“We need a North Star.” Most product designers have been asked for one at some point, and it usually causes us to internally groan and roll our eyes (if not externally, too). We’ve all worked on North Stars that are a frustrating waste of time and served no purpose, and where the sole burden was on us to “come up with the vision.”
But many of us have also created ones that painted an inspiring vision, getting a team excited about the road ahead and keeping them on track to deliver that vision.
I led a discussion in a product design meeting at LaunchDarkly to learn about the team’s experiences with North Stars. What made for good ones, and what made for bad ones? What follows are some takeaways from that discussion.
A design “North Star” is a visual output (commonly a video, although it can also be a storyboard, a series of hi-fidelity designs, etc.) that explains the high-level narrative of why an idea or concept will improve people’s lives.
They should be inspiring, get people on the same page and excited about a vision, but still be realistic.
It’s not a roadmap, a spec, a detailed design mock, nor does it answer every question about how an upcoming product or feature should work. What eventually gets built won’t be exactly like the North Star.
They can be used for projects as big as a whole new product or service, or as small as individual features.
Julie talks about North Stars as very future forward, and primarily videos, but myself and the team have created ones for individual features, and the output was just static screenshots. I’ve also called them “hero shots” and “concept mocks.” You could argue these aren’t “North Stars,” but spiritually they’re the same: get people excited about the future they’re building.
Do’s and Don’ts for North Stars
Simply put, good North Stars distill complex concepts to their essence, and get people excited about the future they’re building towards. These “Dos” and “Don’ts” will guide you to successful North Stars.
Don’t
Design for an unspecified time in the future
Redesign every screen or specify every interaction and design detail
Put all the work on the designer
Have too many cooks in the kitchen
Spend multiple quarters making one
Do it “for fun”, or because someone said you’re not “innovating enough”, or because you’re bored with the current experience
Do
Set a target timeframe for when this could be achieved. In my experience at high-growth startups, a timescale of 6–24 months is best for most features or products, but it will depend on your project and needs.
Scope it aggressively to 1-2 screens, a handful of use cases, a persona — something to set the focus on the most important aspect of a future product or feature. You’re trying to sell a vision, not answer every question. Good North Stars should tell a story in just a couple of screens.
North Stars should be a cross-functional effort, like any product work. Expecting the designer to “come up with the vision” without input from engineering, PM, and other stakeholders is doomed to fail.
Conversely to the above, too many people involved slows down the process, leads to too many opinions, and takes too long to get to consensus. The triad (design/eng/PM) is usually the right group size.
A north star should take somewhere between days and weeks to create (maybe months if it’s a multi-year vision with filming and editing to do), depending on the time frame and scope of the future vision you’re trying to communicate.
North Stars need to be tied to concrete initiatives that are actually going to be built. Doing them speculatively will be a frustrating waste of time for everyone involved.
North Stars That Worked
At both LaunchDarkly and my former company, Gladly, we’d make “hero shots” of features we’re planning to build for roadmap presentations and sales decks. They’re a single screen that communicated the feature to prospects. We’d usually spend a few hours designing this 1 screen to represent a whole concept. It forced us to distill complex features down to their essence. When design and development actually kicked off, they kept our focus on the purist version of the idea. There were a few times when features were getting too complex, or we were over-optimizing for edge cases, and the “hero shots” reoriented the team back to the essence of the concept.
Hero shot for LaunchDarkly’s “global search”
Hero shot for approvals in LaunchDarkly
North Stars That Didn’t Work
While at Optimizely, myself and a couple of other designers worked on a “North Star” (which we called a “concept car”) to envision what the product would do in some far off future (we didn’t have a specific time frame in mind). We were tapped by the co-founder to do this as a way of getting the company excited about the future of the product, get investors bought into our vision, and to sell candidates on joining the company. It was not tied to any product initiatives, nor did it feed into product strategy.
We spent months speculating on a bunch of cool new features, redesigning the UI, and rethinking the core flows. The end result looked awesome and was packed full of new stuff that solved existing pain points. The company was excited about this potential future we could build.
Optimizely’s “concept car”
But it went nowhere. It was shared with the company, shown to some investors and candidates, but ultimately none of it was built. It was way too broad in scope, had a non-specific time horizon that was too long, wasn’t tied to any product initiatives, wasn’t an input to product strategy, didn’t tell a story, and wasn’t cross-functional. Basically, we did everything wrong.
When used properly, North Stars can be a fantastic tool to accelerate projects and sell a vision. But when used incorrectly, they’re a frustrating waste of time. Hopefully now you have some guidance on when and how to do North Stars.
As I’ve been building out the team at LaunchDarkly, I realized my eye for visual design details had gotten a lot sharper. I was seeing rough edges and ways to improve UIs that I wouldn’t have caught a few years prior. This was cropping up in the UI work I was doing myself as well. I hadn’t explicitly tried to improve my visual design skills, and professionally have spent more time in management than IC work, so how had this happened?
Looking back on the past few years, I realized some independent threads had come together to improve my visual design skills without me noticing. I thought it would be fun to document those, and to be a resource for others who are looking to improve their designs (spoiler alert: there’s no silver bullet here, just deliberately and consistently putting in the work).
One of the first websites I designed back in high school for my friends’ band, The Local Oafs, circa 2002 (roughly). It’s actually kinda dope, in an amateur-ish, grunge aesthetic way.
Lettering
The first thread is hand lettering. (See my journey here). Back in 2017 a couple of Optimizely designers and I hung out after work, ordered some Pizza Hut, drank beer and doodled with a bunch of pens and brushes. I started messing around with a brush pen and fell in love with the thick and thin strokes and the overall feeling of making marks with it. I had always admired hand-lettering and sign painting, so I got my own brush pens and started drawing letters. I copied a bunch of Instagram artists to start, and then got some books to help me improve even more. I kept practicing ever since, expanding into drawing letters with a pen & pencil, laying out phrases, and doing calligraphy (which I actually did as a kid also).
I started doing this just for fun, and to get back to analog creative activities that didn’t require a computer, not to get better at design. But hand lettering helped me develop my eye for typography, to see the subtle curves that define a character’s personality, and just general layout and details and color. I now have much stronger opinions about fonts and all the small details that define their mood and character.
Some books that helped me the most:
House Industries Lettering Manual by Ken Barber
The ABC of Lettering by Ivan Castro
In Progress by Jessica Hisch
Handstyle Lettering published and edited by Victionary (a great visual reference, but won’t teach you how to draw letters).
Optimizely’s preview tool, which I redesigned back in 2013. This is what shipped, but to my eyes today this looks like a first round wireframe.
Type & Color & Branding
I also read a lot about typography, color, and branding over the past few years. The type books further trained my eye and attuned me to the subtleties of every character and how that lends personality and uniqueness to each font, making typefaces that previously looked almost identical look vastly different now.
On the color front, I kept buying palette books for inspiration. Inspiration for what, exactly? I don’t know because I didn’t have any projects that needed them. I just liked them.
The palettes also developed my eye, but by far the biggest book that changed how I see color is Interactions of Color, by Josef Albers. This book is a series of exercises that trains your eye to see how color will look different depending on the circumstance, how they interact, and how they influence each other. I couldn’t recommend this book more if you want to get better at using color. Read about the exercises and my experience with the book in this blog post.
I also got a lot more interested in branding during this time. I read some books on branding, but the bigger influence has been subscribing to Armin Vit’s brand review site, Brand New. It further honed my eye for branding, typography, and color.
Some of my favorite books on color, type, and branding:
Logo Design Love by David Airey
The Designer’s Dictionary of Color by Sean Adams
Sagmeister & Walsh: Beauty by Stefan Sagmeister and Jessica Walsh
Thinking with Type: A Critical Guide for Designers, Writers, Editors, and Students by Ellen Lupton
The Secret Lives of Color by Kassia St. Clair
The Designer’s Dictionary of Type by Sean Adams
Palette Perfect by Lauren Wager
Draplin Design Co.: Pretty Much Everything by Aaron James Draplin
My original website, circa 2012, compared to my refreshed website, circa 2019. The old one was fairly bland and safe and avoided making mistakes, whereas the new one has a lot more personality, bolder font choices, and a more evocative color palette. Read about the design process here.
UI resources
Even though I said I didn’t set out to improve my UI design skills, I did read two UI focused resources: Refactoring UI, and Learn UI Design (not a book, but a website & blog & course [I did not take the course]). These are both very practical resources that focus on actual techniques to use when designing UIs, as opposed to theory which I have found leaves a gaping chasm between itself and how it applies to actual UI design. So these were great for both developing my eye for details, and also giving me specific tips and tricks to to use in UI design.
Before and after comparison of a side project I worked on in 2020/21 called Center.
Creativity
The final thread is general creativity. I’ve always been fascinated by the creative process, and love reading how people from other creative disciplines do what they do. These have helped me think more about how I work, and given me techniques to try from other disciplines to break through creative obstacles or find novel solutions.
By far the most impactful book I’ve read in this category is The Artist’s Way by Julia Cameron. Saying I “read” it does it a disservice. It’s a 12-week program that shows you how to shed your inhibitions and find your inner artist. You can read more about my general experience with the book here, and a follow-up post about artist dates here.
Creativity books I recommend:
The Artist’s Way by Julia Cameron
Making Music: 74 Creative Strategies for Electronic Producers by Dennis DeSantis
Working by Robert Caro
On Writing by Stephen King
Keep Going and Steal Like an Artist by Austin Kleon
Bird by Bird: Some Instructions on Writing and Life by Anne Lamott
Draft No. 4. On the writing process by John McPhee
The Gift by Lewis Hyde
Understanding Comics by Scott McCloud
LaunchDarkly’s workflow builder, circa 2021 (worked on in collaboration with other designers & PMs).
So that’s it! Now you know all my secrets: just read a ton of books and put in consistent practice to an artistic pursuit like lettering for years. Easy, right?
But seriously though, all of this did help me become a stronger visual designer without me explicitly setting out to do so. And one of the biggest changes between now and 5 or 6 years ago is how much I’ve developed my eye. I didn’t appreciate how important it is to tune your eye to all the small details that really elevate design work. There’s no shortcuts, but anyone can do it as long as you’re willing to put in the work.
2021 felt like a slow year for reading for me, what with vaccinations and my social life and work life picking up. In actuality, I only read 4 fewer books than last year (24 compared to 28). Not as bad of an outing as I was expecting.
Some interesting stats:
2 books were over 1,000 pages (Master of the Senate by Robert Caro and Antkind by Charlie Kaufman)
Only 3 were fiction
21 were non-fiction
10 of those non-fiction were art and design books (still my favorite category, obvs)
Only 4 were by a person of color, and 6 were by women. I tried to continue my anti-racist reading, and reading perspectives of under-represented peoples, which I did, but this wasn’t a huge improvement over the previous year. It also highlights that my most dominant category, non-fiction (and specifically art and design) are primarily white and male.
Some of my faves (all links are Amazon affiliate links):
House Industries Lettering Manual (Ken Barber) — Amazing lettering book with tons of great techniques, styles, and lessons to up your lettering game. Highly recommended for anyone who wants to letter, or even just admires the art form.
The Vanishing Half (Brit Bennett) — Great story of light-skinned black twins who take divergent paths in their adult lives — one passes herself off as white and leaves behind her black heritage, the other remains in black society. An illuminating tale on the arbitrariness of race. (Also, this book has a great cover).
The New Jim Crow (Michelle Alexander) — A damning case for how we’ve used the war on drugs and the prison system to systematically keep black people in the lowest social caste in America. These programs don’t specifically target any races the way they’re written, so they don’t technically violate the Civil Rights Act of 1964, but the implementation of these systems target black Americans (and other communities of color). This makes fixing this broken system really difficult since it’s not explicit like the Jim Crow laws were.
Master of the Senate (Robert Caro) — Caro’s fourth volume of the Lyndon B. Johnson biography does not disappoint. This was a fascinating look at the inner workings of the Senate, its storied history, and how LBJ was able to pass bills despite the institution being designed such that “the rights of a minority must be protected against the tyranny of the majority” (as Caro put it [and in different words, the founding fathers]). Very interesting to read through the lens of today’s political climate as it really highlights why it’s so difficult for any bills of real change to pass and why the Senate is broken. I’d be curious to hear Caro’s perspective on the functioning of today’s Senate given all of his research.
This Is Your Mind on Plants (Michael Pollan) — Pollan’s next foray into the effects of chemicals on our brains and consciousness is just as interesting as his previous book. He focuses on just 3 drugs: an upper (caffeine), and downer (opium), and an “outer” (mescaline). He includes their history and a trip report for each (or in caffeine’s place, an anti-trip), which was especially interesting for mescaline since I didn’t know much about that drug (it’s the active chemical in peyote).
Full reading list
As always, you can view the full list (past or present) in Notion.
Validating Product Ideas by Tomer Sharon (finished December 31, 2021)
In pursuit of inspiration by Rae Dunn (finished December 20, 2021)
This is your mind on plants by Michael Pollan 👍 (December 19, 2021)
The typography idea book by Steven Heller & Gail Anderson (December 12, 2021)
Master of the Senate by Robert Caro 👍 (November 25, 2021)
River Days, River Nights by Mark Abramson (October 24, 2021)
Twenty Bits I Learned About Making Fonts by Dan Cederholm 👍 (September 25, 2021)
Twenty Bits I Learned About Design, Business, & Community by Dan Cederholm (September 21, 2021)
Logo Design Love by David Airey 👍 (September 19, 2021)
The Art of Letters by Kris Sowersby (September 14, 2021)
The Cuckoo’s Egg by Cliff Stoll 👍 (August 22, 2021)
The New Jim Crow by Michelle Alexander 👍 (August 14, 2021)
The Wreckage of my Presence by Casey Wilson 😆 (July 19, 2021)
The Outdoor Kitchen by Eric Werner (July 18, 2021)
A Field Guide to Whisky by Hans Offringa (June 12, 2021)
Uncanny Valley by Anna Weiner 👍 (May 4, 2021)
Cubed: The Puzzle of us All by Ernö Rubik (April 18, 2021)
Making Music: 74 Creative Strategies for Electronic Producers by Dennis DeSantis (April 17, 2021)
The Vanishing Half by Brit Bennett 👍 (April 3, 2021)
Eat a Peach by David Chang (February 28, 2021)
Demand-side Sales by Bob Moesta with Greg Engle (February 15, 2021)
Antkind by Charlie Kaufman (February 12, 2021)
Sign Painters by Faythe Levine and Sam Macon (February 1, 2021)
House Industries Lettering Manual by Ken Barber 👍 (January 11, 2021)
A common mistake I see product designers make is that they start the solution exploration phase by cobbling together UIs out of the components and patterns in their design system (often skipping lo-fi, broad explorations, which is a separate rant [and one that Figma makes far too tempting with its shared libraries #endrant]).
“But I want to be consistent with the rest of our product! Shouldn’t I be using existing components and patterns? Why is that bad?” I hear you protesting.
I applaud your instinct 👏 It’s coming from a good place. But don’t do it. You’re artificially constraining the solution space before you’ve found the best design for the specific problem you’re trying to solve. You’re potentially overlooking better options by only using what currently exists.
“So what do I do? Ignore the design system altogether?”
No, that would make the design system pointless, wouldn’t it? But actually, yes — kind of. The proper time to reach for the components in your design system at the end of solution exploration, when you’ve nailed down the interactions and flows, have validated it with customers, and your team is ready for you to create the final hi-fi designs for engineers to build.
At that point you can take what you have (which should be mid-fi at most), and seek out the components that most closely match what’s in your designs. A mature, robust design system should have components for the majority of the UIs you create. There may be some things that you did slightly differently than the standard component, and you can adjust your design to fit what exists with little to no impact to the usability of your feature.
“But what if there is no component that meets my need?” Now this is where things get interesting. In this case, you should go to your design systems team to get their input on your designs.
First, confirm that you didn’t overlook or misunderstand anything in the system. It’s possible there’s a component you should use, which the team can educate you on.
Assuming there is no component you can use, you can now work with the team to determine next steps. There are 2 options here: either your thing is a snowflake (i.e. it isn’t a generalizable component that can be used elsewhere), in which case your team can build it as part of the feature; or, the design system needs to be extended.
If it’s the latter, congratulations! You have a contribution to the design system. You have a specific use case for a component or pattern for a feature that’s been validated with real users, and no known equivalent in the existing system. You can work with the design systems team to flesh it out into a generalized pattern.
Design systems are meant to be living systems that grow and change as products grow and change (in my opinion. Some people may think they’re a tightly controlled system that everyone should conform to, but those people are wrong). The best way for them to grow is organically — meaning through contributions from specific features that identify gaps in the current system. Not from hypothetical, “I saw this pattern in Material Design and thought it would be cool to add to our system…”
So there you have it! Next time you’re entering the solution exploration phase and you feel the instinct to reach for your Figma component library, STOP! 🛑 ✋ 🙅. Do not pass go. Do not collect $200. Start with as few constraints as possible and explore broadly before honing in on the best solution. Only then should you translate what you have into the design language provided by your design system.
Last fall, Optimizely was acquired by Episerver, signaling the official end of Optimizely as I knew it. I’ve been re-connecting with old Optinauts and reminiscing on the magic of those early days.
I joined the company in 2012 as employee 29. It was pre-series A, everyone fit in 1 office in downtown SF, and the average age of employees was about 27. Not too long after joining we had the 4th highest valuation of all YCombinator-backed companies (behind AirBnB, Dropbox, and Stripe). There was a ton of energy and momentum behind us. We were all young and hungry and full of ideas and eager to prove ourselves. We had a lot of freedom to try out ideas, fail, learn, and grow. It launched the careers of most of the people who were there, including mine.
What follows are a collection of my most cherished memories.
Every Friday afternoon was Show-and-Tell. We were small enough for everyone to gather together around a couple of couches, grab beers, and plug in our laptops to show what we’d worked on that week. Engineering, design, marketing, sales, success — everyone just showed stuff. There wasn’t a format or agenda, really. It was just show-and-tell :)
That would transition into more beers and people hanging out and playing ping pong, Starcraft, poker, whatever. It would just turn into a party. That would often transition into ordering food or going to bars. The company was young and unencumbered with responsibility, plus a lot of people were new to SF, so the conditions were right for our work lives and social lives to blend together.
I remember the week I joined, we had a happy hour at House of Shields, the bar on the ground floor of the office. A candidate was interviewing for a Solutions Architect role, so we invited them to join us for the happy hour. Dan, the CEO, convinced them to sign our offer on the bar. Literally, on the bar.
A couple of months after I joined, we had our first company retreat to Santa Cruz. There were maybe 40 of us total. We stayed at the Dream Inn, right on the beach. The bus ride down was a party, with everyone drinking and enjoying each other’s company. We had some sessions about plans for the coming year, but most of it was just having fun. I can remember everyone getting sloshed at the company dinner, then getting more drinks at a bar, trying to break into the jacuzzi long after it had closed, running out to the beach instead, getting yelled at from the balcony of a room which turned out to be the after-after party in the CEOs room, which we then joined to keep drinking. I was still quite new and just amazed at how fun the people and culture were.
Drunken photo of us in Santa Cruz
On the Sunday we were returning, most people (including me) were tired and hungover and slept on the ride home. But not the CEO. He got a 30 pack of Coors and kept drinking with the sales team the whole ride home.
The following year we had our second (and I believe final) company retreat to Tahoe. It felt just as fun and collegiate as the first. My main memory from that trip was one person broke their back skiing (same person who signed their offer on the bar at House of Shields). He had to be airlifted to a hospital in Reno. One of the co-founders stayed with him until his parents arrived.
At some point we ran out of room of that first office. I can remember squeezing desks into every corner of the office and there being just enough space to walk past each other. Eventually we rented a second office nearby and moved sales there temporarily. (Which I seem to recall turned into a frat house).
When we finally did find a new office space big enough to re-unite the company (the space on Howard that Optimizely was most well known for), we were all so excited to move in. It had tons of space. Downstairs was dedicated to lunch, show-and-tell, 3 kegs, a speakeasy (which ended up not getting built), and games (we had 2 ping pong tables, a ping pong robot, and a foosball table). No desks or conference rooms. The first floor was sales, marketing, and success, and the mezzanine area was for product, engineering, and design. We quickly expanded into the 3rd, 4th, and 5th floors. (Although I don’t think we ever occupied all of them at the same time).
My wife and I in front of the new Optimizely office (this is from our engagement shoot)
I can remember going to the office on a Saturday to help set it up for our first day that Monday. Getting desks ready, organizing the kitchen, that type stuff. We made little welcome gifts for everyone that included an Optimizely branded pint glass, some swag, candy, and a few other things. It all felt very exciting and like we were on an unstoppable growth trajectory. (I still have the pint glass).
In April of 2014, we had our first annual user conference, Opticon. It was on the top floor of the Metreon, in a cluster of small conference rooms. Only a few hundred people attended, which felt huge at the time. It was so electrifying. The whole company worked hard to pull it off — planning and marketing the event, booking speakers, building features to announce, and so on. It was only one day, but the whole week felt like a big celebration. Customers were jazzed. We were jazzed. I remember going back and forth between there and the office and just having a ball hanging out with customers and coworkers.
Countdown to the first Opticon
The next Opticon was at the cruise ship terminal, and expanded to two days and closer to a thousand people (I think. I’m going off of memory here). It was everything the first one was, but bigger and better. We were firing on all cylinders — the product was doing great, customers loved us, and revenue was strong.
Opticon’s main stage, where we announced Personalization
That early design team also had a magic about it that I haven’t been able to re-create since. When I joined, there was one full time designer, and one contract designer who worked full-time hours. I wasn’t technically on the design team (I started as a frontend engineer), but I spent all my time with the 2 designers.
Then we expanded by hiring a researcher. I suggested this, and the full-time designer got the req opened (I don’t remember there being any push back). In retrospect, it was way too early for a researcher. But somehow we found a great one with a ton of experience from Salesforce. Why she decided to join this rag-tag group of young, inexperienced designers is a mystery to me, but we were all thrilled she did.
The original D-team 4
I remember shortly after we hired her there were a couple of designers we were considering making offers to. She asked (and remember, she came from Salesforce and, thus, was the most experienced member of the team), “How much headcount do we have?” And the full-time design/design manager responded, “We don’t have a fixed headcount. We just hire good people on a rolling basis.” Which is just insane! But at the time I didn’t see anything wrong with it. Looking back, it’s not a smart way to run a business. The company of course grew in lopsided ways and added roles that we didn’t need long term, and had layoffs a couple of years later, but at the time I thought it was incredible.
From there we tried to hire more product designers, but it was really hard. We interviewed a ton of people and a lot weren’t any good, and then the first few we made offers to all declined us. At the time I thought they were crazy, but looking back it’s clear why: we were all super inexperienced and had no idea what we were doing, which is obvious to anyone who’s worked at a more established team.
Early design team lunch
But once we got going, we hired a killer team. We ballooned to 20 product designers, UI engineers, communication designers, and researchers within about 2 years. That early design team had an inexplicable camaraderie and joy and closeness to it. A lot of them came to my wedding.
I’m not sure what made it such a close knit team. Obviously we all got along, but I think more than that we were all young and eager to learn, believed in the mission, and had free reign to try stuff out and fail and learn and try again. There wasn’t much process or oversight or anything. It was a feeling of, let’s just build cool shit together.
Some of us at another designer’s wedding
In August of 2016, we decided we should have an offsite. And not like, a one day team building event. No, we should rent a cabin in Tahoe for a few days. For what purpose? In truth we just thought it would be fun, but we rationalized it by saying we’d build design.optimizely.com (now defunct) to house our design system, brand assets, and info about the team. (Which we did build, and it came out great).
Somehow my boss scraped together enough budget by combining 2 quarters worth of our regular “team bonding” budget, and combined that with some of our education budget and some other funds floating around. We found a cabin that could house all 18 or so of us (I can’t remember exactly how big we were then), and spent 2 or 3 nights building our little sub-site.
The team gathered around the table at our cabin in Tahoe
It was a great success in that we had a great site at the end, and had a ton of fun doing it. We rotated cooking meals for each other. Everyone had different chores assigned. And we had a lot of fun playing ping pong, going to the lake, and gambling in Nevada.
While we saw the value in it, the rest of the company was like, “Why is the design team doing this big offsite?” My boss’s boss, the VP of Product, was upset with my boss that he cobbled together this budget for a “frivolous” offsite.
At the time, we couldn’t have cared less. We enjoyed ourselves, became even closer as a team, and I’m still proud of the site we built to represent ourselves to the world (and in fact, it did become a valuable resource that the whole company used to find product and brand resources. If I could find screenshots I’d include them, but alas I couldn’t find any).
Hack Weeks were a mainstay of Optimizely’s culture during this time. One of the designers decided to make a “UX Bar.” In other words, a physical wooden kiosk we could push around the office to do user testing, help people with design questions, and so on. I immediately joined him to help out. We bought wood, screws, wheels, a flag pole (all on the company’s dime), and constructed a physical bar. We even added rails to hold wine glasses. And painted the top with whiteboard paint so we could draw on it.
Our finished UX bar, built in this weird dead space in the office that was going to be built out as a kitchen but ended up never being used for anything
It actually came out really great. It was at the office for years. I would use it to hold office hours during my tenure there. I can’t recall what happened to it. Between moving from floor to floor it eventually disappeared.
One year, the design team had a Secret Santa gift exchange. We each drew a name out of a hat, got that person a gift, dressed up in pajamas and exchanged our presents in the office. Reliving that now, it was such a goofy thing to do. But we had a ball.
Us dressed in our PJs, exchanging gifts with each other
This was also the era during which we would take a team “holiday photo” and send it to other design teams in the tech community. Why? I dunno, it was just a fun thing to do.
Our team’s holiday photo, right after the PJ gift exchange
So much of what we did in those days feels so random and silly now, but felt completely natural at the time.
The most enduring reason Optimizely will always hold a special place in my heart though, by far, is because I met my wife there. We met at Wine Thursday, which was one of those organic, employee organized cultural staples where people gathered on Thursday evenings to drink wine (which actually started as Wine Wednesday, a much catchier name, but was moved to Thursday once to accommodate someone who had a date that night and then it just stuck on Thursday). We eventually expanded it to include cocktails as well.
It was at one of those that I met my wife, Becca. She had some complaints about — no joke — the documentation of the CSS of our design system, which my team was in charge of. I already had my eye on her, but hadn’t had an opportunity to talk to her (read: I was too shy 😰), so when I heard this I knew I had my in. I chatted her up (yes, about CSS documentation), and we immediately hit it off.
My wife and I, holding a sign of the original Optimizely logo
The next wine Thursday was an “end of the quarter” one (which we somehow convinced leadership to give us money for), so we decided we should dress up and do a wine tasting at CB2 (yes, the furniture store. For some reason they held a joint event with Winc). It was supposed to be a group thing, but only Becca and I dressed up. The fact that I put in that “extra effort” (which was really just wearing a bow tie) won her over 🥰.
Since this wine tasting was at a CB2, there was a large painting of Abraham Lincoln in a space helmet shooting a lazer gun for sale. Since our company theme was rocketships and space, we thought it would look great in the office. One of our entry-level engineers convinced everyone to chip in 20 bucks to buy it. At the next show-and-tell, he got in front of the whole company and drunkenly told everyone how we bought this as a gift to the company. It remained in the office until they closed it earlier this year.
An engagement photo of us under Opti-Abe
A group of us went to Mikeller’s after that to keep drinking. As the night wore on people slowly peeled off. I was hoping it would winnow down to just me and Becca, but alas one of the engineers wasn’t taking the hint and kept hanging around until eventually all 3 of us left. We started officially dating shortly after this. We consider the Opti-abe night our “zero-eth” date.
Optimizely was my first real tech job, which is why the experience is so special to me. We were tech darlings, on track to be a unicorn, and felt like the world was ours for the taking. I learned and grew more than I ever imagined I would. I was able to move from frontend engineering to product design to management to leading the whole product design team. All of which happened because we needed people in those roles, so when I asked to move into them the response was, “Sure, sounds great!” No other interviewing or trial period or anything. Which is just unthinkable to me now.
The conditions that made Optimizely so special are hard to pinpoint. Most of it is the people, of course. We hired really smart, ambitious people who were early in their careers and eager to prove themselves.
We were also well-funded and had a ton of momentum from positive press and hockey-stick revenue. We didn’t have much oversight and had a lot of space to just try out crazy ideas, fail, and try again.
But it’s more than that. There was an ineffable alchemy that created the conditions for the best place I’ve ever worked.
Hero shot for LaunchDarkly’s “global search”
Hero shot for approvals in LaunchDarkly
Optimizely’s “concept car”
Drunken photo of us in Santa Cruz
My wife and I in front of the new Optimizely office (this is from our engagement shoot)
Countdown to the first Opticon
Opticon’s main stage, where we announced Personalization
Some sweet chalk art that greeted attendees
The original D-team 4
Early design team lunch
Some of us at another designer’s wedding
The team gathered around the table at our cabin in Tahoe
Our finished UX bar, built in this weird dead space in the office that was going to be built out as a kitchen but ended up never being used for anything
Us dressed in our PJs, exchanging gifts with each other
Our team’s holiday photo, right after the PJ gift exchange
My wife and I, holding a sign of the original Optimizely logo
An engagement photo of us under Opti-Abe