One Bold Move a Day
Do a single deliberate bold act every day for 30 days to rewire the habit.
- Difficulty
- Starter
- Time to result
- ~days to results
- Steps
- 3
- Confidence
- 82%
Cohen's most actionable prescription is to make one bold move a day for 30 days. The moves start trivially — asking for a discount, salad dressing on the side — precisely because low stakes let you practice the asking muscle without fear. The reps build comfort, and comfort with small asks transfers directly to bigger, more consequential ones. She frames it as her single actionable takeaway: start acting bold with one deliberate move each day.
Origin
When asked for one actionable thing listeners could do, Cohen prescribed one bold move a day for 30 days. She illustrates it with a friend who spent six months asking everywhere for local discounts, turning the practice into a game.
Core principles
- 01Small daily reps beat rare heroic acts.
- 02Practice on things you don't care about to lower the stakes.
- 03Asking is a repeatable behaviour that gets easier with reps.
- 04The byproduct of asking often exceeds the original goal.
- 05Comfort with small asks unlocks comfort with big asks.
How to run it
- 1
Commit to the 30-day challenge
Decide to make exactly one bold move every day for thirty consecutive days to build the habit.
- 2
Start with low-stakes asks
Choose small requests you don't really care about — a discount, a menu change — so fear of the outcome doesn't stop you.
Pro tip Doing it when you don't care removes the pressure and makes the rep pure practice.
- 3
Escalate as comfort grows
As small asks become easy, progressively ask for bigger things where the outcome actually matters.
Pro tip Notice the byproducts — the friend who asked for discounts saved $7,000 without that being the goal.
In the wild
A friend of Cohen's spent six months asking everywhere he went — coffee shops, clothing stores, movie theatres — whether there was any local discount available, purely as a test of what happens when you ask.
→ He discovered discounts nobody knew about and saved roughly $7,000, and, more importantly, became completely comfortable asking for anything.
Common mistakes
Waiting for a big moment to be brave
People skip the daily reps and wait to be bold only when it counts, so they never build the underlying muscle and freeze when it matters.
Only practicing on high-stakes asks
Jumping straight to consequential requests keeps fear high; starting on things you don't care about is what makes practice sustainable.
Is it for you?
Best for
Beginners who want a concrete, immediately actionable way to start building boldness.
Not ideal for
People already comfortable making high-stakes asks who need advanced challenges.
From the transcript
“They can start acting bold by doing one bold move a day for, for the... 30 days.”
“He saved like $7,000 in six [months]. By just asking the question... It was a test to see... what happens when you ask”
From the episode
Jennifer Cohen: Bigger, Better, Bolder. How to Get the Life You Want by Being Bold
Jennifer Cohen