The Task You Keep Moving to Tomorrow Is Probably the One That Matters Most

It's summer, and I have a list.

Not the urgent kind. The other kind. The slightly bigger, slightly scarier kind that I keep telling myself I'll get to once things calm down. A few strategic decisions. A conversation I've been putting off. A plan I know I need to sit down and actually write, not just think about while I'm doing other things. Things to prepare for the Fall Semester before I’m deep in the weeds.

Every year it's the same pull. The sun is out (sometimes!), the days are long, and there's a real, legitimate voice in my head saying enjoy this. Take the walk with Maizey. Sit on the porch. Don't spend the whole season working. And I believe that voice. I think rest matters, and I think founders and leaders especially are bad at taking it.

But there's another voice underneath it, quieter, that I've learned not to ignore. It's the one that knows exactly which task I'm avoiding, and exactly why (well, sometimes!).

The pattern I see in every client

Here's something I've noticed over and over in my work with founders and leaders: the thing you're avoiding is almost always the thing that matters most.

Not the busywork. Not the inbox. Not the easy wins you keep doing because they feel productive. I mean the one task that sits quietly at the bottom of the list, week after week, that you have a dozen good reasons for not starting yet.

It's rarely about time. If it were just a time problem, you'd find thirty minutes for it eventually. It's usually something else: it's a hard conversation, something you feel you aren’t an expert at, a decision you're not fully ready to make, a piece of feedback you don't want to deliver, a number you don't want to look at, a plan that means admitting something needs to change.

Avoidance isn't laziness. It's information. It's usually pointing directly at what's most important.

So, what are you avoiding?

I'd ask you to actually sit with that question for a second. Not the polished, professional version of the answer. The honest one. (You don’t have to tell anyone!)

What's the task you keep bumping to next week? What's the conversation you've rehearsed in your head but haven't had? What's the decision you keep gathering "just one more piece of information" before you make?

That's usually the one.

Why summer is actually a good time to face it

This is where I've changed my own thinking over the years. I used to treat summer as a season to survive, to get through with the to-do list mostly intact and pick everything back up properly in the fall. But the slower pace of summer is actually a gift, if you use it right. There's a little more room to think. A little less noise. It's a good season to finally sit with the thing you've been avoiding, instead of waiting until the fall sprint makes it impossible to give it real attention.

You don't have to solve it all in one sitting. You just have to stop avoiding it long enough to look at it clearly.

Looking ahead

This is exactly the kind of thinking I want to dig into with a small group of founders and leaders this fall. I'm putting together a retreat for this September or October, a space to step back, get honest about what's truly important, and start shaping real clarity before year-end planning season hits in December. More details to come soon, but if that sounds like something you need, keep an eye out.

For now, though: take a minute, name the thing you've been avoiding, and ask yourself why. That's usually where the real value begins.