This year I’ve spent a lot of time thinking about how I work. I think the tendency for people is to do this when they come into one of a few different situations, or multiple. But more on that later. I’ve been thinking about how I work because I want to do better work quicker with less headache. That’s a lot of problems to solve and you could imagine saying, “slow down, take that one at a time!” But that’s the premise of the challenge, right? Find tools or strategies or ways to achieve all these improvements together, intuitively. I spent the first half of the year thinking about different strategies that make sense to my way of working, then spent the second half of the year searching through different tools to enable these goals. I’ll talk about both in turn, but want to discuss what I learned from a meta sense during this process.
Strategies for Work
Here I’ll list out the strategies I’ve had success with over the past year. A lot of these are specific to how I think about problems, and I wouldn’t prescribe this as a one-size-fits-all toolkit for everyone. But they could help you next time you feel stuck.
Asking questions until you can’t help but understand something
This is my favorite method to get involved in product strategy and get opinionated about my design when the project is in a super ambiguous state. The process looks like taking the problem being solved, and writing out all my questions about that problem, trying to be exhaustive. I don’t prescribe an order or hierarchy or importance to these questions, but I make sure to get them all down. From there, I go one by one, taking each question in isolation, and I make my best guess forming an opinion or hunch about what the answer might be. I’ll end up revealing other questions and issues that might get between me and creating solutions for the problem at hand—which is great! Revealing these second-order questions is valuable, I’ve been able to do rounds of self-feedback by being honest with myself if my solutions or hunches don’t make sense. This tool is amazing for helping get all my stakeholders aligned—if our mental models are off by degrees or off by a lot, we’ll figure that out quickly once they start going through my hunches. It’d be strange to think that any of these hunches will hold up when building product, but early stances others can react to has been hugely valuable for getting everyone together early and going wide in our thought process.
Going deep on wireframes
This isn’t a new concept at all, but I’ve been using wireframes as sacrificial lambs to conversations more and more lately. Giving others something visual to point to can shape how people think about their problems quickly and inform my own design work by getting specific feedback early and often. Waiting until something has entered mid-fidelity to get it in the hands of leads is a death knell to progress when building product at my company. I’ve been training leads that they can engage at lower and lower levels of fidelity over the course of this year, and it’s been incredibly helpful in getting to meaningful discussions about product at a fast cadence.
Designing from ideal first
There were times in the past where I would immediately start design work with constraints in mind. Whether those were time, technical, or feasibility constraints, they loomed over explorations for early projects in my mind. I thought I was being crafty—skipping a step, designing something I knew my engineering teams could build quickly and achieve what we needed. I was selling the product short—I wasn’t able to expand my mind to solutions that would require an army to build, or more time than I had to design the high fidelity version of, but those were the designs I needed to see, needed to show my stakeholders to set vision. These days, I start from my ideal, from an opinionated place that lands the concept in the best way possible from my skills. As you improve your craft, the ideal comes faster, the clean-up takes less time, and you have time to set the vision and have a goal in mind. Even if creating that ideal is a gargantuan task, I could at least point to it with any constrained designs I do from that point on. Those constrained designs end up better for it, every time.
New Views
This one is interesting to me. I’ve recently been tinkering with new tools and hobbies almost weekly. I’m writing this on a writing app I started using two days ago, to see how I work when I use it. I’m going to write this list to be tool-agnostic, I think it’s better to find tools that suit your own taste, rather than relying on a recommendation from me. I wonder if it’s my curiosity about what other people are building, or me exploring how I can play around with my own work stream to feel better about my work and achieve that lofty goal I set out for at the start of the year. Either way, here are a few of the tools I’ve been using to help me do what I consider to be better work.
A film camera, like a Nikon FM3A
This has been one of the biggest things that changed my view on the world in the past decade. I’ve always had a camera of some kind, a digital micro-4/3s camera was the one before this. But then I got the inclination to dive into the world of film this year, and it’s changed the way I view the world around me and the work I do on any project, whether at work or not. I started shooting much more, and more intentionally. Each shot costs me about a dollar on 35mm film, making it count matters. In the same way, I’m trying to be more intentional in a lot of different aspects of how I’m spending my time. It’s been super gratifying to see myself become happier, healthier, and feel more balanced through being more intentional, even if it sometimes feels like I’m trying too hard.
A new design tool, like Play
Design tools are awesome, and as a designer it feels meta to look at a tool created for someone like me by someone like me. Design choices made here and there—you can tell what is in service of retaining designers, what’s in service of growing to new ones. This new tool is built with a lot of love baked in. It’s the first tool I’ve used to successfully create an intuitive mobile app designer on mobile. You can design a mobile app straight from your mobile phone. And do it well. This is not an easy thing to achieve, and to see that has inspired me to think about the intersection of novelty and intuition. How can you create a brand new experience that changes the way people think about all their other experiences, while feeling familiar?
A new writing tool, like iA Writer
Who needs anything other than Google Docs? That’s what I asked myself when contemplating the thought of paying for a writing tool in 2023. But curiosity got the better of me. I’ve been thinking a lot about content ownership of information and artifacts—whole companies have started with a user-first ideology around content ownership. I’m using one of those writing tools right now. It exports into .txt, and it looks great. It’s a focus-oriented tool, to reduce clutter and cut through to getting pen to paper. I’ve been able to write more focused, better crafted documents using this tool than I have in three years. I wish that were hyperbole. Now, am I writing more because I have sunk cost paying for a writing tool? Maybe. But I find it to be more engaging and enjoyable, much like the film camera I described above when compared to a digital one. The tool makes me want to write more, and aspire to be a better writer. I could’ve achieved the same end by sitting down to Google Docs, but... who wants to do that?
A photo and link aggregator, like mymind
I want to believe that we’ll see a lot more of these in the near future, leveraging all the new AI tech coming out right now. The promise of these tools is a brain dump—a concept that has existed since long before the first computer, but has been getting closer and closer to its platonic ideal over the last few years. Place on object into an endless bag along with hundreds, thousands of other objects. Months later, when you need that exact object and objects like it, you reach your hand in and immediately retrieve it. That is the promise of these tools, and I’d like to believe it will enable better work, with more focus and clarity in time. It’s likely to kill any sense of information retention when used in isolation, but if you take the time to form opinions about each thing you place in, you’ll develop a strong semantic web along with any artificial web this tool layers over your artifacts.
A niche social network, like Posts
I’m learning a lot about how to put myself out into The Public more, both as a content creator and engager. It’s been an exploration in learning what I feel like sharing, finding content that both feels enjoyable and relatable, while expanding my mind in a fun way. Sounds crazy to say that finding a small community of internet strangers has inspired me to do better work, but it has. The community has taught me how to develop stories around what I share and talk about. This could take the form of friends, a community in your workplace, or a group of strangers you stumble upon online. But learning that your opinions are valuable and valid can do nothing but benefit you as you go about your life.
Wrapping up
I can’t say what led me down this path to find new ways to work and think, but it’s been super enjoyable. I’ve been able to be authentic with myself and give myself the grace to explore things that interest me, even if they’re stereotypical or nerdy or off the beaten path. It’s been a good year.