10-Attempt Target
Build boldness by making ten attempts at what you want most
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 96%
The 10-Attempt Target treats boldness as a skill built through deliberate repetitions. Choose something you want, then commit to ten attempts rather than making success on the first try the test of your ability. Begin with small, ordinary asks to strengthen the behavior before escalating to larger opportunities. Each attempt has two possible benefits: it may produce the desired result or reveal an unexpected opening along the way. Repeated exposure also makes rejection feel less exceptional and therefore less painful. The target shifts attention from an outcome you cannot fully control to a practice you can complete. After ten attempts, review the responses, opportunities, and increased comfort with asking instead of judging the exercise solely by whether the original goal was achieved.
Origin
Jennifer Cohen describes the idea as central to her book and TED Talk, using ten attempts to pursue a desired outcome while becoming more comfortable with failure and rejection.
Core principles
- 01Boldness is a learnable skill, not an inborn trait
- 02Small asks prepare you for consequential asks
- 03Repeated rejection reduces its emotional sting
- 04Attempts create opportunities even when the original goal is missed
- 05Trying is preferable to lasting regret
How to run it
- 1
Choose the target
Name the outcome you want most and can pursue through clear requests or actions. Keep the target specific enough that an attempt is observable.
Pro tip Choose a target that matters enough to justify ten genuine tries.
Watch out Do not use persistence to override another person's boundaries or a definitive prohibition.
- 2
Start with a small ask
Practice on a low-stakes request, such as asking a service provider whether a better package is available. Use the small move to get comfortable initiating an ask.
Pro tip Pick an everyday request you can make immediately.
- 3
Plan ten attempts
List ten distinct, legitimate ways to move toward the target. Count actions you take, not favorable responses from other people.
Pro tip Vary the channel, person, or formulation instead of repeating one identical request.
Watch out Ten attempts are practice, not permission to pressure the same person ten times.
- 4
Make the attempts
Carry out each action while accepting that rejection is part of the exercise. Move to the next attempt rather than treating one no as the end of the process.
Pro tip Record the attempt as complete before evaluating its outcome.
- 5
Review every opening
After ten attempts, assess whether you reached the target, became less sensitive to rejection, or uncovered another opportunity. Use those observations to choose the next target or refine another round.
Pro tip Include indirect opportunities in the review, not only the original yes-or-no result.
Watch out Do not label the practice a failure solely because the original target was missed.
In the wild
Someone who rarely asks for anything starts by calling their cell phone provider and asking whether another package could save money or offer a better plan. The call is deliberately low stakes: its purpose is both the possible saving and one repetition of initiating a request. Whether the provider says yes or no, the person has practiced the behavior needed for larger asks.
→ The caller either improves the plan or gains a completed boldness repetition without serious downside.
A professional wants a larger role but normally waits to be noticed. They define ten legitimate attempts: asking for a stretch assignment, requesting feedback from several leaders, proposing a small pilot, and approaching relevant collaborators. Some requests are declined, but one conversation points them toward a different project that better demonstrates their ability.
→ The attempts reduce avoidance and create an opportunity that was not visible at the start.
Common mistakes
Making success the only score
Judging the exercise only by the original outcome ignores the increased tolerance for rejection and unexpected opportunities created along the way.
Starting with the hardest ask
A high-stakes first attempt can reinforce avoidance. Build momentum with a small everyday request before escalating.
Confusing boldness with pressure
Being willing to ask does not justify rudeness or repeated pressure after a boundary has been set.
Is it for you?
Best for
People who avoid opportunities because they fear hearing no or believe boldness is innate.
Not ideal for
Situations where repeated requests would violate boundaries, consent, rules, or professional norms.
From the transcript
“boldness is a skill like anything else”
“a really easy step is to pick something really small that you do every day like your cell phone like calling yourself service provider and…”
“making 10 attempts at whatever you want most”
From the episode
Episode 320: How To Become Bolder