Month: January 2025

Crippled CEO Blog #184:

The ocean doesn’t care if you’re a good swimmer.

The universe doesn’t care about your plans.

And gravity doesn’t give a damn how expensive your phone was.

There’s this weird idea people have that if they just mean well enough or try hard enough, things should work out. That if they show up prepared and put in the effort, life is obligated to go easy on them. But that’s not how any of this works.

The ocean is going to do what the ocean does. If you jump in without knowing how to handle a current, it’ll swallow you whole—regardless of how many YouTube tutorials you watched beforehand.

The universe? Yeah, it does not give a single shit about your five-year plan. You can have the color-coded calendar, the vision board, the perfect strategy. And then—boom—your supplier vanishes, your car breaks down, your girlfriend leaves you for a guy with better abs, and suddenly your whole timeline looks like a toddler’s crayon scribbles.

And gravity? If you trip on a crack in the sidewalk, gravity is not pausing to consider how much you paid for that iPhone 15 Pro Max. That thing is going down, and if you’re lucky, only your screen protector will die a hero’s death.

What’s the lesson here?

Adapt.

You don’t argue with the ocean—you learn how to swim. You don’t yell at the universe for ruining your plans—you pivot. And you sure as hell don’t try to negotiate with gravity—you just buy a damn case for your phone.

Life doesn’t get easier because you’re ready for it. It gets easier because you get better at dealing with it.

The waves are coming. The detours are inevitable. Shit is going to break, people are going to disappoint you, and your best-laid plans will absolutely, 100% get wrecked at some point.

So stop expecting the world to play fair. It won’t.

What you can do is learn how to ride the waves, roll with the punches, and get better at fixing things when they break.

Because the ocean doesn’t care if you’re a good swimmer. But it does reward the ones who figure out how to stay afloat.

(Do you know who was absolutely not fighting the current last night? Your mom. She also gets a text from me every Sunday with a link to the latest blog post. Send a text to 561-726-1567 with the word CRIP, and you’ll get it, too.

Also, I’m on YouTube now. Go search for Crippled CEO and subscribe. Unless, of course, you enjoy making bad decisions.)

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Crippled CEO Blog #183:

Here in Boynton Beach, we have a road called Old Boynton Road. It connects to Boynton Beach Boulevard, like any normal road might, but as you follow it, something weird happens. It takes this odd, unnecessary curve, bending way out of the way, as if there’s something there to avoid. But there’s nothing there.

There used to be, though. A long time ago, there was a body of water right where the road curves. The lake was drained years ago, and now it’s just developed land with buildings and parking lots. But Old Boynton still swerves to avoid… nothing.

And I think we all have our own Old Boynton Roads.

We have habits, routines, and ways of doing things that made sense at one point. There was a lake, so we built a road around it. But then the lake disappeared, the reason went away, and yet… we’re still swerving.

Maybe you wake up early every Saturday morning to mow the lawn, even though your new HOA covers the landscaping now. Maybe you still send a detailed report to your boss every Friday, even though he hasn’t asked for one in years and only skims the emails. Or maybe you’re still holding on to that apology you feel like you’re owed, from someone who probably doesn’t even remember what they did.

We keep curving around these empty spaces in our lives, doing things because we’ve always done them, even when the reason for them disappeared ages ago.

And the funny thing is, we don’t stop to question it. We just keep following the curve like it’s the only way forward.

I wonder how many times we waste energy, effort, or even happiness on things that don’t matter anymore. It’s not even conscious most of the time. We don’t realize we’re doing it. It’s just… habit.

But if we pause for a second, if we actually look at the road we’re on, maybe we’ll realize there’s no lake there anymore. We don’t have to swerve. We can go straight.

And that’s a pretty cool thought.

(Do you know who didn’t take the long way last night? Your mom. She always knows the quickest route. Your mom also gets a text from me every Sunday with a link to the latest blog post. Send a text to 561-726-1567 with the word CRIP as the message to get the link as soon as it’s up.

Did you know that I have a YouTube channel now? I do! I’m posting two videos every week. Go search for Crippled CEO and you’ll find me. I’d love it if you subscribed.)

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Crippled CEO Blog #182:

There’s this weird little gap in life. You’ve probably noticed it. It’s the chasm that exists between feeling like you’re “not ready” and realizing it’s “too late.”

It’s sneaky, too, because it’s almost never an actual timeline. It’s a feeling. A mindset. A story we tell ourselves. And if you’re like most people, you’ve probably stood in that gap, stuck, more times than you’d like to admit.

The gap shows up in all kinds of places.

You’re not ready to start the new project, the new relationship, or the new habit… until one day, you look back and think, “I missed my chance.”

You’re not ready to speak up in a meeting, pitch your idea, or apply for the job you really want… until someone else does, and the opportunity is gone.

You’re not ready to reach out to someone you miss, someone you love, someone who hurt you… until they’re gone for good, and it’s too late.

This gap is where dreams go to die. It’s where regret sets up camp.

And the thing is, the gap is almost always imaginary. That “not ready” feeling? It’s rarely true. You’ve probably been ready for a while now—you just haven’t given yourself permission to act. And that “too late” realization? More often than not, it’s just your brain being dramatic.

The reality is that most of the time, you’re as ready as you’re ever going to be.

Let me tell you a story.

When I was in my early twenties, I wasn’t ready to run Life Saver Pool Fence. My dad had retired, and suddenly, this entire company was on my shoulders. People were looking at me like I knew what I was doing, but I didn’t. I felt like a fraud. I wasn’t ready.

But guess what? No one cared if I was ready. The business didn’t care. The employees didn’t care. The customers didn’t care. Ready or not, it was time to go.

So I figured it out. I stumbled. I made mistakes. Some of those mistakes were really stupid, like “what-the-hell-was-I-thinking” stupid. But I kept going. And somewhere along the way, I became ready.

Here’s the thing: readiness is a lie. It’s a mirage. It’s the procrastinator’s best friend and the perfectionist’s excuse. If you’re waiting to feel ready, you’ll be waiting forever.

Now, don’t get me wrong—there are actual deadlines in life. There are moments when opportunities really do expire. That’s why I’m writing this. Because the only way to bridge the gap between “not ready” and “too late” is to stop waiting for readiness and start doing something. Anything.

Feeling unprepared? Start small. Start messy. Start scared. Just start.

The best things in life happen when you step into the gap and act before you feel ready. When you stop overthinking, stop hesitating, and stop worrying about all the ways it might go wrong.

If I can run a company while feeling like a clueless kid who had no business being in charge, you can take the next step toward whatever you’re hesitating on.

And if you’re worried it’s too late, let me remind you: my dad didn’t start winning until he was 40. You’ve got time.

Just don’t waste it standing in the gap.

(Do you know who never hesitates? Your mom. She was ready last night, and she didn’t waste a single second. Your mom also gets a text from me every Sunday with a link to the latest blog post. Send a text to 561-726-1567 with the word CRIP as the message to get a link to the blog as soon as it’s up.)

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Crippled CEO Blog #181:

There’s a lie we all love to tell ourselves. You’ve told it. I’ve told it. Your mom told it to me last night. (She’s a compulsive liar.)

Here it is: “I’ll be happy when…”

You know how it goes. “I’ll be happy when I lose 20 pounds.”

“I’ll be happy when I get the promotion.”

“I’ll be happy when I buy the house, get the new car, finally launch my business, make six figures, hit seven figures, find the right person, get married, have kids, send the kids to college, retire, move to Florida, or whatever.”

Let me save you some time: no, you won’t.

Look, I’m not saying those things won’t bring you joy. Achieving your goals feels good, no question. When Life Saver hit eight figures, I cracked a big, stupid smile, treated myself to an irresponsibly expensive watch, and did a little internal victory dance. (OK, it was external. Charlotte saw it, and I’ll never live it down.) But here’s the thing: that happiness? It’s fleeting. It’s a sugar high.

A few hours later, your brain says, “Cool. What’s next?”

That’s why chasing happiness by stacking accomplishments is like trying to fill a colander with water. No matter how much you pour in, it’ll never stay full.

You think you’ll feel complete when you get there, but here’s the truth no one wants to hear: there doesn’t exist. The goalpost keeps moving, and you’ll always find another “when” to chase.

So, what’s the alternative? How do you stop running on this treadmill of misery disguised as ambition?

You stop treating happiness like a finish line. You stop tying your joy to some future, hypothetical event. You start looking for it where you are, right now.

I know that sounds like some hippie nonsense, but hear me out. If a guy who can’t walk, dress himself, or wipe his own butt can feel genuinely, stupidly happy on a regular basis, I promise you can, too.

Here’s what’s worked for me:

1. Celebrate the Small Stuff

I’m serious. Did you make a killer cup of coffee this morning? Hell yeah. High five yourself. Did the dog finally stop peeing on the rug? That’s a win. Acknowledge it.

2. Gratitude is a Cheat Code

Look around. Right now. What’s good? Maybe it’s the fact that you’re reading this blog on your magical, glowing pocket computer while sitting in air-conditioned comfort, not dodging wolves in the wilderness. Pretty sweet, right?

3. Enjoy the Game

If life is a video game (and let’s be real, it totally is), then the fun part isn’t beating the final boss. It’s the journey—the grinding, the leveling up, the random side quests. Happiness lives in the little moments, not in the leaderboard.

4. Detach from Results

Work your ass off, absolutely. Chase big goals, yes. But don’t tie your happiness to the outcome. The process itself is where the magic happens.

Listen, I’m not saying you shouldn’t dream big or aim high. Ambition is awesome. Just don’t put your happiness on layaway. Don’t wait for “someday” to start enjoying your life.

Because “someday” isn’t guaranteed. You’ve got today. Be happy now.

(Do you know who was happy last night? Your mom. And let me tell you, she didn’t wait for ‘someday.’ Your mom also gets a text from me every Sunday with a link to the latest blog post. Send a text to 561-726-1567 with the word CRIP as the message to get a link to the blog as soon as it’s up.

Did you know that I have a YouTube channel now? I do! I am putting up two videos every single week. Go search for Crippled CEO and you’ll find me. I would appreciate it if you subscribed.)

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