What happens when a team that’s already winning decides not to settle
We recently hosted one of our monthly W Days. For us, it’s a chance to step back and be honest about what’s working, what’s not, and where we need to push ourselves next.
Every W Day has a theme. This time, the theme was ‘Get Uncomfortable’.
When you’ve got a team that’s firing on all cylinders and playing at a very high level, that theme can feel a little counterintuitive. Things are working. Momentum is real. The natural instinct is to protect what you’ve built.
So the obvious question becomes: what do you even push on next?
For us, the answer is discomfort.
We’re already a team that gets uncomfortable every day. We press hard. We take on tough conversations. We add new services, new ideas, and new ways of working. In that sense, the theme almost feels funny. But that’s exactly why it matters.
Comfort has a way of sneaking in quietly. Not as laziness, but as routine. As familiarity. As doing what’s already working because it’s safer than testing something new.
Most companies say they value innovation. Very few actually behave that way.
Innovation doesn’t come from labs, titles, or slogans. It comes from motion. And motion creates friction. Friction creates discomfort.
One of the biggest mindset shifts I’ve learned over time is this: discomfort isn’t a warning sign. It’s a signal.
It usually means you’re testing something before it’s perfect. You’re questioning an assumption that’s gone unchallenged. You’re letting data tell you something you don’t want to hear. You’re admitting something isn’t working and changing course. You’re putting real work into the world before you know how it will be received.
None of those feel good in the moment. All of them are necessary for growth.
A lot of organizations confuse discomfort with failure. The moment something feels awkward, messy, or uncertain, they retreat. They polish. They slow down. They wait for certainty.
The problem is, by the time something feels comfortable, someone else has already moved.
Discomfort doesn’t always show up in big strategic decisions. Sometimes it shows up in smaller, almost silly ways.
Our office, for example, is occasionally littered with phone chargers. I once asked someone to order “like a hundred” chargers. She actually ordered a hundred. It’s not exactly minimalist. But everyone’s phone is charged. No one’s scrambling. No one’s distracted.
Is it perfect? No.
Is it functional? Absolutely.
That’s a small example, but it reflects a bigger idea. Choosing progress and effectiveness over optics and comfort.
When a team is already performing at a high level, the challenge isn’t motivation. It’s complacency disguised as success.
The teams that continue to innovate are the ones that stay willing to feel awkward trying something new. They normalize change instead of fearing it. They treat discomfort as part of the job, not a problem to eliminate. They keep raising the bar without raising their voices.
Getting uncomfortable doesn’t mean being reckless. It doesn’t mean going cowboy. It means testing, learning, adjusting, and moving forward with intention.
At Dakota, we expect some things not to work. That’s part of the deal. The real failure is standing still, polishing what already exists, and calling it progress.
Game-changing businesses don’t stay great by protecting what they’ve built. They stay great by continuing to push into new territory, even when things are going well.
That’s why days like W Day matter to me. I get to see the whole team. Feel the energy in the room. Hear people think out loud about how they’re stretching themselves.
Being okay with being uncomfortable isn’t a side idea for us. It’s central to how we operate.
If you’re uncomfortable, you’re probably learning.
If you’re learning, you’re probably improving.
And if you’re improving, you’re doing the work that actually matters.
Stay curious. Stay disciplined.
And get uncomfortable.