When A Habitual Overplanner Is Winging It

Back when I was single, traveling was easy.

I’d book a trip with my friends and lob clothes in a suitcase the night before departure. At best, I’d pick up a new swimsuit and fresh sunscreen, but that would be it – if there was anything I desperately needed and forgot, I’d buy it at my destination. My only priorities were getting to the airport on time and making sure my passport was up-to-date. Travel guides can be read on airplanes, after all.

And then I had kids.

My motto soon became “be prepared”, just like the boy scout I never was. I researched everything, learned all the secrets, the places to see, the things to miss. Winging it as a singleton was fine. Winging it with a couple of toddlers in tow was disastrous, particularly when you have kids who thrive on structure.

Soon enough, decision-making became fraught with frustration because I’d dig too deeply and come up with too many options. Making decisions for small, relatively unimportant (in the bigger scheme of things) things became harder and harder.

Now, one of my goals for this year is to reclaim order and organization in my life. When spring break loomed ahead I lobbed a long pass at a friend who is starting out as a travel agent. “Find me something warm, not sell-a-kidney expensive, and a short flight from Texas.”

She sent me options from a few places in Cancun, and by golly we chose one that day because apparently, everyone had the same idea as us and rooms and flights were being bought up like there might be a travel ban looming. Done. Take my money,  just don’t make me plan.

I lectured the family that THIS year would be different. THIS year I would not be scurrying around at the last minute, picking up things they forgot they needed. They WOULD try on swimsuits and shorts, and I would NOT be shopping like a madwoman.

I have been to Target 752 times in the past week and a half.

I do not exaggerate.

My daughter today tried on the swimsuit that I bought her on February 6th. It did not fit. She will squeeze her skinny backside into an old suit.

I also took my son to buy “nice” shoes, as he owns trainers and cleats, and a pair of sport sandals.
Today. He’s been asking for a pair of preppy boat shoes like his cousins and I was elated to think he might have something nice, finally, so drove him to DSW as fast as I could. (He bought a pair of Vans, instead.)

We leave tomorrow.

Do we have round trip transportation to the hotel? <I think so.>

Do I have everything we need packed? <I don’t care.> “Do you have underwear, swimsuits, a coverup and a toothbrush? Yes? You’re fine.”

I have made a quick check though the bags. I have my Kindle, a few paperbacks, swimwear, sunscreen and my camera. I’m good.

Everyone else pulled their clothes on their own and brought them to me to shove in a suitcase. I didn’t actually check what they packed. I saw underwear and swimsuits, so as far as I’m concerned, they’re good.

I don’t even know who I am, but  I DO know that for the first time, I WILL get to bed before 11pm tonight, all while finishing one load of stinky soccer gear from today’s game.

This is me, winging it.

This is me – also knowing that there is also a Walmart in Cancun…



  1. Relax. Have fun. They can all deal.

  2. Relax. Have fun.

  3. Oh my gosh, I love this post! I am the same way, and when our kids were younger, I eventually migrated to winging it with the kids/spouse and left their packing up to them. BUT, it still seems that I am the one fully responsible for everything related to our house being empty. Plants, yard, pets, mail, newspapers, pool? It’s not like we can just walk out of the house and it will tend itself. Makes me want to sell the too big place we are living in (mostly empty nesters except when we’re not and one or two or all five decide they’re just going to “hang at home” for a few days/weeks/months.). Just glad that in spite of all the hurdles, you are getting away! Enjoy, relax, and I hope there are no Walmart trips in Cancun!

  4. Gmom Phyl says

    I love it!! What ever you did, you are all having fun!

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