Small Business Toolbox: Plan Backwards
- 17 hours ago
- 3 min read
A Letter From My Future Self
Start Backwards
Most financial planning tools ask you to start with today. What do you earn? What do you owe? What can you save this month? These are important questions. But they’re the wrong place to start.
If you don’t know where you’re going, it’s hard to make decisions about how to get there. Should you hire that person or wait? Take the loan or not? Pay yourself more now or reinvest? These feel like financial questions. They’re actually vision questions in disguise.
That’s why we use a simple exercise with the small business owners we work with: a letter from your future self.*
The idea is straightforward. You write a letter — not to anyone else, but to yourself today, from the version of you that exists ten or fifteen years from now. That future self describes their life: where they live, who they’re with, what the business looks like, what they’re proud of, what they had to overcome to get there.
It sounds soft. It isn’t. Done honestly, it surfaces the things that actually matter to you — which are often different from the things you spend your time and money on today.
AN EXAMPLE
Dear Carmen,
Hello! This is your Future Self, 58 years old. I’m currently working in catering — but now we mostly do corporate contracts and I have a manager who runs the day-to-day. When I’m not working, I enjoy cooking for fun, which sounds funny, but it’s different when nobody’s paying you. I live in the same neighborhood because my mother is here and that matters more than I used to admit.
The business employs seven people, most of them women from the neighborhood, which makes me most proud. Our sales are around $800,000 a year. What got us here was finally accepting that I couldn’t do everything myself — and hiring a bookkeeper before I thought I could afford one.
To get where I am now, you had to overcome the feeling that asking for help meant you were failing. You did this by joining a peer group of other business owners and realizing everyone was struggling with the same things.
The very best part of my life is Sunday dinners. I have time for them now.
Sincerely, Your Future Self
Carmen wrote that letter in about twenty minutes. Then talked through it.
She had written down $800,000 in revenue almost without thinking — but she had never said that number out loud before. She had written “seven employees, mostly women from the neighborhood” and then got a little quiet. That sentence told her something about why she was doing this that her profit-and-loss statement never would.
And the part about the bookkeeper? She had been putting that off for two years.
The letter didn’t give Carmen a financial plan. But it gave her something a financial plan can’t give you on its own: a reason to make one.
We use this exercise as the first step in our financial health work with small business owners because the numbers mean more when they’re attached to something real. A savings goal is easier to stick to when you know what it’s for. A hard decision is easier to make when you know where you’re trying to go.
Try it.
Set a timer for twenty minutes. Print the form below and write the letter. Don’t edit yourself.
Then look at what you wrote and ask: what would I have to do differently this year to make that future more likely?
Download the
*Exercise adapted from the U.S. Consumer Financial Protection Bureau (2024).
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