Two Things Can Be True at the Same Time. That’s Not a Crisis. That’s October.

On the both/and mindset, why complexity isn't a problem to solve, and how to lead well when everything is moving at once.

Jen said something in her article this month that I’ve been thinking about.

“The excitement and the fear don’t take turns — they show up together, at the same time, in the same body.”

If you’ve ever tried to explain to someone that you are genuinely thrilled about something and completely overwhelmed by it and watched them look at you like you need to pick one — you know exactly what she means.

We are not great, as a culture, at holding two truths at once. We want things to be good or bad, exciting or scary, a win or a loss. The moment someone says, “I’m so grateful and I’m also really struggling,” half the room tries to talk them out of one of those feelings. Usually, the struggling one. Which is, of course, the one that most needed to be said.

This is something I work on with clients constantly. And it turns out, the ability to hold complexity without collapsing it into something simpler is one of the most useful skills a person — or a leader — can develop.

The Both/And Mindset

Most of us were trained in either/or thinking before we were old enough to question it. You’re confident or you’re scared. You’re ready or you’re not. The business is going well or it’s struggling. Pick a side.

The problem is that real life — and real leadership — almost never works that way. The most honest description of most meaningful seasons is and. I’m excited and I’m terrified. This decision is right and it’s costing me something. I’m proud of what we built and I’m ready for what’s next.

Researcher and author Jennifer Garvey Berger, whose work on adult development I refer to often in my coaching practice, describes this capacity as one of the hallmarks of mature leadership — the ability to hold multiple, sometimes contradictory perspectives without needing to resolve the tension prematurely. It’s not wishy-washy. It’s the more sophisticated move.

The either/or thinker sees complexity as a problem to be solved. The both/and thinker sees it as information to be navigated. One of those approaches tends to produce better decisions under pressure. I’ll let you guess which one.

What Leading Through ‘All of It at Once’ Actually Looks Like

Here’s what I’ve noticed in the people I coach who are navigating genuinely complex seasons — the ones where the business is changing and the personal life is heavy and the calendar has approximately zero margin and someone keeps adding things to it anyway.

The ones who come through it well are not the ones who hold it together perfectly. They’re not the ones with the best system or the most color-coded calendar. (Though I will say, a well-organized calendar doesn’t hurt).

They’re the ones who stay honest about what they’re carrying. Who resists the urge to perform fine when they’re not. Who gives themselves permission to move more slowly through the hard parts without deciding that slower means failing. Who keeps a short list of what truly matters right now and let the rest be genuinely, deliberately less important for a season.

That last one is harder than it sounds. High achievers are not naturally gifted at letting things be less important. We tend to treat everything on the list as equally urgent, which means we treat nothing as truly essential. And when everything is moving at once, that approach will grind you into dust.

What complexity demands is not more effort. It demands better triage. Knowing, with clarity and without guilt, what gets your full attention right now and what gets handled at 80 percent until the season shifts.

The Question Worth Asking This Month

If you’re in your own version of “all of it at once” right now — and October has a way of finding the people who are — I’d invite you to consider with this:

“What are the two or three things that genuinely cannot slip right now? And what am I spending energy on that I could honestly release, delegate, or simply let be good enough for a while?”

Not forever. Just for this season. Because seasons, as Katherine May reminds us in Wintering, do actually end. The winter that feels permanent is still winter. It still turns.

And in the meantime: you are allowed to be excited and scared. Grateful and grieving. Proud of what was and genuinely ready for what’s coming. You don’t have to choose.

If you’d like help sorting through what’s essential and what can wait — or just want a thinking partner for a season that’s asking a lot of you — that’s the work. Reach out. Let’s figure out what this season honestly needs from you, and what it doesn’t.

Chris

Circle Of Life Wellness & Massage

Coaching for the seasons that don’t fit neatly into a category.