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Throwing Your Hat Over The Wall

There are a thousand and one reasons not to do it.

What’s that? Take on something big, challenging, scary, and all-encompassing in your life or your business.

You know, there’s nothing wrong with settling into a routine and getting comfortable, but when you feel called to do something BIG, you feel called to do something BIG.

And there’s that moment when you’re waffling back and forth. Should I take this on with all the demands I know it’s gonna put on me or should I pass entirely … or wait for a more auspicious time?

Well, my experience is that it’s really easy for people to wait “until they’re ready.” Ha. That’s like waiting for the perfect time to have a baby. You know, when it won’t be too disruptive. Yeah, right. I understand the motivation and yet, there’s never really a convenient time to turn your life upside down.

So, what do you do in that moment when you know that you could play the waiting game forever?

You throw your hat over the wall.

It’s an expression that many attribute to John Fitzgerald Kennedy’s grandfather. (That’s where the name Fitzgerald came from.) He and his pals would walk along a tall stone wall in Ireland on their way home from school and as kids will do, they dared him to try to climb over the wall. The wall was imposing and scary. He decided the only way he could ensure that he’d not only take on the challenge, but complete it, was to throw his hat over the wall, so that he’d be committed to retrieving it. The hat was part of his school uniform and he couldn’t come home without it.

Think of the importance of that story for JFK, a guy who declared that “before this decade is out, we will send a man to the moon and return him safely.”

The only problem? The guys who’d have to make it happen had no idea at that point how to do it. That’s throwing your hat over the wall in a big way.

I know the phrase from my work with Landmark Education, an organization whose programs I highly recommend. It’s one of the distinctions they created that made all the difference for me in making the commitment to leave my good paying secure job with benefits and start my own coaching business. And it continues to inform my decision-making today.

Just recently, a new client, another Landmark alumnus, said to me, very matter-of-factly, that he was ready to throw his hat over the wall with regard to a new direction for his business, and it got me thinking again about how important this concept is.

How do most of us approach taking risk? The safe way. Let me give you an example. We coach a lot of folks who want to use speaking to build their businesses, as I’ve done. We suggest the following approach to them when it comes to booking speeches.

Decide on two topics you want to speak on that will appeal to your target audience. Write up a one-paragraph description of each, and create a few brief bullets that say what the audience will get out each speech. Then call the people who book the speeches to see which one sounds like the best match for their group. Once someone is ready to book the speech, then create it.

This freaks some people out. They’d rather know they have something created and polished before they make calls. They aren’t ready to toss their hats over the wall. But think about it. You think that speech won’t get created if someone says, yes, we’d love to have you come to our September 10th meeting? Hardly. Otherwise, it might never get done.

And, if you think that’s a scary proposition, consider this. We have an actress/playwright/screenwriter friend who booked an off-broadway theater for the production of her own one-woman show before she ever wrote the thing! Now, that isn’t throwing your hat, that’s hurling your hat over the wall.

That’s how you do big things in life. When that moment arrives, you take a deep breath and either walk away, because you know it isn’t right or isn’t in you … or you commit. No in between. You throw your hat over the wall and you follow it.

Safe risk taking is an oxymoron.

You just gotta go all in 100%.

Best wishes,


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Meet Denise: Denise Hedges is a Business Development Coach and Speaker Coach for small business owners who want to be more comfortable, confident, and successful with their sales and marketing efforts. She specializes in helping them use speaking as a way to dramatically improve their results!