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.

When Leadership Reaches a Crossroad: A reflection for leaders in the middle

I love leadership — because I love helping leaders.

Not the spotlight version of leadership. Not the polished, platform-driven kind. I love leadership because I love seeing people thrive. I love helping leaders carry responsibility with clarity, courage, and faithfulness — especially when no one is applauding.

That desire didn’t start with a brand or a content plan. Start Strong | Lead Well wasn’t something I set out to “build.” It emerged naturally from who I am and how I’m wired. I’ve learned something about myself over time: if I’m not positioned to help others, I’m not fulfilled. My purpose is tied to seeing people grow — spiritually, emotionally, relationally, and as leaders.

My life motto reflects that: So Others May Live.

That’s the heart behind this space.

How This Started (and Why I’m Reflecting Now)

By most standards, Start Strong | Lead Well is still very new. I began sharing these weekly reflections last year — not as a finished product, but as an offering. An experiment. A discipline of reflection meant to help leaders begin their week grounded and lead it well.

And because it’s new — and still emerging — this feels like the right time to pause and reflect.

That’s something leaders should do, especially early in a journey.

Reflection isn’t hesitation.
Re-examination isn’t weakness.
Sometimes it’s wisdom.

The Quiet Questions That Don’t Go Away

Leadership doesn’t always break down in crisis. Sometimes it slows down in quiet questions you can’t ignore anymore.

There comes a point when continuing the same way starts to feel less faithful than re-examining why you began in the first place.

This isn’t burnout.
It isn’t quitting.
It isn’t a lack of discipline.

It’s leadership pausing long enough to tell the truth.

The Question Beneath the Questions

If I’m honest, there’s a deeper question underneath all of this — one I’ve wrestled with privately for a while:

Am I helping leaders merely consume encouragement… or helping them carry leadership differently?

There are countless leadership voices online. Many are sharper, louder, more prolific, or more established. If Start Strong | Lead Well were to stop tomorrow, the internet wouldn’t notice. The algorithm would move on. Content would keep flowing.

And that realization isn’t discouraging — it’s clarifying.

Because this space was never meant to chase attention. It was meant to serve leaders.

Leading From the Middle

I deeply respect leaders who shape thinking through books and platforms. Their work matters. Their influence has shaped me, and I’m grateful for the mentorship they provide from a distance through their words and teaching.

But most of my leadership life hasn’t been lived on stages.

It’s been lived in the middle.

No bravado.
No gloss or glamour.
No spotlight.

Just responsibility. Day after day.

Reporting up. Caring down. Managing pressure. Solving problems. Navigating tension. Showing up for a team. Being present for a family. Answering to a boss. Carrying weight quietly.

And I believe there are leaders who need reflections from that place too — from the middle, where leadership is lived more than it is explained.

Not the Many — the One

Leadership isn’t always about reaching the many.

Sometimes it’s about being faithful to the one who needs encouragement right now.

That idea is deeply rooted in my faith. Jesus spoke about leaving the ninety-nine to go after the one — not because the many didn’t matter, but because the one did.

That’s something I’m realizing more clearly about Start Strong | Lead Well.

I’m not trying to go viral.
I’m not chasing scale.
I’m not building for clicks, likes, or applause.

I’m writing for the one leader who’s tired but still faithful.
For the one who feels the tension but keeps showing up.
For the one who needs clarity, not noise.

If that’s a small group, that’s okay.

Faithfulness has never required an audience.

Why I’m Sharing This

I’m not writing this to resolve the tension — but to name it honestly.

Because leaders everywhere are navigating similar crossroads. Deciding whether to continue, adjust, refine, or release. Wondering whether consistency is still aligned with calling. Asking whether what they’re building is truly serving others.

These are good questions.

And leaders don’t need more answers shouted at them. They need space to reflect.

That’s what this post is — and what I hope Start Strong | Lead Well continues to be: a quiet place for leaders in the middle to think clearly, lead faithfully, and remember why they began.

If this tension feels familiar, you’re not alone.

And you’re welcome here.

12 Leadership Decisions That Will Shape Your Year

Strong leaders don’t drift into good years.
They decide — early — how they’ll lead.

Over time, I’ve noticed that leaders who experience clarity, health, and sustained influence don’t rely on motivation or momentum. They make intentional decisions before the year begins to move too fast.

Not resolutions.
Not goals.
Decisions.

John Maxwell puts it simply: “Life is a matter of choices, and every choice you make makes you.” Leadership formation works the same way. Over time, our decisions shape our character, our influence, and the environments we lead.

Scripture reminds us that intentional leadership isn’t about control — it’s about alignment:

“The heart of man plans his way, but the LORD establishes his steps.”
— Proverbs 16:9 (ESV)

Here are 12 leadership decisions that quietly shape the year ahead.

1. Decide What You Will Protect

Time, energy, health, and relationships don’t protect themselves. Without clear boundaries, leadership demands will slowly erode what matters most. Deciding what you will protect early in the year creates margin that sustains you when pressure increases.

2. Decide How Your Calendar Will Reflect Your Priorities

Your calendar reveals your real values, not your stated ones. Strong leaders don’t just react to requests — they intentionally schedule what matters most. When your priorities live on your calendar, they stop competing with everything else.

3. Decide How You Will Communicate Expectations

Many leadership frustrations aren’t people problems — they’re clarity problems. Deciding how and when you’ll communicate expectations reduces confusion and builds trust. Clear expectations give people confidence in how to win.

4. Decide How You Will Develop People

Leadership that lasts multiplies. Growth doesn’t happen accidentally — it happens through intentional coaching, feedback, and opportunity. Deciding who you’ll invest in ensures your leadership impact extends beyond your own capacity.

5. Decide What You Will Say “No” To

Focus requires restraint. Every “yes” carries a cost, whether you see it immediately or not. Deciding ahead of time what doesn’t belong in your year helps you preserve energy for what does.

6. Decide How You Will Handle Pressure

Pressure is inevitable in leadership, but panic is optional. Deciding in advance how you’ll respond under stress keeps emotions from driving decisions. Prepared leaders respond thoughtfully instead of reacting impulsively.

7. Decide How You Will Care for Your Health

Leadership is demanding, and neglect eventually shows up somewhere. Physical, emotional, and spiritual health directly affect how you show up for others. Deciding to care for your health isn’t selfish — it’s responsible leadership.

8. Decide How You Will Build Trust

Trust grows through consistency, integrity, and follow-through. Small, repeated actions shape credibility far more than big moments. Deciding to be dependable in both visible and unseen ways builds a foundation others can rely on.

9. Decide How You Will Course-Correct

Strong leaders don’t avoid adjustment — they expect it. Deciding now that feedback and correction are part of growth keeps pride from blocking progress. Course-correction is not failure; it’s leadership maturity.

10. Decide How You Will Finish the Year

Strong finishes don’t happen by accident. Deciding early how you want to close the year influences how you pace yourself throughout it. Leaders who finish well build momentum that carries forward.

11. Decide How You Will Measure Success

Busyness is not success, and visibility isn’t impact. Deciding what “winning” actually means protects you from chasing the wrong metrics. Clear measures of success bring focus and reduce unnecessary pressure.

12. Decide What You Will Carry Forward

Every year leaves something behind — habits, lessons, and patterns. Deciding intentionally what you’ll carry forward helps you build on growth instead of repeating mistakes. Reflection turns experience into wisdom.

Final Thought

You don’t need a perfect plan for the year ahead.
You need clarity.

Strong leadership starts with intentional decisions — and those decisions quietly shape everything that follows.

Start Strong. Lead Well.