Choose what you’re going to fail at today.
That sounds like irresponsible advice. Most of us spend our days trying to prevent failure, not schedule it. We double-check the email, soften the question, delay the call, and wait for more certainty. If we are careful enough, maybe we can get through the day without being told no, looking foolish, or discovering that we aren’t as ready as we hoped.
Chris Voss recently shared the story of a man who deliberately chose five things to risk failing at each day. Then he wrote down what every miss taught him.
He wasn’t choosing five ways to cause damage. He was choosing five meaningful attempts whose outcomes he could not control. That’s a very different thing.
A failure quota sounds backward until you realize it is really an action quota with the ego removed.
Sales makes this easier to see. At a dealership, we measure calls because a call is controllable and the result is not. A salesperson can dial the number, follow up, ask a useful question, and invite the customer to take the next step. He cannot order another human being to answer, trust him, show up, or buy.
That uncertainty makes avoidance attractive. A salesperson can’t hear “no” on a call he never makes. His record remains clean. Unfortunately, his month usually does too.
The scoreboard may say he avoided rejection. The calendar says he forfeited an opportunity.
The same trick applies outside the showroom.
A writer who never shares the work can’t be rejected by the readers. A manager who keeps postponing a difficult conversation can’t mishandle it today. A person considering a career change can’t be passed over for a job he never applies for. In every case, doing nothing protects us from an immediate loss while quietly guaranteeing that nothing new can happen.
Avoidance protects the record by forfeiting the season.
I understand the instinct because I am good at finding responsible-looking ways to obey it. There’s always an email that needs answering, a report that could be improved, a drawer that suddenly deserves organization, or another hour of research that feels almost like movement. Safer errands do not announce themselves as fear. They arrive wearing work clothes.
Once, I even ended a good relationship because I didn’t want to risk it becoming bad. But that’s a separate post altogether.
That’s why a failure quota can be useful. It exposes the difference between being busy and being available for an outcome you cannot control.
The quota doesn’t require five disasters. It might mean making the calls you have been avoiding, sending the application before you feel perfectly qualified, asking for the opportunity, letting somebody read the draft, or beginning the conversation that has been living rent-free in your head. The purpose isn’t to collect rejection for its own sake. The purpose is to make enough honest attempts that rejection no longer has the power to organize your life.
There’s another benefit to recording what each miss teaches you. Failure stops being a verdict and becomes information. The customer’s objection sharpens the next conversation. The unanswered application reveals where your résumé or network needs work. The confused reader shows you where the writing is not yet clear. The hard conversation teaches you which words opened the door and which ones closed it.
None of this means every attempt is wise. Repetition doesn’t excuse sloppiness, and courage is not the same as recklessness. A good failure quota still requires preparation, judgment, and a willingness to adjust. It simply refuses to let perfection become the price of participation.
At the end of the day, five unsuccessful attempts may look like a bad day on paper. But compare it with the day spent circling every risk and accomplishing only what could not reject you. One produced bruises and information. The other produced a full schedule and no evidence that fear was ever challenged.
The goal isn’t to become comfortable with losing. It’s to become more loyal to the work than to the image of yourself as someone who never misses.
If rejection belongs to the work, put it on the calendar before fear fills the day with safer errands.
