Sometimes I Still Feel Like a Milkman (And Other Impostor Syndrome Confessions)

There are days I’m giving advice in a meeting, people are nodding, I’m holding court like I have a clue—and in the back of my brain, a voice is whispering:

“Sir. You are a former milkman. What are you even doing here?”

I laugh it off. Play it cool. But the truth is: I still feel like that 21-year-old guy hauling crates of dairy into convenience stores at 5 a.m., hoping I didn’t forget the chocolate milk.

Impostor syndrome? Yeah, we’re close. Like “text-each-other-dumb-memes-at-midnight” close.

🍔 The Fast Food Philosopher

When I was 16, I worked in fast food. Not the glamorous, drive-thru, headset kind. The grill guy who smells like grease for three days kind. Back then, my biggest worry was whether the sandwich I just handed out actually had the right number of pickles.

Now I’m out here leading projects, mentoring people, and getting tagged in posts like I’m some sort of expert.

Spoiler: I still worry about the pickles. They’re just metaphorical now.

👟 Retail Me This

At 19, I worked at a Footlocker. You know, the store where every customer either thinks they’re the next D1 athlete or acts like you personally insulted their family by recommending the wrong Jordans.

I spent my shifts pretending to know which colorways were “hot” and which ones were “dead stock,” all while trying not to mix up the endless wall of identical black boxes in the back.

There were moments I’d tie a perfect display knot on a size 11 and feel briefly like I had my life together. Then I’d immediately drop the shoe, trip over a stack of socks, and return to my natural state: confused, sweaty, and doubting every life choice.

So yeah—when someone asks for my take on dev team strategy, part of me still expects a guy in a snapback to shout,

“Yo, you sure you even work here?”

Because deep down, I'm still the guy who once gave a sneaker recommendation based entirely on the shoe being “pretty comfy, I guess.”

💻 The Brick Wall Intern

When I landed my first dev gig, I sat at a folding table against a brick wall. No ergonomic chair. No dual monitors. Just a hand-me-down laptop, a bottomless imposter complex, and the crushing fear that someone would discover I didn’t know what git stash did.

Honestly? Sometimes I still feel like that guy.

Even now—years later, projects delivered, teams led, systems built—I catch myself thinking:

“They’re going to figure it out. They’ll realize I’m just winging it with better lighting.”

😅 Real Talk: Impostor Syndrome Doesn’t Go Away

Not completely, anyway. It just changes shape.

You go from “I’m not qualified to be here” to “I’m not qualified to lead here” to “I’m not qualified to be giving talks about leading here.”

It levels up with you, like a very clingy NPC that just won’t leave your party.

But here’s what I’ve learned after all these years of questioning myself:

🔹 Most people are winging it.

Some are just better at smiling while doing it.

🔹 You don’t have to feel confident to be valuable.

Your experience, mistakes, weird job history, and folding-table battle scars all count.

🔹 If you care enough to wonder if you belong, you’re already ahead of people who never do.

Doubt means you give a damn. That’s powerful.

🎤 So Here’s Me, Still Showing Up

Still feeling like that milkman. That fast food kid. That intern with shaky hands and a brick wall backdrop.

But also?

Still helping people. Still learning. Still leading, somehow.

Impostor syndrome might be loud, but it’s not in charge. It can sit in the back and heckle all it wants—I’ve got code to write and people to support.

And if you’re reading this wondering if you belong too?

Spoiler: You do.

Even if you once delivered dairy in a truck that smelled like regret and spoiled yogurt.