Come Before Winter

A reflection on leadership, preparation, and the cost of waiting

Texas doesn’t do cold well.

So when a deep freeze shows up in the forecast, everything suddenly becomes urgent.

This weekend was no different. Like thousands of other Texans, I spent the days leading up to it scrambling — putting spigot covers on, re-wrapping exposed sprinkler pipes, checking pool equipment, pulling plants indoors, moving the outdoor beverage fridge into the garage, rearranging the garage so both cars would fit.

It was chaotic. Reactive. Exhausting.

And somewhere in the middle of all that movement, a quiet but brutal leadership thought hit me:

None of this mattered… until it mattered.

Most of what I was rushing to do could have been handled weeks ago. Slowly. Intentionally. With far less stress.
But because it wasn’t urgent then, it got postponed. Ignored. Deprioritized.

Until suddenly it wasn’t optional anymore.

That’s often how leadership works too.

We wait to winterize until the temperature drops.
We wait to prepare until pressure shows up.
We wait to address the small things until they’ve compounded into bigger problems.

And by then, we’re not leading — we’re reacting.

When Preparation Is Relational

I’ve seen this play out most clearly in relationships.

There was a season when a leader on my staff reported directly to me — someone incredibly talented, committed, and valuable to our team. Over time, small issues surfaced. Nothing explosive. Nothing unfixable. The kind of things that were absolutely coachable.

But instead of addressing them, I chose to overlook them.

Not because I didn’t care — but because the conversations felt awkward. Inconvenient. Easier to postpone than to step into. I told myself they weren’t urgent. That things would smooth themselves out.

They didn’t.

Those unaddressed moments slowly turned into tension. What could have been growth became distance. Eventually, we reached an impasse, and she moved on.

I look back on that season with regret — not because she wasn’t capable, but because I failed to lead proactively. I didn’t give her the opportunity to grow through honest conversation. My lack of winterization contributed to an outcome that didn’t need to happen.

She was a great leader.
And I should have been a better one.

But I’ve also seen the opposite.

There was another leader on my staff who, at one point, began butting heads with me. The tension was real. The frustration was mutual. More than one person told me it would be easier to let him go and move on.

He was in a key role. He brought real value. And I cared deeply about him and his family.

So instead of walking away, we chose to lean in.

We humbled ourselves. We had the awkward conversations. We named expectations. We addressed the friction instead of avoiding it. It wasn’t fun — but it was necessary.

And it changed everything.

That relationship didn’t just survive — it strengthened. To this day, we remain close friends, and we’re both grateful we chose to winterize that relationship rather than abandon it when the weather turned cold.

Sometimes preparation isn’t about systems or strategy. Sometimes it’s about having the conversations you hope you won’t need — before you desperately do.

Winterizing relationships isn’t comfortable.
But it produces longevity.

It keeps things running when conditions change.
And it prevents catastrophic failure when pressure shows up unannounced.

Scripture’s Quiet Wisdom on Readiness

The Bible speaks to this kind of wisdom with surprising practicality.

“Go to the ant, O sluggard; consider her ways, and be wise. Without having any chief, officer, or ruler, she prepares her bread in summer and gathers her food in harvest.”
— Proverbs 6:6–8 (ESV)

There’s no panic in that passage.
No urgency.
No crisis.

Just quiet, disciplined preparation.

The ant doesn’t wait for winter to show up before getting ready. It doesn’t need a supervisor or a warning siren. It simply understands that what isn’t urgent now will eventually be unavoidable later.

That’s leadership maturity.

Coming Before Winter

There’s another brief line of Scripture that has been echoing in my mind this week.

Near the end of his life, the apostle Paul writes to Timothy and urges him to come see him — but with a specific sense of urgency:

“Do your best to come before winter.”
— 2 Timothy 4:21 (ESV)

It’s a short sentence, but it carries weight.

Paul wasn’t being poetic. He was being practical. Winter would make travel harder. Circumstances would change. Opportunities would narrow.

What struck me wasn’t just the request — it was the timing.

Paul understood something leaders often forget:
Some things must be done before conditions shift.

Before conversations get harder.
Before distance grows.
Before urgency replaces intention.

“Come before winter” is a reminder that preparation isn’t just about readiness — it’s about timing. About recognizing that faithfulness often requires action before things feel critical.

Waiting until winter comes can mean waiting too long.

Do the Winterizing First

Here’s what I keep coming back to.

Most leadership breakdowns don’t require new strategies. They require leaders to do the work they’ve been putting off.

The conversations we delay.
The expectations we don’t clarify.
The preparation we assume we’ll get to later.

Winterizing leadership isn’t dramatic.
It’s deliberate.

And it’s almost always easier to do before conditions change.

So here’s the question I’m sitting with this week — and maybe you should too:

What have you been putting off because it didn’t feel urgent yet?

Not because you’re careless.
Not because you don’t care.
But because leadership got busy, loud, and demanding.

Before the forecast changes…
Before pressure forces your hand…
Before small things become costly problems…

Come before winter.