Stepping Stones — Designing your Career with Intention

“How did you get to where you are in your career?”

I hear this question a lot. Answer: Setting reasonable, actionable goals and giving myself time to achieve them.

My career has been a mix of serendipity and intentionally designing my career by identifying milestones and goals.

Back in 2014, when I was looking for my next job, I took an extended time off to figure out what I wanted to do next. Working part-time as a consultant gave me the space I needed. I set a few intentional goals during this exploration time. Consulting part-time gave me time for lunch and coffee dates with friends and former colleagues, more exercise, leisure reading, and lots of quality time with my 4 year old twins and husband.

My 2014 Job Expectations:

• Product that improves people’s lives at a large scale.
• Bottoms-up culture — innovations come from everyone.
• Diversity and inclusion are valued. Including a broad range of ages and backgrounds, not just gender and ethnicity.
• Healthy workplace, respect for employees. No jerks.
• CEO and executive leadership who value product design and research.
• Inspiring design leadership whom I can learn from.
• Talented designers, developers and product owners.
• My role should include coaching and training the next generation of designers and shipping quality products at scale.
• Reasonable commute that includes walking and public transit.
• Total compensation provides for my current lifestyle and desire to save for kids’ college education.
• Stepping stone to VP of Design — stretch goal to get there before 2020.

This list helped me prioritize which companies I wanted to work for next. I landed at LinkedIn in the Fall of 2014, leading the design teams in the newly opened SF office. Most of the list above was achieved at LinkedIn and to my delight, it was an amazing and transformational 3.5 years for me personally.

24 Years of Stepping Stone Goals

So what about the other goals over my 23 year career? Here are the various parameters I set for myself that will hopefully get you thinking about how to define your stepping stone goals and inspire you to continue to raise the bar for yourself and your future employers.

Worth noting, I had no intention of being a design executive when I started out, mainly because design executive jobs were virtually nonexistent back then. And any executives I met early in my career were frankly unrelatable. I only decided to strive for a VP role in 2014.

The list below shows the dates when the goal was set, not achieved. Goals take time. It’s rare to find someone with an accelerated career and there is massive title inflation in many markets these days. The reality is life can throw you curveballs. If you find yourself getting frustrated with where you are in your career, consider pacing yourself as I did (and don’t compare yourself to your peers or the 30 under 30 lists!). All of my results took years to achieve, but they all led me and my husband to the rich and thriving life we have now.

— 1994 No Trust Fund = Find Career that Pays Well —

I graduated in 1992 (recession still going) and I was struggling in the fine arts community, working at many different arts organizations. In 1994 I worked at an art gallery for very little money and was struggling to make ends meet. I quickly realized everyone around me had a benefactor. Parents, spouses, and literal trust funds were able to balance the cost of living for my peers. I didn’t have this privilege. My reality was paying off student loans, credit card debt, and no family backing. So I started investigating creative careers that paid well. I landed an unpaid internship in 1995 and by late 1996 I left that role for a freelance career as a developer/designer/producer making ten times the gallery job. The dot-com wave began!

— 1999 Big Brands —

My degree is from a state university, hard to compete early in my career with MIT, UCB, Stanford, Cal Arts, Pratt, RISD grads, so I intentionally focused on getting jobs with big brands. This has served me immensely well. Doors open with pedigree degrees and big brands. Period.

— 2003 Honing my Craft and Design Practice —

The effects of the dot-com bust were still painfully obvious in 2003. I reflected and figured out I really enjoyed software design and, in spite of the impossibly few design roles open after the dot-com bust, I decided to focus on interaction design. I took a 50% pay cut, no benefits, no vacation time at LeapFrog. This paid off with an introduction to a head hunter by a coworker and landed my job at Samsung. My time at LeapFrog and Samsung were foundational years of honing my craft as an interaction designer. I refer to my days at Samsung as my grad school.

— 2006 Building Design Community —

One of my interests while at Samsung was sharing knowledge and building a place for the design community to come together. Through the IxDA website and former coworkers from 1999, I got connected with Danielle Malik. She started hosting happy hours near her place in the SOMA area of SF after work. We eventually cofounded IxDA-SF, one of the first IxDA local chapters which continues to host events in SF to this day. Fun fact: I interviewed with Peter Merholz at the Hotel Utah at one of the events in 2006 for my job at Adaptive Path!

— 2007 Sharing, Public Speaking & Embracing Ambiguity —

I decided to focus on overcoming my fear of public speaking and embracing ambiguity in the design process. I left Samsung to work at Adaptive Path so I could share my knowledge that I gained while honing my craft at Samsung. I also realized I hated the beginning of the design process — lots of fear and worry with the fuzzy front end of design. With my projects at Adaptive Path, I intentionally focused on how I could embrace ambiguity of the design process and I was able to break through my fear of public speaking with Adaptive Path’s events platform. I am forever grateful for the 2 years working with such an amazingly talented group of people!

— 2011 Design Community Focus —

Working at Palm/HP, I missed the knowledge sharing from my days at Adaptive Path and felt extremely isolated being a design leader in a predominately business and technology company. Having been a Local Leader for IxDA-SF in 2006–2009, I got accepted onto the IxDA Board in 2011. Served for 4 years. Love my global IxDA family!!

— 2014 VP of Design Aspiration —

As I mentioned, during my time off in 2014, I decided I wanted to eventually become a Head or VP of Design at a product company that values design and user experiences. I gave myself 6 years to do this, by 2020. The responsibilities I had at LinkedIn were a great stepping stone to my next role. Plus I focused on leveling up — speaker training, public speaking, improving the copywriting of my portfolio, and career advice from mentors and executive coaching. It all paid off. I started at Zendesk at the VP of Product Design and Research in February 2018!

— 2015 Get Back to Public Speaking —

When my kids were little, I limited my travel to two times a year for IxDA Board obligations, but as they got older and I left the Board, I was able to shift my volunteer board time back to sharing knowledge. I started saying yes to public speaking gigs in 2015. Starting with fireside chats and panels. Now I do about two events a year. I really enjoy seeing the spark in people’s eyes when they hear an idea that resonates with them.

— 2016 From Surviving to Thriving —

This wasn’t a goal, this was a delightful outcome of a lot of hard work. Through executive coaching provided by LinkedIn (thank you again!), I learned a ton about myself and was able to shift my mindset from surviving to thriving. LinkedIn is a special place, I’m so grateful for the opportunity to have worked with such a talented group of people and to have managers who were my champions in helping me become better at my job.

What’s Next?

So what’s my next goal? I’m still ramping up on my new role at Zendesk, getting to know the design and research team which spans 7 offices around the globe. I have a laundry list of specific product and operations goals for myself and my team but the primary goal is truly to help my team thrive and deliver products that help our customers succeed in their businesses.

I hope this list of goals is helpful for anyone trying to figure out how to move their career forward. Bottomline is to set the intention, be vocal with mentors and managers about your goals, and stay focused until you’ve achieved them.

In the comments, let me know what goals you’re working on as well as the goals you’ve achieved, so we can publicly celebrate them together!