The Level Up Leader Newsletter
I’ve got a story this week that’s a mix of regret, sarcasm, and a whole lot of leadership gold if you’re willing to pay attention.
I was working with a client. Another consultant. A smart guy. Big presence. Big energy. Big opinions.
The kind of guy who doesn’t just walk into a room—he enters the scene like he’s being introduced at an awards show.
He had the résumé.
The credentials.
The stories from ten years ago that he still tells like they just happened last week.
You know the type.
From the outside looking in, the metrics didn’t lie. Things were stalled.
Flat numbers.
No momentum.
And if you were brutally honest, you might even say… washed up.
But I didn’t see him that way. I saw a guy who needed a reframing moment.
I saw wisdom. Depth. Experience that, if aimed properly, could be gold to any company willing to receive it.
But here’s the part I’m not proud of.
Instead of leading with my frameworks and sticking to the systems I know work, I let him call the shots.
He told me how to do my job.
He told me what he “needed.”
And I—against every bit of instinct and experience—let him.
Why?
Because I didn’t want a weekly wrestling match.
Because I thought maybe if I gave a little, I’d earn his trust.
Because I wanted the best for him, and I convinced myself I could serve him his way.
Spoiler alert: that never works.
I didn’t stick to my process.
I didn’t hold the line.
I caved.
And you know what I learned?
When you give up conviction for comfort, you lose both.
This wasn’t about who was right or wrong.
This was about fit. And this was not a fit.
Eventually, he started having to make hard decisions.
Where to invest. What to stop funding. What to let go.
I had my perspective.
He had his.
And we didn’t agree.
And that’s fine. Seriously.
This isn’t a rant about a bad client. It’s not even about him.
It’s about this:
Sometimes the smartest thing you can do is stop.
Stop investing time, money, and energy into things that no longer produce results.
Stop doubling down on old ideas just because you’re emotionally attached to them.
Stop clinging to “your way” if your way hasn’t worked in five years.
Let me get even more specific.
How do you stop paying for a team that’s been with you forever but isn’t actually moving the needle?
How do you walk away from a system that feels comfortable but no longer works?
How do you admit that the thing you created, built, poured yourself into… is no longer serving your future?
Here’s the brutal truth:
We fall in love with our systems more than we love the outcomes.
And that’s backwards.
Systems are tools.
Outcomes are the mission.
So here are the questions I want you to sit with this week:
- What are you still doing that’s not producing results, and why are you still doing it?
- Where are you letting comfort keep you from making the decisions you know you need to make?
- Are you leading with conviction, or are you adjusting to avoid tension?
- Are you more loyal to your systems or your outcomes?
You might not like the answers. That’s kind of the point.
As for my story—there’s no perfect ending here. Not yet.
I still want that client to win. I’ll always be in his corner. But I’ve learned my lesson.
When you know what works, you stick to it.
When you’re the guide, you don’t let the hiker take the map.
When you build something proven, you don’t let ego run the show.
And when it’s not a fit, you don’t force it.
You release it. And you move on.
Level Up Leader Tip: Your Calendar is a Mirror
If you want to know what matters to you—look at your calendar.
Don’t tell me you value growth if you’re not blocking time to build.
Don’t say you care about strategy when every hour is spent in someone else’s emergency.
Here’s the move this week.
Do a five-minute audit.
Pull up your calendar and ask:
- What should I stop giving time to immediately?
- What’s missing completely that needs a dedicated block?
- What am I doing out of guilt or habit instead of purpose?
Leaders who own their calendar own their outcomes.
Stop saying “I just need to manage my time better.”
Start making decisions that reflect what actually matters.
This Week on The Level Up Leader Podcast
Coming up this week, I sit down with Jeffrey Hayzlett, Chairman of the Board for the C-Suite Network.
This guy knows how to scale, how to build high-trust leadership, and how to challenge you without sugarcoating a thing.
We talk about real influence, executive presence, and what it really takes to stay relevant at the highest level.
Do not miss this one.
Listen and subscribe now: www.levelupleaderpodcast.com
Available on YouTube, Spotify, Apple Podcasts, and wherever you get your content
Keep Showing Up
This newsletter exists to challenge the way you think, the way you lead, and the way you build.
No fluff. No filler. Just frameworks, questions, and bold moves.
If this story hit home, I’d love to hear it.
If you’ve had to make a tough stop lately, reply and share.
If you’re clinging to something you know you need to release—what’s holding you back?
Keep leveling up.
You were built for better.
Until next time,
Michael
About Michael King
Michael King is an award-winning executive coach and the founder of Teams.Coach, Gawker Traffic, and CatalystCo. With two master’s degrees in Leadership and Executive Coaching from Bellevue University, he helps high-performing executives simplify complexity, optimize their leadership, and build teams that actually work.
A certified executive coach, Michael has spent years guiding Fortune 500 leaders, entrepreneurs, and teams through the real work of leadership—creating clarity, building systems, and driving results without the burnout.
When he’s not coaching, Michael is an accomplished singer/songwriter and music producer with over 100 published songs to his credit. He’s also a Ducati aficionado, a die-hard Apple fan, and probably has a Starbucks in his hand right now.
