Combat boots and a T-shirt dress from H&M.

That’s what I wore to my first professional interview a decade ago.

A lot of thought went into this outfit choice. I didn't wear dresses often but common wisdom for interviews was that you had to look neat and put your best foot forward, so I pulled this casual blue number out from the back of my closet. Now, if I was going to wear a dress to look polished but not stay true to my authentic style, I had to do something to show off my edgy self. The answer? My combat boots.

I was thrilled to have gotten this interview in the first place. I had grown up an avid music fan, wasting away my youth wandering around the sticky floors of DC concert halls and waiting at the bar (black sharpie X's prominently displayed on the backs of my hands) to oh-so-casually bump into my musical idol at the time (MGMT, Tame Impala, The Vaccines, Vampire Weekend, Twin Peaks, Temples… many a "spontaneous" encounter). Now I was entering the east coast musical Mecca of the 9:30 Club to potentially work here?! Albeit just for the summer, I could not have been more excited.

I never debriefed with my old grassroots marketing supervisor what actually landed me that first gig. It was a group interview, me in a lineup of 11 other people, one of the 4 sessions they ran over the course of a few weekends. But in my mind, in a row with people looking stuffy in suits and masking their personality, my combat boots played a key role in landing me the offer. That or maybe my answer to the interview question "If you only had 5 words to say to Kanye West, what would you tell him?"

A few weeks ago I was back in the 9:30 Club, watching my friend's boyfriend's band perform upbeat pop-funk-soul fusion hits. Looking around the venue, I found myself reflecting on where the last ten years had brought me.

I've lived many lives in the last decade. When I toured the BBC Headquarters while working in London, I never could have imagined that 8 years later I'd be doing Live TV and Radio interviews with the acclaimed British broadcaster. “The Ethics of Entertainment Media” was my favorite class in college, the one that challenged my mind like no other. Little did I know I'd spend my late twenties building an online brand around the same questions I wrestled with for my degree. I moved to California to work on film sets of all things… and by some detour I found myself in the tech industry. And the blog I regularly contributed to for the 9:30 Club? A decade later, I'm writing a weekly newsletter for my own wonderful community of nearly 800 folks who are curiously minded and like to challenge the status quo.

I sometimes take all of this for granted, until someone a few steps behind me on their journey asks how I got there. Yesterday I sat across from my football teammate at Tryst, an Adams Morgan institution, sipping a beer during what was intended to be a "coffee chat" — our defeat on the field earlier in the day had been hard-felt. Or maybe it was just the heat. A couple of us have been playing together since last September now, and we slowly have moved past the phase of sheepishly asking for each other's names again and small talk about where we're from to now being decent friends (aided by a few boozy nights out, as tends to give the assist).

He's figuring out his next career steps. Do I quit my job to build this product I've been tinkering on? Do I move to New York City or San Francisco to gain more exposure to people in the field? He's impressed by the amount of risks I've taken (and, as I interject to remind everyone I have these conversations with, the sheer amount of luck I've had). That said, the luck has consistently arisen from the risk.

I was recently exposed to a name for this concept, which I always find funny when I come to something intuitively only to discover someone else packaged it up in a "framework" and now uses it to sell books.

Somehow, I'd been doing this all along in little ways. I never engineered my luck on purpose, but I have always felt called to follow my curiosity or passion of the moment and do the thing while always being my true self. The "Telling" part was never strategic… I just love to share what I'm excited about!

As I sit here typing this week’s edition from my favorite neighborhood coffee shop, warding off a small sparrow eyeing the crumbs left by the patron before me, I realize I am in fact wearing Doc Martens. Sandals, not boots — it's a high of 90 degrees and I'm not that much of a masochist. But it's that same inclination — to refuse to show up as anyone but myself.

I told my teammate yesterday (the mentee, though I'll admit I spent half our outing wondering if it was a date, the classic conundrum I face given I'm only attracted to professionally ambitious and creative people), whatever path you take will only feel fulfilling if you can be authentically yourself throughout the process. I don't have answers to his every question, and Lord knows I’m figuring out my own. But that part? That part I'm sure of.

Curiously,

Kate