What I Wish I Knew Twenty Years Ago

A question on design twitter prompted me to create this short list of the things that ultimately helped me navigate a career in tech and design.

1. Understand that the bulk of your work is actually about understanding human behavior and not about any specific tools or deliverables. Direct your energy appropriately. Tools are going to change, human behavior not so much.
2. It’s fine to pay attention to what Design People are saying on the Twitters, but always be suspicious of anyone talking about My Great Method or Tool or Framework that Fixed All the Things. Especially if they are benefiting financially from a specific approach or viewpoint. (You eventually learn in this business that there are people who make their living from doing the work, who occasionally talk about it, and then there is a whole category of people who make their living by talking about the work, while rarely actually doing it. Direct your attention appropriately.)
3. Keep project journals. Use whatever format works for you. Document your expectations, the things you tried that worked, and those that didn’t, your progress, the pivots you had to take and how you felt throughout the process, what you’ll do differently next time.
4. Encourage your team to do regular retros if they aren’t already. This allows you to learn from what your team is learning. If your team isn’t doing this and you don’t have this level of influence, do retro-style research on an individual basis with friendly team members. (The exact format of the retros matters a lot less than the practice of doing them consistently, with one exception: don’t let them devolve into bitch sessions. There’s a time and place for venting but this isn’t it. This is for learning.)
5. Start thinking about what it means to deliver value instead of just thinking in terms of deliverables. This is a huge topic you can explore, and expand your education to professionals outside of design (particularly those who are doing product management well).
6. When you get stuck, reach out to someone else in the field and see if you can hop on a call to talk it through. They don’t have to be more senior than you. Being forced to articulate a challenge to someone else, who understands the type of work we do, will give you clarity.
7. The work is messy. Get used to it. Look for mentors, virtual or IRL, that openly talk about the challenges of the work and share their failures. (This ties to #2 above: be suspicious of professionals who only talk about success and never mention failure. Failure in this industry is a feature, not a bug.)
8. There is no one right way to do this work. Don’t worry about what Current Tech Hero Company is doing. The experiences and feedback of the people who use your products/services and your teammates are your most important benchmarks of success.
9. The number one metric of success is how healthy your team & projects are. Nothing else matters if everyone is miserable. It doesn’t have to be that way. Designers are often the canary in the coal mine when it comes to declining team health. Take care of yourself.