Desk Departure USA

When it’s worth being crazy to travel

Chicago beach skyline

“You’re crazy.”

That’s what they told me. “They” being nearly everyone I encountered and shared my plan with.

The plan: Work all day Friday. Come home to a family party hosted at my house. Leave around midnight to drive 311 miles from Metro Detroit to Chicago, solo.

“But what about your family party?”
What about it? I’ll be there. I won’t miss it. I’ll leave when it ends, regardless of the time.

“It’s dangerous for a girl to drive alone in the middle of the night.”
Nobody will even be on the road. It’s dangerous for a anybody to do a lot of things.

“You’re going to be exhausted.”
I’ve got coffee and adrenaline. Plus I can pull into a rest stop if I get THAT exhausted…

“What if you get lost?”
I won’t. GPS and road signs.

“But you’ll be all alone.”
I’ve got my podcasts and sliced nectarines to keep me company.

“Did you bring your pepper spray?”
Of course, if you insist.

“It’s such a far drive!”
Maybe, but I’ve driven double that distance solo.”

I understood their concern. I understood that everyone cared for me and my safety. I cared too. Nobody would be more careful and conscious than me. There was no way in the world I was missing a family party. There was no way in the world I was missing wedding dress shopping in Chicago for my friend. Sure, the timing of the two may not have been the most convenient, but when has travel been about convenience?

Trust me — I wouldn’t do it if I didn’t think I could. Drive 5 hours in the middle of the night to Chicago? Yes. Run a half marathon? You’ve gotta be kidding me.

But it was difficult to channel their concern away from self-doubt. Every “you’re crazy!” manifested into second-guessing my capabilities. Am I crazy? Can I really do it?

Of course I can.

A little encouragement and reassurance would have gone a long way. I guess you can say I relied on my own personal drive to make the drive. Pun definitely intended.

But no words of concern jarred me more than this comment: “Why are you doing this? It isn’t worth it.”

Wait. What?

Sure, I suppose that prepping a whole week for a big family party, and only getting a few hours of sleep before working all day, hosting said party, and driving straight through the night to Chicago is a bit intimidating or peculiar, but not once did I even question whether it was “worth” it.

Chicago penthouse skyline

Glittering views from a downtown penthouse.

Every late hour on the road was worth putting in the hours at work.
Every late hour on the road was worth spending time with family at a party we hosted at our home.
Every late hour on the road was worth crashing on my friend’s couch at 4 am and waking up to my college friends eating homemade breakfast casserole.
Every late hour on the road was worth watching my best friend try on wedding dresses.
Every late hour on the road was worth laughing until I cried.
Every late hour on the road was worth spending time with some of my best friends who had been dispersed around the country and somehow ended up being together during the same weekend in the Windy City.

So was it worth it?
The answer is an astounding yes. At least for me it was. It might be slightly crazy to some people. But it’s definitely definitely without a single shadow of a doubt, worth it.

Then I thought deeper about the comments I received. What I heard as concern from others was a bigger reflection of what I hear about weekend trips, or travel in general.
Through their concern, I was given permission to make excuses.

Excuses like:

“I’m worried about my personal safety.”
“I don’t want to travel alone.”
“I have to work.”
“I have family obligations.”
“I need time to get sleep.”

All excuses I could have made when others were trying to convince me that I’m crazy.

You see, travel isn’t always simple fun. Sometimes it takes a little bit of sacrifice and a little bit of grit to make it happen. Sometimes you need to give up your early bedtime to wake up in a new city. Sometimes you need to make the journey alone to arrive at a destination of friends. And most of the time, it’s worth it.

Chicago Friends

wedding dress shopping in Chicago

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  • Aaron Cruz

    Can definitely relate. Drove overnight from Charlotte area to middle Michigan quite a few years back. Had to get back for an event. I had been visting family. I did that so I could maximize family time down there. Didn’t give it a second though. On a side note I’ve driven to Chicago on a whim just for pizza then driven back. People thought I was nuts haha. :)

  • I’ve made plenty of crazy trips like this myself – it’s almost ALWAYS been worth it!

  • I LOVE this! So inspiring. I’ve been on the other end of “crazy” for long drives/late excursions, but even then, it’s difficult to justify doing it all by myself. I’m challenging myself to try more and live more freely!

    • And P.S. – that Chicago photo is AMAZING!

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