If you want to know how long I’ve wanted to own a weekender bag I will tell you. It’s been 9,033 days.

I was standing on the corner of 83rd and Lexington when I saw a woman who was definitely not Carolyn Bessette Kennedy walk out of a building and stroll down the street to catch the jitney which would whisk her off to the Hamptons where the young, rich, and beautiful engaged in their seasonal mating ritual. Or something.

I have no idea because I’ve never been on the jitney. And the reason I’ve never been on the jitney is clear: I did not have a weekender bag. I had luggage. And only a boob would take luggage to a weekend in the Hamptons.

 
Approximately 550 days ago, my friend K rolled into Porto with a pink carry-on that turned my head so fast that all my hair fell out. Because you and I both know what that bag was except what you don’t know is that it was seriously called, “THE WEEKENDER.” Like, not as a category of bag. That was its First Letter Capitalized Proper Name.

Well, I had questions.

Questions that started with where did she get it and ended with how much did it cost and within minutes, my questions were answered and I. Was. Satisfied.

I mean, not satisfied enough to actually go and get one for myself.

Please. I like to stalk my prey before I pounce. There’s a reason my friends call me Stealthy.

 
OK fine. Nobody has ever called me Stealthy.

What I do answer to is Woman Who Enjoys A Prolonged Evaluation Period.
Because for 550 days I have been “evaluating” this bag. Picturing myself strolling through the airport with it, exuding all of the airs of casual, yet chic and faintly otherworldly. Imagining strangers smiling at me and bartenders winking and waving my credit card away while bringing me unlimited bloody marys with mini hamburgers on top because a Weekender Woman has got to eat.

I spent entire evenings debating whether I wanted the Classic Weekender or the Mini. I lost days to considering whether the citron was too fluorescent or the black was too basic. The Weekender went on sale. The sale ended. Discount codes came and went while I hemmed and hawed and could. Not. Make. A. Decision.

 
Until 9 days ago, when I did what I’ve been saying I was going to do for over 9,000 days: I opened a new tab, emptied my cart of all but the Beige (which I prefer to call White Sand because come on, Béis, we can do better—feel free to reach out for more suggestions) and I bought that sucker. I may have then clapped my hands because I believe in celebrating all the wins.

2 days ago, The Weekender appeared at my door in the arms of a man who wore a red baseball cap. And I was so out of my mind excited that I was freakishly able to have an entire conversation with him in Portuguese. I mean, the words just flowed from my brain to my lips like I was born to the language and I was like, OMG! Who am I right now!

I’ll tell you who I am.

I am someone who finally made a decision.

After 550 days of hemming and hawing.

Not because I didn’t want the bag. But because I wanted the right bag.

The right size. The right color. The right amount of “who’s that girl” as I walked through the airport.

And I didn’t want to make the wrong decision.

So I looked.

I compared.

I reconsidered.

I waited for the moment where I would just know.

 
As it turns out, that’s often what’s going on when we delay making decisions about what to do with all of the stuff we’ve got shoved in our closets.
All the stuff in there that makes it impossible to get to your contact lenses without knocking over all the lotions.

The stuff forcing hand-to-hand combat with your toilet paper to get your suitcase out of the closet.

The stuff making the simplest things feel hard.

 
You’re not exactly confused about what to do to fix it.

You’re definitely not lazy.

You’re just hanging out in the quiet hope that if you wait a little longer, think a little harder, and look at the red leather culottes that haven’t left your closet since the Obama administration a few more times, then the right answer will reveal itself. And you’ll never have to risk the regret of making the wrong call.

So you move things around. You buy some cute bins. You tell yourself you’ll deal with it when you have more time, more energy, a better plan.

You dance instead of decide.

You can live a long time in the suburbs of Someday. Unfortunately, they aren’t serving bloody mary’s with mini hamburgers over there.

 
When I finally clicked “buy,” I let go of the possibility that I will ever walk through an airport with a bag that probably glows in the dark and I said: “Beige. This is the one.”

And just like that, it was done.

Not because the right answer suddenly came to me, but because I was tired of waiting and wondering and waffling. I had enough information to make a thoughtful, reasoned choice and trust it.

 
At some point, you’ve thought enough and looked enough and know enough to stop circling.

At some point, more thinking isn’t helping you decide better. It’s just keeping you from deciding at all.

At some point, Stealthy, you have to pounce.

 
Your friend who now apparently speaks fluent Portuguese,
Vivian

 
P.S. If making decisions about your stuff feels harder than it should, you don’t have to do it alone. This is what I do. I help smart, capable women decide what stays, what goes, and whether the red leather culottes still belong in their lives. I work with women all over the world over Zoom. Book a free intro call here.