Its Thanksgiving, 2013.
I'm sitting in my parent's living room, cradling a dotgrid sketchbook and wishing direly I was better at lettering. My parents were in the kitchen, my mom was running the phone while cooking, fielding every friend or family member's call to kvetch about the turkey, swap jokes, or tell them what her band was up to.
I appreciated the break, as I was in the middle of a startup bootcamp's full-time dev course. I was trying to pivot my career towards actually building things! I would 'graduate' at the end of December and I had to have a portfolio. Everyone did - it was part of the curriculum. I was fresh off of some artistic successes at my previous agency gig, so I jumped at the chance to do work on my own terms, for me, finally.
I worked that whole holiday, keeping my sketchbook on me just in case I found a moment to draw on some inspiration between the green bean casserole and a heated inter-generational 'is open-source secure?' argument.
All that effort got me relatively little: I found a pretty 70s nostalgic serif typeface, made a few solid sketches of a custom letter forms for a logotype, and used dozens of pages for my brain to furiously run in circles. No matter how much of myself I put in, or how capable I thought I was, I couldn't seem to apply that capability for myself.
The original custom letterform sketch from 2013
It wasn't that I was remarkably better than anybody else, nor did I aspire to live as a tortured auteur. I only mean to say that I had capability, and I could push myself to get a lot done with it, just never for myself.
So, a week goes by, two, a month... how did it come out? Not terrible, but despite working on it for over a month, the source code looked like it could have been coded in a day. It was a single page of plain HTML & CSS, an unsplash photo of stars at night for a background, with my name at the top, featuring the custom letterform I did on Thanksgiving. That's it. It had a decent design. The words sounded nice, if a bit insincere. The contact form didn't work when I shipped it, because I ran out of time.
In short, it was sufficient, but it was hollow. I begrudgingly accepted compliments, a burning shame of how bad it was drowning out praise. I was already plotting its redesign & rebuild. I'd fix that contact form first.
"It's the worst winter in Boston's history,"
we were told, as 2014 limped into the snowmapocayplsageddon of 2015. The startup I was working with died. I was applying to jobs, leaning on my Github contributions graph and LinkedIn.
I mean, I couldn't use my portfolio; it was over a year old with no improvements, the contact form didn't even work.
Boston's Seaport District, in winter
I had half of an idea for a redesign the year before (see above), just never chance to follow up on it. I had been bouncing from startup to startup, nothing sticking. There were several attempts of a new portfolio scattered across my hard drive, each a momento for a promising idea scuttled onto the craggy shores of executive dysfuction and dissociation.
It felt like a metaphor for my whole life. No startup job I found lasted; almost all would implode due to stress or lack of money. My imposter syndrome was having an easier time (read: field day) of selling me the idea that I was the common problem at all these ventures. I didn't want to lose everything I had worked for. I pushed myself harder.
But I found a job - a remote, freelance one - thanks to AngelList. I couldn't complain; it was easier than a portfolio and free. Sudden I had resources and no obligation to spend two hours of every day stuck in a gross, sweaty tube in a frigid city with icy sidewalks.
So I announced my plans to go remote. There was a wonderful goodbye party from wonderful friends. Then I hit the road with my partner, leaving everyone and everything I knew behind.
I'm in North Carolina for the first moments of 2017
We're celebrating new year's eve, or at least trying to. Its been a hell of a few months for everybody, but I was especially done. After realizing that remote startup work meant I couldn't spend my time on the places we were visiting, I had finally found what should have been a stable engineering job. That would fix everything, right?
By the end of the year, I was burned out, badly. Too many months of six day workweeks. I buried my dog. There were the elections. We got robbed.
The first new friend I made in Durham was the one who robbed us. Trust issues suck.
Durham was a crucible that burned away the last vestiges of the lies I told myself. In that terrifying chaos that I realized I was trans, I had always been. I knew almost nobody in NC, hadn't had a doctor in years, and my health was rapidly deteriorating. I realized I needed to get out of North Carolina, ASAP. I had some friends and family in CA. I could get medical care there. Medocino & Sonoma were a lot cheaper than most of the Bay area, too.
I had been talking to my manager about moving for months by new year's. I was getting out as soon as my lease was up. Apparently my manager forgot to tell his manager about it. If he had, he would have been able to tell me that the company had adopted new staffing policies and they wouldn't employ anybody in California. But he didn't. So I, closeted trans woman living in NC, was given a choice: keep my job or move to CA.
Which is to say, no choice at all. But, I direly needed employment, which meant I direly needed a portfolio, ASAP. The previous year I unceremoniously took down my old portfolio, contact form still broken. In its place was a wordpress blog with a basic, unmodified theme and two short posts. I hadn't touched it since. I still haven't.
In new and terrifying ways that I could tell nobody about, my portfolio was my sole lifeline. Which should have shaken me enough to complete it, but all it did was render me increasingly nonfunctional.
That's fine, you don't need a portfolio on Upwork, right? My resume was enough to get me in the door. In fact, my first upwork job came in before I could finish even redoing a simple, static version of my old portfolio. It was... not a great gig, but I was terrified we'd run out of money before we find a place in CA, or the car would break down. What was the alternative, though?
I say goodbye to everything and everyone again. There's no party this time. We leave North Carolina. I don't look back.
It's 2019 now. A lot has changed.
I have a name now - it isn't that I didn't have one before, but my deadname felt more like a SKU or UUID than an identity to me. It wasn't me. It was just the sticker that my parents put on my blisterwrap.
My name's Sarah by the way (she/they pronouns), thank you for reading this far. It really does mean a bunch to me 💖
Its not all roses - I've managed to survive the hazards of transition so far, though just barely at points. Every few months, there's a new existential threat that threatens the financial, medical, or legal safety of myself or my loved ones.
In return, I have everything I never knew I wanted, and more.
My fiance and I sailing on Richardson's Bay in early 2019
Joy so raw and honest I still tear up when thinking about it. Acceptance, healing, love so wild and deep that I dove in head-first and have yet to find the bottom. I have discovered depths to my strength and kindness I never knew was possible. Euphoria is the correct term, but it is the understatement of a lifetime.
For the first time in years, I felt myself get better at programming instead of worse. Not coding, not outputting LOC, not writing tickets - programming. Concepts started to click that I struggled with for my whole career. I realized that my passions shared more primitives than I had previously believed.
So I started building. And writing. And now, here I am. This blog isn't 100% what I want it to be... yet. But it'll get there, slow & steady, with lots of love.
So, how do you make a portfolio to grow your career when you have crippling face and identity dysphoria? Answer: Half a decade of painful experience and growth, and around a week of actually coding.