A Letter to Myself in Ten Years

Many, many people write letters to their past selves, advising their earlier selves to avoid mistakes that they’ve made. I thought it might be interesting to take the opposite approach and write myself a letter today to read on my fortieth birthday.

Dear Trent,

Today is your fortieth birthday. Your son is twelve years old, your daughter is ten years old, and you’ve been married for fifteen years. Right now, I can scarcely believe that’s possible. I don’t know what frustrations and joys you will have experienced between now and then, but I just wanted to pop in with a little reminder of the things you value now, so that maybe you’ll sit down and use your fortieth birthday as an opportunity to really look at your life and make sure that it’s still centered around the things that you value.

I guess that’s the first thing I want to say. Right now, take a few hours and set it aside to really reflect on your life. You probably don’t remember the day to day realities of your life when your daughter was a newborn and your son was two, but you spent it working full time at a job and at two side businesses, plus you devoted time to your children and your wife, spent time on your hobbies, and still squeezed in a bit of time for reflection, too. The times in your life that you’ve been melancholic have been the same ones where you failed to take time to reflect on things. So, take that time right now. Go for a walk in the woods and think about where you’re at right now.

When you get back, do these things.

Take that wonderful wife of yours, the mother of your children, into your arms, give her a kiss, look her straight in the eyes, and tell you that you love her. Right now, she is the emotional center of your life, and even if that has changed somewhat in the intervening ten years, let me assure you that right now, as I write this, she is the reason to get up in the morning. Don’t let little aggravations get in the way of things.

Give each of your children a hug, too. You and your wife used to spend every evening completely devoted to them, and they’ve likely grown into interesting people as well. You’re probably wondering where the time went, and asking yourself when your son turned into a budding young man and your daughter transformed from a soft, snuggly little baby into a nuanced and thriving child. Hug them both, and don’t let these last few years of their childhood slip past. Take some extra time to spend with them, and never hesitate to let them know that you love them.

Think about what you really want to do. Right now, I’m planning on spending much of my thirties making the strongest possible foundation I can for you, one of financial security for you and your wife and those kids. Why? So you can do some amazing things now. Go on a few deeply memorable vacations in the next few years. Take your family and visit every continent in the world. Do some things that will build your family’s connections, but also enable your children to grow and see new things. I’ve spent much of my time over the last few years worrying about how I will be able to take care of those children, but they’re growing up now and the worry should be less, so use those resources you’ve got to experience some new things.

Right now, our family’s plan is to build a new house when I’m about your age. We want to build it out in the country, and we’ve already started planning for it financially. Ask yourself seriously, is this still the dream? Talk about it as a family, and then use those financial resources in whatever way you think is the most valuable for you.

Most of all, never, ever stop dreaming. Your dreams of writing made The Simple Dollar possible and has (hopefully) led to some great writing opportunities over the last decade. Don’t stop. Listen to what your heart is telling you and do it. You should be close to complete financial freedom now – take that leap and just run with whatever it is that’s in your heart.

One final thing: she still wants to go on that Bahamas trip, you know. See if you can leave the kids with her parents for a week or two and just go. It will probably be the best thing you guys have done since, well, your honeymoon.

Best wishes,
Your twenty nine year old self

No matter where my life goes between now and then, the contents of that letter will mean something when I read it again in 2018.