Questions for my Older Self

elderly man sitting on a bench

Lately I’ve been seeing quite a few blog posts written by seasons professionals reflecting on their careers and all the advice they would have given their younger selves. Often given a title like “A letter to my younger self” or “Things I wish I knew when I was 20,” these reflections are equally thought provoking as they are filled with regret and remorse. This got me thinking, Instead of waiting until I’m 50 and writing a post about all that I’ve learned over the years, what if I wrote something that outlined some of the commonalities lamented in so many of these midlife tell-alls? While I can’t pretend to anticipate much beyond a few hours in the day, I thought that a letter to my future self was an interesting idea. 

As I started trying to jot down my thoughts and come up with some nice, succinct correspondence to quinquagenarian Steve. I found it nearly impossible to capture all of the things I wanted to keep top of mind. We’re talking about a couple of decades between now and then, so a lot can change–values, experiences, ideals, etc. Furthermore, it’s impossible to outline what life lessons one will learn over the course of the next few years. Thus, my letter morphed into a list of questions. Ones that I hope to contemplate on a regular basis over the next few years.

  • Does your wife feel like she’s the most important person to you?
  • Is your marriage still growing and strengthening? What are you doing to care for it?
  • Are you forging lasting relationships with your kids?
  • Are you accessible to your kids? Can they talk to you whenever they need you?
  • What does your lifestyle say about what you value the most? Is family more important than money/material things?
  • Have you managed your body with care and respect? Are the things you’re putting into it making you better or worse?
  • Does your travel schedule cause you to miss games, recitals, or other events in your kids’ lives?
  • Do your kids feel loved by you or managed by you?
  • Does your wife love and respect you or simply tolerate you?
  • Do you hug your loved ones and friends enough?
  • Are you investing time into your most important relationships or are you just waiting for relationships to happen to you?
  • Have you lived below your means and saved money with the right goals in mind?
  • Do you live with integrity that others see? Is there anything you need to rectify?
  • Is there anyone you’re trying to please or impress? Is it worth it?
  • Do your words have meaning to others or do they ring hollow when spoken?
  • Is there enough in your life you can laugh and smile about?
  • Are you feeling fresh and alive or do you feel burned out?
  • Are you still learning/educating yourself? What have you read recently?
  • Do you maintain perspective on what’s truly important? Are your actions proof?
  • Are you being challenged to grow, learn, and adapt?
  • Are you happy with how you’ve spent the first half of your life?

So there’s a decent start to my list of questions to contemplate. If you had to come up with your own list, what would you challenge yourself with? Feel free to comment with your ideas below, I’d love to hear them.

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