39 Days Out and No Plan

In 39 days, I’m supposed to go to Minnesota with my daughter, Toria, and my granddaughter, Zoe. Zoe is going to be the flower girl in a friend’s wedding, and I agreed to come along to help with her so Toria could enjoy the wedding.

We have no hotel reservations.
No plane tickets.
No plan.

And for me, that causes stress, anxiety, and worry.

Will there be flights available? What will they cost at this late date?
Will the hotel still have vacancies? Why are we this close to a trip—and still acting like it’s optional?

A Flashback to Another Plan-less Trip

This isn’t the first time I’ve faced a trip without a plan.

One summer, early in my relationship with my now-husband, we decided to go camping in West Virginia. Gear packed, food loaded up—we hit the road. Thing is, we had no reservation, no destination.

I remember him saying, “We don’t need a reservation—we’ll find a place when we get there.”

Hours later, after dark, we still hadn’t found a single campsite with a vacancy. This was before GPS and smartphones, and we were running out of options. Tired, hungry, and frustrated, we finally called Pipestem Resort—a place I had visited as a kid. They had a room available, so we booked it and stayed there for the night.

The next day, we finally found a campground.

Glenn was unbothered. Me? I was irritated, exhausted, and seriously questioning how people live without plans.

Planners and Floaters

There are planners and there are floaters.

Me? I’m a planner. Or at least, I used to be. The kind who would panic over a change in plans—or need time to recover from a sudden shift. Then I met Glenn. Divorced like me, three kids to my one, and absolutely allergic to structure. Glenn doesn’t do plans. He doesn’t even like rules. He’s the type to say, “We’ll figure it out when the time comes.”

So now, we’re headed to D.C. with friends in June. We’ve booked the Airbnb—but not having every detail nailed down three months out? It made me twitchy. The what-ifs spun in my head like a carousel.

But here’s the thing: every feeling, every situation, is an opportunity to learn and grow—if we’re willing to look at it.

So Here I Am: 39 Days Out

We’ve known about this wedding for at least six months. Not one conversation. Not a single plan.

How did I let this go?

Maybe I thought it would change. Maybe I assumed Toria wouldn’t actually go. I mean… taking a two-year-old across the country to be a flower girl? That felt like a stretch—and a big expense.

Or maybe, as my friend often says about Toria, “Just wait a day, and things will change.”

But here we are. Thirty-nine days out, and nothing has changed.

The Shadow Side of Planners and Floaters

And maybe it’s not just about this trip.

Let’s be honest—there’s a dark side to both planning and floating.

Why People Become Planners (The Shadow Side):
• Control as a shield – Fear of chaos makes them over-plan to feel safe.
• Fear of failure or judgment – If things aren’t perfect, they’ll be blamed.
• Lack of trust – After being let down, they’d rather just do it all themselves.

Why People Become Floaters (The Shadow Side):
• Avoidance of responsibility – No commitment means no accountability.
• Fear of decision-making – Better to leave it open than get it wrong.
• Learned helplessness – “What’s the point in planning? Life just happens anyway.”

I used to be labeled controlling. But the truth is, I like knowing what’s happening. Planning saves time, money, and stress. And I’m good at it. A natural leader.

So why did I abandon that part of myself?

A Hard Truth: Self-Abandonment

Here’s the deeper truth:

My daughter is a floater. I’m a planner. We’re supposed to go to a wedding in 39 days and there’s no plan. And the truth is… I don’t even want to go. But I said yes.

And I’ve been sitting in a fog of dread, wondering how I, the lifelong planner, got stuck in someone else’s way of doing life.

Because this isn’t just about a wedding.

This is about how easily we let go of what we need to keep the peace. To not be difficult. To go along.

And suddenly, we’re 39 days out from something we never wanted in the first place—without a plan, without clarity, and without ourselves.

As I sat with this, I started seeing it everywhere. Other places I was self-abandoning.

The Woman I Used to Be

Back in the day, by now, I would’ve planned the outfits, mapped the days, chosen restaurants. I probably would’ve had it all in an Excel spreadsheet.

But somewhere along the line, I left her behind. I thought it was better to go with the flow. I live with floaters—it just seemed easier.

But how does that feel now?

Who am I really?

Midlife or Monthly Wakeup?

I’m 55. Shifting how I dress. Reclaiming parts of myself I hadn’t realized I’d left behind. We’re living in a house that, on paper, makes sense to stay in—but part of me still dreams about a different space. A new chapter.

I’m involved with the family business, and I’m good at it. I’m proud to support what keeps us going. But at the same time, I’m building something of my own—leaning into my writing and the creative work that calls to me.

Back in the day, they’d call this a midlife crisis. But for me? It’s more like a monthly check-in. A situation shows up, and I choose to grow through it—if I’m paying attention.

The Text That Terrified Me

Yesterday, scared to death and heavy with guilt, I texted my daughter:
I’m not going to Minnesota.

And while it felt like the right move, I was instantly afraid.

What will this do to our relationship?
How will she manage without me at the wedding?
Will she be mad? Disappointed? Will she feel abandoned?

But here’s the truth I’m finally learning:
She’s an adult now. Capable. Resourceful. Fully able to make her own decisions and handle the outcomes.

The Real Question

And as I unravel this, I’m seeing it more clearly:

Did I stop planning because others let me down too often?
Because I was told to “go with the flow”?
Because I was taught not to be bossy or take up space?

Who am I now, and what do I want?

Can I handle the disappointment of others if it means staying true to me?

That’s the work now. That’s the question.

And it’s taken 55 years to be willing to ask it—out loud, and without apology.