and kindness. The world already offers plenty that will knock us down. Rudeness, shaming, and cruelty are choices that are never required or needed – that includes the way you speak to yourself.

And finally, no matter how old you are, today could be your last. That isn’t meant to scare us; it’s meant to wake us up. Live your moments. Reach out. Tell people they matter. Say “I love you” sooner rather than later.

So now I’ll turn the question back to you. What advice would you give? What has life taught you so far? If you feel like continuing the conversation, do so! Grab a friend, have a conversation. I’d love to hear from you, too. You can reach me at lesslee@regardingthejourney.com.

After all, wisdom isn’t meant to sit quietly by the fire. It’s meant to be shared.