Wetsuits Don’t Lie

In early February my girlfriend and I decided to go surfing after an unintended several-month hiatus due to the holidays and other commitments that interrupted our normal weekly trips. Someone (I’m going to assume it was her) suggested that we put on our wetsuits before we left since it had been so long and it might be good to “just check” that they still fit. As anyone who has put on a wetsuit knows, there is a bit of a dance/contortion that happens after you get your feet in and start pulling the suit up towards your head. While I expected it to be a bit more snug than usual, we didn’t expect that we would encounter some bulges around the mid-section that would get in the way of our wetsuits coming properly up around our necks and sealing to prevent too much water from entering. To put it frankly, there was “no joy in Mudville” that day. It was an important moment for both of us, because even though we skip out on the pre-bagged, processed stuff and cook a lot of our own food, that doesn’t mean we necessarily eat “healthy”. I believe her initial reaction was “we don’t really eat that poorly, and we don’t have desserts that often” which then led to an accounting of just how many desserts we’d really had recently. It was quite shocking when we laid it all out. It was also an inflection point where we both really committed to adjusting our diets and losing weight. Having it laid out so starkly by those neoprene critics was the honest assessment we needed to make that change.

Our path from realizing there was a problem through designing and implementing a solution got me thinking about other times in my life when I had a jolt of honesty that acted as a forcing function to make some real changes in my life. Another notable health-related episode occurred in my mid-20s when my girlfriend of five years ended our relationship and during the rather emotional breakup one of her criticisms was that I had “put on a lot of weight and wasn’t really attractive anymore”. That’s about as real as it can get at that age. As painful as it was at the time, it was also what made me realize that I needed to make serious changes and pushed me down a path of losing 50 lbs over the next six months and becoming a more healthy, active person. It also motivated me to evaluate where I was at that point in my life and where I wanted to go, and ultimately ended with me relocating from the East Coast to San Francisco and effectively rebooting my life.

When I started working on my first startup with my co-founder Jon, I was really on top of the world. It felt like an inevitable step after cutting my teeth in the San Francisco tech industry for a few years, progressing from an apprentice software developer to something more akin to a journeyman. What I didn’t realize was the difference between saying you “founded a startup” and actually getting down to brass tacks and doing it. While I was spending all the time I could focusing on the product, talking to users, and iterating on ideas there was a certain lack of urgency that I was missing and I know Jon felt it. After I dropped the ball on something important he took me aside and gave me some hard truth; he needed someone who was as focused and committed to the idea as he was, and was willing to go farther and push harder to keep moving the ball forward for our idea. It wasn’t just about working long hours (which we were doing) but about being strategic and focused, and always chipping away at the mountain of work that was important instead of getting distracted by smaller, more inconsequential tasks. The talk he gave me still sticks with me to this day, and it motivates me not just professionally, but in all endeavors I undertake.

Which brings me to my central thesis: in anything you undertake it’s important to find a wetsuit. Something or someone that will unabashedly give you the true feedback you need to hear, not something spun to be upbeat and positive and make you feel better. I’d rather have some hard truth that stings but ultimately lets me move forward than a temporary band-aid that makes me feel better about myself. We can all be our own harshest critics at times, but when you have someone to give you honest feedback what you find is that they are acknowledging real problems they see in front of you which may actually not be about you, but about circumstances you can take control of. That gives you permission to ease up on yourself and direct your energy at solving what’s really important, like getting into a wetsuit.