Jan 3 • Governance & Transparency
Some Lives Look Like Straight Lines. Yours Probably Doesn't.
This is not actually a story about "Tamara." It's about YOU—the reader who has worn more hats than you can list, who has made decisions you regret, who sometimes looks at your own life and thinks, "Did I mess this up… or is there something I'm not seeing yet?"
Welcome to Puzzles to Pictures, Criminal to Cowboy. This is a blog for the person who needs to believe their scattered past is not wasted—and that there is still a picture on the box, even if all you see right now are pieces.
---
WHEN YOUR LIFE LOOKS LIKE A PILE OF PUZZLE PIECES
Think about your own resume for a moment.
Maybe you've:
- Started and left jobs in totally different fields
- Dropped out of something important (school, a relationship, a career path)
- Gone back later, or tried to
- Had seasons that felt like pure survival, not strategy
From the outside, it can look like instability. From the inside, it often feels like shame: "Why can't I just pick one lane and stay there like everyone else?"
That's how it felt to me, too.
Behind my name is a list that makes people raise their eyebrows:
High school dropout. Montessori teacher. Real estate licensee. DCF caseworker. COVID investigator. Prison nurse. Public health worker.
And before all of that, a little girl with trichotillomania, pulling out her own hair to manage feelings she didn't know how to name. A girl whose biological family was threaded through the prison system. A girl adopted into a family that ran Montessori schools, then grew up to sell the very school her father had poured his life into—and regret it more than almost anything.
From the outside, those facts look like contradictions. From the inside, they felt like failures.
But here is the lesson this blog is built on:
💡 What looks like instability on paper may actually be God, life, or fate handing you puzzle pieces for a picture you haven't seen yet.
And that lesson is not just mine. It's yours.
---
THE BIGGEST MISTAKE… AND WHY YOU'RE STILL HERE
Every person reading this has a "biggest mistake." You can probably name it in one breath.
- The thing you sold or walked away from.
- The job or relationship you burned down.
- The school you dropped out of.
- The moment you "betrayed" your own values or your family's work.
For me, it was selling my family's Montessori school. It felt, and still feels, like selling out my father's legacy—decades of sweat and service exchanged for a momentary sense of relief. If you have ever signed something, said something, or walked away from something and immediately thought, "I can't ever take that back," you know the taste of that.
But here is what time, and a lot of tears, taught me:
If I hadn't let that school go, I would never have been forced into the wilderness of other work. No DCF. No health department. No prison nursing. No barns. No deep understanding of courts, case files, and the way idleness eats people alive from the inside.
Without my biggest mistake, I would not have the handful of puzzle pieces that became LettersToRon.org.
You have your own version of that story. A decision you'd reverse in a heartbeat… except that the person you are now is shaped precisely by having lived through it. The question is not "Was it good?" The question is:
💡 "What will I do with who I am now because of it?"
This blog is an invitation to stop treating your regret as dead weight and start treating it as raw material.
---
CRIMINAL TO COWBOY: WHY YOUR PAST DOESN'T DISQUALIFY YOU
"Criminal to Cowboy" is more than a catchy phrase. It's a way to talk about transformation in identity and environment.
Criminal is not just a legal status. It's a role: the one who is watched, doubted, written off, contained.
Cowboy is not just a costume. It's also a role: the one who shows up at dawn, handles dangerous responsibility, reads the weather, earns trust through action, not talk.
Maybe you've never been arrested—but you know what it is to feel like the "criminal" in your own story:
- The one everyone expects to fail again.
- The one trying to outrun a file, a label, a rumor, or a past choice.
- The one who gets invited into programs that keep you busy but never really trust you with anything real.
Inside, though, you might actually be built like a cowboy:
- You think better when you're moving and working, not sitting still.
- You calm down when you have responsibility, not when you have nothing to do.
- You feel most like yourself when someone hands you real tools and says, "I'm counting on you."
"Criminal to Cowboy" is the shift from being managed to being trusted with real work. It's the journey from idle time to purposeful labor. And if your life has ever brushed against the justice system—from the inside, the outside, or just the edge—this is your terrain.
The point isn't that everyone needs a horse. The point is that everyone needs:
- A structure.
- A role that matters.
- A place where their hands, brain, and heart are actually needed.
If no one has given you that yet, your story is not finished.
---
PUZZLES TO PICTURES: CONNECTING YOUR PRIOR KNOWLEDGE
If you're wired anything like me (classic ENFJ energy), you probably:
- Feel everything deeply.
- See patterns in people and systems.
- Tell stories to make sense of chaos.
- Carry a quiet belief that your life is supposed to matter to someone beyond yourself.
ENFJ or not, your brain is always trying to turn puzzles into pictures. It wants a narrative that makes your past make sense.
Here's how to start seeing it:
1️⃣ List your "random" roles.
Every job, every unpaid responsibility, every label you've worn—especially the ones you're embarrassed by.
2️⃣ Ask: what did each one actually teach me?
Not just tasks. Insight. People. Systems. Pain. Skills. Limits.
3️⃣ Look for repeating themes.
Do you keep ending up with:
- People in crisis?
- Systems that are broken?
- Young people on the edge?
- The same kind of injustice or need?
4️⃣ Ask the dangerous question:
If all of this was preparation, what might I be being prepared for?
---
This is what happened to me, piece by piece. Montessori and special education taught me how environment and structure shape behavior. DCF showed me what happens when they're missing at home. Real estate showed me how land and access work. COVID investigation showed me how quickly stability can vanish. Prison nursing showed me the cost of idleness and hopelessness on a body and soul.
Individually, they were puzzle pieces. Together, they became a picture: a nonprofit built to replace idle time with structured, meaningful work for people who were never meant to have access to a "nice program."
You are not reading this by accident. Somewhere in your own life is a similar picture trying to emerge.
---
YOUR TURN: FROM READING TO RE-WRITING
This blog is not here so you can admire someone else's story. It's here so you can re-read your own.
If you take nothing else away today, take this:
✅ Your "instability" may be training.
✅ Your "criminal" chapters do not disqualify you from becoming the "cowboy" in your own life.
✅ Your "biggest mistake" might be the very thing that pushed you into the experiences you needed to build what only you can build.
So here are three questions to sit with, journal on, or talk about with someone you trust:
❓ Which three moments in your life feel like scattered puzzle pieces that don't belong together?
❓ What kind of person do those three pieces prove you've become (resilient, perceptive, protective, relentless, etc.)?
❓ If your life were quietly preparing you to build or lead something that doesn't exist yet, what problem would it exist to solve?
You don't need a nonprofit, a barn, or a program to start. You just need to be willing to look at your life with new eyes.
---
A QUIET INVITATION
LettersToRon.org exists because one woman finally realized her puzzle wasn't broken—it was just incomplete. It exists because one inmate's honesty turned scattered experience into a clear mission. And it exists because a mother decided that no other mom should have to watch a child disappear into idleness and systems with nothing meaningful on the other side.
This is your story, too, whether you're:
- A parent afraid for your child.
- Someone with a record trying to build a future.
- A worn-out helper who has seen too much and still wants to believe humans can change.
- Or just a person whose life looks like "too many pieces" and not enough picture.
If you want to:
- Support work that fights idleness with real responsibility
- Help create spaces where "criminals" can become "cowboys" in their own lives
- Or simply stay connected to a story that reminds you your past is not wasted
then consider this your invitation to stay, read, share, and, when the time is right, step into the arena—whether that's through giving, partnering, referring, or starting your own version where you are.
Because the real miracle isn't that my puzzle became a picture.
It's that yours can, too.
---
📚 REFERENCES & FURTHER READING
For readers who like to know the roots:
- Von Wedel Montessori School and its legacy in North Miami.
- FTBOA Member Spotlight on Tamara's background, equine connection, and Gentry family lineage.
- Coverage of Juan Alvarado's training career and work ethic in the Thoroughbred industry.
- University of Miami education background and brain-based teaching and learning focus.
---
💬 Want to share your own "puzzles to pictures" story? Drop a comment below.
0
0 comments
Some Lives Look Like Straight Lines. Yours Probably Doesn't.
powered by
Suggested communities
Powered by