Halfway There; Living on a Prayer

Sorry to leave y'all hanging for a month. I attended my first industry conference, learned a lot, upgraded some gear and put all the new skills to work with my first barber pop-up. And all while closing in around 750 hours completed towards my barber license. Lemme break it down for you.

I got a LOT out of my first-ever experience of the Beauty industry writ-large at America's Beauty Show a few weeks ago. I picked up a student pass and went all three days. I took several classes, helped my instructors from barber school with their first time presenting at a conference, and insodoing did some fine networking.

Ashlee Norman's talk on how to do color on curly hair was really instructive. I could geek out on clay lighteners and what that means for being able to do better color control on coily hair by helping lock that stuff in place on the balayage board... yeah, I'm not even in the color unit yet of instruction. It took all my focus to not spend a ton of money on hair color stuff. it looks fun to work with.

I was really fortunate to meet some great barbers who offered different perspectives on how to approach similar cuts. Unlike going to a learning & development or an HR or even a tech conference, very rare are you encouraged to gather round a speaker who's literally doing the thing you're there to learn. But I got to see multiple barbers give a break down of different approaches to fades. Jesse Fonseca, Matt Sabella, Steven Wren were each patient and structured in their approaches to doing fades. I've pulled a little something from each of them into my process and my fades have really elevated in the two weeks since ABS.

I also caught multiple sessions on how to do a shag haircut in my attempt to get more training on working with shears, but the instruction I got from Jesse Perez Gil was outstanding, when he visited Erskine Reeves Barber Academy just a few days after the show, demonstrating a shag cut but really focusing on how to approach the cut with the use of point-cutting.

It feels like I first learned of a first-of-its-kind mobile barbering chair within my first days of barber school back in October. I've been mobile-first throughout my entire tech career, blazing the trail for others to follow in being able to work from anywhere.

I remember thinking, why should barbering be any different?

Now, six months later, here we are, making a new self-investment for an entirely new type of business venture.

I'm in an interesting spot; I'm in the middle of barber school. I've learned all the broad skills to succeed as a barber. I lack all the experience I need to be the barber I want to be. I am not ready to be a full-time barber, yet I need more cuts so I have more experience. Figuring out risk vs. reward, opportunities vs costs... how do I create opportunities to cut more hair and develop a Chicago-local community that is down with the JFDI-ness of getting better and better with every cut?

This new mobile barbering chair is a catalyst for me coming into my own as an entrepreneur and as a barber. I ordered a 10x10 pop-up tent with sidewalls to help control for wind, lighting, seating, a large battery generator, portable hot towel warmer... and the weekend after America's Beauty Show, I JFDI'd a pop-up barbershop in Portage Park, nabbing three takers for free haircuts in the four hours I was up and running.

Free Cuts Pop-up no. 2 is planned for Saturday, May 16 at Portage Park, again, 11am-3pm.

It seems when I was DOGE'd in February 2025, and then two months later I got some separation paperwork so I could move on, I was never dropped by the F.E.P. - the insurance program because they did not receive any notice that I was to be dropped from the program.

Because I was let go outside of the standard operating procedures that ensure b.s. doesn't happen when you let an employee go, just as a matter of process.

So, because of this, Medicaid is no longer paying on doctors bills and medications because, ha-ha, I'm showing up on a report that says I'm covered by the F.E.P. They need an email from the provider I had when I was a fed, to let them know that I've not been covered.

I call the provider I had with the F.E.P. They needed an email from the National Archives (or a completely different agency, because who knows which agency is doing what HR jobs for whom now). As of writing, this isn't resolved.

But I have a stack of provider bills and explanations of benefits from two different insurance providers telling me all the things they're not gonna do. On top of gas hitting $4.99 a gallon, and groceries doubling since January while the cash I budgeted to get through barber school is depleting a lot faster than planned.

When you can't even lay people off correctly, it has consequences and that shit always rolls downhill. Shrugs.

I'm coming into May a better barber. Because of the people in my life, I'm coming into it a better person. I can't say that I'm happier than I was a month ago, but I am hungrier. Hungry is a lot more useful to me as I stare down the second half of this journey towards a barber's license, and have to master things I don't like much, like working with relaxers. There's a lot of it ahead, and it's messy. And did I mention there will be a lot of it ahead of me? Yeah...

Anyway, being hungry for the experience of cutting hair and being a barber is a good thing right now. Nothing gets me right like having a client in the chair. I have more and more autonomy and confidence in my ability to get a client looking and feeling right. My clients are getting me with an upgraded kit, whether it's in a pop-up or at barber school, and yeah the pleasure of working with quieter, sensory-safe tools that cut with better sound, feel more comfortable when they're lining or shaving a bunch of hair off... those little things are a lot. I was able to do a lot within a constrained budget in April. I'm excited for the growth in front of me.