You will lose people you love.
You will lose money, some of it through mistakes you could have avoided.
You will lose a business or a job, friends who stop calling, and years you spent chasing the wrong thing. If you live long enough, you will bury your parents. If you don’t, they will bury you.
Nobody gets out of this.
The richest man you can name will watch his friends die. The fittest woman at your gym will one day need a hand to get out of a chair.
Most people know this and still build their lives around dodging pain; they skip the hard call, the risky launch, the honest talk, the mountain. They think they’re buying safety; really, they’re buying a slower, less owned, and less controlled kind of pain, and they pay more for it in the end.
You can’t choose whether you feel pain.
You can choose when you pay, how much you pay, and what you get back.
Run the numbers
You start ten businesses over your career. Six lose money. Three limp along. One works and pays for the other nine.
You can’t buy the winner on its own; you buy all ten because, at the start, you can’t tell which one will win. Founders who quit after the first two failures never reach the tenth.
Sales lives and dies by the same math. Make a hundred calls and ninety people tell you no. Ten say yes, and those ten pay your rent. You don’t get the ten without the ninety. The folks who make three calls, hear three nos, and decide sales “isn’t for them” have paid for three rejections and collected nothing. They felt the pain and quit before the payout.
Most people judge a loss by how they feel on the day. Judge it by what it buys you over a hundred tries.
Never shrink the sting
The first time a prospect hangs up on you, you’ll replay it all evening.
By the fiftieth hang-up, you’ll forget it before you dial the next number. You haven’t stopped caring; you’ve given your brain enough data to stop treating a no as a threat.
Athletes, comedians and salespeople all know this. Comedians bomb at open mics for years before they build a good set. Tennis players lose hundreds of matches before they win one that counts. They don’t learn to like losing. They learn to lose faster, with less drama, and then get back to work.
You’ll publish your first fifty posts to almost no one, and you’ll hate half of them a year later. The writers who keep going past fifty write better at post one hundred than they did at post ten, and they care less when readers ignore a post.
You can do the same with any pain you choose.
Pitch more, publish more, ask more.
You’ll hurt less with each round, and you’ll get more back.
Two kinds of pain
You’ll face two kinds of pain.
You choose the first kind: the workout, the cold pitch, the hard talk with your cofounder, the month you spend learning a skill you’re bad at. You pay up front, and you know the price.
You don’t choose the second kind. You get fired. Your partner leaves. A client who brings in 40% of your revenue walks. Your doctor calls with test results. You don’t pick the timing, and you can’t haggle on the price.
People who avoid the first kind still get the second. They just meet it weaker. The founder who never learned to sell loses her biggest client and has no idea how to replace him. The man who skipped the gym for twenty years gets bad news at fifty and has no strength to recover with.
You train for the pain you can’t choose by choosing pain on purpose.
Practice losing
Seneca, the Roman Stoic, told his friend Lucilius to set aside a few days to live on the cheapest food and the roughest clothes he could find, and to ask himself whether this was the thing he’d feared. Tim Ferriss has pushed the same idea for years and runs his own version of it.
You fear most losses because you’ve never tried living without the thing. So try. Pick something you think you can’t do without (your phone after 8 pm, your car, takeaway, your morning coffee) and go without it for seven days.
After seven days, you’ll know what the loss costs you in practice, not what you imagined. Most people find they guessed far too high. They also find they think about the thing far less by day five.
Try it with money too. Live for one month on half your income and bank the rest. You’ll learn how much you could cut without missing anything, and you’ll know your number if a big client ever walks.
Fear-setting
Take the decision you’ve put off longest, the one you keep “thinking about.” Grab three sheets of paper.
On the first page, draw three columns.
Define. List everything that could go wrong if you do it. Be specific. “I lose $40,000 and have to take a salaried job for a year” beats “it fails.”
Prevent. Next to each item, write what you could do to make it less likely.
Repair. If it happens anyway, write what you’d do to fix it. Who would you call? How long would you need to get back to where you are now?
On the second page, write what you’d gain from trying, even if you only half succeed. What skills would you pick up? Who would you meet?
On the third page, write what you lose by doing nothing for six months, a year, and three years. Include money, health, relationships, and how you feel about yourself.
The third page is the hardest. We’ve priced the pain of acting down to the dollar and set the pain of waiting at zero. You pay plenty for waiting. You lose three years. You lose the lessons you’d have learned from failing. You lose the second attempt, the one you only get after the first one fails, and the one you often win.
Pay early, pay small
You pay less for most pain when you pay it early.
You can have the awkward pricing talk with a client in month one, or the angry one in month twelve, after you’ve resented them for a year.
You can fire the wrong hire in week three, or in year two, after they’ve trained five people to work the way they do.
You can tell your cofounder you want out now, while you still like each other, or later, through lawyers.
You can see a doctor this month about the ache you’ve had since spring, or wait until you can’t sleep through it.
You feel the loss either way. You only choose how much interest you pay on it. Founders who make the hard call early lose a little. Founders who wait lose a lot, and then lose the same thing anyway.
The losses you can’t fix
You can’t run a framework on some losses. You lose a parent. You and your partner end a fifteen-year marriage. Your kid gets sick.
You can’t fear-set your way past grief. You can’t optimize it or pay it early. You go through it.
You can still do two things.
First, run the math on the people you love while they’re here. Tim Urban at Wait But Why ran it on his own parents. If you see yours twice a year and they have twenty good years left, you’ll see them about forty more times. Most people who run that number pick up the phone that week.
Second, admit now that you will lose them. People who look straight at a coming loss don’t hurt less when they lose someone, but they often have fewer regrets, because they said what they wanted to say and showed up while they could.
What to do this week
You’ll lose things whatever you do.
You can at least choose some of the losses and get something back for them.
Start with these five:
Collect ten nos. Make ten asks you expect people to turn down: a raise, a podcast spot, a discount, a meeting with someone you think won’t take it. Count the nos. Note how many yeses you get anyway.
Give up one comfort for seven days. Pick the thing you’re sure you can’t live without.
Run fear-setting on the decision you’ve put off longest. Give it thirty minutes and a pen.
Do the parent math. Count the visits you have left, then book the next one.
Have one talk you’ve dodged for more than a month. Do it this week, while it costs you the least.