There are few things I value more than getting the opportunity to learn from those who are older and wiser than me.

Over the past few months, I’ve had the chance to sit down over coffee with several men that fit this description. Each of them is in their mid-sixties or early-seventies. Each has experienced incredible success in their careers — be it in marketing, finance, or business. Each is respected and viewed as a man of integrity and influence.

The (Somewhat) Encouraging Lesson I Learned from 3 Wise Men

But as I began to ask them about what’s currently going on in their life — I recognized a pattern. In each conversation, the men described how they were trying to determine what’s “next” for them. Admittedly, each was still wrestling with the same challenges and questions I’ve wrestled with over the past decade.

To be honest, I was a little caught off guard. Here’s why… As someone who just turned 30, I’ve always thought this was the season of life I’d wrestle with questions like “What’s next?” I assumed I wouldn’t wrestle with the questions and doubts as I got older – especially by the time I reached 60.

Here’s the (somewhat) encouraging lesson I learned from these men over the past few months:

There will be certain questions, challenges, doubts that we always wrestle with throughout our lives.

I saw “somewhat” in a sense that this can be a little disheartening to realize at first. The idea there will be a point in our lives where we’ve “made it” is a lie. That reality can be a tough pill to swallow.

But I do believe it’s ultimately an encouragement in this — we’re all in the same boat, experiencing the same longings, dealing with the same frustrations, wrestling through the same challenges.

So What Can We Learn from This Lesson?

Here are some ways this new reality has shaped the way I go about each day…

We’re all in the same boat, experiencing the same longings, dealing with the same frustrations, wrestling through the same challenges.


  • Recognize the “journey” nature of life. We tend to think the trajectory of our lives should always be up and to the right. It isn’t. Learning these men are still asking the same questions helped me realize that we’ll never reach a “destination” in this life where all of our troubles and problems are solved. Rather life itself is a journey in which we’re constantly meeting new challenges and opportunities.
  • Be kind to people. It can be difficult to extend grace to others — especially those leaders you’re responsible for following. It’s easy to think they should have it figured out. In those moments, it’s important to remember that everyone (including those older and wiser than us) is fighting a hard, hidden battle.
  • Live in the day, measure by the decade. The reality of a “lifetime” of questions frees me from the worry and pressures of tomorrow. Rather than constantly trying to figure out “what’s next,” I can be more present in truly living for today. At the same time, I don’t have to worry about making an impact right now. Instead, I approach each day recognizing that making a real difference happens over the course of a lifetime.

If you’re frustrated by continually wrestling with the same questions or feel like you should have “made it” by now — take the encouragement from my three wise friends. Recognize these doubts and questions as a part of life. Don’t get discouraged. Embrace each day for what it is — another step in this long, long journey we all get to experience called life.

Photo by Asaf R on Unsplash
The opportunity to learn from those who are older and wiser is a gift. Jeremy Chandler learned an encouraging lesson when he sat down and listened.

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