This Is the Hardest Part of Leadership

Playing to Win

August 28, 2025

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Welcome to the Latest Newsletter
of Playing to Win!

My newsletter is designed specifically to help business owners like you grow your companies with tried & applied bits of business knowledge, all communicated in actionable, bite-sized chunks. I will share insights and advice aimed at enhancing your business operations, boosting your success, and allowing you to focus more on what truly matters. Let's work together to achieve your goals and make your endeavors a reality.

Key Points of the Newsletter

  • Leadership means making hard decisions, even when you care about everyone involved.
  • MIT45 and Uprising offer real support for employee growth, like continuing education reimbursement.
  • Investing in your people’s future is non-negotiable, even when the present is tough.

This Is the Hardest Part of Leadership

 
One of the hardest things to do as a leader is sit down, look at your team, and tell them you care, then still have to let someone go.

I care deeply about the people who support us. About the journey we’re on. I want everyone to win. I want to build something where the long-haul players are rewarded. Where people aren’t just clocking in, they’re bought in.

And that’s what makes the tough moments so frustrating.

Because inside MIT45, Uprising, and Golden Monk, we’re not just handing out paychecks. We’re investing in people. We’re creating opportunities to grow, advance, and get further than you’ve ever gone before.

We offer continuing education reimbursement, $1,250 per quarter. If you want to level up your career, we’ll help you pay for it. Books, trainings, certifications, we cover it. And if you’re pursuing a degree at a credited university and scoring 80% or better? We’ll reimburse you up to $5,850 per year in tuition.

Because I believe in betting on people. Not just in what they bring to the table today—but in who they can become tomorrow.

So when we do have to make cuts, when performance slips or roles evolve, it’s not cold. It’s painful. Because I know what someone’s poured in. And I know what I’ve committed to pour into them.

But leadership isn’t just about celebrating wins. It’s about making hard calls with love, clarity, and conviction.

And through it all, we continue to invest in growth. We keep showing up with opportunities for the people who want to rise. Because when we say “people first,” it’s not a slogan. It’s policy. It’s budget. It’s action.

So if you’re part of this team, or any team, and you want more for your life, know this:

We’ll meet you at your effort. But we won’t carry you. That part’s on you.

Want to work in a place that invests in your future while expecting your best? Let’s talk about what that looks like.

Stay tuned for more insights in our next newsletter. Remember, it's the small adjustments that often make the biggest impact on your business's profitability. Here's to your continued success!

Stay driven to push your business forward,
Ryan Niddel