Embracing the Unknown

My search for and embracement of new challenges and learning opportunities as a designer


Two years ago if anyone had suggested to me that I would be quitting my job at Google and returning to school, I would have written them off as crazy. As far as I was concerned Google was the greatest place to work in the world. There were and still are a great number of people that would agree with that statement.

So it was to the great surprise of my colleagues and friends when I decided to resign my position at Google and pursue a masters degree in Human Computer Interaction as a full-time student at the University of Washington. Hell, it even surprised me a bit that I actually took a leap of faith and returned to school rather than continuing forward with the on the job education I had been receiving.

Although today I am happily employed in a role I love at a company that I hold an immense amount of respect for, the path that led me to my position as a Product Designer at Nextdoor was by no means certain nor was it immediately clear. Fortunately, the Designer Fund’s Bridge program provided me with an incredible amount of guidance and support that made my transition into working for a top startup an easy one.

Even today despite my past experiences, I in no way consider my design education close to completion. I do however consider myself very lucky to have been afforded the opportunity to study design academically as an undergraduate and graduate student and professionally at companies with headcounts as large as 50,000 and as small as 100.

If I've learned nothing else in my journey as a designer, I can say with some confidence that no matter where you are or what you are doing, there will always be opportunities to continue learning. While my own experiences may not be applicable to everyone, I'd like to share the strategies I've employed over the past several years toward the end of improving my own design competencies.


“Prepare for the unknown by studying how others in the past have overcome the unforeseeable and the unpredictable.”
- George S. Patton

Some of the learning strategies I've found to work especially well are:

1. Pursue continuing education

I've always considered a formalized education to be the foundation upon which any fledgling designer can expand and refine their skill set. While at Google I took full advantage of the $12,000 annual education allowance offered to employees by taking part-time computer science and visual design classes at the College of San Mateo and the San Francisco Academy of Art University respectively. I enjoyed being a part-time student enough that I was eventually motivated to return to school and pursue a master’s degree in Human Computer Interaction.

While sitting through lectures alone didn't make me the designer I am today, school did provide me with a framework for understanding and deconstructing design problems. While that’s not to say you can't learn on the job the things you'd otherwise learn in the classroom, being in school full-time allowed me to pursue a means of learning in ways I had struggled with while trying to juggle night classes with my day job.

2. Seek out online resources

If enrolling in full or part-time courses isn't an option, MOOCs are a great alternative. I'm currently working my way through Udacity’s fantastic Android Development course and I've previously relied on the faster-paced Team Treehouse micro design lessons to brush up on technical and design concepts. Udacity is free and Team Treehouse is a bargain at only $25 a month.

3. Always be reading

Using recommendations I was able to elicit from design professionals, professors, and of course from Quora, I assembled a reading list of books touching upon visual design, user experience, and research that I am constantly making small dents in. I bought the majority of the titles on that list used and fairly cheap from Amazon and eBay. Whenever I'm traveling, I make sure to have at least one new book on design that I'm reading.

I also subscribe to several personal blogs of designers that I hold a great deal of respect for. Reading design blogs is a great way to pick up on lessons you're not likely to find reading a book.

If you don't have the financial means to purchase the books from the list I shared above and you happen to be living in San Francisco, email me and I'd be more than happy to loan you one.

4. Expand your network

The greatest resource available to any designer is the advice and insights offered to them by their colleagues and peers. I consider myself extremely lucky to have found mentors first at Google, later at UW, and now at Nextdoor who care about me both professionally and as an individual.

As a member of the Designer Fund’s Bridge program, my network of design professionals and friends has grown in ways that I never would have imagined possible. The peers I worked with during Bridge III are among the smartest and most sincere I have ever known and I in no way doubt that I am a far better designer today than I was a few months ago for having worked alongside them. Being able to learn best practices from industry veterans each week in addition to receiving critiques on projects I was working on from my peers at other top startups proved absolutely invaluable in helping me settle into my new role at Nextdoor.

If you lack access to more formal design networks, seek out ways to create your own. Reach out to designers you follow on twitter or other social media and let them know what you think of projects they are working on or posts they are sharing. If you happen to see issues, design or otherwise, negatively impacting products you enjoy using, figure out who might have been the responsible designer and let them know you tripped over something. Do this in a sincere and respectful way and I guarantee you they will be appreciative you took the time to let them know.

5. Look for the harder problems

One of the best ways to get better at something is to place yourself in situations where success will never come easy. Working on difficult problems that matter has always been one of my biggest drivers as a designer and in general.

In my current role at Nextdoor I'm working with an incredible team that’s trying build stronger and safer neighborhoods by bringing neighbors together through meaningful connections. It’s a hugely difficult problem and one that’s important to solve. It also means that I’m eager to arrive to work each day and don’t mind staying late when somethings needs getting done.

I've personally always found situations where I'm struggling to swim upstream far more rewarding than those where I've simply been treading water.


While the five methods I mentioned above worked well for me, they probably aren't for everyone. Figuring out what works best for you, surrounding yourself with a strong support network, and having the motivation to see your goals through are what really matter and what will ultimately allow you to succeed in your own pursuits.