The Irony of Calculated Chaos and The Beautiful Journey
How Chasing Success Led to Something Better: Growth
Plans are Just Plans
When you’re going to shake life up and do something big, you spend months or even years crafting the perfect plan. Every step is mapped out, you build up a safety net, calculate your risks, make sure you’re okay with them, and make a plan for if you fail. You’ve created a dozen spreadsheets of how things could go and you’re okay with accepting even the worst case scenario.
Finally something prompts you to take a dive, and you jump. And Immediately every calculation goes out the window.
The Surprising Beauty of the Riddle
The plan was clean, linear, and logical. You’re an engineer. You’re used to “If this, then that”. You also have a list of things that equal success, and things to avoid. Seems simple enough? Nope!
You thought every decision would be logical, like a math problem, but its more like a riddle. Nothing in business or life is predictable. You’re “vibe-living” your way through life. You even have to dig into your retirement account because you believe in today’s version of you more than your 65 year-old self.
The wild part is: life isn’t going as planned, but somehow you have more underlying joy than you’ve ever had. You’re taking punches to the face regularly, and somehow you’re still happier than you were when your life was comfortable. You’re doing things you never thought you could do with ease. New problems come up, big problems come up, but you’re Mike DiPasquale, you’ve got this (If you’re from KC you know the reference 😂).
Every day you question if you should give up. You tell your closest friends and family you might give up. They think you’re going to. You keep talking about it, but you’re just talking through it — you know deep down that you won’t, you just need to hear yourself say it out loud to motivate yourself to keep digging. You still believe in yourself. You still have hope. You realize you can't wait for all the info—you have to make calls with incomplete information and trust you'll figure it out. You’ve never lived like this before, it feels foolish, but it feels rewarding.
When Your Why Changes Everything
When you’re in the middle of some beautiful chaos, something shifts.
You started with impure ambitions — wanting people to notice you, prove old bosses wrong, whatever. But somehow that seems like a different life, and a completely different person.
When you see your daughter, when you take the afternoon off to go to Science City, when you start work late to get a vegan breakfast wrap at Mildred’s, you realize this is what matters. She’s your everything. All the original reasons you started feel so small. You have nothing left to prove — you just want to provide for her and have a job that’s flexible enough for you to spend half days with her.
You’re no longer building your business to escape or become wildly successful. You’re doing it because you realized the struggle is making you a better person. Being an entrepreneur has humbled you. When your day-to-day is just you and your business partner, you can’t hide behind blame and anger anymore. You used to blame everything on other people at work. Now you’re accountable for yourself and you have to self-actualize your life.
Somehow what you’ve learned in business directly applies to your personal life. You were so blind before. You start apologizing to people you've done wrong, going to therapy, realizing the whole point of all of this is to just be a better person. When you have a dry-spell of work, you remember you’re still growing as a person. You used to be scared when a client had an idea you didn't know how to execute. But you always find a way. You can solve impossible problems and you don't need to be hesitant to say so—you know you've got this.
Your 401k growth used to be the scoreboard. Now it's your personal growth that gets you excited to wake up.
What just happened? Who am I?
The Irony of Calculated Risks
I thought I was taking a calculated risk starting Haystack. I built runway, safety nets, and backup plans, but my day-to-day is just a big improv show. Every week brings a curveball (personal or business) and there’s no textbook to help, and no one to bounce it off of.
It’s crazy: when you were 21 you used to have such bad anxiety that you didn't want to try a new restaurant. Now you'll navigate a rocky situation with ease (while also still dying inside, but at least you’re brave, haha)
You spend all this time trying to minimize uncertainty, and then you discover that embracing uncertainty is actually what life is all about.
Staying Power is Everything
The difference between people who are doing what makes them happy and those who aren't isn't talent or luck or having the perfect plan.
It's staying power.
Everything in life feels instant. People don't lock in for the long haul anymore. Everyone wants to do their own thing, but nobody actually does it. People start side projects and abandon them. They want to get strong and give up. They have the desire, the fire, but they also have fear and don't believe in themselves.
You stay in it until you've stayed in it too long to quit. Until walking away would feel like betraying the version of yourself who believed this was possible when nobody else did. And honestly, you'd be throwing away growth, knowing there's more around the corner. There are things you've learned about yourself that would have been hidden your whole life without the pressure, risk, and bravery. You could have lived your entire life with the wrong mental models, trapped in comfort, not growing.
The Beautiful Mess
Some days I think about the 2022 version of myself and laugh. I knew I’d still be running my business now, but I also believed I’d be the same person I was when i started. I’m not. I’m better. And I’m proud.
The plan was about becoming successful. The journey ended up being about becoming a better version of myself.
And honestly? That's way more interesting than any plan i modeled in a spreadsheet.
The irony isn't that planning doesn't work. It's that the real plan reveals itself only after you start walking. And the person capable of executing that real plan? They don't exist yet when you start. You have to build them as you go.
That's the most beautiful, terrifying, exhilarating part of this whole thing.
We make our plans. Then life happens. We adapt. We grow. We become people we didn't know we could be.
And somehow, that messy, unpredictable, impossible journey becomes the point.
What started as a calculated risk has become something much more valuable: a daily practice in becoming the person I was meant to be. There is no ROI on that. It’s priceless.
