What I Wish I’d Known 30 Years Ago: A Letter to My Younger Self

Some books start as ideas. Mine started as a life — with all the wrong turns, late realizations, and moments of unexpected grace that come with actually living one.

While I was writing Wired for Purpose, my publisher asked me to write a letter to my younger self and it turned out to be one of the harder — and more clarifying — things I’ve done in the writing process. What emerged wasn’t a highlight reel. It was an honest look at the habits, relationships, and blind spots that shaped the person I am at 57.

If you’ve ever wished you could reach back and hand your younger self a road map, this one’s for you:

Dear Aaron,
This is 57 year-old you writing to 20-something you. There’s part of me that wants to reach out to “high school you,” but I don’t think he would’ve heard me then.
Let me just start by saying you turned out okay. You married an incredible woman, had a successful career and raised three amazing children. All I can say is it will get difficult at times, but stick with it. You also developed some pretty amazing friendships over the years. But one little piece of advice before I give you my list of, “things I wish I’d known.” Take better care of some of your legacy friendships. Yes, I’m talking about people like Joe Maher, Christopher E. Hornbarger, Michael Stiller, Gregg DiPietro and John Erik Riley. They’ve been with you through thick and thin, and they deserve(d) your attention much more so than others who took energy from you. Ditto with your brother, John, your sister, Heather and your parents, especially after you moved away from New England.
So, I’m a list guy. I guess that means you’re a list guy too. Here are a few suggestions that will help you get further faster in life:
  • For starters, keep your ego in check. You’ve mostly done a good job over the course of your career, balancing confident and cocky, but it will get you in trouble while you are at Fidelity Investments. The result is you spending time and energy digging out of your hole, and it will set your career back at least a year or two. Speaking of, leave Fidelity earlier than you did. Don’t get me wrong, it’s a great company and your time there was invaluable, but you should’ve done a startup closer to 2003 or 2004 before your kids started to grow up and you had settled into a lifestyle. BTW, the ego thing surfaces again after you publish your Dummies book. Stay focused on your friends and your family and be gracious, don’t let any of the bullshit go to your head.
  • Stick with the blogging thing. You turned out to be a pretty good writer. You let go of the skill prematurely while you were at Real Chemistry. You rediscover it after you leave, but it would’ve served you to do more of it.
  • Networking is your superpower. Not a lot to tell you about this one except just know that the time you invest ultimately pays off.
  • While there were definitely times where you could have leaned in more at work, spend more time with your family. There are times in your life were you straddled both and as a result, you were good at neither.
  • When your oldest daughter tells you, she has anxiety in middle school, pay attention. It’ll serve you well as your children go from kids to young adults.
  • Bob Pearson is one of the smartest people you’ll ever meet, but pay closer attention to your relationship with Jim Weiss early and often. You ultimately figure this out but you would’ve saved yourself a lot of pain had you done it toward the beginning. Jim will drive you hard, but he has great instincts and he will be a big part of why you are successful.
  • Not sure there’s much you could do about this because they’re still no real cures for glioblastoma or dementia, but you will ultimately lose your mother-in-law and your Aunt Barbara to glio and your grandmother and dad will be afflicted with dementia. Spend more quality time with them when you can.
  • Speaking of, menopause is going to hit your wife hard. You both ultimately make it through to the other side, but it’s not going to be easy. Learn more about it in your 40s and give Melanie more grace and support once you turn 50.
  • One last health-related PSA. You won’t believe it, but there will be a global pandemic that hits in 2020. It will literally grind the world to a halt and will change how we work, how content gets consumed and how commerce gets done. But your mental health takes a dip during this time, so talk to a therapist earlier, and take better care of yourself because it will impact your relationship with Melanie for a while and neither of you need that.
Oh, one other thing. Stick with the podcasting thing. It will help you with your platform. To that end, your fifth show, the Reaching Higher Podcast is going to break through for you. It will also be the way that you meet some of the most amazing people in your life.
Now there’s a saying, free advice is worth what you pay for it. And while you’re not paying for this advice, I guess you did in some ways with all the blood sweat and tears we put into our life.
Let me conclude with one of your favorite allegories. It’s the story of a man looking down from heaven at his footsteps on a beach that symbolizes his life. He notices that there are two pairs of footprints during some of the better times and only a single pair when life gets tough. He asks God, “why did you abandon me during most difficult times. God says, “I didn’t abandon you. I was carrying you.”
You got this.
Love,
57 year old Aaron