Writing Your Future Self a Letter of Intent

I was working on a new project (it’s going to be great, and will facilitate group/class situations with YNAB in a very powerful way) and came to the realization that every decision you make now affects the future.

Well, duh.

Okay that was part of it.

The other part was me browsing on the app store and seeing an app that would age you. You take a photo of yourself, then say that you want to see yourself 35 years from now (I’d be 66). Laughter ensues of course.

Unless the old person staring back at you is scowling. Or glaring. Or man, what if they’re crying?

It was a trifecta of circumstances I guess, because the third idea rattling around in my brain had to do with an HBO special on Obesity (you can watch it free online). About halfway through the second hour they talk about how once you’re obese, if you lose the weight, you’ll always have to eat less than a person of equivalent weight that was never heavy.

So we’re talking about an irreversible situation based on a collection of choices you made in the past.

Seeing a picture of myself a few weeks ago at my son’s party, undergoing a strenuous hike on Saturday (where I was seriously sucking wind), and watching that “Weight of the Nation” HBO documentary has made me more aware of the choices I’m making now, and how they’ll affect that 66-year old man staring back at me. Hopefully giving me the thumbs up.

You Should Write a Letter to Future You. And Sign It.

Obviously this isn’t a fitness blog, though I sometimes wish it were 🙂

But think about what you’re doing with your money, and how that’s going to affect Future You. Could you write a letter to your 30-years-older self and explain your strategy? Explain how what you’re doing now is going to set Future You up for a life that will hopefully be healthy, fulfilling, and debt free? One where you’ll be able to afford the things you love? One where you’ll have enough to visit the grandkids, maybe travel a bit, and finally finish restoring that classic car?

Mine might look something like this:

Hey Jesse+30 years,

First off, you look good. Julie is as lucky to have you now as she was 30 years ago.

With that out of the way, let’s get down to business. As far as I know, we have five kids. If there are tons more that you know about, that I don’t at the time of this writing… then man, I don’t know what I was thinking. At the moment, I sure feel like five is enough.

Kids’ School

With five kids, college funding is a big question mark. In my heart of hearts I’m hoping for the upheaval of the higher education system by scrappy upstarts that push online education to the forefront. As blogs did to newspapers, I’m kind of hoping the internet will do to crazy-sky-high tuition rates.

But, since we can’t bank on that, I want you to know that I’m working hard with the kids and we’re making their education a top-priority. Scholarships will have to happen in order for all of them to get their degrees. I’ve also been setting some money each year in a 529 plan. It probably won’t be enough, but it will certainly help.

Hey, since my youngest should now be 30, if she’s still in school, we have a problem. She’s the baby of the family but man, you gotta cut her off.


The house is paid for, and all the kids are gone. My plan is for you to downsize, brother. Part of that house is retirement income so let it go and get something smaller that’s cheaper to heat and cool. If you now have a mortgage, then I’m extremely ticked off right now. Because I worked my tail off so you wouldn’t have a mortgage. I’m sure you don’t. You’re a sharp guy. So yeah, downsize and free up some of that equity.

Health Care

I’m going to start an HSA here very soon and will put money in that every year. We will not pull from that account. I’m going to let it grow tax-free, so you can pull from it tax-free and use it for who knows what. Hopefully it’s something awesome like replacing the bones in your legs with adamantium. I’m sure that’s possible by now.

I know this isn’t money-related, but I’m also going to try really hard to keep exercise a part of my everyday routine. Hopefully at the time of this letter you can bust out 30 pull-ups at the drop of a hat, deadlift 2x your bodyweight, and nail a few muscle-ups. This stuff’s important because Julie’s impressed by it.

Just Livin’

I’m doing my best not to leave you in the lurch, cash-flow wise. We both know how much Julie spends (I kid Julie+30 years, I kid!).

I want you to be able to visit the grandkids, travel a little bit, serve in the community, etc. I don’t want you to have to work if you don’t want to. But I do want you to stay involved and busy. Anxiously engaged. That type of thing.

So as far as cash flow goes to fund your modest lifestyle (which includes golf and an awesome gun collection), we’re maxing out our 401k. The business also does a match. Hey, what version of YNAB are you on now? We’re on 3 here. Is the business still doing fine?

I’ve invested the funds in a target-date fund for 2045. So at this point, it should be fairly conservative. Lots in bonds, not too much exposure in stocks, etc. My mentality for these next 30 years will be to invest and forget about it.

Hey, should I buy a share or two of Facebook?

Warm Regards,

Jesse-30 years.

P.S. Are you still driving the 2002 Honda Civic?

Remember that person 30 years from now. Are you doing your best to give them the best life possible? Or are you throwing them under the proverbial bus?

It’s a tough thing, to think about the future when everything around us tries to get us to think about the Now, or the next five minutes. Operating with Rule One, where you have some priorities outlined for the 30-years-older version of yourself, might give you just the clarity you need, to cut through the Now Pressure and set yourself up for the future.