How I Went From “Not Good Enough” to Running Strategy—One Skill at a Time
Most people think they’re getting better just because they’re working. They show up, check boxes, answer emails, and assume that time spent equals skill gained. But if you’re not deliberately stretching yourself—if you’re not training with intention—you’re just reinforcing mediocrity. I had to learn that the hard way.
I Wasn’t Cut Out for This—Yet
After college, I landed a job in communications. I thought I was ready, but I wasn’t. I didn’t know how to write a proper press release. I didn’t understand how to structure a story. I didn’t even know what a lead or a bridge was. My first on-camera interview was a disaster. I was supposed to announce that three people had died in a tragic incident. I delivered the facts—but I forgot to say “thoughts and prayers.” I delivered it cold, like a robot, and my heart sank the moment the camera turned off. I wasn’t cut out for this—yet.
That failure humbled me. It also lit a fire in me. I knew I had to get better, not just for my job, but for myself. That’s when I joined the DC Air National Guard and went into Public Affairs. I didn’t do it because I had it all figured out—I did it because I didn’t. I needed reps. I needed structure. I needed pressure. I needed to earn the kind of skills that would make me undeniable. I was signing up for the challenge because I knew that’s where the growth would be.
The DINFOS Wake-Up Call
After struggling in the field for two years, one of my supervisors—a Marine and a graduate of the Defense Information School (DINFOS)—told me that if I really wanted to be great, I had to go where the best communicators were trained. I almost joined the Marines to make that happen. I stuck with the Air Force, and eventually made it to Fort Meade to attend DINFOS.
At the time, DINFOS had one of the highest washout rates in the military, right behind special forces and translator schools. It wasn’t just a communications boot camp—it was a mental and technical proving ground. For eight hours a day, we trained in deliberate practice. It wasn’t enough to show up—you had to show mastery. Put a comma in the wrong place? That was minus 25 points. Misspell a name or make a factual error? Automatic failure. You needed an 80 to pass, and that margin left no room for laziness or ego.
They’d cut the lights and throw you into high-pressure on-camera interviews. They’d hit you with tough questions, and you had to respond with not just an answer, but a command message. If you fumbled it, you failed. But even then, it was all still just practice. Purposeful, grueling, high-level practice.
From the Classroom to the Crisis
When I returned to my civilian job, there was no easing back in. I was thrown straight into the fire. One of our special agents had been killed. A federal standoff was underway in Oregon. There were news crews, stakeholders, and chaos. And this time, I wasn’t rattled. I wasn’t unsure. I was ready. I had the reps. I had the calm. I had the skills.
That was the moment I realized what all that deliberate practice had prepared me for. It wasn’t just about communication. It was about being the one people could trust when it mattered.
Most People Avoid the Very Thing That Would Make Them Great
Cal Newport talks about this in So Good They Can’t Ignore You. He explains that top performers don’t just work—they improve on purpose. Deliberate practice is the process of targeting specific weaknesses, pushing yourself just past your current abilities, getting consistent feedback, and repeating with focus until your skill becomes second nature. It’s not glamorous. It’s not fun. But it’s where the magic happens.
Too many professionals coast through their careers. They confuse time spent with mastery. But the difference between someone with ten years of experience and someone with one year of experience repeated ten times is deliberate practice. It’s the reps that hurt. The assignments that scare you. The pressure you don’t think you’re ready for—until you are.
Everyone Wants Freedom—But Few Are Willing to Earn It
And here’s the link everyone misses: this is what leads to freedom.
People want creative freedom. They want to work from a beach. They want to start a business. They want to make six figures doing what they love. They want autonomy—but they aren’t willing to put in the work that earns it.
Autonomy isn’t a vibe. It’s a result. It’s the byproduct of someone who got so good, for so long, that people had no choice but to give them space, trust, and resources. Autonomy is built on capital—and capital is built on practice.
If you want that freedom, start with this: pick a weakness. Break it down. Drill it. Get feedback. Do it again and again until that weakness becomes your strength. Until you’re trusted. Until you can trust yourself.
Final Word
DINFOS didn’t make me perfect—but it trained me to operate under pressure. It made me deliberate. It gave me confidence grounded in repetition and precision. It helped turn a kid who bombed on camera into a man trusted to lead communication strategies in the most critical moments.
That’s what deliberate practice builds. Not just skill—but confidence. Not just results—but reputation. That’s how you get freedom. That’s how you become so good they can’t ignore you.