As Otis Redding so accurately captured this moment… just sittin’ on the dock of the bay

A few weeks ago, I went to the corporate offices of a well-known “disruptive” tech company in SF to pitch some content strategy ideas, and I was immediately struck by the overwhelming awareness that I’m not 27 years old anymore. (To be fair, I’m not even 37 years old anymore.) Waiting at reception after I checked in via an iPad (I miss humans), I watched oodles of twenty-somethings walk around carrying half-open MacBook Air laptops in the palms of their hands like a waiter carrying a tray, being followed by prancing puppies clad in denim jeans stopping at dog biscuit stations for treats and then bounding up the factory-inspired metal stairs after their owners. The girls wore classic San Francisco girl outfits — skinny pants, loose blouses, booties, big sweaters, Warby Parker black or tortoise-shell glasses. The guys wore classic engineer duds — gray T-shirts with some sort of logo or cartoon (the more unrecognizable the design, the cooler the dude), jeans, and sneakers. It was sort of cold that day so there were some hoodies. I was wearing a Diane von Furstenberg patterned tunic dress, burgundy leather knee-high boots and a gray wool Vince one-button cape jacket. So yeah, I, um, didn’t fit in. A born-and-bred New Yorker who started my career in fashion, I might be just slightly more aware of what people wear. But — it was soon very apparent that the outfits were very much the book covers by which we all could be judged.

I only met one person there and she was perfectly lovely. Though we spoke quite different languages, we thankfully seemed to be speaking about the same thing. (Score!) During the presentation she mentioned on a few occasions that my ideas were “like so totally awesome.” (Double score!)  I can’t imagine what my slightly pained and very pensive face must have looked like during that meeting. I just really wished I had a millennial dictionary to help decode our conversation while it was going on.

Speaking of dictionaries, I’ve recently rediscovered my love for Strunk & White’s The Elements of Style. I have the third edition, published in 1979 and handed down to me from my older brother, who was also an English major and a grammar nerd. I’ve found one other grammar nerd here, he’s 30 so technically still a millennial but not as much of a logo T-shirt-er as his peers. We can nerd out almost endlessly about affect vs. effect and the correct uses of the word “hopefully” (there are very few, in fact). And I really appreciate this nod to concise and grammatically correct speaking and writing. Many, if not all, of my publishing peers in New York would think of these efforts as a given, but sadly in the young San Francisco tech scene, I yet again seem to be a fish out of water.

That same week I was also at the corporate office of another well-know “disruptive” tech company in SF for another meeting. The offices were stunning. Draw-dropping, crank your neck, mouth-wide-open stunning. A modern glass and open-plan space juxtaposed in a 96-year-old warehouse building, it is a design masterpiece. But when I looked around the dining room, casually eating my grilled chicken schwarma and still oogling at the tap bar from which I chose an awesome local sour wheat beer, I noticed that everyone looked, um, well 27. Trying to imagine myself working there, I just couldn’t get past feeling like a dinosaur. I guess in dog years in the tech world, I am. At least the building was older than I am.

All this to say, my life is different now. It’s been just slightly over a year since I left my corporate VP job and starting blazing my new trail. And it’s taken me that entire year to step back and get some perspective on it all. Some days are fucking scary. Others are amazing. Most mornings when I wake up to start the coffee brewing and start motivating myself, I don’t know which kind of day it will be. Although I don’t regret any of the adventures I’ve taken in life, I do miss the times when I had friendly faces of encouragement around me always. I do miss having coworkers. I realize now that the “we’re all in this together” hokey stuff is very comforting.

I was struck by an article I read recently on medium.com entitled Blind Positivity Sucks. After a bit of harsh reality around how much people on the Internet seem to be obsessed with positivity, motivation, and inspiration, it goes on to say:

Blind positivity is believing that your dreams will come true instead of putting in the hard work to make it happen.

That line actually gave me some reprieve around my approach to life lately. Because damn have I been hustling. Hustling for $0, it should be noted. Promises of payment or contracts or longer-term working relationships, yes — but actual money, no. So it probably goes without saying that there are only so many consecutive days that you can hustle for $0 that you don’t occasionally stop and ask yourself, “What the feeeck (as the Irish say) are you doing? Do you really think this will work?” And honestly, I have no feeecking idea.

I’m not 27. I live in a city where everyone is obsessed about the next big thing and disrupting anything and everything that could possibly need disruption. Many of my “peers” are brilliant and will go on to do great things. Many of them don’t use “your” and “you’re” correctly, but will still go on to do great things. I don’t really want to disrupt things as much as I want to make them better. I want to teach little kids how to cook. I want to show them where their (not there) food comes from. I want to help the awesome chefs and bakers and food people in this city spread their knowledge and their research and their amazing food with others. I want to connect those amazing people with the little ones like I’m Cupid with an arrow made out of bread. And every so often I want to put on my chef’s whites and open my knife bag and get cooking somewhere awesome. I just need to stop and remind myself — I’m doing all of those things. For $0, yes, but I’m doing them. I’m now on the Board of Directors for Bay Leaf Kitchen, an amazing non-profit organization that teaches kids about cooking, farming and food sustainability from age 3. I’m helping Chad Robertson with anything and everything related to the future of bread. He has taken to introducing me as, “This is my friend, Alexis. She came to me to bake bread and then I found out who she was.” It makes my heart sink every single time. And this weekend I’m going to cook somewhere awesome — at the Taste of the NFL charity dinner the night before the Super Bowl, which helps fight hunger across the country.

So the hustle is not for naught, but the true test is reminding myself every day that I’m putting in the hard work. It’s been crazy to leave a world where you define yourself and your successes from a corporate perspective. Audience growth, product engagement, unique users, PNL, percentage change year-over-year, etc. etc. — it all plays like a game of corporate bingo. If nothing else, I’ve learned from blazing this new trail that I need to redefine what success means to me.

And there is no better reminder about how much hard work can pay off — AND how sometimes we just need to see what we have — than this scene from The Pursuit of Happyness. Especially because it was filmed on a street that I walk down almost every day.

*SPOILER ALERT — if you haven’t seen the movie yet, you should watch it first. Right now, in fact. It is one of the best.