I Wrote Down a Hundred Million Dollars and My Wife Called Me Dude
I Wrote Down a Hundred Million Dollars and My Wife Called Me Dude
The night before we recorded this, Jana and I emceed the Love Moves the World Gala for Chair The Love.
She calls it a gala. I call it a gala. We have been married a long time and we have never once agreed on how to say that word, and neither of us will move, and at this point I think the disagreement is load-bearing.
It was a good night. A room full of people doing what Jana described as defying gravity with their hands, which is a generous way of saying they kept raising auction paddles. We raised a ton of money. Possibly half a ton. The accounting on that is still open.
But standing up there watching people give money away on purpose put me back in a room from several years ago, in Tennessee, where this whole thing started with a sentence I had no business writing.
The week in Tennessee
Jana and I spent a week with our coach, Berta Medina of Dreamers Succeed. Not a workshop. A week. A deep dive on where we were going, personally and as a business, and — the hard part — on getting one vision out of two people.
I should explain how we handle that, because it's the reason the rest of this happened.
We don't believe in compromise. Compromise is where two people each give up a piece of what they actually wanted and shake hands in the middle, and what you end up with is a life that's smaller than either person was aiming at. Both of you lost and you're calling it maturity.
What we do instead is each write the whole dream down. All of it, unreduced, out loud, on paper. And then we get creative enough to make the two of them meet upward — into something better than either of us would have built alone.
That is significantly more work than compromise. Compromise takes an afternoon. This takes a week in Tennessee with somebody who won't let you off the hook.
The centennial exercise
Coach Berta had us do an exercise.
Jana calls it the centennial exercise. It's the centenarian exercise. She has called it the centennial exercise every single time it has come up for several years running, including on the podcast, and I have corrected her every single time, and we are both fully committed to our positions. Centennial is a hundred years. Centenarian is a person who's a hundred years old. I understand why this is confusing. I also understand that I'm going to be correcting it at my own funeral.
Here's the exercise. You pretend you're a hundred years old. You look back across the whole marriage. And you write a letter to the other person about what you're proudest of having done together.
So we each wrote one.
One of my lines was that I was so proud we gave away a hundred million dollars to charity.
Jana read it and her mouth dropped open. She looked up at me and said, dude. You are living in dreamland.
It was the first time in our entire marriage she had ever called me dude.
And she wasn't being unkind. She was being accurate. We did not have a hundred million dollars. We did not have a plan that produced a hundred million dollars. We did not have a path to a plan. I had written down a number with no mechanism attached to it, in a letter, pretending to be a very old man.
She'd also never heard me say it before, which is the part I didn't think about at the time. I had never said it out loud. I'd never been asked what my dream was in a way that required an actual answer, so I'd never produced one.
Why that number
People assume the big number is a motivation trick. Write something audacious, scare yourself into action, go earn it.
That's not what was happening.
Here's what was actually underneath it. I know we all get a limited amount of time here. And I'm going to be forgotten. Not in a dramatic way — in the ordinary way that everyone is. I wrote a book so that something would live past me. Then I wrote another one. And they might live forever. They might also end up in a landfill and never get published again, and nobody would be at fault for that. That's just what happens to most books.
A trust doesn't go in a landfill. Something that keeps giving after you stop being around to administer it doesn't depend on anybody remembering your name.
That's the math I was doing. It came out as a hundred million dollars, and it came out in a letter from a hundred-year-old man, because that was the only setting in which anyone had ever asked me the question in a way I couldn't duck.
Then the phone rang
Here's the part that surprised me most, and it's the opposite of how I'd have told the story if I were making it up.
We didn't go looking.
Chair The Love found us. They came across the Facebook Lives Jana and I were doing at the time — the ones that eventually turned into this podcast — and they reached out and asked Jana to come speak for them.
And then they said something I thought was exactly right. They said: in order for you to speak to our CEOs, we'd like to send you on a distribution trip first. Go be an ambassador. Go hand somebody a wheelchair.
Know what you're talking about before you start blowing out your blowhole.
So we went. Mexico first. Then Nicaragua. We filmed the first one and put it on YouTube and it's still one of our highest-performing videos, which tells you something about what people actually want to watch.
Between the trips, we have personally put a little over 550 people into chairs.
Living Lucky® Practice
The Centenarian Letter
You're a hundred years old. You're writing to the person you've spent your life with, looking back across all of it.
Don't write what you think you're supposed to be proud of. Write what you'd actually be proud of. Nobody reads this but the person you hand it to.
01 What I'm proudest of, looking back.
Five or six things. Write past the obvious ones. The fourth and fifth are where it gets interesting.
02 The line that surprised me.
Something came out that you didn't plan to write. That one. Put it here by itself.
03 What's on my calendar this week that didn't make the letter.
Some of it has to be there. Some of it won't survive the comparison.
04 One unreasonable thing I'm doing this week.
Toward the line from step two. Small is fine. Sensible is not required.
The honest math
Five hundred and fifty wheelchairs is not a hundred million dollars.
It isn't close and it isn't on pace. Measured against the sentence, I'm failing badly.
But I wasn't going to do any of it. And now I've done some of it. And the sentence is the only reason why.
That's the real use of a goal that size. Not that you hit it. That it makes the small, comfortable, reasonable version of itself look like nothing. If my line had been I want to give generously, we'd have written a check at Christmas, felt good about ourselves, and that would have been the end of the story. There was no sensible first step available for a hundred million dollars, which meant the only step left was an unreasonable one, and the unreasonable one is the one that moved.
What came back sideways
Jana's wheels have custom art covers on them. She makes them. She's made over a hundred of them now — gifted a bunch, had two hung in an art gallery, and she builds them for sponsors, which means she's rolled a sponsor's logo onto three different stages, across the starting dock in Australia, and up to the podium five times at the World Championship in adaptive water skiing.
That whole thing started on a wheelchair distribution trip, when Glen Mather — the CEO of the foundation — looked down at her wheels and said, I think you've got a business here.
He wasn't the person she was there to help. He had nothing to do with why we went. He just looked at her chair and said the thing, and his saying it is what made her take it seriously.
That's how it tends to come back. Not from where you sent it. From somewhere off to the side, later, usually from a person who had no idea they were returning anything.
The ten minutes
The other thing that came back sideways was an education, and Jana got it by keeping her mouth shut.
Distribution trips involve a great deal of bus. Long rides, rough roads, hours with nothing to do. And the people who fund this work and keep coming back year after year tend to be financially free. So Jana sat on those buses and didn't speak, didn't ask questions, and just listened to people talk about real estate development and investing and how they actually structure things. Not a seminar. Just what those people talk about when there's nothing else going on.
One habit kept showing up. In the morning, over coffee, they'd check out of the conversation for about ten minutes, look at their investments, and then come back and pick their coffee up. Sometimes once more before the market closed. That was it. The rest of the day was theirs.
I'm not telling anyone to go trade options. We're not qualified to advise anybody on that and it's a fast way for an inexperienced person to lose real money.
The transferable part isn't the instrument. It's the ten minutes. Measure it briefly, on purpose, at a set time — and then put it down and go live. Most people run the exact opposite program, which is to never look at it and worry about it constantly. That's the worst available combination and it's the most common one.
Why contribution gets you unstuck
Every one of these threads started with us feeling stuck at some point, and here's what I've noticed about being stuck.
Every instinct points inward. Think about it harder. Analyze what went wrong. Figure yourself out.
And it doesn't work, because the thing that's stuck is the same thing you're using to get unstuck.
Going and doing something for somebody else breaks it almost immediately, and not for mystical reasons. You physically leave. You end up around different people. Your attention gets handed a problem that isn't yours. That's the whole mechanism and it's enough.
You cannot ruminate about your business while you're lifting somebody into a chair. There's no room for it.
Where the formula sits in all this
Run it back through the four questions and you can see the shape of it.
What do I want to experience? Giving away a hundred million dollars in my lifetime. Written in a letter, by a hundred-year-old, because that's what it took to get it out of me.
How do I want to grow? Into the person who could do that. Which meant learning things I didn't know existed — on buses, from people I'd never have met otherwise.
How do I want to contribute? We kept meeting people who needed a chair. I can do that one. That's not abstract.
How lucky am I? That's the fertilizer. It doesn't decide what grows, it just feeds whatever's already in the soil, which is why it matters a great deal what you've got planted.
Four questions, interwoven. That's the Living Lucky® Luck Activation Formula, and this entire story is one long answer to it.
The Living Lucky® Practice
Exercise: Write the letter. You're a hundred years old, looking back, writing to the person you've spent your life with — or to yourself, if that's who it is. What are you proudest of?
Reflection question: What would my hundred-year-old self say about what's on my calendar this week?
Journal prompt: What's the small, comfortable version of my real goal that I've been quietly settling for?
Action: Take the most unreasonable line in your letter and do one thing toward it this week. It does not have to be sensible. Sensible is what's been stopping you.
Frequently asked questions
What is the Centenarian Letter exercise?
You imagine yourself at a hundred years old and write a letter to your spouse or partner looking back at what you're proudest of having done together. Evaluating your life from its endpoint tends to surface what actually matters to you and makes this week's worries look about the size they really are.
Why write down a goal that seems impossible?
Because a reasonable goal has a reasonable first step, and a reasonable first step is easy to put off forever. A goal with no sensible entry point forces an unreasonable action instead, and the unreasonable action is usually the one that changes something.
Does writing a goal down actually do anything?
Writing it is the cheap part and it isn't magic. What it does is make the goal statable — which means other people hear it, and some of those people turn out to be able to help build the road. The sentence does nothing by itself. It makes a lot of things possible.
How does helping other people get you out of your own rut?
It moves your attention off a problem it's been circling without result, and it physically changes where you are and who you're around. That shift does more than any additional amount of thinking about yourself.
What financial habit is worth copying from financially free people?
Brief, deliberate measurement. Check your position for a few minutes at a set time, then stop and go on with your day. The common alternative — avoiding your finances entirely while worrying about them constantly — costs more and produces nothing.
Do I need a coach to do this exercise?
No. The letter takes twenty minutes and a piece of paper. Doing it with somebody who then reads yours is what makes it uncomfortable enough to be useful, and a spouse or a good friend covers that.
Jana says the whole thing is the circle of life. She's not totally sure she's got the words right. She's fairly confident the Lion King didn't either. The part she's sure about is the opening: somebody holds you up and points you in a direction.
That's all the letter did. It held the thing up where I could see it.
We Create Our Luck®.
Hear the full conversation on the Living Lucky® Podcast with Jason and Jana Shelfer — Season 11, Episode 42: "We Plan To Give Away $100 Million." Listen to the audio, watch the video broadcast, and tell us what your hundred-year-old self would thank you for starting today.
