Hey everyone: it’s your boy Josh Rubenoff, product designer and org culture enthusiast.
Reminder: I use this newsletter to work and think in public. You probably subscribed on my website or via Twitter @joshsj. If you’d like to unsubscribe, there’s a link at the bottom.
In December 2017, a 50-person startup bought my employer. After talking to a few people there, I realized I didn’t want to stay. So I quit without another job lined up.
This decision gave me some pause. I felt confident I could get hired elsewhere, but also knew I was picky. I wanted to work somewhere that:
This ruled out 95% of jobs in the Bay Area. My partner’s family lives here, so moving was not an option. Fun!
I reviewed thousands of job listings and applied to 132 companies. 27 requested an interview, giving me a response rate of about 20%. Of those 27, I was rejected or ghosted by 17 teams, and I withdrew my candidacy from 8 after realizing they were a bad fit.
In March, I contracted with a startup under a “trial period” to become a full-time employee. It didn’t work out. Two months later, I applied to the City and County of San Francisco’s Digital Services team. After a protracted screening process with city HR, I finally started in August 2018.
All told, it was demoralizing. During this time, I became quite depressed, and thought about leaving the industry. I also ran out of money twice, accruing $6K in debt before my start date. (Over the following months, I worked it off with a part-time second job.)
Despite this, I’m doing it all over again! I gave notice to the city a month ago, and my last day was January 31st. I hadn’t even started applying until a few days ago. And my job criteria haven’t changed.
I’m very fortunate to have more savings this time around, so I’m not as worried about running out of money. But towards the last few months of my unemployment, I felt pretty hopeless. When I was considering whether to quit the city, I wondered how I’d avoid sinking into despair.
It’s not like I was unemployable: there were lots of easy opportunities I chose to not pursue. Even so, it still hurts to get five rejection letters in a row, or even worse, no responses at all. What would keep me from feeling like I was hopeless or unwanted?
To answer that, I first had to figure out what had made me feel that way in the first place.
I relied too heavily on hiring managers for feedback. To improve my resume and portfolio, I only asked for feedback from hiring managers who rejected me. This was actually super helpful and I learned a lot. But it also meant that, to get any feedback at all, I had to wait for them to send a rejection letter saying they no longer wanted to consider my work. Then, I had to bug them to reconsider my work anyway, and send multiple follow-ups to ensure they replied. It didn’t feel great.
I was obsessed with my “conversion rate” (gross.) I methodically tracked responses for each place I applied. In theory, I wanted to confirm that my desirability as an applicant was improving over time. In practice, I checked my inbox 50 times a day for responses, making me super anxious. I also became paranoid about minor issues on my resume that ultimately didn’t matter.
I placed too much importance on my day job. I haven’t had too much success with cultivating a healthy side project, or building a creative community, to complement my job. So I looked for companies where I could find total professional and creative fulfillment. I ended up looking for way too long time.
I focused inwards, not outwards. Instead of sharing work on a regular basis, I spent much of my time writing a 6,000-word case study for my portfolio. This was my thought process for doing so:
If this case study explains my work in sufficient detail, hiring managers will really appreciate the rigor I put into everything I do.
I still haven’t published it.
I’ve learned from all of this. I’ve promised myself I’ll do the opposite of everything I just mentioned.
For example, I still think hiring managers should give feedback to anyone who asks for it, and has taken the time to apply. (It’s what I’ve done when I’ve hired in the past.) But if someone can’t take time out of their schedule, it’s not worth beating myself up over. Also, I already know where I have room to improve! Instead of waiting to see whether hiring managers notice my flaws as a designer, I’m going to try and fix them myself.
I’m also going to care much less about whether a random hiring manager responded to my resume. Hiring practices are wildly inconsistent across the industry and often totally subjective. If I have concerns about my portfolio, it’s easier to form a community of designers I trust and ask them for feedback in person.
And I no longer think a day job is a prerequisite to evolving my design practice. Unless I start a business, the existence of a perfect role that indulges all my interests is outside my control. I don’t need to “ladder up” in my career to be happy, but I do need to feel like I’m moving forward. This can mean taking the time to learn new design skills that don’t intersect with my day job. I think I’m more comfortable with this than I’ve been in the past.
Finally, the easiest way to avoid getting stuck in my own head is to consistently put myself out there. That means reaching out to other human beings. But it also means putting creative work out into the world. That might be this newsletter, new design work, or something else altogether.
With that in mind, I’m going to try writing about the thought process behind my job search going forward. That’s what’s occupying my head these days, and I haven’t seen a mid-career person write about this topic with any level of vulnerability.
Hopefully you’ll find it of interest, but if not, I’m still writing about culture. Speaking of which…
DIAMANTINO, Gabriel Abrantes & Daniel Schmidt (2019.) The B-movie we need right now (with all the cliché and naïveté that phrase implies.) The plot and characters strain belief, and I yelled at the screen more than once. But I can’t say I regret seeing it. The filmmakers’ narrative invention, scrappy production design, and obvious passion for this project shines through the screen. Instead of trying to explain what it’s about, I’ll just refer you to the trailer.
MASTERS OF DOOM, David Kushner (2003.) A chronicle of the formation of id Software, the creators of Doom and Quake. On the one hand, the author’s perspective feels outmoded in Ga*er*ate’s wake: Kushner’s uncritical of crunch mode and booth babes, and earnestly describes co-founder John Romero as “the ultimate gamer.” On the other, so much reads like an origin story for our present day. Romero and Carmack are obscenely wealthy, abusive executives with no sense of gratitude for their early supporters and zero compunction about stabbing their partners in the back. Carmack is the prototypical antisocial tech libertarian hailed as a genius. Romero reads like the Musk of the 90’s, obsessed with press and notoriety to the detriment of his personal relationships and ability to ship work on time. Alluring like a nightmare; amusing like a sick joke.
LA POINTE COURTE, Agnes Varda (1955.). Varda’s debut, and the first I’ve caught in her Pacific Film Archive retro. She shot this for under $150K in today’s dollars, right out of the gate, her confidence as a filmmaker is incredibly inspiring. The main narrative thread centers itself around a troubled mid-20’s relationship that I could have done without. But the remainder consists of wonderful slice-of-life segments in the small coastal town where it’s filmed.
CONTAGION, Stephen Soderbergh (2011.) Looks ugly, but for once the muddiness of late-2000’s digital video suits its subject matter. Made me miss studio movies made for adults. For more, read K. Austin Collin’s piece on the film’s resurgence amidst the coronavirus.
DRY COUNTY, Rich Tommaso (2018.) A graphic novel too tame to succeed as Florida fiction and too prosaic to succeed as neo-noir. Some nice compositions, though!
Thank you, sincerely, for reading.