Snowstorms and Sunshine

Betting on Yourself, Losing, and Choosing to Start Over Anyway

There’s a certain kind of pain that comes from doing the brave thing.

Not the “I tried something new and it didn’t work” kind. I’m talking about the big swing. The one where you bet on your family’s future. You pack up your life, move across the country, and tell yourself, “This is our next chapter.”

And then six months later… it’s gone.

My wife was recently let go from her executive role. The very role that brought us from Texas to New York City. We didn’t just change zip codes. We changed routines, weather, support systems, and the little comforts that make life feel steady. I walked away from a company I spent eight years with. We traded a quiet community for the full-volume intensity of the city because we believed this move would improve our future financially, professionally, and personally.

And the bet didn’t pay off.

That’s the part people don’t say out loud when they tell you to bet on yourself. Sometimes you lose.

And this kind of loss doesn’t just hit your bank account. It hits your confidence. Your identity. Your sense of control. It makes you replay every decision like you’re in court and you’re both the lawyer and the defendant.

But here’s what I’m learning in real time: this isn’t the end of the story. It’s the part where we decide what we learned, who we are now, and what comes next.

The trap after a loss

When something doesn’t work out, we tend to judge the decision purely by the outcome.

If it worked, it was smart.

If it didn’t, it was stupid.

That’s not wisdom. That’s hindsight pretending to be leadership.

A good decision can still lead to a rough outcome. A bad decision can accidentally work. Companies change. Leaders shift. Budgets tighten. Things that look stable on paper can vanish fast in real life.

So here’s what I know for sure right now: Losing doesn’t automatically mean you were wrong.

We took a swing. We were willing to trade comfort for growth. That’s not foolish. That’s courageous. I would rather be someone who tries and gets humbled than someone who never tries and calls it “being practical.”

The second truth is a harder pill: Every opportunity costs something.

In our case, the cost wasn’t just a move or a job transition. We left a home we loved. We left a community that felt safe. We left a pace of life that fit us. And our Texas home is still on the market as I write this, which means we’re still carrying that financial weight.

I also left a team I cared deeply about. People who supported my family and me for years. People who were blindsided and hurt by the timing of our decision. I’ll always be grateful for their kindness, friendship, and the way they cheered us on even after we left.

New York has been a culture shock. It’s loud, fast, and intense. It has its charm, but it asks a lot of you. Our son is thriving here because kids adapt like it’s their full-time job. He’s soaking up life like it’s brand new every day.

But my wife and I have had to admit something that’s both honest and uncomfortable:

We’re not as happy here as we thought we’d be.

That isn’t failure. That’s information, and adults are allowed to change course when new information shows up.

How I’ve learned to look at failure

Throughout my life, I’ve lived moments of shame and embarrassment. Real ones. The kind that make you want to shrink, disappear, or pretend that season never happened.

But I can honestly say this - I thank God for the failures in my twenties and thirties.

Not because I love pain. Not because I’m trying to put a shiny filter on something hard. I’m thankful because adversity taught me lessons success never did. My mistakes humbled me. They sharpened me. They built a version of me that was ready for the best parts of my life.

They led me to my wife. And eventually, to my beautiful son.

That’s one of the strange gifts of failure - you rarely see the purpose while you’re in it. Sometimes loss is doing work in you that comfort never could.

Snowstorms and Sunshine

This morning my wife said something simple that stuck with me - she’d take the Texas heat over the New York snowstorms.

It wasn’t really about weather. It was about pace. Familiarity. Feeling grounded. The kind of life where you don’t have to fight the environment just to breathe.

And that’s where I’ve found an unexpected sense of hope.

Snowstorms feel harsh. They shut cities down. They make progress feel impossible. But snow also protects what’s underneath. It hydrates deeply when it melts. It creates conditions that help plants and crops survive winter and germinate in spring.

So maybe that’s what this season is. More than a storm. A layer of protection. A kind of deep watering below the surface. A setup for growth we can’t see yet.

Starting over doesn’t have to be dramatic. Sometimes it’s just choosing what fits. Choosing what’s best for your family. Turning around not because you quit, but because you learned.

What we’re taking with us

For anyone else walking through their own storm, here are a few lessons we’re carrying forward:

1. You can’t control outcomes, but you can control alignment.

   You can do a lot right and still get blindsided. The focus now is alignment with what matters most: family, stability, health, and peace.

   
   

2. Your identity can’t be a job title.

   A role can be taken. A paycheck can pause. But character, resilience, and leadership are portable. They travel well.

   
   

3. Starting over usually means starting wiser.

   We’re not back at zero. We’re back with experience, clearer standards, and fewer illusions.

   
   

4. Going home is not a downgrade.

   There’s a pride trap that says returning means you failed. I don’t buy that. Choosing your foundation is how you build something that lasts.

   
   

5. The only real loss is letting this make you smaller.

   This kind of hit can shrink people. Make them bitter, cautious, and closed off. Or it can refine you. We’re choosing refined.

   
   

We’re still in the season of snowstorms, but we’re looking toward sunshine. Not because sunshine is easier, but because it’s ours.

A question for you

If you’ve ever taken a big swing and it didn’t work out, what helped you keep your heart open while you rebuilt?

To sunshine,

Hector

Chris’s Comments

One of the hardest things to admit as a leader is that sometimes the bravest decision doesn’t come with a clean win attached to it.

We’re taught to tell the story after it works.  After the turnaround.  After the promotion. After the “see, it was all worth it.”

But leadership isn’t built in hindsight. It’s always built in the middle - when the outcome is still unclear and your confidence feels thinner than you’d like.

What stands out to me in this season isn’t the loss. It’s the refusal to let the loss define the people involved.

There’s a quiet strength in saying, “This didn’t fit us the way we thought it would,” without turning that honesty into self-criticism. Too many leaders stay stuck because they confuse persistence with pride. They keep pushing not because it’s right, but because stopping would feel like admitting failure.  Choosing alignment over ego isn’t quitting.  It’s leadership maturity.

Starting over doesn’t erase what you’ve built but rather it reveals what actually matters enough to build around.

And if you’re reading this while carrying your own version of a snowstorm - professionally, personally, financially - hear this clearly:

You are not behind.

You are not broken.

You are not weak for reassessing.

You’re learning.

You’re recalibrating.

You’re becoming more honest about the life you’re trying to lead.

That kind of clarity doesn’t come from comfort. It comes from weathering the storm and deciding - consciously - what you’re willing to carry forward and what you’re ready to put down.

The damaged leader isn’t the one who stumbles. It’s the one who refuses to grow smaller because of it.

And that choice - to stay open, reflective, and human - that’s where the real leadership work begins.