20 insights / 20 years of designing

What do I have to say after working 20 years as a designer?

Wait. Has it really been twenty years since I started designing interfaces & interactions within this field known as “UX” (User Experience)? 😬 This milestone feels both astonishing — time truly flew by while busily cranking away! — and exhausting — mentally cataloging thousands of hours of making wireframes, flows, prototypes. And all those endless, tedious debates with mutually dissatisfying compromises with imperious cross-functional peers… Whew! 😅

Perhaps it’s surprising for some, but I did not expect to find myself in the current position that I’ve been very fortunate and privileged to achieve — a design leader with community presence via articles & talks. I truly had no idea of what was going to happen upon receiving my degree in interaction design at Carnegie Mellon that beautifully warm sunny day in May 2001. I had never worked in “industry” before, so I had no conception of what to expect or how to navigate among the possibilities. Like a young Groot heading out into the world, all I could say was “I am a designer” — but not truly knowing what that really meant. 🤔

A potent piece of advice given to me long ago: Always be learning and connecting! Be both sponge and glue. I took that to heart, always observing, capturing, reflecting, and creating my “playbook” along the way…

My career journey has been highly organic and improvisational — but not for a lack of a career path model. Indeed, my first job was at Oracle, which had a well-developed career path in place, along with a large team of seasoned managers & leaders from places like Apple, Sun, Netscape, Palm — the places then known for HCI, UX, human factors, etc. And certainly, I could have followed that model in a prescriptive manner.

But I don’t really do prescriptions, as my friends & colleagues know 😁 I prefer to invent my own recipes, just like when I cook at home. Being in that mode of continuous discovery & experimental execution. Try it out and see what happens! Rarely choices that are made in your career (or in your kitchen) are irreversible — if reasonably made 😇 And just learn! So you can pass it on to others…

So, I quickly realized that a) I wanted to own my path of pursuing contexts & challenges that pushed my interests and abilities, and b) by doing that I’m expanding my repertoire, shaping my own narrative of personal and professional growth. It’s about ownership and establishing a personal mark, a signature expression of advancement. I wanted to collect a diverse range of experiences, comprised of a mix of “habitats” — scenes of collaboration, leadership, creation, iteration, tackling all kinds of problems, with all kinds of tools and technologies. By learning new things and trying new approaches I satisfied this insatiable curiosity and hunger to keep seeking — What else is out there? What else can I create and solve?

It’s worth noting that what ignited my intrigue for design in the first place — other than making beautiful humanized products (Thank you RISD Summer Program!) — is the tantalizing aspect of addressing competing interests, as captured by Eames’s famous diagram, to arrive at something innovative and beautiful. It just seemed like some impossible challenge! And I can’t resist a challenge 😏

The Eames Design Diagram, aka ‘Statement of the Eames Design Process’ as displayed in the 1969 Exhibition Qu’est-ce Que Le Design? (What is Design?) at the Musée des Arts Décoratifs in Paris.

I love how the overlaps are always fluctuating yet never quite the same for any two projects, because of… well, people! And their motives, politics, values, goals, and also constraints. And yet, as the designer you must arrive at some sort of balance that advances a set of principles or a vision for an improved state. And it’s really for at least that particular moment in time (aka, that release cycle!).

I’ve found that conviction & compromise dance along to an invisible tune; composing that tune is the difficulty — and opportunity!

This somewhat correlates with Clement Mok’s early definition of design in the 90s/2000s: “Design is the art of causing change in accordance with taste and intent.” 🧐 Every job, project, or role I’ve had was an expression of that in some way — and likely yours too! Sometimes successful, but often not so much. My own self-professed impatience and imprudence at times, hastened by a fierce ambition and desire to achieve what felt so obvious & necessary, can get in the way, causing jumps to other jobs, sometimes a bit sooner than deemed practical. Sigh.

We may contain multitudes; yet we are flawed, in our own ways. Therein lies the fun of working with people!

Thus, at every company I worked at — no matter the type of engagement (contractor, or full-time lead) or brevity of timeframe (my shortest was…3 months? 😋)— I was constantly observing and reflecting upon the organization, its culture, its politics, and the leadership models. 🤔 How is the “art of causing change” really happening, or not, in those places? What can I learn and apply? What should I not do? A bit like a self-guided role-playing game you are continually picking up such golden nuggets here and there, saving them for a future moment, for a just use.

It’s often said that “the grass is always greener”. But be careful, there are many shades of green, and what looks brown to you might be a different shade of green to others.

So I’d like to share a set of 20 insights and lessons gained from the past 20 years. Hope you enjoy and find some benefit for your own career path! 😌

  1. A designer’s power comes from wielding craft + influence, together.

2. Avoid yes/no questions with Engineers; instead, use conversations to drive the next steps, and identify what’s possible (or what’s needed).

3. Always question your assumptions and dependencies. This can help mitigate costly or painful misunderstandings early on!

4. Assume good intent, but flawed approaches. We’re all people…

5. The best team-building activity is building (and shipping) a product together.

6. 90% of design work is throwaway — accept it! It’s necessary to help you understand the real problem, and foster dialogues you need to have with others.

7. Emotion is just as important as “data”. Emotion IS data. Use it well!

8. Designing is a political act. You’re asking to change things (visuals, behaviors, services, etc.) which some may have a very strong personal interest (or investment) in protecting. Build up your allies!

9. You must protect the fragility of your ideas. Everyone wants to slay them, not from malice but fear or misunderstanding. (or “we gotta ship now” vibe!)

10. Relationships > prototypes. Yes, “show, don’t tell” still matters. But if you haven’t done the necessary groundwork of getting key stakeholders bought in early, explained how it connects to their agendas, and enables their success, your prototype spectacle will fail.

11. It’s not about failing fast, it’s about learning quickly and developing resiliency for the long haul.

12. Imposter syndrome is very real at every level in an ongoing career journey. But trusting in your demonstrated abilities and expertise, with your colleagues’ support, will keep you afloat. Persist!

13. UX (Design) and Agile are fundamentally at odds with each other; trying to make them fit into each other isn’t the point. Perhaps it’s more of a “productive coexistence”? [still trying to figure this one out, I admit…]

14. Design + Eng + Product: it’s less of a “three-legged stool”, but more of a “system of checks and balances” engaged in constant, earnest debate guided by a set of core principles. (Sound familiar? It’s like government!)

15. When it’s time to walk away, be gracious. Always. It’s a very small field and — even after a dozen-plus year — former colleagues will reach out to you for a remarkable opportunity that you never imagined.

16. You’re always evangelizing (educating others) about design, research, content, strategy, etc. to some degree, no matter your role or job. Because that is a part of your job no matter what!

17. When meeting a new stakeholder (product manager, engineering lead, etc.) I’ve found that asking “How can I help you be successful?” is an effective charm tactic that provides useful information. Be genuine, not sleazy!

18. When interviewing for a job, ask about the organizational maturity of UX and the levels of investment today and beyond. How does your role shape that, in their view? (Also ask that of PM and Eng, for their view!)

19. You can’t “how might we” (HMW) fundamental problems of culture, value, purpose, vision. Those require deep interventions with group therapy sessions! (facilitated workshops, etc.)

20. Remember: there is no perfect design. It’s all a game of balancing imperfections — and discovering & learning along the way while teaching others about “the way”. 🤓

Bonus: Designing UX isn’t for everyone. It’s not the game everyone should play. And not everyone will give it the proper respect, or investment, or support needed. That’s OK. Just keep moving forward or onward. 😎🌅

I want to especially thank all the mentors, coaches, and guides along the way — some of them intentionally assigned, others a bit more implicitly discovered — who provided useful nuggets of wisdom, or at least thoughtful perspectives to counter my own views! Seek them out. They’re wonderful resources, and sometimes, become very good friends, too. 🙏🏽 😌



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Uday Gajendar

Design catalyst / leader / speaker / teacher. Always striving to bring beauty & soul to digital experiences.