Get Crazy and Bring Someone Along With You


I write this on Sunday night. The wind is howling through the trees and rattling the windows in cottages all around the Mackinac Straits. In 9 hours, 50 swimmers will enter the Straits to swim the four mile distance from the Upper Peninsula of Michigan to Mackinaw City in the Lower Peninsula. Hopefully the wind will diminish and allow the white caps to settle and smooth, so the swimmers can enter. Even if the waters calm, the currents beneath will make the four mile swim in 60-degree waters seem much further.

Why do it? The answer, a bit like the classic answer to climbing Everest? Because it’s there! That’s what Carole McAlvey, 51 year old mother of four told me. She said every time she has driven across the massive bridge, which celebrates its 50th year this year, she has thought, “I wonder what it would be like to swim it?” I continue to believe there ought to be something similarly CRAZY and wild in all leadership. I suspect the best personal leadership is always born with “crazy” questions: Why do we have to be at war? Why can’t we end slavery? How come our office doesn’t recycle? Why does my mom have to use drugs? Who says we have to tolerate racism? Why shouldn’t I run for mayor and make things better? How come no one sells a ___ that . . . ? Why don’t our schools have . . . ?

Years ago Jim Dreyer wondered: Why can’t I swim across Lake Michigan, and Erie, and Huron, and Superior – and Superior – and Superior – as he tried multiple times and was pulled out half-dead from the unforgiving, frigid and forceful waters. He finally survived the Superior crossing, and a new question occurred to him last year. He wondered: Why is it just me swimming for Big Brother Big Sister? Why don’t I get others to join me? And so this time he recruited 50 swimmers to cross the Straits of Mackinac, all raising at least $500 for “the Bigs.” He now expects his “Dire Straits Team” will raise around $40,000.*

So, on this Labor Day, here are two questions for you: First, what wild objective are you not pursuing? Dreyer risked drowning, hypothermia, kidney failure, you name it, 100 times – to “just do it” (and to raise money for BBBS, but Jim, you know there were easier ways to do that!). So, what are you not doing cuz you think you might sink or drown? And how real is your fear? Second, what great stuff are you trying to do on your own, when others could help? I asked Jim where the fifty swimmers came from. He said, “crazy people like me usually have crazy friends, so that’s where the first of the fifty came from. And then they had other circles of “crazy” friends.” The help you need is probably similarly right around you!

As Margaret Mead wrote: “Never doubt that a small group of thoughtful, committed citizens can change the world, indeed, it’s the only thing that ever has.”

You’ve got be a little crazy and find a few friends, if you’re going to

Lead with your best self,

* (It’s not too late to contribute:

Members of Dire Straits team hearing final instructions from Captain Dreyer 

Preparing to take the plunge! 

  • Crazy? Paris-Brest-Paris! Twelve hundred kilometers, seven hundred forty-five miles (actually 745.65 – but who’se counting), in an elapsed time of 90 hours or less, on a bicycle. A sixty-fourth birthday present to me and a fundraiser for adoption. The date? Third week of August every fourth year. The next one? 2111. The training already started. Any takers?


  • I can’t agree with you more. About nine years ago, I saw a commercial for the Make-A-Wish Foundation. I looked into how I might get involved with them. I decided I would participate in their 300 mile bike ride, which is done over 3 days, always the last weekend in July. The first year I rode myself, met some great people, who motivated me through that first year. At the end of the 3 days, I was greeted by the wish child, who I was raising money for that weekend and, by about 100 other wish children, who were sponsored by other bikers that weekend. It was an incredible experience. I shared that experience and pictures of my wish child, with those who had sponsored me. Year 2, my team (3 or more riders) had 6 bikers. Year 8, which was this year, our team had 86 bikers and, our team (Team W.O.W.) raised over $132,000. I have told my fellow bikers that this was my last year for riding. Believe it or not, I am not a biker and, my training hours are limited. I am not sure if I will be able to really not ride this next year but, I know that the team will continue and, I will support them. It is amazing what you can accomplish, if you just give yourself a chance and be a little “crazy”. There are other “crazies” out there just looking for an opportunity to get on that ride with you.

  • Hey Dan-

    This is Becky O…I met you before the swim and as I was the first girl to finish:) You totally helped me accross the rocks. Thanks so much for making the day so great, it was great to meet you and Jennifer and you little guy. I was so honored to have been part of this team and making history in michigan. As Jim will tell you I am huge on the way fitness can change a persons life. I attached the link to the tri team site that I coach. Although that has changed a little. The weekend before the swim I finished my third Ironman:)

    Anyway, I just wanted to say thanks so much. I am also doing Ironman again in April in Arizona, and this past year I did it for 2 nonprofits…I will be doing Arizona this year as an Adopt and Athlete helping a school to see the benefits of physical fitness and also chosing to raise money for the Marin Foundation and I am thinking of maybe doing it for Mentor Michigan.

    Let me know what you think.

    Thanks so much and have a great day. Give Jennifer and your son my thanks too.

    Becky O

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