Daily Picks
← Back
Life & WorkWESTENBERGJA Westenberg2026-10-08

You can't avoid the pain, but you can pick when to pay for itThe Pain Is Coming. Choose When You Pay.

Loss is unavoidable, but the timing of the bill is negotiable: choosing pain early costs far less interest than letting life collect it later.

You will lose people you love. You will lose money, some of it through mistakes you could have avoided. You will lose a job, friends who stop calling, and years spent chasing the wrong thing. Live long enough and you bury your parents; not long enough and they bury you. Nobody gets out of this.

Most people know it and still arrange their lives around dodging the ache: they skip the hard call, the risky launch, the honest talk. They think they are buying safety. What they are buying is a slower, less controlled kind of pain, and they pay more for it in the end.

Run the numbers

Start ten businesses over a career. Six lose money, three limp along, one works and pays for the other nine. You cannot buy the winner on its own — you buy all ten, because at the start nobody can tell which one wins.

Sales runs on the same arithmetic. Make a hundred calls and ninety people say no; the ten who say yes pay your rent. You do not get the ten without the ninety.

So do not judge a loss by how it feels on the day. Judge it by what it buys you over a hundred tries.

The kind you cannot choose

Pain comes in two kinds. The first you pick: the workout, the cold pitch, the showdown with your cofounder. The price is known and you pay up front.

The second kind picks you: the layoff, the partner who leaves, the doctor's call. People who dodge the first kind still meet the second, only weaker — the founder who never learned to sell loses her biggest client and has no idea how to replace him.

So choose some pain on purpose, as practice for the pain you cannot choose. Pick one thing you think you cannot live without and go seven days without it, to see what the loss actually costs.

Pay early, pay less

The same loss costs less interest if you pay it early. The awkward pricing conversation with a client can happen in month one or month twelve, after a year of resentment. The wrong hire can go in week three or in year two, once they have trained five people to work their way.

Some losses have no framework — a parent dies, a marriage ends, a child gets sick. Those you walk through. Two things are still possible: while people are here, count how many visits you have left; and admit now that you will lose them.

In the end, pain is a bill that cannot be dodged. The only question is whether you pick when to settle it, or wait for someone to collect it with interest.

Why it matters

Most people treat endurance as free, and so book the cost of not deciding at zero. This one puts a price on waiting: the year you stall costs not just money but the second attempt that only a first failure earns you — and the second attempt is often the one that wins.

Share to
Read the originalWESTENBERGThe Pain Is Coming. Choose When You Pay.

You might also read

5 articles worth reading every day

Curated from high-quality sources, with concise summaries and key takeaways.

Daily Picks

5 articles worth reading every day

Curated from high-quality sources, with concise summaries and key takeaways.