The Price for Playing Small
Most entrepreneurs don’t fail because they lack talent. They fail because they lack courage.
Most entrepreneurs don’t fail because they lack talent.
They fail because they lack courage.
Courage is the multiplier. The “brass balls” factor. The guts to raise your hand, raise your prices, and raise your standards.
And the marketplace? It takes you at your own appraisal. If you undervalue yourself, everyone else will happily agree.
Where Playing Small Shows Up
Let’s be brutally honest. Playing small doesn’t always look like fear.
It often hides behind good behavior:
Charging “reasonable” fees so you don’t scare clients away.
Saying yes to clients who aren’t a fit because you “need the revenue.”
Accepting the stage you’re invited to instead of asking for the stage you want.
Here’s the kicker: the market rarely pushes back on smallness. No one argues when you undercharge. No one complains when you over-deliver for free. No one stops you from working yourself into the ground.
But the cost? Massive. You erode your authority. You blend in. You get clients who see you as a vendor, not a trusted advisor.
A Story From My Own Playbook
Years ago, I was sitting across from a potential client, quoting a fee that made me sweat. I had practiced the number in the mirror because even my own face didn’t believe it yet.
I said it anyway. Straight-faced. Calm. Quiet.
And you know what happened?
They said yes.
That moment taught me two things:
The market doesn’t pay you what you’re worth — it pays you what you ask for with conviction.
If no one ever flinches at your price, you’re charging too little.
It wasn’t my talent that shifted that day. It was my courage.
Courage Compounds
Bold moves stack.
The first time you raise your prices, it’s terrifying.
The second time, it’s liberating.
By the third time, you wonder why you ever accepted less.
The first time you fire a misaligned client, you worry about revenue.
The second time, you feel relief.
By the third, you realize problem clients were costing you more than they paid.
Courage compounds like interest. Each bold decision buys you leverage for the next one.
Check Out Dr. Dorothy Martin-Neville and what she has to say about working with me in my 8 week accelerator! Even an accomplished coach, can take some great takeaways from spending time in a group all doing the work of raising the game!
The Real Cost of Playing Small
Let’s call it out:
Playing small keeps you stuck at the $100K–$250K plateau.
Playing small fills your calendar with busywork instead of bold moves.
Playing small means you’ll never build authority, because authority requires audacity.
Every entrepreneur I know who broke through to half a million or more did it the same way: they asked for more. More money. More opportunity. More respect.
And they didn’t wait for permission.
The Challenge
So here’s my challenge to you:
What’s the one bold ask you’ve been avoiding?
Raising your prices by 30%?
Asking for the stage instead of waiting to be invited?
Saying no to a client who drains your energy?
Pick one. Do it this week.
Because the only thing standing between you and your next level isn’t another funnel, or another course, or another marketing hack.
It’s the courage to stop playing small.
Final Word
Entrepreneurship rewards the bold. Not the most talented. Not the most qualified. Not the ones with the longest list of credentials.
The ones who step up, look the market in the eye, and say: “This is what I want. Take it or leave it.”
So — what’s your bold move?
This is the work we do inside my ecosystem every single week — helping entrepreneurs stop playing small and step into their next level. If you know you’re ready for that kind of bold move, get in the room. Start here →