I’m ready to get real and vulnerable. Lately, I’ve started to see my own journey in Derek Trucks’ path to mastery.
I’ve always held Derek in the highest regard. Just as people from my parents’ generation reminisce about seeing Hendrix live, I believe that 40 years from now, people my age will proudly say, “I saw Derek Trucks live.”
And I have — twice. God willing, this October will make it three times.
Derek isn’t old — he’s just a couple of years younger than me — but he’s been one of the most incredible guitarists on the planet since he was in fifth grade. Music runs in his family. His Uncle Butch was a founding member of the Allman Brothers Band, a band Derek joined at just 19.
If Derek keeps playing at his current level for another 25 years, his legacy could easily rival that of Eric Clapton, an artist he toured with for several years.
While researching for Hello Again, I read Gregg Allman’s autobiography. One story about how Gregg first met Derek really struck me.
The Allman Brothers were recording in Miami, but the atmosphere was tense and plagued by addiction. Frustrated, Gregg retreated to his hotel room to take a nap. But then, Butch Trucks knocked on the door. “Get dressed, there’s a guitar player I want you to see.”
Gregg reluctantly agreed. Butch, Gregg, and possibly Warren Haynes found a small club where two kids were playing catch outside. They snuck in and took a seat in the back to avoid being recognized. On stage, those same two kids were performing. One of them sat behind a drum kit, and the other picked up a Gibson SG that seemed almost as big as he was.
Gregg was captivated by the guitarist, who was tearing it up on a slide guitar — no small feat, even for seasoned players.
A few songs in, Gregg had an epiphany. He tapped Butch on the shoulder. “Wait a minute, that’s your nephew, isn’t it?”
“Yep,” Butch proudly replied.
Derek took a unique path to becoming the guitar master he is today. He started with the slide, and as his hands grew, he eventually moved on to fretting notes. Through countless hours of practice and thousands of live shows around the world, Derek has become one of the greatest guitarists of all time.
And he’s only getting better.
So, why am I talking about Derek Trucks? What does his story have to do with me?
I feel like I’m at a turning point in my life. With my business growing, the possibility of moving, and a complete life reset on the horizon, I’m realizing that I need to approach practice in a new way.
Derek had a natural talent for playing slide guitar, but he still put in the work to improve and become the master I admire.
For a long time, I believed that if you weren’t good at something, no one would ask you to do it — so no one would pay you for it. This belief is why my coaching business is only now starting to gain traction. I finally have some practice under my belt.
But here’s the truth: I’m terrified of failing. I’m scared of looking bad and of facing my own imperfections. Embracing activities I’m not yet good at brings all of these fears to the surface.
One of my biggest fears is being exposed as a fraud. Someone once angrily told me, “You’re such a fraud,” and it really hit me hard.
But I don’t want to go through this alone.
I don’t think I can do this alone.
I want to build my confidence by doing hard things — like running, creating clients, and talking to beautiful women. I’ve never failed when I’ve pushed myself to take on difficult challenges.
I also want to get in tune with my emotions, no matter what they are. This means being mindful of how I feel physically. Am I anxious? Do I feel comfortable in my skin? Am I numbing myself by scrolling through my phone, watching pointless content, or listening to music without really enjoying it? When I notice these things, I want to ask myself what I’m feeling and where that feeling is coming from.
Lastly, I want to practice financial literacy. I’m going to revisit some of the books I avoided in the past — books about money, getting clients, and so on — because I was too scared to put their advice into action.
I’m going to fail. I’m going to stumble. I might embarrass myself. But as long as I keep getting back up, I can’t lose. As someone once wisely told me: everything works out in the end. If it hasn’t worked out, then it’s not the end.
In closing, I want to start a conversation. Let’s talk about practice. What are some things you want to improve in your life? What are you practicing, and how are you going about it?
Let’s practice together.
