Relax, find your purpose

These past seven years, I have run from start-up to start-up… from innovation studio to the spin-out, to acquisition, followed by another incubator, a pandemic, another spin-out—this time complete with a pivot, and then on to the next start-up! I was moving so quickly all I could focus on was what was coming next, and whether I could keep my head above water.

I needed a break.

I needed to catch my breath, take some time to decompress and to reflect on what gives me meaning, gives me purpose. So after my last start-up ended after an early morning call with the CEO and my other co-founder, I took the generous severance they offered and after I got the logistics squared away —health insurance, budgets, etc., I spent the next couple months doing nothing.

Then I relaxed.

I spent time with friends. I started painting again, and I read. Not the professional books you need to stay current, but fun books—graphic novels, mysteries, and biographies. I painted both as an expression and an exploration, working on a couple new series I explored new directions, and again, like with the books, with no professional goal in mind. (I have previously sold work through galleries—but art is a business, with all the things that come with that, I just wanted to paint.) I also started writing, something friends have been encouraging me to do for a while. Finally, after a couple months, I was able to feel relaxed. I had reached that point when the first thing I looked at in the morning wasn’t my calendar. The days just blended together.

The last time I was there was 20 years ago… I had just left a start-up and I had planned on taking a six month sabbatical. I managed to stretch that out to almost three years. At one point about 9 months in, I called up a friend to see he if was interested in grabbing breakfast—after a pause, he pointed out it was Tuesday and he was at work. I said I would have sworn it was Saturday (this was before the iPhone) and said we should grab breakfast on the weekend. Fast forward 20 years, it was time to do that again.

If you have never been at the point where you no longer wake-up knowing what day of the week it is, you need to relax and make that happen. Being in a place where you don’t have to save up all the fun things for the weekend is awesome. I had cleared my head and pushed out the anxiety, and was able to forgive myself for rushing through the last seven years. I felt I was finally in place where I could objectively think about what I wanted to do next, where I might be able to find meaning again.

For the last seven years I had been running both Product Management and Design every place I worked. I am a good product manager but I am much better designer. Thinking about what gives me meaning, I realized I needed to focus on design and let go of the product management. That while I am very good at setting strategy and focusing on building solutions that deliver value, in the day to day I would rather be in front of a white board than in a spreadsheet. So with that internal guidance I started doing my homework; I started looking at what companies where hot? what market sectors where trending? where were VC’s placing their bets? And which companies where in need of a design leader.

I started working my network and getting introductions. After a few conversations, I got an offer from an early stage start-up looking for a Head of Design. Great culture, well funded from a top tier VC, and focused on an interesting market that desperately needs to be disrupted. But given their size, while the title was Head of Design, the position was an individual contributor role. And they had no immediate plans to grow the team but at some point if things worked out, that would be an option. Frankly, from my experience that made perfect sense and if I were in their position I would make the same call, in fact I did.

Two years prior I had co-founded Zeitworks where I was the Head of Product, which meant I was the only product manager and the only designer. There was no way to justify bringing on additional designers (or product managers) given our size. So I rolled-up my sleeves and got things done, I created our website, defined our customer journeys, created collateral, built mock-ups and visualizations, wrote requirement docs, and spent late nights working with the engineers on trade-offs. I even designed our logo and branding, down to the fonts and color palette. While it was hard work, it was also energizing to be actually designing a product again—a rarity when you are in design leadership. To be playing with the layouts, workflows, and creating design language and translating that into a scalable system. Really, it was a blast.

Fast forward two years, and I am sitting in front an offer for an almost identical role. I thought about this offer in front of me and honestly, I was excited about the prospect that I would be able to design again like I had at my previous start-up. But I had committed to myself not repeat the past seven years, so I took a pause.

I talked about the opportunity with friends, colleagues and mentors. During a couple of these conversations I reflected on my career the twenty years in Silicon Valley, and the seven years in Seattle, as well as the reasons behind our move to from the valley to Seattle. During one of these conversations, one of my mentors offered an insight: I love flying solo on designing something that’s mine but that when I really fly, I am building design practices to help organizations reach their next level.

I co-founded Zeitworks, it was my company, and doing day to day, hands-on design work came naturally. It was what the business needed to grow; it was my contribution to the team so we could move things forward. Building Zeitworks gave me a purpose, it gave my (design) work meaning. But prior to that, I had transitioned from designing things to designing teams and processes. I found greater purpose and meaning in (re)building design teams--hiring and mentoring designers, and in working with company leadership to effectively reshape the organization in order to fully leverage design as a competitive advantage. And as my mentor pointed out, I am really good at it.

I reflected on the offer in front of me, given the insight, given its not a company I co-founded, I asked myself if I could find same meaning in doing the hands-on design work for them that I had found at Zeitworks? I reminded myself it will be a considerable amount of time before they are ready to build out a design practice, so if I don’t find meaning in the work, I will have a long wait to do something in which I know I will find meaning.

I declined the offer from the start-up.

That is not a decision I would have made six months ago. I would have grabbed the offer and gotten right back into the race. Instead I told them it would be better to find a designer who will grow with them, someone who can organically shape their design practice rather than someone who will be impatiently waiting for them to get there.

I have always been a designer, and I love designing. And fundamentally I believe there is no difference in designing a product or in designing an organization. However, there is a difference when it comes to the why that is behind any design. And you need to be able to answer the why honestly and objectively. Why are you designing that? What are you working towards? What is it that gives your design meaning, and your work in designing it purpose.

As always, please feel free to share your thoughts.

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