The Dissatisfaction Advantage

I want to wreck your relationships

Looking for time freedom? Good, that’s what I write about. But I’m not going to give you neatly packed 5-point checklists to make it easy on you. Nope, not here. I’m going to try to challenge the way you think, give you some different perspectives to consider, share some insights from other smart people and help you break up your relationships with your limiting beliefs.

The general idea here is if we can just stop our wrong thinking and replace it with better thinking we move ourselves up to a higher plane of existence. I want to help you get all the way to the plane where your freedom goals are. I believe when we become the person that operates at a higher plane of existence, we naturally intersect with our dreams as a no-biggie kind of thing.

In other words, the work I want to help you with is upgrading your character with additional XP and get to that level where the bosses are harder but you have way better armor and weapons and the treasure after the boss-kill is HUGE. Oh, and you build your own castle and you can do whatever you want all day but you still choose to do epic stuff because it brings you joy.

Sweet Not Savory

I've been thinking about something Ray Dalio (his book Principles is soooo good) said about life stages: something about achieving versus savoring. Maybe I can't relate to the savoring part because I'm still deep in the achieving phase. Or maybe they don't need to be separate stages at all…

Here's what I know: I'm not satisfied.

Not with my business. Not with who I am as a leader. And I'm starting to think that's exactly where I need to be.

We live in a culture obsessed with contentment, with having "enough," with finding peace in where we are. But what if dissatisfaction isn't dysfunction, what if it's fuel? What if the moment we get too comfortable is the moment we stop becoming who God designed us to be?

I believe this life is preparation for eternity. We take our knowledge, our relationships, our skills with us. That means every day I'm not growing, I'm missing an opportunity that has eternal consequences.

So yes, I'm dissatisfied. And I'm counting on it being a strength, a driver. Kind of like a setting on a thermostat, but also different. Always a bit discontented with where I’m at so I’ll keep moving, learning, growing, stretching into discomfort. I’m also learning how not to be the guy on the heavy cart whipping the mule to pull the cart faster. In this metaphor I’m both the whipper and the mule. I felt that way through most of my 20’s and 30’s.

The Stage 2 Awakening

Right now, I'm working to level up both personally and professionally. I've moved beyond Stage 1 where I was the bottleneck, the hub with assistants spinning around me. I've built a business that runs without my daily involvement, with managers who own their departments.

But Stage 2? This is where it gets interesting. Harder and easier at the same time.

Last week I had three conversations that significantly advanced my understanding of what it takes to scale: [Ray Hespin on hiring superstars], [Taylor Hou on incentive structures] (who admitted to drunk-texting me predicting my failure on this next hire), and [Sam Eddinger on serious leadership development].

Here's what I'm learning: A business is a collection of people. If you want a better business, you need better people.

Sounds simple. It's not.

The Hardest Truths About Hiring

Ray hit me with something that challenged everything I thought I knew about giving people chances. He said he can spot the superstars within 30 days, the solid performers within 60 days, and never after that.

Never. After. That.

This goes against every nice-guy instinct I have. We want to believe in people's potential. We've all heard stories about the receptionist who became a COO. But here's the thing: when you're building something that matters, when you're trying to create value that extends beyond yourself, you can't afford to hope people into roles they're not built for. That receptionist turned rockstar COO always had it…

The most loving thing you can do, for them and for your mission, is to see people clearly and act on what you see.

Taylor drove this home with his obsession with incentives: "Incentives drive behavior." He's all-in on this idea, and his results prove it. The cost of keeping the wrong person isn't just their salary, it's the opportunity cost of not having the right person, the energy drain on the team, the mission drift that happens when you're managing instead of leading.

The Internal Battle

But here's the real shift I had to make moving from Stage 1 to Stage 2, and it wasn't tactical—it was psychological.

I had to release myself from performance-based self-worth.

For years, I was the bottleneck because I needed to be. My identity was tied to being indispensable. I over-promised things only I could deliver. I micromanaged because their mistakes felt like my failures. I swooped in to fix things because their imperfection threatened my sense of worth.

All of it traced back to a deep need to feel like I mattered, to feel worthy of love.

Once I shifted my self-worth from performance to commitment, from what I could do to who I was called to be, everything changed. I gave myself permission to charge more while personally getting involved less. I gave my team space to learn through their own mistakes. I stopped being the hero of every story.

That's when the business became more scalable.

The Competing Truth

Now, I know some of you are thinking: "But what about developing people? What about seeing potential? What about grace?"

These are valid tensions. There's real wisdom in investing in people's growth, in believing the best, in giving second chances. The parable of the talents teaches us that faithful stewardship often means multiplying what we've been given—including the gifts in others.

Grace doesn't mean lowering standards, though. Love doesn't mean tolerating consistent underperformance.

The most graceful thing you can do is help people find where they're naturally gifted to thrive, even if that's not in your organization.

Where Are You?

Where are you in your journey?

Are you in Stage 1, still thinking of yourself as indispensable, and unconsciously crafting a world around you that shows you you’re right about that? Are you the hub with assistants, telling yourself you're building a business when you're really just buying yourself a job?

Or have you made the psychological shift but you're struggling with the practical realities of Stage 2? Are you afraid to pay what top talent costs? Are you hoping mediocre people into critical roles? Are you avoiding the hard conversations because they feel unloving?

I’m accepting more and more we can’t hope or force people into something they are not right now. I’m also thinking about this idea: The primary power we have in life is the ability to say no. To dysfunction. To misalignment. To relationships that require more energy to maintain than they create. Saying no means we don’t tolerate mediocrity or dysfunction. Saying no means we install and act on boundaries.

Boundaries are the foundation that makes everything else possible.

The Call

This week, examine your relationship with dissatisfaction. Are you running from it, thinking it means you're ungrateful or unhealthy? Or are you learning to see it as the compass pointing toward your next level of growth?

Look at your business, your team, your leadership. Where are you settling because changing feels too hard or too risky? Where are you managing problems instead of solving them? Where are you hoping people into roles instead of hiring for them?

The people who got you here won't get you there. And that's not an indictment, it's just reality. The question is: What are you going to do about it?

Stay dissatisfied,

Mark

P.S. If you're in the stage I'm describing—building beyond yourself, hiring for leadership roles, scaling something that matters—I'd love to hear from you. What's the hardest part? What are you learning? Hit reply and let me know.