Predictability junkies, analysis addicts, safety-netters… comfort seekers. You know the type…
They sit, wait, and negotiate with themselves and with you. They tell you why something won’t work, why it’s better to hold off, why every step needs another round of “careful thought.” And they’re so damn good at convincing you—especially if you value the truth.
Because they don’t just toss out vague warnings—they use facts… selective facts. They wield “what-ifs” and “better-safe-than-sorry” like a scalpel, slicing the soul out of your wild ideas before they even get a chance to breathe.
They’ll make you doubt yourself, not because they’re right, but because they’ve infected you with their fear, their worry, and it becomes YOUR anxiety…
They don’t even do it on purpose, they actually mean well most the time.
But, if you let them influence your decisions…? Well… I’ve got a story about that.
The Perfect Planner Who Nearly Killed My Business
Years ago, I was trying to carve my own path in life—something bold, something mine… and that included bootstrapping my first business, while chasing a dream that felt risky and real.
One of the first things I did, under the suggestion of my peers, I brought in a friend (yeah yeah… don’t work with friends), one who thought differently than I did, and I told myself “Well… Self: look.. he’s smart. AND he’s cautious. He’ll keep me from screwing up… his methodical, by-the-book approach will balance my crazy ideas.”
Honestly, He was kinda Mr. Perfect… always dressed like he was heading into a business meeting, spent hours filling up spreadsheets with plans, analyzed every choice down to the tiniest detail. He wanted everything safe, predictable, risk-free…
…and he almost suffocated my rebel spirit—and my business—before I could even get it off the ground.
No matter what I dreamed up—whether it was doing a big sale or event promotion, ditching the 9-to-5 that I was hanging onto, traveling the world to go to shows, or even just speaking my mind publically—he pushed for the safe route, the one that didn’t include any of that.
The safe route for a rebel? That’s a slow, soul-crushing death.
It meant saying no to risks, delaying dreams until every detail was “perfect,” rejecting anything that might shake things up. I watched as I started sinking into analysis paralysis, drowning in perfect little plans.
The worst part? He was right—on paper. His logic made sense. But life doesn’t live on spreadsheets or checklists. The only way to thrive is to move… to stumble, adjust, and keep pushing forward. Playing it safe doesn’t keep you alive—it just stretches out your misery.
I had to make a choice: keep playing it safe until I lost myself, or take back control. So we parted ways. It hurt, but he went on to build his predictable, comfortable perfect little life—with the trad wife and trendy named kids, all happy in a routine, while he kept stacking titles and accolades. Win-win… I guess.
Turns out, perfect and predictable weren’t enough—years later, he reached out, considering an affair with a “sexy” female co-worker who he’d been going on sales calls with, asking me to talk him out of (or into?) it. True story.
Anyways… where was I… oh yeah, when I started taking risks again—listening to my gut, defying expectations—that’s when I started to feel alive, and my business actually began to grow.
Over-thinkers vs. Over-planners
Over-thinkers question, run scenarios, and worry… but through all that, they still take steps. Over-planners? They sit still, waiting for the “perfect moment” that never comes. They have no sense of adventure, no hunger for the unknown. These are the people who spend years in school, stack up degrees, become “experts,” and then settle into a cubicle (or maybe a corner office) and call it a career—hoping one day to retire.
And you know what? They’re happy about it. They’ll tell everyone how much they love their safe, orderly life, with plenty of certificates and praise to prove it.
Why? Because their “success” isn’t about living or creating—it’s about being right. They watch sports to see if their predictions pan out, they love puzzles that serve no purpose. Meaning? Soul? Those are optional—as long as they can say, “I told you so.”
And you want them to lead your life?
Hell no.
They can manage. They can optimize, refine, tweak… but they can’t lead.
Rebels Feel the Need to Take Risks
Why do rebels crave danger?
Why isn’t safe and simple ever enough for us?
Why are we comfortable making bets that might not pan out, or moving early and often, even when we don’t have all the answers?
Because we know—nobody ever has all the answers. Life’s too messy, too unpredictable for that… playing it safe isn’t just boring—it’s a slow, soul-crushing death.
We’d rather leap into the unknown than wither away in a cage of caution.
Waiting for certainty? That’s really just waiting forever. Nothing’s certain except death… and maybe taxes, if you want to get cynical about it.
What’s the Danger?
Unfortunately, sticking close to over-planners will kill your spirit, drain the magic out of your dreams, and replace them with stress and anxiety… leaving you with something safe—but utterly dead.
Do you want to build a life that feels like an adventure, one that feels good no matter what happens?
It takes courage!
Some people will never want to go higher, faster, or take the risks, and that’s ok… but don’t let their roof keep you pinned down, just because the’re afraid of the heights you crave.
Find the ones willing to understand that life itself is risk and anything worth doing, has the chance of failure.
Rebels need rebels, because going against norms can feel lonely as hell.
The rest? Let them set their routines, let them analyze, let them build their predictable, boring lives… maybe nudge them to step out and have some fun.
But never let them write your story.
Hey Rebels!
Don’t forget about our weekly X live audio spaces! Join us this Wednesday, and talk about Changes, or just hang out with other Rebels… set a reminder here:
Hope to see you there!
-Rick & Ani
RebelSpeakeasy.com by Ani Alexander • Rick
Find us on X @NFTrebels & @unl0c7
