Adding this one item to the top of my to-do list changed everything

Making a plan and planning to fail

This newsletter is about my midlife reinvention in progress. It’s me rescuing myself from drowning in other people’s expectations (and maybe throwing a line to you too).

How not to plan

The other night, on a group Zoom, the facilitator suggested we use mind maps to think about our writing goals. She shared an image of a cluster of overlapping thought bubbles. “I like these shapes because they remind me of clouds,” she said.

“Clouds?” I glanced at the screen to make sure no one caught my eye. Heads were nodding across the grid of tiny boxes.

I thought of the PowerPoint file “2024 Goals” open on my laptop—all bullet points, tables, and infographics. There was not a cloud in sight.

Mt. Batty summit at sunrise, looking over Penobscot Bay, Camden, Maine 2019. Photo by Catherine H Palmer (moi!)

But first, a confession

Last fall, I wrote a post about my self-management style—how my life wizard told me that the plans and list-making I used in my business career inhibited my intuition. Since then, I thought I was, I don’t know, cured. I’d uninstalled planning apps like Trello, given up spreadsheets, and torn up the weekly aspirations I used to post above my desk.

But when

Alana Kirk

of “Your Midlife Matters” commented on that post, noting she used a “colour-coded Trello board,” my mind sped into multi-task mode—searching for my Atlassian password while configuring the perfect rainbow-shaded project plan.

I tapped a heart onto Alana’s comment, then replied in a way I hoped didn’t sound as smug as I think it does now, ‘I rely on my intuition as my guidance system.”

That was a bit of bullshit.

I’m a planner by birth and by training

Before I took my first step down the reinvention road, I made a list. My January to-dos looked something like this:

• Train the dog

• Reach 1,000 Instagram followers

• Learn to make donuts, knit, code, play the guitar, etc.

• Plant a garden

• Write a book

• Raise chickens

• Paint the bedroom

Lacking ideas was not my problem, but would fresh tomatoes, a crooked scarf, or a well-behaved dog help me build the life I wanted to lead in my third chapter? Did I even know what that looked like?

And yet, month after month, I grew increasingly frustrated. “I haven’t done anything!” I’d whine to Felix, who repeatedly reminded me, “There’s no pressure for you to do anything.” 

If I didn’t tick all the boxes—this was my thinking—I was failing. Five years later, not one of those items is complete, but all, save one, have been crossed off.

I was trying to be SMART

In 2018, I had a secret blog. Secret only because I’d told no one about it. I wanted it to be perfect before sharing it with the world (i.e., my 113 Instagram followers). And because list-making and planning are every perfectionist’s procrastination go-to, I opened PowerPoint and got to work.

In a business context, lists might take the form of objectives—Specific, Measurable, Achievable, Relevant, and Time-Bound indicators of success. I was used to creating these kinds of plans.

My objectives were SMART, with targets for reach, followers, and engagement. I created messaging, audience profiles, a content strategy, a color palette, and a mood board.

What I didn’t do was write—blog post, essay, or scene. Not a single word in the weeks (and weeks) I polished my PowerPoint plan.

But that was dumb

By summer, I was tired and defeated. Reviewing my old notebooks (another great procrastination technique), I came across this question my Life Wizard asked a year earlier when I’d insisted that updating my LinkedIn profile was my top priority.

How can you be confident writing your story when you don’t know what it is?

My beautifully formatted blog promotion plan distracted me from what I most wanted to do—write. Worse, my SMART objectives (like those 1,000 Instagram followers) made it seem like I was constantly failing—at everything, all at once.

My saboteur struck again

This time, the self-talking bully masqueraded as a strategic guru to keep me frittering away time on a PowerPoint deck (a document no one else would see!).

Maybe you should take those objectives down a notch. You need to redo the whole plan. And make a logo while you’re at it. No one is going to take you seriously without a logo.

I downloaded Canva. It was safer to bury myself in comfortable old work habits than begin the vulnerable work of writing.

My saboteur wanted me to believe that I couldn’t begin until I perfected the plan, and I would never get the damn plan right because I’d missed the Life Wizard’s point—I wasn’t clear about the story I wanted to write for my future.

I needed to start with clouds

That’s it. Begin in the clouds—the one to-do list item that changed everything.

Establishing a vision for the life I wanted to build—a single, clear aspiration—helps me set boundaries and make better choices about using my time.

My 2024 plan reminds me of what I want most and gives me permission to fail at everything else on my to-do list. 

Feet on the ground, head in the clouds

Trello boards are great for organizing your business deadlines and priorities. Life requires some head-in-the-clouds, big-sky thinking.

To be fair, Alana did distinguish between business planning and life planning, saying she preferred to use “words as guides, intentions rather than To-Do’s...” And I kind of shit on this idea in my response simply because I’d once picked the wrong word at the wrong time.

So, I’m sorry, @Alana Kirk, for not thinking more deeply about your comment before responding, and I’m sorry to the leader of my writing group for poo-pooing your clouds.

And just so you know, my words for this year are curate and boundaries. But I still have a PowerPoint presentation.

Keep reading to see my 2024 plan and learn tips to create your own.

Work hard. Be Brave. Believe.

Catherine

Tips for Planning Your Next Chapter

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