Milestone Reflections and Unsolicited Advice for Designers
Over the holiday break, I took a little time to reflect on my journey as an individual contributor (IC) designer in leadership. The career path for IC designers is something near and dear to my heart. Now that I’m closer to retirement than I am to starting out I wanted to share some thoughts and reflections about what it’s like to be an IC in leadership and some tips and ideas for what’s kept me sane and allowed me to keep at it for so long. I’ve collected many great moments, and while my path has not been typical, along the way I think I’ve learned a lot.
Isn’t it our job as humans to be collecting great moments? Photo taken in Reykjavik, Nov, 2024. Mural by Herakut
Ten years ago today I started a new job working for Atlassian.
I was one of two designers working on Bitbucket. This quickly became one designer—me—and then our PMs left the company. Just me and a bunch of excellent engineers for a while. I miss those days. For most of my first couple of years, I was one of 50-ish designers in a company that was only just getting its mind around how to work with design. We grew quickly; it was a wild and rewarding ride. In those ten years, a lot has changed. I’ve grown, the company has grown, and we’ve had a few ups and a few downs.
But Atlassian—the people, the products, our customers—has been the best place I’ve ever worked, I’m eternally grateful for the opportunity and I’m looking forward to many more great years there. Like many reading this, I’m sad and concerned with the direction many tech companies are heading, and while Atlassian isn’t perfect by any means, and some of those concerns apply there as well, I’m mostly proud of the work we’re doing and the way in which we’re doing it.
What follows is a slightly altered reflection I posted on our internal Confluence, primarily for other Atlassian designers. Still, I figured I’d share these thoughts and the unsolicited advice here, too.
Over the holiday break, I took a little time to reflect on my journey as an individual contributor (IC) designer in leadership. The career path for IC designers is something near and dear to my heart. Now that I’m closer to retirement than I am to starting out I wanted to share some thoughts and reflections about what it’s like to be an IC in leadership and some tips and ideas for what’s kept me sane and allowed me to keep at it for so long. I’ve collected many great moments, and while my path has not been typical, along the way I think I’ve learned a lot.
As with most things, your mileage will vary, and you might even disagree with some of these, but I hope they get you thinking.
Ask a lot of questions.
That’s it—that’s my number one piece of advice. It’s a wonderful opportunity not to know something. I like to think my primary responsibility as a designer is to ask questions and consider the answers.
Actively look for problems and opportunities.
Stick your fingers into other people’s pies; just be friendly and helpful about it. Ask to help, ask questions, and dig into the work to find ways to improve it and yourself.
“Share early; share often” is fantastic advice. Do that.
Be proactive and seek feedback whenever you can. Don’t be afraid to show messy work and be sure to include outside perspectives if you can.
Soft skills are more important than technical skills most of the time, and they become more important the longer your career goes.
It’s particularly important to become a good, clear communicator and know how to manage your time.
Get comfortable with ambiguity and being able to shift altitude.
This means learning about product, business, and strategy and being close with your leadership teams while at the same time getting and staying as close to the work as possible. As you move up and your responsibility and influence increase, it’ll be more challenging to stay close to the work, for good reason, but do what you can to remain as close to the work as possible.
Specialist vs generalist? Why not both?
(Yes, I realize that doesn’t make sense. But sometimes things just don’t add up.)
Either can work and often, your work will push you toward one or the other. I’m more of a generalist, but I have the mindset that I can specialize when needed. I like to say my design specialization is design.
If you identify as an introvert like me, you might want to practice being extroverted.
Design is a team sport most of the time, so practice playing as and with a team. I fully believe you can get more comfortable with people if you’re introverted, but it takes practice.
Practice all of the crafts. Color outside of the lines and be flexible.
Become part engineer, lean into product management or research. Exposing yourself to many other skills and work is a good idea, even if you are a specialist. Practice that beginner’s mindset throughout your career.
Learn how to facilitate and bring others into the design process.
Look for opportunities to run workshops or help with design sprints or strategy sessions. Volunteer for these things if they come up; don’t wait to be asked.
Work on your rationale and understand why you’re doing things. Also, examine the rationale of others.
I often think of design as similar to legal practice. You need to research and investigate, have hypotheses to test and learn from, and build and present a case for your ideas and solutions.
Work on your writing.
Written communication will always be a part of what you do. Don’t let AI do too much. People can often tell, even if they don’t say anything and too much reliance on AI prevents some of the personal benefits you get from writing. (AI can be helpful; just don’t let it do all the thinking and phrasing for you.)
Find a way of working that works for you, but don’t be afraid to keep trying other things.
It’s good to mix it up. I find my perfect process is the one that’s working for me at the moment. Sometimes, I write to think; sometimes, I sketch; sometimes, I prototype; sometimes, I explore and make a big mess; sometimes, I’m analytical and dive into research and data. Some people have very solid processes they go to, but even then, in a collaborative environment, you need to be flexible. There is no one right way to do things.
An iterative process is usually best when shipping a great product to customers.
Build relationships with PM and ENG so you can move fast, get better at prototyping, and do enough research so your team can test to learn and get the next iteration over the line. Lean into working this way when you can.
Develop a sense of quality but don’t let unknowns and a quest for perfection slow you down too much.
A Good, better, best approach (something we embrace at Atlassian) is an excellent framework for this. We should build at a level of quality we can be proud of and not rely on our customers to tell us where that bar is.
Practice and growth never stop, but they do get trickier as responsibilities pile up.
It’s terrific to have side projects and hobbies for those times when you don’t have time or energy for “on-the-job” growth. This is doubly important as you naturally move from implementation to influence. Keeping sharp will not only benefit the work, it’ll be more fun.
Practice giving direction and leveraging the work of others.
Even if you stay an IC, you’ll do less and less “hands” work as you move into leadership, and it can be a tricky transition. Not always being the one doing the work is more difficult then you’re probably thinking. I know it was/is very difficult for me. But as many manager-types will tell you, there is a lot of value, and a lot of reward, in facilitating and supporting the work of others. The shift is challenging, but you’ll likely to find that leaning into it will free you up to do more overall, and increase your impact.
Don’t fear mistakes.
Failure isn’t fun. I’ve never been a fan of glorified failure, and it’s not the only way to learn. In my experience, what's essential is being resilient and willing to experiment and take risks. So don’t see out mistakes, but don’t let fear of them hold you back.
Stay humble, helpful, and easy to work with, but protect your energy.
Don’t shy away from pushing back when you need to, and ask questions when things don’t seem right; sometimes, things are not correct, and you might be the only one who sees it. We’re all in this together, so don’t be afraid to be the squeaky wheel. Having said that…
Sometimes, it’s best to dive into the work and see what happens.
We’re not always going to know the best way to do things, and sometimes the best way to move forward is to jump in—together, as a team—and figure it out.
Hello 2025: On Resonance
I’ve had a bit more free time the last couple of weeks than I usually do, and in that time, I’ve done a fair amount of thinking, planning, and scheming for the new year. This is something I’ve done almost every year throughout my adult life. I look forward to it, in a way I think I’m kind of addicted to it. There is something about the act of planning self-improvement that makes me feel good and productive. I’m also one of those who is able, most years anyway, to keep my plans and schemes going through the year.
A scenic sunrise taken somewhere in my neighborhood.
I’ve had a bit more free time the last couple of weeks than I usually do, and in that time, I’ve done a fair amount of thinking, planning, and scheming for the new year. This is something I’ve done almost every year throughout my adult life. I look forward to it, in a way I think I’m kind of addicted to it. There is something about the act of planning self-improvement that makes me feel good and productive. I’m also one of those who is able, most years anyway, to keep my plans and schemes going through the year.
So, yeah, for the most part, I feel good about it.
But in recent years I’ve realized that what I’m feeling is more around the progress towards the goal. It’s about ticking off the days, the tasks, the objectives, the measurements and counts, and the impact. And I’ve come to question whether or not I’m interested and feeling good about the right things.
I’m not sure I know the answer yet. But what I do think I’ve realized is that I’m putting more effort into the systems I’m creating and the order and control those systems seem to provide me than I am into the things that I want to get out of them.
Don’t get me wrong; there is a huge benefit in these systems and in the structure they provide. But as they relate to my life, I think they are more on the “means” side of things than the “ends” side. And I’m hoping to shift that balance. To what? I’m not entirely sure, but the word I think I will go with to describe what I’m looking for is “resonance.”
I like the idea of a theme word to help guide me through the year, especially when I’m feeling a little lost, which happens. So this year, I’m going with resonance as my theme word.
I didn’t come up with it on my own. As life sometimes does, it provides clues and waypoints to guide yourself, and this one I found in the intro to a book I’m working through: Meditations for Mortals by Oliver Burkeman. This book is about embracing our imperfections in ourselves and our lives. And letting go of the drive to be perfectly productive. It’s about learning that life as an imperfect human being isn’t something that needs to be solved. I read this intro, and it instantly resonated (heh) with me. This is double-bonus cool because a section of the intro was about resonance, specifically, and how we might find it.
Burkeman writes that when we lack resonance, life feels empty and meaningless. He describes it cleverly as a contrast to how we should feel when we’re “productive” and doing all the “right things” but still feeling unsatisfied. We’re doing things, but they’re not filling our cup.
Reading this made me feel instantly sad, as it spoke to something I think has been lurking at the edge of my mind for many years. I feel this way sometimes, not all the time, but enough. I’ll not bore you—or myself—recounting all the ways why that is; I’ll just say that it resonated with me.
But it also excited me in a few ways. Understanding, even just a little, this feeling, this lack of resonance, triggered a strong desire to find out why and how I could change things, at least try something new. I realize it might be a trap. It could be just another self-improvement carrot to dangle in front of my gob as I run through the motions, resulting in feeling the same way on the other side. But maybe it’s not. Maybe there is something to it. I’m motivated to find out.
It was nice to see Burkeman speak to that very feeling and admit that he, like me, sometimes struggles with productivity addiction and a desire to design and implement systems to help bring life into control. Yep, that’s what I do all the time. I’m a huge fan of systems.
Like most new years, I see this new year as a reset. I’m not going to bin the systems I’ve got in place, but I’m also not going to try to improve them. They’re there, they work. I don’t need to justify their existence or my ability to be even more productive by putting more work into them.
Instead, I will take a step back and focus on looking for resonance in the things I do. I’ve got things I want to do, but plans and goals are a bit looser than usual. I’ll follow the energy wherever it leads me, trying not to impose too much order and control over where life goes, working on doing one thing (work, play, exercise, reading, etc.) that feels like the best next thing to do.
We’ll see how it goes. I’m excited to return to work and my job benefits from a fair amount of structure. At the same time, I’m often told that I try and do too much, so maybe a slight pullback will be good.
Goodbye 2024
I didn’t do any blogging during 2024. This was mainly because I was head-down-focused on the first draft of my first novel. I made some good progress on that, too. Not so much that I’m going to let anyone read it, but enough that I’m very proud of my work and the things I’ve learned along the way.
I didn’t do any blogging during 2024. This was mainly because I was head-down-focused on the first draft of my first novel. I made some good progress on that, too. Not so much that I’m going to let anyone read it, but enough that I’m very proud of my work and the things I’ve learned along the way.
2024 was, in most ways, a good year. I traveled a lot—spent some weeks in the spring in Germany and Switzerland, which was beyond incredible, and had a few trips along the way to San Francisco—my old home—and a trip to Iceland for Iceland Airwaves. That was fantastic. SXSW was also great this year and Kerri and I had a lot of fun at Bottlerock Festival in Napa.
Lots of good music this year. If you’re into long, eclectic Spotify playlists, here’s what I have for you:
I also went to Sydney—my favorite city—a whopping four times, which was great. Most of that time down under was for work, but I enjoy connecting with my co-workers in person, and I feel so much better about work in general when I’m face-to-face with people.
I don’t have much to say at the moment. I’m feeling fairly exhausted even though I’ve had a lovely week or so off to celebrate the holidays. 2024 has been great, but it’s taken a lot out of me. I don’t think I’d go as far as to say I’m feeling the dreaded burnout, but this time of year is usually a nice pick-me-up, and in years past, I’ve come into the new year feeling energized. Not so this go ‘round.
Still, I’ve had enough energy to do some blog tinkering and get this thing up and running again. I’m not 100% sure what I plan to do with it, but I need some alternative to social media, which completely drains me to engage with, let alone keep up with, in any tangible way.
More to come, but for now, here are some of the many photos from this year.
Kagen The Damned by Jonathan Maberry
This book was bonkers in many ways, lacking in subtlety and slipping some sneaky/interesting ideas between blood, gore, and horror. The tone falls between a hacker flick and an epic fantasy novel, which I didn't expect and liked more than I would have guessed. Most of the over-the-top violence here serves a purpose, but sometimes I felt it was a bit much.
⭐⭐⭐⭐
File under: Cosmic Horror meets Epic Fantasy, with a side of a lot of other stuff
Wizard-level reading challenge: A book written by a new-to-you author
This book was bonkers in many ways, lacking in subtlety and slipping some sneaky/interesting ideas between blood, gore, and horror. The tone falls between a hacker flick and an epic fantasy novel, which I didn't expect and liked more than I would have guessed. Most of the over-the-top violence here serves a purpose, but sometimes I felt it was a bit much.
Jonathan Maberry is a “new-to-me” author (which marks one off my list), and—I didn’t know this going in—he’s most well-known for horror, which explains a lot.
Overall, though, I liked it. But I also like grimdark, cosmic horror, and bonkers-kitchen-sink-type novels, so this was right in my wheelhouse. YMMV, for sure, and I expect some people to hate this one.
Oh, an aside: I would have loved a better map. :)
Images of Heaven by Peter Godwin
Throwing it back to a classing 80s dance cut.
Hey Journal, it’s your lucky day. Yep, that’s right—it’s Throwback Thursday! I don’t do this every Thursday, but when I do, you know you’re in for a treat. This time, it’s a simple share of a particular song that I’ve loved for many a year. It was recently reminded to me, as the melody in “Faded State” by Home Front is a bit similar.
“Images of Heaven” by Peter Godwin. Released in 1982 on the EP Dance Emotions, this was a frequent dance-floor banger, popular amongst wavers and goths alike as it had both haunting melodies and an excellent, simple, and danceable beat. “Torch Songs,” also from Dance Emotions, was also good.
James Jean
A few words about my favorite artist.
James Jean - Pinocchio Move Poster
I think James Jean might be my favorite artist. I saw his art first, I think, on the cover of Fables, the magnificent comic series by Bill Willingham. James Jean is a Taiwanese-American artist who works across mediums and, I think it’s safe to say, is prolific. His Instagram is something to behold; the volume, speed, and quality on display are inspiring.
His style is so unique and his imagination so wild, it’s…well, it’s hard to imagine a single conduit for so much. I’m in awe of his talent and find myself impressed over and over with his latest and greatest. My favorite work of his might is one of the most simple: Maze from 2008.
Lifetracking with Notion
For a few years now, I’ve been tracking goals, aspirations, projects, and a lot of other things in a fairly complex Notion-based setup.
For a few years now, I’ve been tracking goals, aspirations, projects, and a lot of other things in a fairly complex Notion-based setup.
Over the years, I’ve modified, tweaked, and designed my way to an easy-to-use and robust system that works well. It’s flexible and useful and requires limited input, except where I’ve designed it to do more heavy lifting.
I used to track things day-by-day, but after a couple of years doing that, I decided the value was not worth the effort. Now I’ve got a weekly/monthly/quarterly/yearly set up that covers mostly the highlights and essential markers, leaving the minutiae to automated things. This has freed up a fair amount of time and brainpower to spend on other things while still allowing for a regular cadence of learning from reflection, which I think is highly valuable.
While it’s a low priority, I would like to share the system. Either in template form or via write-ups. It took quite awhile to build, both initially and as it was refined over time, and I think it could be of great use to others. The seeds of my system were built from scratch, following guides and advice provided by August Bradley, Marie Poulin, and others, and over the years, I’ve changed it a lot. If anyone stumbles across this journal and wants to learn more, I highly recommend checking those two out. In the mean-time, here’s a shot of what it looks like. The front door, so-to-speak. I’ve got one of my projects—my novel work—exploded. That’s another template I’d like to share at some point. It’s based off of something I found via Reddit a while back, but I’ve heavily modified it and will continue to do so.
My Notion set up
Robert Gould
Appreciating the work of fantasy artist Robert Gould.
Elric of Melniboné by Robert Gould
One of the things I love the most about many of the books I read as a youth is the covers. I’m still a sucker for a great cover, but something about the artwork and design of books from the 1970s and 1980s sticks with me. Among my favorites, one artist stands out, and, in many ways, I think shaped and inspired my interest in both art and design. That artist is Robert Gould.
Sadly, I couldn't find a lot of info on him. I did, however, find a lot of his work, so much so that I got a little lost looking for info about him. I’m a reasonably talented internet sleuth, but this one has me stumped. And it’s odd, right? His art is so fucking good, and there is a lot of it out there. He did a lot of covers back in the 80s, and I can find all sorts of ephemera from him, but not a lot about who him. I’m alright with that; I’ll chalk it up as a mystery. Having said that, I’m not done, I now have a goal to own some of his work, and I think I might need to put considerable effort into that.
Off to Canada! And a small reflection.
I’m traveling to Canada today to go snowboarding up in Whistler for a much-needed break.
Hey Journal. I’m traveling to Canada today to go snowboarding up in Whistler for a much-needed break. I think I’ll still try and keep up this daily practice, but if I don’t, I don’t, and I’m going to be alright with that. I need the break and could use some time and space just to let my mind be free and enjoy life, so I make no promises.
Life has seemed especially difficult lately; things seem to have more friction, and it’s been harder and harder since Covid started—to find flow and joy. Work is more challenging than ever, and celebrating wins has not been easy. It turns out that working from home, while it does have its perks, also has many problems. Mostly I miss people, but also, it’s just been higher and higher stress and less certainty. The world seems to shift daily, both in my own life and in the life of those around me. I’ve been working my entire life to achieve stability, and right when I thought I’d got there, everything started to change. Though I’ve done all the right things and set myself up for success, I’m living in a limbo state with a lot of uncertainty. Thankfully, my efforts have placed me on solid footing to deal with that uncertainty, but, damn, I was looking for life to chill a bit. So I’m hoping, for the next week anyway, I can leave my worries behind, shred the mountain, and enjoy some hard-earned rest and relaxation. And, yeah, maybe take some good photos, work on some personal projects, and use that free time and space to move the needle on some things that matter more to me than to someone else.
When The Tiger Came Down The Mountain by Nghi Vo
Another short tale within a tale from Nigh Vo.
⭐⭐⭐⭐
File under: Fantasy
Wizard-level reading challenge: A book with dual timelines
“When you love a thing too much, it is a special kind of pain to show it to others and see that it is lacking.” Here is one of many beautiful lines of prose found within this short, entertaining tale. In the follow-up to The Empress of Salt and Fortune, we find the intrepid cleric Chih telling stories again. Or, rather, swapping tales. This time with a band of ferocious tigers.
I don’t want to say much more other than to share that I liked this quite a bit, and I’m excited to read the next one.