The Entrepreneur's Dilemma: Trapped in a Cage of Your Own Making

Jackson Calame stared at his reflection in the mirror. Dark circles under his eyes. A weary smile. The look of a man who'd been through the entrepreneurial wringer... twice.

Two divorces. A failed startup. And a nagging back injury that robbed him of his favorite outdoor pursuits.

This wasn't how the story was supposed to go.

But in that moment of brutal self-reflection, Jackson stumbled upon a truth that would transform not only his life but the lives of countless entrepreneurs:

The solopreneur is a myth. And it's killing your business.

"I've never, ever met a successful solopreneur, ever," Jackson now declares with the conviction of a man who's seen behind the curtain. "I have met people who will claim it, but as soon as you see behind the scenes, they either stepped on all the people who helped them get to where they are, or it's a complete lie."

Harsh? Perhaps. But it's the wake-up call you didn't know you needed.

Jackson's journey from struggling entrepreneur to founder of Vision Pros Live wasn't a straight line. It was a series of hard-won lessons and painful realizations.

Lesson #1: Start with Who, Not Why

Forget Simon Sinek's "Start with Why." Jackson takes it a step further. Before you can even articulate your why, you need to focus on the who.

"If we really gravitate towards who is the type of person we want to work with and who we are as leaders, what are our values, what are our virtues, then we establish the why we're doing what we're doing."

It's not just about finding warm bodies to fill roles. It's about aligning with people who share your values and can complement your weaknesses.

Lesson #2: Embrace Radical Candor

Remember those yes-men surrounding you? They're not doing you any favors.

Jackson learned the hard way that surrounding yourself with people who only tell you what you want to hear is a recipe for disaster. Instead, he advocates for radical candor - feedback that's both kind and brutally honest.

Find people who love you enough to tell you the hard truths. Your ego might take a hit, but your business will thank you.

Lesson #3: Time is Not Your Enemy

Think you don't have enough time? Think again.

Jackson's blunt assessment: "We have to stop telling ourselves that lame excuse that I don't have the time. No, if I didn't make the time, then I say I did not make the time, but I am not going to make the excuse that I didn't have it. We all have it. We just choose to do different things with our time."

Ouch. But he's right.

Jackson recommends tracking every minute of your day. It's painful. It's eye-opening. And it's the first step to reclaiming your time.

Lesson #4: Play the Long Game

In a world of instant gratification, Jackson's advice is counterintuitive: think quarterly, not daily.

"Most small businesses fire most of their people and change their systems within a matter of one quarter or two quarters. They are get-rich-quicking. We have to own where we are on the get-rich-quick bandwagon."

Stop chasing the next shiny object. Give your strategies and team members time to prove their worth.

Lesson #5: Get Outside

Jackson's back injury robbed him of his beloved jet skiing for years. But it taught him a valuable lesson: there's more than one way to reset your mind.

He now swears by a practice involving deep breathing and visual focus exercises outdoors. It's a simple yet powerful way to get present and recharge your entrepreneurial batteries.

The Journey is the Destination

Perhaps the most powerful lesson from Jackson's journey is this: success isn't about reaching a destination. It's about how you show up each day along the way.

"Today needs to be my best day. I need to just do my best today. And if I do that, knowing that part of today is planning tomorrow and the next day and so on and taking care of my people, I can go to bed happy."

It's time to break free from the cage of solopreneurship. To surround yourself with the right people, embrace honest feedback, manage your time wisely, and remember to step outside once in a while.

Because at the end of the day, it's not just about building a successful business. It's about creating a life you don't need to escape from.

Are you ready to make that shift?

If Documenting Your Journey Feels Hard, Weird, or Like You’ve Got Nothing to Say?

Are you tired of staring at a blank screen, desperately trying to conjure up content that doesn't sound like it was written by a robot with an MBA?

Do you find yourself drowning in a sea of generic posts, wondering why your message isn't resonating with your audience?

You're not alone.

The struggle is real, and it's killing your business.

Every day, we hear “Document your journey!”

And every day, we go, “Cool. Um… how?”

Sometimes we’re just too close to the business to SEE it anymore.

Sometimes, we’ve lost touch with the emotions behind the problem we solve, or how much loving the people we serve drives us every day.

Sometimes, we just have flashbacks of our 7th grade English teacher.

Whatever’s driving it, we end up taking WAY too much time to create our content - if we ever even do.

Yeah?

So, who here would find it extremely helpful to see my workflow for creating deeply engaging, emotionally resonant content that sounds exactly like you - without writing a single word?

I’m going to hold a free workshop, "Break Free from the Content Creation Cage.”

You'll discover:

• The secret to tapping into your business's emotional core (hint: it's not where you think)

• Why your inner fourth-grade teacher is sabotaging your writing (and how to shut her up - Mrs. Doll at Melvin H. Kreps, I’m looking at you)

• The counterintuitive reason why talking beats typing when it comes to authentic content

• A step-by-step workflow that turns your verbal ramblings into polished prose

• The tools that will make your content creation process a breeze (no more hours wasted on social media)

This isn't about following some cookie-cutter formula or mimicking the latest trends. It's about finding your unique voice and using it to connect with the people you're meant to serve.

But here's the catch: This is for entrepreneurs who are ready to dig deep, get vulnerable, and do the work to create content that truly matters.

It’s time to stop hiding and start shining. Your audience is waiting.

You want in? (We’ll sort out details soon - just trying to read the room here.)

Anyone else hate shopping?

My hubby loves that about me lol.

My goal is… Get in. Get the thing. Get out. Nobody even knew you were there.

My take on getting the news I actually need to know about is similar.

The media has one goal: to capture your attention. Even better if you get so absorbed in it that you can’t turn it off.

If I get wrapped up in just one horrible news story, it can take me hours or even days to get my brain space back.

I don’t know about you, but I can’t afford to surrender one extra brain cell to that. I’m on a mission. No time for that nonsense.

That’s why I pared my news consumption down to THIS (plus Morning Brew, which I just like because of the writing style).

Maybe you’ll like what it does for your brain, too. The info you need, without the hysteria you can live (better) without.

Daily News for Curious Minds

“I stopped watching the news, so sick of the bias. Was searching for an alternative that would just tell me WHAT happened, with NO editorializing. I found it. It’s called 1440. It assumes you are smart enough to form your own opinions.”

Sign up now!