At a Fond du Lac County orchard, market – a ‘Little’ goes a long way
Family Roots Greenhouse – rooted in family, friends and plants
December 1, 2025
I sat in the audience recently watching 10 entrepreneurs walk across a stage to pitch their ideas.
Two awards, 10 brave souls and a spotlight on people who likely would have preferred to be anywhere else.
Because here’s the thing: for most of these folks, public speaking is not their thing.
Pitching in front of a crowd – not how they usually spend a Thursday night.
But there they were anyway.
Mic’d up.
Spotlight on them.
Speaking passionately about the dreams they’ve been building in garages and coffee shops and spare bedrooms.
And I realized: this is what stepping into the arena actually looks like.
Not quote-worthy.
Not Instagram-polished.
Just people doing the uncomfortable thing because they believe it matters.
Theodore Roosevelt gets a lot of credit for his “Man in the Arena” speech – the one about credit belonging to the person “marred by dust and sweat and blood.”
It’s framed nicely and quoted a lot, but most people are still choosing the sidelines.
Not because they don’t want to grow, not because they don’t believe in themselves, but because there’s a gap between knowing you should step up and actually doing it.
And that gap?
That’s the real work.
I’ve coached leaders long enough to see this pattern clearly: You can train someone on every leadership skill in the book, but training someone and having them actually use what they’ve learned are two different things.
There’s something in the middle – something between knowing and doing.
That something is what separates people who grow from people who just attend workshops.
Start with what actually matters to you
I talk to a lot of people who’ve chosen a goal based on what they think they “should” want.
The title, the salary band, the achievement that looks good on a LinkedIn profile – and it never sticks, not really.
Here’s what I’ve learned: If the goal doesn’t spark something real for you, you won’t do the uncomfortable work it takes to get there.
Not when things get hard.
Not when it would be easier to stay where you are.
Pick something that would genuinely change your confidence, your relationships at work, your business, your life.
That spark is what carries you through.
Stop believing your work speaks for itself
I hear from emerging leaders all the time: “If I’m ready for the promotion, they’ll ask me,” or, “My work speaks for itself.”
I used to believe that, too.
It cost me opportunities I didn’t even know existed.
Your work does matter – but it doesn’t automatically translate into visibility.
Leaders aren’t ignoring you – they’re assuming that if you want something, you’ll say so.
Your silence looks like satisfaction from where they’re sitting.
The most practical, courageous step-into-the-arena moment might just be saying: “I’d like to be considered for that opportunity.”
That’s not pushy – that’s clarity, and leaders respect clarity.
Take steps forward, not leaps off cliffs
Reasonable risks look like: presenting before you feel perfectly polished.
Volunteer to lead a project that stretches you.
Ask for feedback you know might sting.
Speak up about your goals.
Applying for something that scares you just a little.
These aren’t leaps off a cliff – they’re steps forward, and forward is what matters.
You don’t have to have it all figured out to move.
Build your support system before you need it
No one succeeds alone – not in leadership, not in business and not in life.
You need a mentor who tells you the truth kindly.
A peer who’s growing, too, and isn’t threatened by it.
A boss or leader who knows where you want to go.
A friend who reminds you to rest, breathe and not lose yourself in the grind.
The people who last are the ones who know they don’t have to do it alone.
Who’s on your team?
And more importantly – who are you showing up for?
A different arena altogether
If you own a business, especially in a community where you know people and people know you, you’re playing a different game.
Your arena might be competing for a grant that could actually change your business, even though the application process feels overwhelming.
Pushing past that voice that says you’re not cut out for public speaking, pitching or promoting.
Taking on one more responsibility when you’re already juggling payroll and marketing and literally sweeping the front steps.
And here’s what I want you to know: Sometimes that opportunity that feels like “one more thing I don’t have time for” is actually the one that breaks the bottleneck.
That grant might let you finally hire help.
That pitch could connect you with exactly the right partner.
That extra responsibility could unlock the solution you’ve been looking for.
Business owners step into arenas every single day without even realizing that’s what they’re doing.
Give yourself credit for that – courage matters.
Compete with yesterday’s version of you
One of the most freeing things you can learn as a leader or business owner is this: You’re not competing with anyone else – you’re competing with yesterday’s version of yourself.
Instead of comparing yourself to others, ask yourself: Am I more confident than I was 90 days ago?
Am I communicating more clearly?
Am I delegating tasks instead of hoarding them?
Am I having the tough conversations sooner?
Am I stretching instead of shrinking?
Those small changes compound faster than you think.
That’s not about perfection – that’s about progress, and progress is everything.
So, here’s my question for you: What’s the arena you know you need to step into next?
Not someday.
Not after you feel ready.
Not after the fear stops talking.
Now.
This week.
This month.
The people who grow – the ones who move up, build strong businesses and create meaningful change in their communities – aren’t the ones waiting to be invited.
They’re the ones who step in.
Dusty shoes, imperfect plans and all.
They’re the ones who figured out that the gap between knowing and doing gets closed by taking one small step.
And then another, and then another.
As for those 10 entrepreneurs on stage that night?
I’ll be watching them.
Some will succeed spectacularly.
Some will struggle.
Some will win and then hit a wall they didn’t see coming.
That’s how it goes.
But I’m hoping they keep stepping into the arena anyway.
That they don’t let one setback convince them to go back to the sidelines.
Because the people who change things aren’t the ones who get it right the first time.
They’re the ones who keep showing up even when it’s messy.
That could be you.
And I’ll be right here in your corner, cheering you on.
