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Milwaukee's Daily Magazine for Thursday, Oct. 2, 2014

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Cooperstown road trip in 1999: an early bucket list fill up.
Cooperstown road trip in 1999: an early bucket list fill up.

Don't forget to fill those buckets

I am an extremely fortunate person, and an even more fortunate Milwaukeean. By founding OnMilwaukee.com at such a young age – I was 23 at 1998 – I’ve had too many amazing experiences to count. Almost every opportunity to do something cool in this city has been at my disposal, and I never forget that, even when I’m having a bad day at work.

But becoming an entrepreneur in my early 20s also presented some challenges. I never had the chance to backpack around Europe. I haven’t taken one of those long, detached vacations where you turn off your brain and stop checking your email. I had to take the decade more seriously than most of my peers, because running your own business is serious business.

Throughout this time, however, I’ve made it a priority to cross items off my bucket list. Visiting Cooperstown to see Robin Yount inducted into the Hall of Fame; driving my own car on the Autobahn at 135 miles per hour; hanging out with the Violent Femmes post-show; flying above Milwaukee with the Blue Angels, and much, much more.

One more bucket list item, though, awaits me this weekend, and just in time. On May 27, I’ll turn 40, and I’m not overly excited about this milestone. Three days later, one of my oldest friends, Eron Laber, also hits the big 4-0. To commemorate it, we’re finally doing something we’ve talked about for years: hitting all the Brewers’ minor league teams in one weekend.

That’s right; this afternoon, we’re driving to Beloit, then Montgomery and finally to New Orleans to catch road games of the single-A Wisconsin Timber Rattlers, double-A Huntsville Stars and triple-A Nashville Sounds. It’s a ton of driving in a very short time.

Eron and I haven’t taken a road trip like this in many years, probably since we decided to actually drive to Phoenix for Brewers Spring Training (another bucket list item) in 2000. We have to give major props to our wives for being OK with this trip, because they’ll be single parents while we speed south to Bourbon Street on Saturday night.

And of course, there is a work component to this trip. I’ll interview players at each stop and return with a great feature article. But this is certainly mostly about having fun the weekend before we turn 40.

Because, as I’ve learned, no one is going to fill your bucket list for you. If you don’t take the opportunities, and sometimes force them, they don’t happen. And all you’re left with is regret.

Like I said, I’ve been extremely lucky. I’ve seen most of what I set out to see. And I’m looking forward to filling that bucket again this weekend. Even if I have to drive a few thousand miles to do it.

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