Response Crafting


2016 Review

A Few Good Machines

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Photo cred: Christopher Dugas

2015 was the year of broad shoulders and the bay – moving from Chicago to San Francisco to see about startups and product management; more specifically, to figure out i.) what, if anything, made a good founder vs. a bad one and ii.) what it was about SF and iii.) which companies, if any, needed to be started there.

After a few months I got what I needed to know, and this all segued into 2016, the year of a few good machines. And a worthy problem.

I started a company.

I was frustrated with women’s clothing. There are big problems with the way it fits, the poor quality, the inefficiency of shopping. There’s a lot I could write about this – and a lot that I already have – but, in short: shit’s broke, yo.

I worked backwards from retail through production until I stopped getting bullshit and excuses from people in the industry telling me why it couldn’t be solved. I ended up going all the way back to machinery and motors, because they’re honest and clean, and built the company with my own industrial equipment for production and a motorcycle for client meetings.

I shared the frustrations, and clothing was also something I could touch, which meant it was something I could test and then stand up myself. Costs were low, turnaround time was low, and I developed a pretty intimate understanding of the production that, now that I’ve brought on support, has really benefited the delegation. Which is the next step

THE COMPANY

TL;DR – Made to measure dresses. I went from not even knowing how to sew to having my dresses worn on Steve Harvey in under a year. So I guess you could say things are getting pretty serious.

In that timeframe, we also collaborated with local businesses and organizations (such as Glowout Salon, BLVDier, Forth Chicago, and Windy City Cosmo) as well as individual influencers, female founders (such as Bela Gandhi of Smart Dating Academy, Mal and Coco Strong of Goldplaited, and Rebecca Borges, President of Chicago’s FemCity), stylists (Meghan Jedlinski, Mallory Sills, and Hanna Lee), fashion bloggers (including Lauren Nolan), podcasts, blogs, etc. 

We have averaged double-digit growth in sales per week since it started, and if that’s good enough for Paul Graham of Y Combinator, it’s good enough for us. (August was pretty sweet, being our fifth month in a row of 20%+ weekly growth.) Plus, virtually all of that growth has been word of mouth, which is extra cool.

Clients have worn their dresses at speaking engagements, offices, date nights, bachelorette parties, rehearsal dinners, weddings, holiday parties, New Years Eve parties, and 30th and 40th birthday parties (including my own.) 25% of the dresses are ordered as gifts for sisters and friends and daughters and wives.

We have seamstresses and a small factory and soon we’ll have sales people, and then new prints and fabrics and styles. But most importantly, we have clients who are excited about an attempt at a solution.

It’s clothing, but it’s not about fashion. It’s about people. Because people deserve better.

HIGHS

Look, like many firsts, nothing beats the feeling of the first customer.

I say our sales started in April, but really the first sale was in March, from a stranger, before I even asked for or expected it. I was still learning how to make dresses, using a bunch of “guinea pig” women I’d found online, and one of them insisted on paying me. Frankly, it was a total turn-on.

Similarly awesome feelings: hitting revenue growth goals a bunch of months in a row, getting word of mouth, getting traction, getting visibility, and that feeling when a client loves your product so much she shoots you a candid photo of her wearing it at 10 pm Friday night. That’s pretty cool.

LOWS

Worst part of starting a company is the period of deafening white noise between quitting your job and getting your first customer, when you’re not sure if this is a thing or people value it.

Thankfully, this period was relatively brief for me. I pushed hard to get a client asap, so it was just a couple of months at the beginning of this year when I was still figuring out patterns and sewing and practicing on those “guinea pig” women. (It made it harder that this was during the winter. But one main saving grace was that it was a relatively mild one, and there were quite a few dry, mid-30’s days when I could at least take the bike out for short rides.)

It’s better once you get started, though it still sucks when you disappoint a client – her dress needs alterations (again), or it takes longer than expected, or – god forbid – you make a mistake in design (it’s only happened once or twice, easily fixed.) The only thing you can do is show up, own your part (and then some), take your blows, and then bend over backwards for as long as they’ll let you try to make it right. But behind closed doors, that low-belly sinking feeling still sucks.

BIGGEST LESSONS LEARNED

(1) By far the biggest lesson this year was: Neurosis is not the same as introversion. 

I can’t believe I got this far in life not knowing this. But I’m also glad I figured it out when I did. Introversion is healthy. Neurosis is not. It’s totally okay to be reserved, or recharge on your own, or prefer books to parties. What’s not okay is to succumb to actual social anxiety, and too often we don’t realize that and chalk it up to “introversion.” It’s not.

Some helpful tips:

  • Always assume people like you. People want to like other people. Normal, healthy ones do, anyway, and those are the ones you want to work with.
  • Similarly: never assume it’s you. People are busy and they have entire lives outside of getting back to you. If you don’t hear back after they expressed initial interest, keep following up until you do. It’s not you. It’s them.
  • Worry is wasted energy. The best solution for anxiety or stress is action. Do something already. Nothing will ever happen while obsessing over your manic scribble-lists and stress notes. The last year has given me a much deeper appreciation for composure – the only thing sexier is decision and action, and very little is unsexier than panic. I still get nervous every single time I see a client. If I waited until I was 100% ready, I’d still be sitting on my floor surrounded by bad scrap fabric.
  • Oh my god, just smile already. It’s not a sexist thing. I assumed it was, too, until I hired an interpersonal coach and the first thing she did was film me interacting with her. It took less than 10 seconds of watching that footage for me to be convinced. Smiling makes a huge difference. I’m still working on it.

(2) Context is king. Time and place is everything.

In the same sense that you wouldn’t want to be hit on at your grandma’s funeral, there’s a time and place that people want to be sold to. Even talked to.

(3) You’re not special.

I say this in the most loving way possible. The sooner you realize you’re not the only one with your problems and frustrations and idiosyncrasies, the sooner you can capitalize on them. You think you’re the only one who loves coloring books or forearms? Wrong. Find your people.

(4) Put your best foot forward, but don’t spend a ton of time convincing people.

Another way sales is a lot like dating. Focus your energy on those who want you. The others will come around when they’re ready. Or not.

(5) Nothing is really that hard.

You throw energy at it every day and eventually it’ll yield. It’s amazing the headway you make if you just sort of lean on things.

This time last year my biggest concerns were: figuring out how to use an industrial sewing machine, make patterns, and find customers. At the time, they all seemed nebulous and daunting. Now they’re all part of my everyday life, and my new biggest questions are: how to scale production, improve pattern accuracy, and build a sales team. A year from now, these will ideally be “everyday” too.

(6) Incidentally, a lot about patterns and clothing production. And quite a bit more about sales.

OTHER THINGS

(1) The bike

I picked up the second bike, a Ducati, in early November, after months of trying to just make it through the season on old boy and finally caving (mostly because his front end threatened to.) The Duc doesn’t have a name (neither does old boy – it’s not really “old boy”), but he does have a personality, though perhaps not what you might expect: it’s the light, floating prance of an Arabian horse. Or a jingle horse (“pick up your feet.”) Sometimes he’s an actual duck.

…Or the bouncing DMX llama:

In short, he’s adorably light underhand, which makes him super playful and fun.

(Incidentally, old boy’s personality has always been best summarized with the gif of Clint Eastwood having coffee, from Gran Torino. Still a little badass; mostly sick of your shit. Though, as of late, he can also be characterized by this horse. Because: front end, as I said.)

(2) The apartment.

Probably the “sexiest” apartment and my favorite while living in Chicago (apart from my tiny white box in Oak Park, which served a very different purpose and was loved for entirely different reasons.) This one has the doorman and quartz countertop pizazz to please the boy, but also the warehouse history and matchstick hardwood grit for me. And perhaps most importantly, space. So much space. For all of our hardware and machinery and the work we both do. All without leaving our ‘hood or sacrificing walking distance to our favorite spots.

It’s also the only apartment I’ve ever named, and her name is Anita.

(3) The 30th birthday.

Threw a couple of bomb-ass birthday parties. And bought a bike (see above.) It was great.

(4) The Whilk and Misky concert.

Still one of my favorite artists, and they delivered. They played a ton of shit I’d never heard and played it all well and at the end I applauded them using their real names and they ignored me. It was great.

(5) Dat final, winning play between Bryant and Rizzo, game 7 of the World Series.

Okay. Yeah, I got sucked in. I said I wasn’t gonna get sucked in – even swore I was gonna hate the city of Chicago even more than I already do if they won – but in the end I couldn’t not get sucked in.

I’m not a sports fan, let alone a baseball fan, but I watched the games in the way everyone in Chicago was watching the games. They were on everywhere. You couldn’t not.

I was mid-conversation with someone during the game and didn’t even see that final play live, but when the replay surfaced the next day, I rewatched it like a million times.

Everyone fell in love with Kris Bryant and his idiot grin. And sure, I did too. But what I loved even more was the moment just after it: first baseman Rizzo, knowing, his arm outstretched and unmoving, no adjustments, just rock steady like “right here, buddy. Get it here and I gotchu.” Like Snow reaching for Rickon in Battle of the Bastards. And like Kevin Costner’s character reaching for the letter in the final scene of The Postman. I apparently have a thing for this, and Rizzo put out. Afterwards, I tumbled into a 24-hour rabbit hole of Rizzo first-base highlights. I could watch that guy dive for hits for days.

Everyone fell in love with the Cubs – and the Cubs fans. Nobody hates a Cubs fan. If the Cubs were the lovable losers, their fans poured on enough love to make them lovable, too, and the whole city was a cesspool of affection. During their losing streak, you never heard a hateful word from a fan. On the contrary, the whole city trekked up to Wrigley to chalk their love and encouragement all over the stadium walls.

People were worried there’d be riots if the Cubs won, and I was like “have you seen these fans?” Midwest right to the end, even the parade was a cordial “no please, after you – let’s cheer together!” affair.

TRAVEL

Not this year, bro. It just didn’t excite me in the ways it usually does. The only trips I made were for work or fam (my brother and his wife went and had themselves a baby, so some for that. Because #niecelove.) Next year, more. Probably much. Still work, in other ways.

WRITING

Took a hiatus from this blog, mostly because I was focused on the company, thinking about other shit, and writing about it all elsewhere. Will probably share it eventually, but it’s mostly your garden variety first-year-of-a-company questions, baby “revelations,” and other notes.

READING

I read 75 books this year. Mostly business. Some better than others.

  • 15 on clothing, fashion and manufacturing
  • 11 biographies and autobiographies, mostly from entrepreneurs
  • 7 dating books intended for men (“player books”) in an effort to figure out women, and 2 on love + relationships in an effort to figure out me
  • 17 other introspective / “self-improvement” ones
  • Only 2 works of fiction: Atlas Shrugged and – wait for it – The Call of The Wild
  • Way too many (like, 20) business books, most of which were what I call “bullshit business books” – the ones written by people who have only studied and never actually done the thing they’re talking about*. You know, the books sold in airports and shit.

The best of all 75 were:

  • Shoe Dog (Knight)
  • Scaling Lean (Maurya)
  • The Woman I Wanted to Be (DVF)
  • Made in America (Walton)
  • Grinding it Out (Kroc)
  • Let My People Go Surfing (Chouinard)
  • Pour Your Heart Into It (Schultz)

I don’t normally include film mostly because I don’t watch a ton, but in the same vein as the best books: I watched Coco Before Chanel like half a dozen times this year, which obviously isn’t typical (for anyone, but especially me) but it’s so good. Coco Chanel is my spirit animal.

*A word on “bullshit business books:” about a year ago I reached my saturation point and tolerance level for authors out there who lacked firsthand experience with a subject and yet still felt entitled to write (and sell) books. This includes everyone with “credentials” such as “expert,” “insider,” “advisor,” “thinker,” “chairman,” etc. associated with “forums,” “organizations,” “committees,” etc. (One author included that he’d traveled to 41(!) countries in his bio – for a technology book. Dude, this impresses nobody except you – and other insecure, fake-accolade-motivated people.) In short, all of these authors are inferior to any author with an actual degree in the domain, especially if it’s science or engineering, and/or anybody with “founder” following their name (when it’s associated with an actual company, not a committee, forum, or org.)

As an aside, “expert,” like “couture” or “humble,” is one of those things you should never call yourself. Weirdos.

The problem, of course, is that the “theorists” – unsurprisingly – make up the vast majority of the books out there (since the doers are busy, you know, doing.) So unfortunately they do sometimes slip in. But what the doers write, when they do write, is so much more valuable, and I’d take a single poorly-written paragraph from a doer over 100,000 words of rambling nothingness from a theorist any day.  But we do what we can.

SCATTER SHOT SUMMARY

This year…

Tasted like: beer. So much beer. Also white cheddar popcorn, burrata and arugula pizza, feta cheese, and black coffee.

Smelled like: gasoline, faintly, from a leaky gas tank cap. Good cologne. Dude deodorant. “Leather” and “wood” scented candles.

Sounded like: MØ, mostly. But it started with Gomez / Same Old Love and Beiber / Love Yourself and ended with La Roux / Sexotheque, K Flay / Blood in the Cut, Johnny Cash / Hurt, Cigarettes After Sex / Nothing’s Gonna Hurt You Baby.

Looked like: patterns, pattern paper, rulers, ink smudges on your hands. Thread, needles, stitches, seams. Ribbons, roads, addresses, front doors. The good fit of a dress done well; the alterations – usually hips – of most others. The bodies, but moreover the eyes, of clients.

Felt like: the rush of several new clients or successful client meetings in a row, the rush of brushing up against new things. And people. The anxiety of each new client meeting. The warmth of getting it right. The thrill of being in charge – and free of bullshit. Pushing yourself to do something even when you don’t want to. Wondering if you’re doing enough. Wondering how to do more. Leaning, prodding. Bad fabric, better fabric. The instability of a bad front end, the joy of taking a curve on a more stable and sporty bike. The pleasure of riding, either way. Pain in your wrists, from bike riding and fabric cutting. Apprehension and courage and joy.

MAJOR THREADS + UNANSWERED QUESTIONS

Things I’m still chewing on but haven’t fully figured out:

  • The idea of a thing vs. the thing itself. (Also looking for better ways to describe this.)
  • Accurate vs. false logic / the right reason to do things
  • A bit on love and being a woman
  • Production

NEXT YEAR

More travel, as I said.  More books. More sales. Far more robust production. Maybe a kid.

Lolol, just kidding.

The company’s my kid.

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Okay, but now let’s talk about good men.

There’s a lot of hostility towards men right now. Yeah, a lot of us are upset that Trump won and really worried about what that means for women and minorities and probably most other people who are not white men (though, by “white men” we really men “white men of certain income tax brackets,” but whatever.) But even before Trump, there was just so much… tension. A lot of shit being directed at dudes in general, mostly because women feel it’s directed at them in general. We have to take a stance against dudes being let off easy for sexual assault, and mansplaining, and making more money, and controlling our reproductive rights, and everything else they do.

And I get it.

I get the political issues. But I also have sympathy for men socially. I’m not sure where women expect dudes to stand anymore, because it’s not even clear to me. Women have an issue with some men or most men or the patriarchy in general, and take it out on all dudes, most of whom are actually pretty damn decent and just want to understand how, if at all, to approach you at a bar. (We still do that, right?) And when it comes down to it, it’s the good men who are the ones hit hardest by this. The ones who don’t care never will. But the ones who do care don’t understand what’s acceptable anymore.

I’ve already said before that sometimes I don’t do a very reassuring job of being a woman, and I rub women the wrong way when I say things that they perceive as a betrayal to our own kind. I don’t see my role in most “women’s issues” discussions, don’t appreciate being reeled into them on basis of gender, and frequently take the opposite stance, ruffling all kinds of feathers and raising concerns about how little I understand “what’s going on” (which, frankly, is incredibly ironic, because best I can figure “denying people their own experience” is kinda core to the women’s fight. But what do I know.)

I recently discovered Red Pill Theory. For the first 24 hours after I found it, I couldn’t peel myself away. I pored over the articles and forum posts, both aghast and fascinated by the content. On the one hand, yes, it is sexist to the point of being insulting — as much to men as women, if I’m being honest. (And it is also insulting to the point that the dudes driving this content — and the women who subscribe — strike me as tragically insecure, which I guess saves me from taking it all too seriously.) But on the other hand, I almost kind of understand where they’re coming from, in the way I almost kind of understand — but do not share — a number of fetishes. I don’t support what they say — I think they took too extreme of a position — but I can sympathize, I guess, and sort of understand how an era with ever-fluid gender roles can create insecurity and frustration. I see where people might retaliate by drawing these severe gender role lines.

So, look. The thing is, I like dudes. I like them in their imperfections and complexities — I like them as human beings, of course — and I also adore them in their simplicity. I forgive them for their social indiscretions, and I appreciate them for their intentions. Because you guys, I’ve met so many incredible men in my life! And with all the man-negativity floating around, I wanted to at least offer my short list of Good Men that I’ve met.

So here’s a very short list of several good dudes I know — and good interactions with dudes I’ve met:

First, my dad is a good man. Let’s just get this one out of the way and start this list off right. People ask me what my dad’s like and my 1-second answer is: “He’s a good man.” Easily one of the best, if not the best, I know. Sometimes, depending on my mood and whether I like the person, I leave the answer that clean and simple. Other times, a drink or two further in with the right person, I’ll bring up the “stepdad” technicality just to point out and drive home how good — that he loved and supported his biological kids and then took on my brother and me in the same capacity, gave in ways other men didn’t, and never chose favorites. We were all his, and he was all of ours, and we all adore and respect him. On top of being a good dad, he’s a thoroughly nice person, a good, honest worker, and has loved our mom steadily, and at the end of the day those things are pretty much the short list of a good man.

For the most part, my guy friends are good men. I could call in a 3-am favor in the middle of a snowstorm with most of them and I’m pretty sure they wouldn’t bat an eye. And overall, most of the men I’ve dated were good men. Even at their worst, they meant well, or were only living out their own realities in those moments they are unknowingly hurtful. We all do this.

Most of the men in tech are good men. I don’t know why men in tech get such a bad rap. The most sexism I’ve ever gotten at work has actually been from the older guys in corporate environments — just for comparison, at no point has any “guy in tech,” developer or otherwise, told me that my clothes don’t show off my figure enough, or exclaimed, the first time I worked up the nerve to wear a skirt: “my god, you’ve got legs!” They’ve never said “I remember girls like you” or “you’re attractive, but not a size 2.” No, that’s the handiwork of the middle-aged corporate man. The tech dude has always been nothing short of an eager ally, and I appreciate and adore him for it.

Chicago men, in general. I don’t like Chicago. But the one thing I do like very much about the city is the men. They are not the pompous, over-preened chauvinists of the east coast, nor are they the tender children of the west coast, the latter of whom come at you like 9 year olds with crushes on their babysitter. Midwest men are creme de la creme — they’re adept enough to banter a bit and open a door, but in a deferential rather than patronizing way. They’re boyish but also rugged, and it’s great.

All of the dudes who offer to help when my arms are full. Look, there’s a difference between being physically able to handle it on my own — and actually needing some help. I’ll turn you down if it’s the former but I will readily accept the latter, and I appreciate you continuing to put yourselves out there. (I also appreciate those of you who laugh and don’t get offended when I offer to help when you’ve got an armful. Because it’s a human being thing, not a gender thing.)

All of the guys who magically manifested out of nowhere every time I dropped my motorcycle the first year I had it. Most of these “drops” were really just the sad, slow-motion, setting-down of the bike when I lost balance while parking, before I figured out how to wield it at very low speeds — or stand it back up. Every time, someone appeared out of thin air to help. But there’s a special shout out to the dude who was there the one time I actually crashed, who stood the bike back up for me and then quietly hovered nearby until someone I knew got there, hanging out even when I tried to convince him from my seated, dizzy position on the curb that I was okay. I wasn’t — I later lost vision for a hot second — and it was cool he stayed to make sure I got somewhere. (I recently ran into him again — I didn’t recognize him but he instantly remembered me, so fortunately I had a chance to properly thank him.)

Tucker, my old roommate’s boyfriend and the darling of our apartment. Maybe I’ve made him out to be something different in my memory, but I do know homeboy was a chef by day and that we had this big happy-house apartment where the door was always unlocked and between the three of us who lived there and our three boyfriends and numerous “drop-in” friends, several people were always there and, as I recall it, we’d often come home from work to him cooking enough for all of us. And it was very endearing. As was he.

The car full of dudes who took me home when I was doing that shameful drunk-crying on the street thing — that one time I did it. I’d gone out with a few friends, and we left the bar together. But they were going one direction and I was going another, so we said our goodbyes and parted ways. A block later I realized I’d left everything — phone, keys, credit card, etc. — inside the bar, but when I went back, the doorman wouldn’t let me in to get them. (In retrospect, that doorman was on some kind of pure shit power-high, and was not a good guy.) My friends were long gone, so in my drunken stupor I broke down, dropped to the sidewalk and just ugly-cried my soul out onto the pavement. A woman actually stopped first. She told me it’d be ok, and it was she who stopped and screened the group of guys for me. I didn’t know them, but I trusted her, and they promised her they’d get me home. And, true to their word, they actually did. It’s sad, of course, that this should be surprising, but I think we all understand that something very bad could’ve happened — but didn’t. I was still thoroughly drunk when I got home and thanked them, but fortunately not so drunk that I ever forgot when the driver of the group said to me in response, “Look, I have sisters. I’m only doing for you what I’d expect some stranger to do for them.”

The doorman outside of Elways on Curtis Street in Denver back in 2010, when my then-boyfriend was losing his shit with me on the sidewalk outside after dragging me out there, berating me because he didn’t like that I was getting happy hour drinks with a group of colleagues, one of whom he didn’t like. The boyfriend had recently lost his mom, so I was putting up with him doing a lot of ridiculous and aggressive things at the time mostly because they weren’t particularly characteristic for him. I was trying to be patient in this moment outside of Elway’s, listening while kinda doing this submissive, deflective thing, smiling sheepishly and allowing myself to be bullied up against a wall and yelled at on a public sidewalk at 5 pm for something stupid.

And the whole time, the doorman was eyeing us, watching. I noticed him and sort of wondered what he was thinking — should I feel embarrassed? For this scene, or getting drinks with colleagues? Maybe he thinks I deserve this? I wasn’t sure. But I did know he wasn’t stepping in, and I assumed it was because I was either in the wrong somehow, or this didn’t look as aggressive as it felt. So I let this go on for a while, letting the boyfriend go off, waiting for it to run its course. But then suddenly I just lost all patience and 180’d. I went from submissive to pissed in about 1 second flat, suddenly moving off the wall, into the boyfriend’s space and said, in flat seriousness “Alright. That’s enough.” And in that split second, suddenly the doorman was rightthere — next to me, his hand between us, and he was facing the boyfriend and saying something to him that made me feel okay and gave me enough space to walk away and go back inside.

Every guy trying to figure out, in earnest, his role — in society, for women in general, or in a particular woman’s life. A lot of these dudes have hearts of gold, and without always having full certainty on what we’d like from them, they still put themselves out there and give it a go, and for god’s sake let’s at least give them that.


On the brink of everything

Last Monday, I woke up to a 7 am text telling me I was on a 9:15 flight. I was up, packed and out the door in 15 minutes. I was flying standby to see my factory.

Truthfully, when I say “my” factory, I mean the one I’ll probably work with, at least for a while. And when I say “factory,” I mean sew shop, which is smaller. But when I call it a “sew shop” people only hear “shop” and then they think I have a storefront and wonder why it’s in another a state. (Then again, when they hear “factory” they think “sweat shop,” so it’s really a lose/lose, which is just part of the reason why I tend to not spend a ton of time getting people up to speed when they ask “how’s business?” That, and I just spend way too much of my day talking and thinking about it as it is.)

I’d been meaning to take this trip for weeks, struggling to fit in between client appointments, production, and capricious flight loads. And now it’s like a perfect storm of “open” across all three and here’s this text on my phone at 7 am, and I’m now making this 24-hour trip to another state. I even got the middle seat, which I love. (Seriously. Don’t make it weird.)

Most normal days, I am on client appointments all over the city and working on production in town for this little company that I started earlier this year, and more often than not, I feel good about the way that company is growing.  I work odd hours and every day, though frankly I kinda dig it. I ride a motorcycle to see my clients, which makes no sense at all in terms of either professionalism or product representation, because I sell dresses, but I don’t care, either count.

I spend most of my time with – or thinking about – clients, playing this game of “being a woman” and trying to better understand them, as it pertains to my business but also in general. And I love my clients and love solving the fit problem for them; love meeting them and making them feel awesome. But part of starting a business is that you will go a little crazy – first from isolation and then from client interactions, because they take on a certain nature that’s deeply satisfying, but only in very particular ways. End of day, I want little more than to crack open a beer and talk to a dude, about anything other than dresses.

It takes a degree of risk-taking to do things. You make these tremendous investments in areas of your life and you’ve got energy outstretched way beyond your core in one direction, you end up doing things to balance it out in others. You toe the line of recklessness and sometimes you have to brush up against the wall to know it’s there. It’s deliberate and it’s rowdy, it’s tender and it’s rough.

You practice restraint in some areas; you bleed out in others.

I love my clients. But moreover, I love the game. And then the game seeps into your life and that right there is the shit.

This December, I turned 30.

I am super excited about this.

I have felt 30 for years – at least half a dozen; maybe more. In a way, I’ve always been 30. One of my dearest guy friends tells me I’ve been 30 since we met in high school, and I’ve been telling strangers in bars “I’m 30” since this time last year. I take pause each time someone asks my age. How old am I? Eh, 30 sounds right.

Designer Diane von Furstenberg wrote, in her memoir “The Woman I Wanted to Be:”

“When I turned twenty and my mother asked me, ‘How does it feel to be twenty?’ I said, ‘Well, I’ve been telling people I’ve been twenty for so long that it doesn’t make a difference.’”

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Christopher Dugas

That’s my 30. I’m finally legitimate. Like most people’s 21, when you can walk into a bar and use your real ID for the first time. Like, yeah, you’ve been drinking for years, but now you’re a real boy! It’s a thing.

I’m even at peace with the less exciting parts. I regard my fine lines with amused interest; the extent of my concern not going much further than assessing whether they’re age or dehydration / fatigue (because there is a difference.) I’ve been eyeing my hairline for my first gray hair for months – and I haven’t anticipated a change in my body with this much attentiveness since I was waiting on my first period. It’s not excitement, per say, but it’s also not dread. Rather, it’s an eager acceptance, like “c’mon c’mon! Let’s get this over with already so I don’t have to be surprised.”

I have so much other living to do.

People started asking me a few months ago what I wanted to do for my 30th, and I told them “a huge blowout!” Then added “and none of that ‘kiss your 20’s goodbye’ sadness!” Because this is exciting – like graduating college. (And I say that as someone who skipped her own college graduation ceremony. To be fair, I was sitting for the CFA exam that day, but that doesn’t change the fact that I didn’t go, which made my mother worry I hadn’t really graduated, a concern resolved only when I asked my alma mater to send a copy of my diploma home to her.)

But I wanted The Whole Thing turning 30: champagne, bottle service at a club, confetti from the ceiling, sparklers, maybe a flying Pegasus – I don’t know. But I wanted my own little personal New Year’s Eve. Because it is.

There was a time when I thought I’d celebrate my 30th by buying a designer handbag. Instead, I bought another bike.

My excitement with turning 30 has a lot to do with shedding the connotations of a girl in her 20’s, which become assumptions, then expectations, then burdens.

When you’re in your 20’s, people put shit on you. And they also strip shit away. Women older than you hate you for no reason at all. They come at you in the office break room, telling you as you’re refilling your Styrofoam cup with bad coffee: “I’d give anything to have my 20’s back. Enjoy it while you can.” And you’re just left standing there with your mousy ponytail and loose-fitting business-casual clothes, too young to know who’s right to feel uncomfortable. Men eye you in uninvited ways, and you haven’t yet figured out how to redirect that. You get a lot of backhanded compliments like “you’re smart for as young as you are.” Or worse, lines like “you’re younger than me. You don’t know.” 

Which, in a way, can be true. Until it’s not.

Finally turning 30 feels like being free of the burden. It’s getting up and announcing to a crowded room: “alright, I’ve played by your rules. Now it’s time for mine.” 

HOW WE GOT TO NOW 

Throughout my 20’s, I had a list of things I thought I wanted by 30. A lot of them were the generic, check-boxy things that people do – and the sort of things we all advise on down the line back to others. I graduated college,  made six digits, invested in the 401k, drank water, figured out some hobbies and interests, strengthened my relationship with my parents…  I also loved, lost, backpacked through Europe, read, ate some Oreos, moved to new cities, figured out what kind of wine and whisky I like, and discovered that not only is friendship harder as an adult, but intimate relationships are too (both, however, are also a lot more meaningful than whatever we had during school.) 

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Christopher Dugas

But at some point, you’re like “hold up.” Do these things really make me happy?

Because the checklist things can become just things we barricade ourselves with. We build little fortress walls of “achievements” we can point to whenever we wonder about our own lives. Like “nah, I’m alright – I got married” or “I make money; it’s okay.”

And maybe at some point you get serious and ask yourself: what really makes shit worthwhile? And if you could only pick one thing that mattered, what would it be? Because focus is everything.

Mine was starting a company. I got the fever like most women my age start to get frenzied about marriage and babies. It’s been everything since I started. And it was a major step in meaning and purpose and problem solving. 

And if that’s the snapshot of meaningful work as I round 30, there’s also a snapshot of thinking. About business and people. Friendship and love and life.

HOW TO “LIFE” and other things I think I know

Look, I don’t have it all figured out. But I have thoughts on a few things. And at this point, here’s what I’ve got and what I’m working on…

My own big list of Do This, Not That:

  • Pursue meaning over happiness. Chasing happiness for the sake of happiness, especially if it’s in the form of hedonism, isn’t real. Happiness is a side effect of pursuing purpose and problem-solving. 
  • Make decisions out of growth, not fear. And sometimes fear looks a lot like “comfort.” It can also be avoidance or escape. Don’t do things just because you’re afraid of the alternative. Don’t not do things because you’re afraid of the outcome. Live balls out and see how far it gets you. (You’d be surprised how far it gets you.) If you’re not growing, you’re dying. 
  • Choose creation over consumption. The latter is only sadness. 
  • Action over deliberation. At some point, planning becomes procrastination. Do something. 
  • Don’t be scared; just try. 
  • Assume a position of ownership over victimhood. Take responsibility. Even if for nothing more than your own response, because that’s always in your control. 
  • People over process. Especially in management, but probably also life. 
  • Progress over perfection. Done is better than perfect. Just ship it. 
  • Move towards, not away. Frame decisions in terms of acquisition, not avoidance. (Though sometimes knowing your “away” can help define your “towards.”)
  • Be “definite” rather than “indefinite.” Lifted from Peter Thiel. Choose something and go deep. Being a little bit of everything means you aren’t much of anything.
  • Invest in things that appreciate, rather than depreciate. When it comes to money and time, but also mental energy and the investments in yourself. Looks fade. 
  • Make major life decisions (kids, work, marriage, etc.) for the right reasons (see above.)

Also, other general good things to bear in mind:

  • People frame things in terms of themselves. The reason people do things is because of and for them, not you. This is good to remember in business and relationships alike. 
  • “Burn the pink candle sculpted like a rose before it melts in storage.” Don’t let things be so precious you don’t even use them. Drive your luxury car, wear your designer shoes, and drink the Dom before some punk kids break into your place and steal it.
  • Or just slum it. If you’re not going to enjoy the car, champagne and clothes, don’t bring them into your life. If you want to appreciate things, don’t get adapted to them.
  • “It ain’t about how hard you hit; it’s about how hard you can get hit and keep moving forward.” And I haven’t even seen the Rocky films.
  • Don’t make excuses. Bonus points for not accepting others’ excuses, either. 

HOW TO CAREER

This isn’t my focus anymore and there’s already a ton of material out there, but here are the two things I’d share with anyone asking:

1. Promote yourself

I understand that loads of people have stuck it out with one company and made great money – that’s fantastic for them. But here’s what worked for me: I worked at six companies between graduation and now, not including my own. I transitioned from corporate banking to custom software to a software startup, and with regard to moving up in a career, understand this: companies are not in the business of promoting you. This isn’t Boy Scouts, and their purpose isn’t to hand out badges. They are running a business and are incentivized to get a job done. To the extent that you’re good and they want to keep you and keeping you involves the occasional bonus or promotion, they’ll do so, but it isn’t a primary goal for them like it probably is for you. You think you’re worth more? That’s on you. “If you know what you’re worth, then go out and get what you’re worth.” Either with them, or elsewhere.

2. If you’re managing people, don’t be a douchetool

This, I do still care about. Deeply. If you’re a manager, care about people, then products, then process. Never the other way around. I’ve had horrendous managers who had no business managing people, and I’ve also had great ones. The difference between them is this:

  • Understand the domain of the work
  • …Then admit to the limitations of your understanding
  • Hire people who are better at the job and/or domain than you are
  • Trust them to do a good job (if you don’t trust them to do the job, you shouldn’t have hired them for it)
  • Praise publicly, criticize privately
  • “Eat last” – take care of your team’s needs before your own
  • If you want them to throw themselves at the work for you, take every blow possible for them
  • Let them take pride in their work
  • Let them take the shot
  • In the very least, I don’t know, read a management book or something. Or, if you’re just real pressed for time, try out Napoleon Hill’s essay on Leadership.  

HOW TO STARTUP

i.e., what I’ve been doing since leaving “Career.” I still mostly have no idea what I’m doing, but here’s what I’ve got:

  1. Do it for the right reason: solve a problem 
  2. To get huge value, give huge value
  3. To give huge value, figure out what they value most.
  4. Understand others by understanding yourself 
  5. Focus on growth above and beyond everything else.
  6. Define growth as “sales,” long-term
  7. Learn how to sell
  8. Manage your mindset

HOW TO BE A WOMAN

I do not do a very reassuring job of being a woman. On the one hand, “how to be a woman,” as a woman, should be as simple as doing whatever the hell you want, because it’s not like a label that can be stripped away. But on the other hand, there are social norms and shit, and I still haven’t decided which ones I care about and how much.

ON BEHAVIOR

I am rough around the edges and perhaps a little reckless. I’ve done some cool shit and like to think of myself as a pretty cool person, but I am not a “lady.”

As women, there’s an overarching expectation to behave. To fit into a situation rather than drive it; to supplement the lives of others rather than lead any charge, and frankly? That’s all bullshit.

I hope to god people have more to say at my funeral than “she was pretty. And pleasant.” 

What a tragic waste of a human life – my own – that would be.

I once dated a guy who thought it was a greater offense when I dabbed my bread into the butter ramekin at dinner with friends than when one of his buddies across the table told me – for the umpteenth time – that my breasts were too small for his taste.

Amy Schumer said “You become a woman the first time you stand up for yourself when they get your order wrong at a diner.” But it’s really when you finally just stand up for your right to a self-respecting seat at the table.

It’s not about being rough for the sake of being rough – I don’t need to make a point of being a “nasty woman” – but it is about confidence and self-worth.

I wanted a motorcycle for about ten years, and over that time dated a dude or two who had one. They never wanted to ride as much as I did and never wanted to teach me to ride on my own and for a long time I sort of thought this was okay. But after I broke up with them and made a certain salary, it suddenly occurred to me: “whose permission am I waiting on?” and I bought one. And to date, it was the best purchase I’ve ever made. That thing brings me immeasurable amounts of joy, rain or shine or cold.

People ask me if I have a bike because my boyfriend does. On the contrary, one of the reasons I am with my current boyfriend is because he knows a thing or two about bikes.

Being a woman – and not a little girl – means realizing you’re entitled to your own seat at the table, your own boobs, your own bike, your own self respect… preferences, opinions, thoughts, and questions. Even when it makes people uncomfortable, and it doesn’t fall in the category of “pleasant.”

“Now that I’m out of school and there’s no threat of a principal’s office looming down the hall, I ask whatever the fuck questions I want. It feels pretty good. Pretty womanly, too.” -Amy Schumer

Humanly, in any case. Which is more important.

ON BEAUTY 

I’m in awe that we think “beautiful” is still the highest compliment we can pay most women – or what many women regard as the highest compliment they can receive.

I’ve never measured my self-worth first and foremost by my appearance, and I’ve never viewed others this way, so I was shocked when the realization caught up to me and hit me like a ton of bricks somewhere in my mid-20’s. Suddenly this “truth” was everywhere and I realized it’d been there the whole time.

“I’m not the first to point out how women are taught that our value comes from how we look, and that it takes a lifetime (or at least until menopause) for most women to undo this awful lie…Women who relied only on their beauty can feel invisible later in life.” -Diane von Fürstenberg

That’s an awful long time to live without valuing yourself properly.

I don’t understand why we do this to ourselves. I mean, have you ladies not heard that nobody can make you feel inferior without your consent?

I’ve met fantastic women in their 30’s and 40’s who are harboring deep unhappiness and will confide in me, over our third glass of wine, that every year their husband gets more and more attractive – while they become less and less pretty. And they let this heartbreak destroy them from the inside.

But the most shocking thing is they put that invisibility on themselves. And they strangle every other part of their being – and everything else that makes them amazing – in their pursuit of something fleeting.

“Counting too much on your appearance limits one’s growth.” -Diane von Fürstenberg

There’s just so much more to life than that. We’ve got so much other living to do.

ON BODY

One of my great gratitudes to my mother is for raising me with a healthy body image. I became vaguely aware of body consciousness in high school, of course, though I wasn’t quite sure how it worked and so was never all that great at it. (At 15, my boyfriend’s mother greeted me with the now-familiar female coo “you look great – have you lost weight?” and I blinked and replied, “I wouldn’t know. I don’t weigh myself.” Looking back, all awkwardness was on her.)

My roommate (and now best friend) and I of course did the college girl thing of hanging photos of Victoria’s Secret models, torn from the catalogues, up in our dorm room. One of my still-dearest guy friends, a digital media student who already knew about all things photoshop, came in one day, took one look at it, and said, “Darling, take that down. You’re comparing yourself to something not even she has achieved.” That is still today one of the most powerful body-image lessons I ever got.

Early-20s phase aside, I am very fortunate – and grateful – to have a healthy, happy perspective of my body. When I am occasionally asked what surgery I would get if I ever did, I shrug and answer, “Lasik?” You may think this comes naturally to someone who has a pleasant build, but you’d be surprised what sort of body image woes plague beautiful women – I have had friends built like runway models who don’t like their knees. I work with women’s bodies every single day, and every single woman – right down to the petite, size-zeros – wishes her belly was just a little flatter. We put this shit on ourselves. I do what I can to not.

…WITH OTHER WOMEN

I often don’t share women’s biggest goals (husbands, babies) and even our higher-level values often feel unaligned. They’re shocked I ride a motorcycle and I’m like “yeah, I mean… there’s not an application or anything.” I’m not real into dresses (despite making them) and makeup and doing my hair; I strike very few people as “soft” or “warm” or any number of other things women are “supposed” to be. Boyfriends’ female friends dislike me, I have a very select number of female friends, and most of my female bosses have fired me or asked me to leave. Just for starters.

I upset a lot of women – and probably some men – with the way I “woman.”

(1) I don’t care for the “women’s issues” conversations. I don’t want to talk about gender issues, and the “women’s fight” is not my fight. I don’t like the way they define the issues as being all women and only women – my favorite example of this being the “women have families” argument in defense of work:life balance. Because not all women have kids. And men have kids too. This stereotype isn’t helping. It’s holding us back. Women come at me with these grandiose statements that are supposed to be about “me,” and I’m supposed to care as a default, but girl, there are only so many hours in the day, and taking some kind of political position for work:life balance is literally the opposite of my jam right now.

(2) I do my best to avoid anything where they’ve put the “women” prefix in front of shit. “Women in tech” events are probably the worst offenders, and they are an absolute waste of my time. Because rather than talking about tech, as women, all they do is huddle around and gab about being women and all of our woes and struggles in tech, all while being kinda hostile to any male allies in the room. I don’t want to circle around and talk about being a woman – I don’t feel compelled to get any better at that. I want to talk about the domain. 

You want to know what’s holding you all back? Bullshit conversations like these. If you want to make headway in anything as a woman (or a man), focus on the thing itself.

I side with Morgan Freeman when he criticized Black History Month, saying,

“Stop talking about [race]. I’m going to stop calling you a white man. And I’m going to ask you to stop calling me a black man. I know you as Mike Wallace. You know me as Morgan Freeman. You’re not going to say, ‘I know this white guy named Mike Wallace.’ Hear what I’m saying?”

I don’t care as much about being a “woman” as I do about being a “human being.” If you want to stop being seen as the “other,” stop calling it out. Men – white or otherwise – don’t stand around and talk about what it means to be a “man in tech.” I don’t want to, either.

A lot of women share this viewpoint. Amy Schumer said, regarding the release of Trainwreck:

It felt pretty demeaning when they called it a ‘female comedy.’ This meaningless label painted me into a corner and forced me to speak for all females… They don’t ask Seth Rogen to be ALL MEN! They don’t make ‘men’s comedies.'”

“The pressure is on. Because the movie doesn’t have to do well so that I can feel proud of it or so the studio can make money – it has to do well for the 50 percent of the population I am now apparently representing… I write about my life and how I see and experience the world, without assuming that my views are universal.”

That. And I go as far as to add: it goes both ways. I don’t want other women’s  experiences being assigned to me either, especially when they expect them to override my own.

…WITH MEN

There’s something here about balance and negotiation and push-pull. Depending on what you want from dudes – friendship or a partnership or professional support – I guess you have to make space for them to coexist.

For a long time I would just do what I wanted to do and let dudes figure out where they wanted to stand in relation to it, but maybe there’s something to say for actually carving that space out in opposites. Which can be frustrating, because “carving out space” for them sometimes looks and feels a lot like “being a lady,” i.e., being warm and soft and pleasant, which I either cannot or will not do enough of, or consistently. (See above.) I shouldn’t have to soften for a man to feel Like A Man, and a man’s masculinity shouldn’t hinge on how convincing my “femininity” is.

Sometimes I think I can get away with being one of the dudes, and I can say and do whatever I want without intimate implications. I once told my mom “I can’t wait to be the age where I can just tell a dude he’s attractive without him assuming it’s on.” And she laughed and goes “oh honey, that’s never.” And I was like, well, shit.

I just want to be able to tell a dude he has nice hands without him and half the dudes within earshot thinking It Means Something.

HOW TO LOVE

Balance, give and take, and what’s healthy

How to give enough. How not to give away too much. What’s okay and what isn’t. Whether you’re improving as a partner and listening better and accommodating… or relinquishing your self worth and self respect. You read these resources on what it means to have a “healthy” relationship and you’re like “surely nobody really nails all of these! That’s just not real.” So then it’s a matter of understanding which are non-negotiable and which are only nice to have, and whether you’re permitted to pick and choose. 

Real love / loving someone for the right reason

Some of the wrong reasons are obvious. “Beauty” and “money” are clear to most people.

But I’m pretty sure there’s a slew of other bad reasons to be with someone, like: you want someone to travel with. Or someone to have kids with. Or because you’re afraid of being alone. Or it’s just time to settle down. Or you’re not sure what else to do with your life. Or everyone else is doing it.

And you may be with someone and think you got it right. But the truth is, nothing will save you from the day you ask the person you love most why they love back and they say “because you’re beautiful.” Full stop.

It’s like that scene from 27 Dresses where Katherine Heigl’s character finds out that the local wedding announcements are written by someone who hates weddings, and she says, “I feel like I just found out my favorite love song was written about a sandwich.”

That, except the “song” is your real life.

Pushed to add more, they may go on to say “and because you agree with me on religion and politics! We’re like the same person.” Which is weird as phrasing alone, but even weirder when you don’t, and aren’t. And you’re just left standing there with your dick in your hand, realizing you wasted good love – with right reasons – on carnival games you were dumb enough to think were the love of your life.

Loving someone vs. loving the idea of them.

Only loving the idea of someone means you actually love a bunch of ancillary things that could easily be stripped away: their looks, their job, the fact that you both have the same hobbies.

It also looks a lot like:

  • Making a checklist of your Ideal Partner and then looking for someone to fit into it
  • Loving only those checklist things, and remaining oblivious or indifferent to anything else about them
  • Falling in love with them hard and fast
  • Calling them your “everything.” No single person should be “everything” to you. If they are, you’ve assigned far too much value to them. It’s not romantic. It’s sad.
  • Loving drastically different things about them than what they love about themselves, especially if your things are “smaller” or less consequential (like, yeah, beauty.)
  • Loving showing them off to friends, family, colleagues – acquaintances
  • Being routinely – or even periodically – surprised by their actions or words
  • Loving how “easy” the relationship is, and cherishing not putting in a ton of effort
  • Feeling impatient whenever they have complaints or concerns you don’t share or agree with
  • Loving them because you love having a girlfriend/boyfriend/husband/wife and they’re yours
  • Losing feelings for them when you meet someone else

I don’t know what it would look like for someone to really love someone for real. That’s why it’s an open question. 

The reality is, to some extent, we all do this. We say we love people unconditionally, but short of parent’s love of a child, we don’t mean that. If your partner went crazy and wanted to spend the rest of his or her life counting out grains of rice one by one, would you stay with them? I mean, that’s the real them now. And it’s different than “the person” you love. 

We all partly only love the idea of someone. We all love people partly because of what they represent. Because we all frame everything in relation to ourselves. We’ll always only have a version of other people that exists in our heads, framed by our own thinking – and the context of our lives at that time. We look for fun when we’re bored, decisiveness when we feel lost, stability when we’re ready to settle down.

Maybe the best case scenario is that we can still strive to see our partners at least as big as, if not bigger, than they see themselves.

Types of Love and Partners

The Greeks had seven types of love – eros (lust; love of the body), philia (love of the mind; brotherly love), ludus (young, playful love), pragma (longstanding love), agape (love of the soul), philautia (love of the self), and storge (love of the child.)

And maybe that’s comprehensive, but I think there are more.

They say eskimos have 50 words for snow. Humans are far more complex than snow, so there’s no reason there wouldn’t be just as many types of love.

Leo Tolstoy wrote in Anna Karenina, “there are as many kinds of love as there are hearts.” I like that — so long as I may take license and interpret it to mean: there is a new kind of love for every combination of each 2 people, forever. (Which is exponentially more than “number of hearts,” just to be clear.)

I love my parents differently than I love my siblings. I love my clients differently than I love my childhood best friend. I have a handful of terrific guy friends, all of whom I love.

I have loved deeply but platonically. I have loved superficially and fleetingly. And I have loved at arm’s length. Some of the greatest loves of my life so far would probably be surprised to hear it.

And, likewise, I have also loved each partner differently, each love an oyster tucked into one singular shell.

Duration

Once I love, I love forever. A lot of my partners – and friends – would probably laugh at this, because I don’t “love hard.” I am more “fighter” than “lover,” a love-avoidant over addict, and often the one to end things. But for what I lack in intensity I make up in longevity – my low-burn love is also slow-burn love, and once I love someone, they are a chapter of my life I neither remove nor rewrite.

Charlize Theron, on a podcast with Sophia Amaruso, said that she “marries” all of her boyfriends. “But I am now divorced from them all.” Because apparently the “healthy” way of dealing with breakups is to erase the person – and all physical reminders – from your life. That’s bullshit. It’s not healthy. If you wouldn’t grieve for your grandma by throwing away everything she ever knitted you, then it’s bizarre to do this to other people we love more.  

The problem is that some people see “partner” as a singular slot to fill – then replace, erase, refill. For many, it’s only ever a snapshot, point-in-time relation. But partners are people on the other side of our own short-sightedness, who existed before we met them, existed together with us, and go on existing afterwards. Tearing each one from our story is denying ourselves – and them – the fullness of our own lives. I’m being honest when I say that people I love stay bound in my binding. My love has an exceedingly long half life.

Diane von Fürstenberg agrees: “Parting ways does not mean erasing entirely someone from your life.” And even when they are but a flicker in the grand scheme of things, “it was a phase, but it was real.”

Needs

In some way-off future, I bet we’ll finally realize that our needs are incredibly complex, and expecting a single person to satisfy all things in our life was always setting ourselves up for unhappiness.

I have friends for different needs. I have the fun friends, whom I can count on for a lighthearted pick-me-up. I have the deeply intellectual, artistic friends who are ready for discussions on psychology and love and happiness and pain. I have stable, consistent friends and offbeat friends; friends who love to work hard and friends who barely work at all. I reach out to them for different things. I would never live my life with one friend. 

A single person simply cannot be perfect at all roles: parent, lover, playmate, best friend, mentor, aid. I think we settle for “good enough” and tell ourselves it’s “perfect” in the name of security and social norms. That, or maybe we’re all just that simple-minded. But I don’t think so.

I say this to people and they assume I mean polyamory, but what I really mean is closer to the role nannies provide support in the parental role. Or chefs for cooking. Or friends, in most anything else.   

I’m not suggesting a company have more than one CEO. But I am saying that, in the same way a company has a role for each person who is good at it, our personal lives might one day also have other “chief” roles. Someone for sex, sure, but also brotherly love, love of the mind, play, and love of self. 

They say that cheating is often about satisfying needs that aren’t met inside the core relationship – sometimes sex, sure, but often appreciation or excitement or, hell, just laughter.

And if the core partner is unwilling or unable to fulfill your needs, as most people can’t do all things, then maybe fulfilling our basic human needs (not sex, but all of these other types of complexity and companionship) elsewhere should be viewed with more love and compassion.

On The Brink of Everything

There is no real concept of past or future, only as we exist as people and the way we spread out as fabric, interweaving with one another and taking up bits of other people as ourselves.

I feel nothing short of awe and anticipation for what’s beyond this; nothing but excitement for the grit and gift of life. Now. Next. Both. Everything as it is and will be and already has been.

Which is everything, really, beyond “pretty and pleasant.”


2015 Review

The year of broad shoulders and the bay.

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If last year was the year of the bike – and running that horse hard from city to country – this year was about broad shoulders and a bay.

The little things: I drank cheap wine, light beer and great whisk(e)y. I learned about good whisk(e)y; learned scotch. I listened to Whilk and Misky more than any other artist, got into my bike’s oil, and finally dragged someone out to a shooting range to show me how to fire a gun. These all matter to me.

The bigger things, they went a little like this:

HIGHLIGHTS – the four most important things of my 2015:

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Cuba. By far the most meaningful trip I took in 2015. I had wanted to go for several years, and went at a time I wanted it most. Cuba offered me the tiny but much needed consolation: “Nah, girl. You different, but you ain’t wrong.”  We came as we were and, with her, we lived off bad food and good coffee, wandered the streets with bottles of $2 beer and got just as drunk on the rainbow of modern ruins; we smoked Cubana cigars in bars, and ran down neighborhood alleys turned to mud in the pouring rain.

San Francisco. A move I had wanted to make for well over two years, while running things out in Chicago. After that long, some people cautioned against having built it up too much and warned me not to make it into something it wasn’t, but I knew what I wanted and wasn’t let down. From day one (okay, maybe day two), San Francisco’s streets already felt as good as mine in a way Chicago’s never had. I also hit the SF apartment jackpot and found an utterly darling place in Nob Hill, living with the coolest person I’ve met in the city.

Why San Francisco? For startups. To learn about “the making of something from something, against something, in relation to something.” To meet people starting startups and funding startups, go to startup pitch fests and  VC panels, and work at a startup. To see what good and bad startups look like, what good and bad founders look like, how their devs compare to the Midwest’s and what, if anything, is essential and unique to the San Francisco Koolaid that makes starting one there so common. Chicago has startups too, but ain’t nobody got the sheer density of startups that San Fran* do, so I went to the mecca to see.

That, and the people always seemed more my people. The city always a little more me.

*”Nobody” calls it San Fran and they all say you shouldn’t either, but I’ve never heard a good enough reason why, so I still do.

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Product Management. As I started looking to make a change in company and city, I was looking to make a change from program to product management as well, and I found an opportunity with a great startup in SOMA in August.

I like product management, though it’s not a forever move. (We all knew it was never going to be a forever move.) I came into it with a few objectives, which really boil down to: learning what goes into the pot. What tools, used in what way. Turns out, tools aren’t that tough. Any good product manager can “tool” and “recommendation.” “Politics,” even. A great product manager, though, knows how to add value, in the way that’s valued most. That’s what I wanted to learn.

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Last: a pivot and a machine. More on this next year. (UPDATE)

On to the rest of the things:

TRAVEL.

Beyond Cuba, I also did the sort of travel most everyone does a little of: Denver, Summit County, Cancun, Vegas, Orlando, as well as first-time trips to Portland, Mexico City, and Cayman Islands.

By the way: Mexico City, originally just a layover from Cuba, is incredible. And hotel Downtown is utterly breathtaking. It’s a renovated 17th Century manor and it is cool AF.

The photo below is not the hotel. This is a cathedral.

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Mexico City Metropolitan Cathedral

This is the hotel:

Portland was cool, too. We spent a couple of nights in this totally darling, secluded place – some renovated, whitewashed barn way off by Mount Hood – hiked to waterfalls, and met goats.

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READING.

I read 60 books in 2015, ranging from management and product development to philosophical essays and fiction.

By far the most important and influential ones were:

*I read both Value Proposition Design and Business Model Generation, both out of the Strategyzer team, and strongly prefer the former, despite value prop only being a fraction of the business model and the latter being recommended more often. Because frankly, if you don’t get value prop right, there’s no use worrying about generating a business model.

**Elizabeth Hawes is legit AF. She made this list twice for a reason, because she had the best damn stance on clothing I’ve ever seen. I was so impressed with “Fashion is Spinach” that I tracked down a reference-only copy of “Why is a Dress?,” now out of print, and rode my bike up to a university to sit in their library for as long as it took to read the book in one sitting. Because the book is tough to find but amazing, I also captured my favorite quotes and shared them for you here.

Other books and essays I highly valued this year include: Rework (Fried, Hansson), Peopleware: Productive Projects and Teams (DeMarco, Lister), The Mythical Man-Month (Brooks), Homesteading the Noosphere (Raymond), The Cathedral and The Bazaar (Raymond), What Customers Want (Ulwick), Naked Innovation (Paradis, McGaw), and Infinite City by Rebecca Solnit, my most cherished writer of 2014, though she had mostly lost me and would have remained distant had it not been for my move to San Francisco, about which Infinite City is written. I wrote about it – and my San Francisco – here.

You can see everything I read in 2015 here.

WRITING.

I published 70 posts to this blog this year (a few more to other blogs.)

I wrote the most about:

I also wrote a lot about work, creativity, my respect for developers and engineers, motorcycles and driving, whisk(e)y, Cuba, San Francisco, and love, among other things that struck my fancy.

My most popular post of 2015 was “the first week in SF.” (Last year, it was “from this place to a new one,” so apparently you guys like reading about my moves.)

My own favorite posts were:

And, in a way, this one.

THINGS I KNOW MORE TO BE TRUE.

The task of management should be taken seriously. More seriously than managers take themselves. Get your priorities straight. People – your customers; your team – always come first. Then the product. Then the project. Then the process. Don’t manage the other way around.

Layoffs are disgusting. Everyone in a company has a job to do, and the job of financial success is foremost the responsibility of the executives. If the company is struggling, then “streamlining” and “headcount cost cutting” should start with the people whose job it was to take care of the company and failed, not with the people who actually held up their end of the deal. There’s a special place in hell for managers who first fail at their job of running the company, and then fail at their job of managing people, charging the expense of their screw up to individuals who actually did their jobs.

I’ve always hated layoffs – a normal viewpoint when you watch your parents lose their jobs this way – but nothing solidified it quite like 2015, when my own company did a round of layoffs in Q1 (I high-tailed it shortly thereafter) and someone dear to me was laid off when his company did a round in Q4. (Oh, but then offered a transfer. I have a lot of respect for his response.)

I will not tolerate layoffs – will not continue working for any company that does them and will sooner surrender my own salary and make changes at the top before doing layoffs at mine. I have no fear about saying this – no fear of one day facing my people and going back on this word. I know who should fall on a sword, and have no appetite for cowards who instead use it to slay others.

There is nothing without something of value. Adding value is the most important act. Figure out who matters to you or cares about what you’re doing, figure out what matters most to them, focus on that and de-prioritize everything else. Don’t waste time doing anything that doesn’t matter to the people you value and value you, including anything that matters a lot only to people who don’t. Only do things that are real. Pushing papers nobody reads, just to look busy? Delaying the delivery of a proposal so that you can perfect every sentence? Creating high-fidelity designs when all your developers needed was a sketch? Writing business plans and whiteboarding instead of talking to customers? All not real. Deciding, developing, deploying. Those are real. And value-add.


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What we choose what we choose: aspiration and avoidance

Do people make decisions to validate what they are or pursue something they want to be? Both? Are decisions complementing or making compensations in contrast? (It’s not both. It can’t be both. It has been said that you can tell a lot about a person by the partner they choose. Some people will choose a partner who almost seem like the same person. Others will choose partners to “set off” or “highlight” things in themselves – the men, for example, who pursue trophy wives or hyper-feminine wives as a means of setting off their success and masculinity.)

The clothing, though… always aspirational?

Is it also always aspirational plus relative? Always pursuing something and also fleeing something else?

As sentient beings, we all desire pleasure and seek to escape pain. So it’s not a matter of knowing it’s pain – and so many producers don’t even get that far – but, rather, what sort.

A flowy, subtly ruffled but shapeless cotton peasant shirt. Aspiring toward comfort, of course, but also an ease and simplicity – a nod to bohemian sensibilities; perhaps farm life. And, as such, an escape from… stress? Modern woes? Mortgages? The 9-5?

A tight-fitting lycra dress – aspiring to be sexy, of course. But also aspiring to be desired; to be seen. Escaping… aging? The monotonous? The mundane?

The feminine type who dress in nod to times past – especially the 1950’s – want the sense of security and stability offered by legacy and tradition. And they seek to avoid the pain of uncertainty, even change.

And the rebel – an archetype called out even by J.C. Flügel’s “Psychology of Clothes,” in which he said that “the rebellious type gets little satisfaction from clothes, and is never resigned to them, feels constricted, impeded, and imprisoned.” She is reluctant even in her t-shirt and jeans, and is ultimately aspiring toward freedom, of course, and escaping rules and anything else that hinders.

Rebels need freedom of movement. It must not hinder and it must come with. Rebels don’t care for feeling restricted in our movement, but we also do not care for clothing that’s too drapey, that we feel we must drag and swing around.

All of us are pursuing something and avoiding some pain in what we do. The matter, in product, is figuring out what it is for a segment of customers.


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There’s room in passion for imperfection.

There’s often this expectation that people will uphold the things they do professionally in their personal lives.

Like this morning, I met a woman who designs textile patterns and, after learning this, I immediately became more acutely aware of her dress. I felt like she would want me to – I looked almost as though I was being asked. But I also looked because I thought, as we all think, that it made sense to do so: that I should find some physical manifestation and extension of her work even in her life outside of it.

That she should be consistent.

It’s the same way we may assume film critics, in their at-home theatres, would never stoop so low as to happily watch “Bad Santa” on a Sunday night. That sommeliers never drink Bud Light and priests always practice what they preach.

We want to believe that most things can withstand the test of consistency and play their part all the time. And for the most part, this probably does hold true. (In cases of ethical questions, it definitely should.)

But there’s also something wonderfully refreshingly genuine about the passionate person who lets things slide sometimes. The authenticity afforded them by the occasional guilty pleasure. Not hypocritical, but honest.

Like the top chefs with a soft spot for McDonalds, and like actors who aren’t always camera-ready and instead run errands in sweats, and like the inventor of the typewriter who, all things considered, very likely still used pen and paper from time to time.

Like the award-winning pastry chef and bakery owner I also met this morning, who admitted that her least favorite thing to make is “chocolate chip cookies.” I immediately envisioned a moment, even if it’s only happened once, when she has torn into Chips Ahoy at home. And I mentally made space in our conversation for that.

Because I like a world where she can.

There’s room in passion for inconsistency and imperfection.

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The second to last sip of beer

I’m at an event, and for 99.9% of the time, my thoughts are on-topic or only immediately tangential.

But there’s a single split second where I zone out, seeing a middle-aged woman a few rows ahead of me.

She takes the second to last swig of her beer and as she lowers the bottle, she reaches up to tuck her hair behind her ear.

Drinking beer from a bottle reminds her of all the other times she’s drank beer from a bottle, all of which already reminded her of all the times before that, which all take her back to the first times and remind her of when she was young. She’s at a conference sitting in a sea of pressed khaki, but when she takes this sip of beer she feels that nostalgic uncertainty and excitement again; feels something that reminds her of youth.

And so gingerly tucks her hair behind her ear.