Hi, I'm Jovon Vaughn: Professional Rule-Breaker and Recovering People-Pleaser

Let's keep it real: I used to be the king of "almost." Almost started that business. Almost left that toxic situation. Almost believed in myself until "almost" started feeling like a fancy word for "scared as hell."

Then one day, I realized: Adulting is just glorified improv comedy. Nobody actually knows what they're doing some people are just better at faking it. So I decided to stop taking cues from a script I never agreed to.

Look, when you've gone from serving cocktails in dive bars to serving on City Council, from selling vacuum cleaners door-to-door to executive directing a Chamber of Commerce, you learn that the system isn't designed for people who color outside the lines. Yet here I am a Black, gay Navy veteran with rescue pitbulls and more career pivots than a basketball player—breaking those same rules that tried to break me.

Between navigating the justice system as a certified paralegal, cooking in resort kitchens, and somehow ending up producing an actual TV Show (yes, I have an IMDB page now, which still feels ridiculous to say), I've learned that the only permission slip you need is the one you write yourself.

The Day My "Almost" Addiction Hit Rock Bottom

Picture this: Me, sitting in my car outside yet another community meeting, rehearsing answers to questions like "Where do you see this initiative going?" while juggling texts from my husband about which dog food our picky pitbull might actually eat this week.

I had three different business plans saved on my laptop. A half-written resignation letter from one of my board positions. Six unfinished community development proposals. And approximately 47 screenshots of inspirational quotes that I was absolutely, positively going to implement... someday.

My husband, a brilliant salon owner from Savannah with enough Southern wisdom to fill a cookbook, looked at me over dinner one night and said, "Baby, you're collecting titles like I collect seashells, but are any of them actually YOU?" Leave it to a Georgian to serve truth with a side of sweet tea.

And he was right. After 20+ years of hustling from the kitchen to the courtroom, from boardrooms to bar service, I wasn't living, I was perennially window shopping for a life. All while my community kept calling me "visionary" and "transformative," which just made it harder to admit I was drowning in my own expectations.

Introducing The BREAK FREE Playbook: Stop Waiting for Permission to Live Boldly

That's when I developed what I now teach as BREAK FREE:

• Belief systems - challenge them relentlessly (something this Episcopalian knows a thing or two about)

• Risk taking - calculated but consistent (Navy training comes in handy here)

• Experimentation - treat life like a lab, not a test (or like a kitchen—sometimes you burn the first batch)

• Authenticity - unapologetic and non-negotiable (44 years on this earth and I'm done shape-shifting)

• Knowledge - constantly expanding your possibilities (from legal briefs to film credits)

• Fear - using it as a compass, not a cage (the same fear that kept me in food service for 20 years)

• Resilience - bouncing back faster each time (something every small business owner masters)

• Evolution - small changes compounded daily (how a telephone salesman becomes a workforce developer)

• Empowerment - taking back your damn agency (because City Council taught me power is both taken and given)

Now I:

• Hack personal growth like it's the Matrix (red pill = my email list)

• Turn limiting beliefs into kindling for my success bonfire

• Approach life like a science experiment (hypothesis: What if I actually tried?)

Last month, I called up my fellow Council members and told them I wouldn't be running again. Was I nervous? Absolutely. Did my voice crack like that time I had to tell a judge I'd filed the wrong motion? You bet. But guess who's writing this blog post from his home office while his dogs snore at his feet and his husband builds his own empire across town? Sometimes the most revolutionary act is simply choosing yourself.

(For the record, my community won't collapse now that I am stepping back. Turns out nobody is as indispensable as their anxiety tells them they are.)

The "What If I'm Wrong?" Insurance Policy: A Key Play in the Playbook

Here's the thing about those big, scary life changes we avoid making: they rarely kill us. But "almost" definitely will, one sad little compromise at a time.

This is a cornerstone of The BREAK FREE Playbook - using fear as a compass, not a cage. So I developed what I call the "What If I'm Wrong?" insurance policy. Before any decision, I ask myself:

1. If this goes terribly wrong, what's my actual worst-case scenario?

2. Could I survive that worst case?

3. If yes, then what the hell am I waiting for?

Turns out, most of my apocalyptic fears boiled down to "the community might think I've abandoned them" or "I might have to go back to bartending for a while." Neither of which, shockingly, is terminal. I've survived worse shifts at dive bars during fleet week than anything corporate America could throw at me. And I've dealt with more complex situations negotiating with my rescue pitbulls about bath time than most boardroom dramas.

Why This Blog Exists: Living The Playbook

This blog is where we trade:

✓ Toxic positivity → For real talk (the kind you get at 2 AM from a veteran bartender)

✓ Cookie-cutter advice → For "oh damn, that actually works" strategies (tested across board meetings and barrooms)

✓ Existential dread → For slightly more organized chaos (my specialty after juggling Chamber meetings and catering gigs)

You won't find me telling you to "just manifest abundance" while ignoring the very real systems designed to keep you small. As someone who's navigated those systems as a Black gay man in America, I know exactly how they operate. But you also won't find me wallowing in cynicism, because that's just another form of giving up, and my military training, small business survival, and courtroom battles have shown me we always have options.

Instead, we're going to get tactical about rebellion. Strategic about authenticity. Methodical about breaking the rules that deserve to be broken.

You're Here Because You're Tired of "Almost." Me Too. Let's Fix That.

Maybe you're:

Stuck in the purgatory between who you are and who you could be (like I was, with one foot in public service and one foot trying to escape)

So busy meeting everyone else's expectations that you've forgotten your own (been there between Workforce Development meetings and trying to remember which dog needs which medication)

Walking through life with one foot on the gas and one foot on the brake (the story of my 20+ career whiplash)

If any of that resonates, welcome home, my friend. This is your tribe.

After spending decades serving others, from literally serving food to serving on boards; from filing legal paperwork to filing into community meetings, I'm finally serving my own purpose. And it turns out that's the most transformative leadership move of all.

The Fine Print

Warning: Side effects may include unexpected confidence, improved standards, and the sudden urge to quit stuff that sucks.

I'm not promising overnight transformation. I'm not selling miracle cures. What I am offering is a bullshit-free zone where we can figure this stuff out together, one "actually did it" at a time.

So bookmark this page. Or don't; I'm not your boss. But if you're ready to trade in your collection of "almosts" for some "hell yeahs," I'll be here, posting new strategies from The BREAK FREE Playbook every week.

Your move.

Jovon Vaughn is the creator of "The BREAK FREE Playbook: Stop Waiting for Permission to Live Boldly." A 44-year-old Black, gay Navy veteran, certified paralegal, television producer, and Episcopalian, he's spent over two decades in roles ranging from chef to City Councilor, bartender to Board Member, and vacuum salesman to Executive Director of a Chamber of Commerce. He's been recognized as a visionary and transformative community development leader but is now transitioning out of these roles to practice what he preaches. He lives with his husband (a salon owner from Savannah, Georgia) and their rescue pitbulls, and can often be found with his nose in a book when not helping others break free from their own "almosts."