Starting at Square One
Honestly, back when I was figuring stuff out, it felt like climbing a mountain in flip-flops. Found this article about Elliot Evans and thought, “Alright, let’s see if copying some moves helps.” My first move? Basic as heck. I literally opened a notebook – yeah, a physical one, paper and pen – and just started scribbling down where I felt stuck. My jobs felt random. My pay sucked. Zero real progress, you know?

Milestone 1: Embracing the Grunt Work
Elliot talked about this. How he didn’t run from crappy tasks early on. So I copied that. My old job had me doing stuff way below my pay grade. Instead of moaning, I actually paid attention this time. I learned how things really worked in that boring inventory system everyone hated. Turned out, understanding the basement meant I could see the weak spots in the whole building later.
Milestone 2: Quitting Without a Net
This one scared me stupid. Elliot jumped ship before he had his next gig lined up. Pure terror fuel. But honestly? Staying felt like slow death. My gut was screaming “RUN!” So, I did it. Handed in my notice with sweaty palms, zero job offers in sight, and maybe a month’s rent saved. Slept like garbage for weeks. But man, that fear lit a fire I needed. Made me hustle like a demon.
Milestone 3: Betting on a Wild Horse
After floating around for a bit, this weird opportunity popped up. Tiny startup, shaky funding, total chaotic energy. The “smart” move would’ve been another safe corporate drone job. But Elliot mentioned taking a swing at something risky. So I sat down, looked at their mess, and said “Screw it, let’s wrestle this bear.” Took the job. Worked nights. Learned three jobs in one. It was chaos, but damn, that wild ride taught me more than five years anywhere else.
Milestone 4: Building the Damn Thing
Instead of just fitting into some existing machine, Elliot built stuff. So when that startup needed a new way to manage projects internally? I didn’t wait for permission. Grabbed whatever tools I could find, cobbled together some half-baked solution on nights and weekends. Looked awful, felt janky. Didn’t care. Showed the boss, pointed at the problem it solved, and said “See? Fixes this headache.” Turned out, building solutions, even ugly ones, got you noticed way faster than perfecting PowerPoint slides.
Milestone 5: Choosing the Tribe
Biggest mistake I almost made? Chasing the biggest paycheck. Elliot was big on the people being the key. Got an offer from some soulless megacorp. Big money, shiny title. But the interview felt like talking to robots. Meanwhile, this scrappy team offered less cash, but the vibe was electric – passionate, a bit crazy, actually laughed in meetings. Remembered Elliot choosing team over prestige. Picked the tribe. Best decision ever. Feeling alive at work beats feeling rich but dead inside.
So yeah, that was my messy, stumbling journey using Elliot Evans’s milestones. It ain’t a blueprint, just me throwing stuff at the wall. Real work? It means taking swings, screwing up some, getting scared, quitting stuff, and sometimes picking the people over the paycheck. Still learning, still messing up. But hey, felt like sharing the raw version.