As I spend the next 5-6 weeks awaiting barber college to start, I'm getting adjusted to all sorts of changes from the routine (or lack thereof) of summer. It's still August, but school's been on in Chicago for a week already, which means my wake-up time is now 5:30am. The temperature has also dropped precariously from the 90s now to the 70s and the 50s overnight. My parents need the AC on so my body doesn't know what temperature it's supposed to enjoy right now. I'm also now three days out from trying out a boxing gym and going way. too. hard.
Getting older is no joke, y'all 😂
My point is life at this moment is more or less pretty chill and while it's too chill for comfort, I appreciate that I can be as present in the moment as I am. So... yeah, I have a lot of time to read, to write and reflect this week. I'm starting to see my story as a refrain told in an epic poem about a generation of people who must go through the same alchemy without anyone ever preparing them for the change the world requires of us that all of the sudden, arbitrarily, the market we've contorted and twisted ourselves to work for/with decides at some point in our midlife we're just supposed to do something else.
Yesterday, I shared a podcast where I discussed the story behind my pivot. This morning I'm witnessing comrades going through it, so I'm following up yesterday's video with details on my process in the hope it finds its way to someone who maybe needs this.
When we all knew the election outcome in November 2024, I did two things immediately that night. First was organize ExtraORDinary Camp which took place in early February 2025 (that timing proved SO CLUTCH). The next thing I did was generate a bunch of value propositions for new businesses or new jobs or new careers. Since the release of Project 2025, with 47 in office, I knew my time at the US National Archives, one way or another, was gonna be limited. I took that job on the heels of being laid off in 2023; taking that job in 2017 was a result of 45 crushing all gov contracts and several Department of Education and Health & Human Services projects, which crushed my contracts working with ADL and a few other cabinet-level agencies, let alone grant-funded programs I was primed to support as my business pipeline went from $349K in December 2016 to $48K in in mid-January 2017. Go figure.
I am tired of this man's hands all over my pockets. 😤
Anyway, for speed, in helping to accelerate the on-ramp to action, I simplified a template to generate Value Propositions for myself. Back in 2011, when I was piloting the first Up to All of Us in NYC (basically the first four hours of the program), Elliot Felix introduced a short-hand to generating robust value propositions as a MadLib exercise. That's always stuck with me and I never altered it until I needed to, when encapsulating the crux of an idea quickly is more important than elaborating full details about an idea I'm not yet committed to.

The "whom" are my would-be customers. The "what" is the crux of what I'd be doing that's of value. For me, doing something that is immediately and tangibly of value is paramount now because as economies get weird, governments get weird, rules get weird. That what I do is so obviously valuable people will pay cash for (or trade in a bartering exchange) is more important than ever for my feelings of security and self assurance. What I would pitch as my secret sauce is the "why."
I did this exercise several times until I had maybe four unique ideas I felt interested enough in to take it to the next level - generating business model canvases, which in and of itself, elaborates on the value proposition.

I sketched mine on 3M Flip Charts at first. I like those because, like post-its, I can put them up on any wall and boom I have a place to sketch and stand and move. Once I can't keep track any more of my scribbles, I'll transcribe the business model canvas (or canvases, as it may be) into OmniGraffle. I love thinking through value chains in OmniGraffle – connecting specific customer segments with specific key activities, color coding the connected but distinct value propositions...
So I had enough good feels from how elaborate I could get in fleshing out food truck ideas that my next step was figuring out how to make that real. So while I had a good idea, now I needed to do some real research on what it takes to make a food truck business work. I talked to food truck vendors with different backgrounds and situations in which they opened their businesses. I talked to restaurant owners. I researched where I could go to school a little, but mostly I was focused more on the "after I'm out of school what do I need to make a business?"
The resources it takes to open a food business of any kind, even just making coffee, and do it legit, are many. Running off just the business model canvases I developed, I did some risk-assessments for a few scenarios I could envision just in trying to do a cheesesteak truck.
- What if there are tariffs or other slowdown on cuts of beef (ribeye) desired for Cheesesteaks?
- What if there's a listeria outbreak and I can't get fresh onions?
- What if I can't source rolls from Philly? What would my backup be locally?
- What if prices go up for key ingredients?
When I worked at Grainger, I would use a matrix that spelled out the Likelihood of scenarios happening versus the Severity of impact or consequence should that risk be met. I can visualize that stuff in my head, so when enough scenarios began to aggregate that weren't low risk, I asked a fundamental question I hadn't asked anyone yet: how many people were doing a food business all on their own, and the answer was a resounding "No one." That compelled me to use a different tool to really gut-check how much I wanted to do a food truck.
I made a time-utilization pie chart identifying the critical tasks that need to be done to just be a food truck vendor in Chicago.

For my pivot to work, I need to be self-reliant and, ultimately, no variant of a food business I strategized for was one I could operate myself. Having shaken a critical success factor out of this process, I went back to the beginning – this time generating value propositions for skilled trades that included becoming an electrician, a pipe-bender, a florist and a barber. I was frustrated about this, but I was very grateful to have learned these tools, to have figured out such a critical piece of the puzzle before spending any resources, let alone launching a business.
When you're on your own, it's empowering, but when you can't afford missing the 2-meter exhaust hole in the Death Star Trench Run... it's humbling.
When I finally got down to both scenario risk assessments and time utilization, I just knew barbering was gonna be for me.
Oh, and by the way, if you're working with the American Jobs Center on a Workforce Innovation and Opportunity Act (WIOA) Grant, this is exactly the kind of thing they like ppl to do in their applications, so when it came time to file that work, I had all manner of artifacts ready to pull the paperwork together.
Feel free to share this with someone you think might need it. It sucks having to figure this stuff out on your own, especially when so many people have been so tragically underdeveloped by employers in their current and previous roles. I hope this helps.