Boldness as a Trainable Skill
Fortune favors the bold, not the brilliant — and boldness is a muscle you can build.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 90%
Jennifer Cohen argues that the real secret to success is boldness, not brilliance, athleticism, or good looks. Crucially, she reframes boldness as a skill anyone can learn rather than a personality trait you're born with. Like building physical strength, boldness is a muscle developed through consistent practice of small bold moves. Each small win compounds into confidence, and confidence into more boldness over time. The through-line across every successful person she knows is that they went after what they wanted instead of settling.
Origin
Cohen was labelled 'average at best' by a teacher and never saw herself as smart, talented, or athletic. Over her journey from an Olive Garden greeter to a celebrity fitness trainer, she realised that boldness — chasing what she wanted rather than accepting what she got — was the secret sauce behind every pivot in her life.
Core principles
- 01Boldness, not intelligence or talent, is the differentiator for success.
- 02Boldness is a skill like karate or a language — practiced, not inherited.
- 03You are not born bold; you build boldness through repeated small acts.
- 04Momentum compounds: each bold win fuels the confidence for the next.
- 05You can be bold without being rude — it's how you say it, not what you say.
How to run it
- 1
Reframe boldness as a learnable skill
Stop treating boldness as an inborn trait. Accept that, like any skill, it can be practiced and improved regardless of how shy or timid you currently are.
Pro tip Use the fitness analogy: you don't get strong from one gym visit, and you don't get bold from one brave act.
- 2
Start with tiny bold moves
Practice on low-stakes asks — request salad dressing on the side, ask for a discount — specifically because they don't matter, so you can build the habit without fear of consequences.
Pro tip If you can't ask for the little things, you'll never be comfortable asking for the big things.
- 3
Do it consistently to build the muscle
Perform bold moves daily so the behaviour becomes a trained muscle rather than a one-off. Consistency, not intensity, builds the skill.
Watch out One bold act won't make you bold for life any more than one workout makes you strong for life.
- 4
Stack the wins into momentum
Let each successful bold move give you the confidence to attempt the next. Small wins accumulate and compound, and something in motion stays in motion.
Pro tip Track your wins so you can see the momentum building.
In the wild
At 12, Cohen wanted a job but was too young to work where alcohol was served. Instead of babysitting like her friends, she walked in and proposed a role standing outside the restaurant as a greeter, opening doors, so she was technically off-premises and legal.
→ The manager, taken aback that a kid invented an opportunity, gave her a shot — her first proof that boldness creates options others don't see.
Cohen prescribes practicing boldness by asking a restaurant for salad dressing on the side — a trivial request that makes many people deeply uncomfortable — purely as reps to build the asking muscle.
→ By rehearsing low-stakes asks, people build the comfort needed to ask for the bigger, higher-stakes things later.
Common mistakes
Believing you're either bold or you're not
Treating boldness as a fixed, all-or-nothing trait stops people from ever practicing it. You can be bold in one area of life and timid in another, and any area can be trained.
Confusing bold with rude or aggressive
People avoid boldness fearing they'll be mean or bitchy. Boldness is taking ownership of what you want and how you act — it's about how you say it, not being overtly rude.
Is it for you?
Best for
Shy, timid, or self-doubting people who want to ask for more in their careers and relationships.
Not ideal for
People genuinely content with the status quo who feel no pull toward change.
From the transcript
“the most important thing for success in anything... it's boldness. is and was the secret sauce for me to get me from where I wanted…”
“I think boldness is a skill. Like anything else, if you want to become good at karate or Spanish or whatever you want, you need…”
“You can be bold and not be rude. You could be bold and not be bitchy.”
From the episode
Jennifer Cohen: Bigger, Better, Bolder. How to Get the Life You Want by Being Bold
Jennifer Cohen