Choosing Purpose Over What’s Cool
Have you ever been stuck in a long line, wishing you could just march right up to the front?
When I was in my 30s, that’s exactly what my friends did at a local nightclub.
At the time, I was mortified.
Yet, deep down inside I thought it was the coolest thing.
They carried themselves like they belonged, like they didn’t need anyone’s permission to take up space.
I remember thinking… maybe that’s what leadership looks like.
Take the risk. Be bold. Do what it takes to get ahead.
It felt like confidence. It looked like power.
And I'll admit ... there are times in my life when I made decisions based on how cool I thought something would make me vs. whether I thought it was the right thing to do.
Over time, I’ve learned that what’s cool rarely aligns with what’s truly lasting.
Cool fades. Purpose endures.
It’s easy to be drawn to what turns heads or makes a strong impression and harder to stay anchored in what’s true, especially when it means standing alone.
Leadership asks something deeper from you.
It requires a willingness to listen for what’s real.
To live with alignment.
To walk forward even when no one’s clapping.
And that's one of the hardest lines to walk in leadership.
Every day you'll be confronted with decisions that will challenge you in ways that you never imagined.
They will put your moral and ethical code on trial or out for bid to the highest buyer.
If you make your decisions based on what you see others around you doing, or what the media says is "normal", you'll always fall short from what God has in store for you.
When I first started my career in Federal law enforcement, I saw the world through a lens of good and evil.
There was no middle or grey area.
And then, over time, I watched colleagues make decisions that didn't sit well with me. Behaviors that left me questioning what the "right" thing to do, has challenged my moral fiber.
We all carried the same badge. We all have the same set of credentials that read, "This officer possesses integrity."
Yet one of my closest partners made choices that eventually landed him in jail and serving time for his choices.
Leadership will reveal what’s underneath.
This is why the people around you deeply matter.
When things get uncomfortable (and they will), you need to be surrounded by people who call you higher.
People who see you for who you are and who you're becoming.
That’s the sacred space we’re creating at the Upside Retreats.
So here’s the invitation:
- Is it time to pause and look at the decisions you’ve been making?
- Is it time to notice who’s around you and whether those voices are helping you stay grounded in truth?
- Is it time to re-commit to who you are, what you want, and why that matters?
Because life has never needed more cool leaders.
It needs more aligned ones.
ACTION: The Upside Challenge for the week is to step back from chasing what looks shiny and start leaning into what’s actually meaningful.
Begin by making a list of three things you’ve recently said “yes” to because they sounded impressive or exciting.
Then, identify the one that feels least aligned with your values or your calling and take one clear step back from it.
That might mean turning down the next opportunity, rescheduling a commitment, or resetting expectations.
Use the time and energy you free up to invest in something that may not be flashy yet fuels your deeper purpose.







