This morning I dropped off my daughter, Bay, for her first day of kindergarten and then drove straight to the Outpost for the first day of the Davidson College school year. These two events are in the same sentence because they both — Bay and the Outpost — were born on the same day, November 14, 2013. While I won’t go so far as to equate raising a toddler to managing a business, the four-minute drive today between the two new chapters instigated some reflections on growing up.
I spent much of that first Outpost year, from November 2013 to the following May, working at the butcher block bar pictured above with Bay asleep in her carseat carrier. She was affectionately known as Summit Baby, and when I wasn’t changing diapers and swaddling a newborn, I was washing dishes and swaddling a newborn (business, that is). Those days and weeks and months run together — they did in the moment, and they do in hindsight. Both were beautiful and terrifying, opportunities to recognize growth and opportunities to dwell in complete and utter fear that you have no idea what you’re doing.
Bay is my oldest daughter, and the Outpost is the first business I ever opened. When I assumed leadership of Summit in 2011, alongside Tim, Basecamp already existed and thrived. But the Outpost was our baby, born on the same November Thursday as Bay. So on this first day of their school years in 2019, transitioning from kindergarten dad to café owner, I felt equally sad and triumphant.
Sad, because of growing up. This day has been coming for months, but it also came out of nowhere. We woke up this Monday, and Bay dressed herself and packed her own lunch, brushed her hair and put on her shoes, made sure we left on time and made sure we knew where we were going. She didn’t need us in those moments. I woke up this Monday, and the Outpost brewed coffee and turned on the lights (maybe in that order to be honest), readied for the new students and new menu items. The Outpost didn’t need me in those moments. And the truth is, even though I have been there for all of the little moments, it hasn’t for years.
Triumphant, though, also because of growing up. There’s a reason I suppose that Bay knows how to get ready for school, and that the Outpost can open for a new year without me pushing the buttons. It’s because we prepared them to succeed, to grow up and to be grown up. Sure, at less than six years old they both have lots to learn and lots more mistakes to make, more victories to celebrate and more tears to shed. But today felt landmark, in a way. That parenting, like leadership, takes on a different shade when your child gets older, grows more capable.
Bay and the Outpost both need more leadership, less management. Bay doesn’t need me to hold her hand to show her which way to go. Bay needs me to hold her hand to offer support and encouragement when she goes her way, and then let her shine. Likewise, the Outpost doesn’t need me to brew coffee or wash dishes. The Outpost needs me to provide a vision for this, its 7th school year, and then get out of the way and let the immensely talented OP team run with it.
In both cases, I’m sure it felt good that I was around — a sense of safety or security or familiarity. But in both cases, it felt like the reasons I was around were more for me than for them. There’s the sad/triumphant dichotomy again. As a parent, you do all you can to set your children up for success, to prepare them to make good decisions and think on their own. Basically your job in raising a child is to teach them how to need you less and less, or at least differently.
Growing a business is no different, in retrospect. In the 70 months since the Outpost opened, I (and a slew of great people) have prepared it to stand on its own, to discover its identity and grow into it. We somehow figured out how to keep it alive in its infancy, and now are working to develop something that’s not only sustainable, but will flourish as it keeps growing up.
If I am being candid, I am a WAY better dad than I am a CEO. I’m sure being good at one probably makes me less able to be good at the other, though I am constantly trying to be the best at both. But on that four-minute drive today from kindergarten to cafe, it occurred to me that there’s a lot I’ve learned from parenting that’s helped me as a leader, and lots more fumbling through things as a CEO that I’ve used to be a better father.
My wife Tyler remarked last night that I’ve had a palpable energy and enthusiasm about the Outpost that has been lacking in recent years. I think getting ready for this kindergarten year, and reflecting on what Bay needs from her dad, has allowed me to get ready for this Davidson College school year, and reflect on what the Outpost needs from me.
The author Jodi Picoult says of growing up, “They outgrow us so much faster than we outgrow them.” On this Monday morning, the first of the new school years, it dawned on me that Bay and the Outpost are growing up faster than I’ve been able to keep up. It’s my job as a father and as a leader to not only let it happen, but shift gears and figure out new ways to help. What was needed from me in 2013 is so, so different than what’s needed from me in 2019. And yes, sometimes it’s nice to just have me around, so I will continue to do school drop-offs and say hello when I grab coffee. But it’s also time to let them flourish, to discover who they are on their own without me getting them dressed, turning on the lights, making the coffee.
I feel both sad and triumphant today, and that’s a wonderful feeling. It means we’re growing up. All of us.