Grateful for snow days

The alarm sounds at 6:30 AM, I chug a glass of water and look at my calendar - full of meetings and loads of work that needs to get done. I don’t have a boss to breathe down my neck if I don’t get this done, but a team of employees and a roster of investors and rely on me to move things forward - I pull off the sheets, swing my feet to the ground and shuffle to the kitchen to make coffee. The house is still quiet, except for my dog who bows her head, bears her teeth and wiggles her butt so vigorously she looks like a furry half donut - time to get my layers on and take her for a walk. The muted light of the sun filters through dense clouds as I step onto my porch and feel snowflakes on my face. A few inches of snow have already accumulated and I glance at my phone notifications and see that school has been canceled. I brace for the cold wind as it envelops my body and think how my wife and I will manage with my son home for the day. It doesn’t feel like fun.

As my wife informs me she’s got back to back calls all day, I settle on the fact that I’m going to take my son snow tubing down the huge hill behind our neighborhood. This may seem like an obvious conclusion, but I had been fretting recently about past years where I missed out on quite a few tubing sessions with my son as I was so consumed with my startup. As a founder, I can set my hours, say no to meetings and mostly do what I want, but the pressure of what I was going through left me wrought with anxiety around being productive and present with my team. As my wife took my son tubing those days with friends from the neighborhood while I stayed home, it didn’t dawn on me that I was only going to get a limited number of chances to flake off from work for one or two hours with my kid and enjoy the pleasures of a New England winter. This morning, for the first time in three years I was post-startup, in so far as we had started to wind down the company and even though I had stuff to do, I realized it could wait.

I’ve been working remotely for a long time now and I prefer it. Whether I was working for someone else, or as an entrepreneur in this stage of life, I appreciate being able to slot meetings and the daily minutiae in a way that works for me. In my life pre-family, rigorous daily structure and execution was the holy grail for a satisfying week of work - where you’re only limited to the productivity you can squeeze out of yourself.

Then there’s parenthood.

I won’t attempt to make your eyeballs violently roll to the back of your head with an analogy comparing being a startup founder to being a parent. The analogy falls apart quickly and depending on which side of the analogy you fall on, you may be too offended and defensive to follow it. But I will say one thing - raising kids (well) doesn’t net out to some perfect formula that works the same for everyone. You can have the most disciplined and loving environment for a family and each member of the family will grow and evolve in unexpected ways. It’s your job as a parent to love your kids unconditionally and meet their needs when they’re young and need you the most.

My son and I started trudging up the road in about 8 inches of snow and he asked me “dad, can I sit in the tube while you pull me the rest of the way?” I had been mindful about saying “yes” to more things when my son asks to bond with me, even when they seem silly and unnecessary. “Sure,” I said, “get in!” I got a nice little workout walking the quarter mile to the hill and we arrived to dozens of kids and their parents flying down this huge hill. To date, my son had never gone down the hill alone, so I had him climb on top of me while I sat in the tube and we flew down at a rate of speed that simultaneously made me nervous, yet also made me remember the breathless feeling of tubing when I was a kid. We took turns pulling the tube back up the hill and descending a couple more times and when he saw a few bigger kids doing crazy stunts on their way down he told me he wished he could try that. My hesitation to encourage him to be reckless subsided after a few seconds of recalling how good it felt to sail down a snowy slope solo and I encouraged him to give it a try. After carefully getting him settled into the tube, showing him where to hold on and gently pushing him over the edge at the top I heard him scream with excitement as my heart stopped as I saw a parent walking diagonally up the hill, something totally careless as my son seemed to aim for that parent in slow motion.

To say this parent got air would be an understatement - my son took him out beneath the knees and he did a full backflip. I sprinted down the hill and checked on the man who instantly knew he made a huge mistake and was apologizing to me before I realized I needed to check on my son too. As I ran up to him at the bottom just sitting still on the tube, partially in shock, he told me the man’s leg hit him, but he felt alright and wanted to go again. I got the entire thing on video and felt embarrassed that I let it happen but also so proud of how my son shook it off and relieved that nobody was hurt.

Of course, he wanted to go again. I helped him pull the tube up one more time and he told me he could do it himself and we proceeded to have the best day of tubing of our lives together. We came home, had some lunch and he went to take a nap to recover from the exercise, cold and adrenaline and I was able to catch up on the work I needed to finish for the day. Realizing I couldn’t take back the times I had missed tubing with my son, and other things I hadn’t chosen to do with him like explore the woods behind our house, spar on the BJJ mats in the basement or read any and all books he’d gather at the library, I felt hopeful that this memory would ground me to do better - not by anyone else’s standard of parently necessarily, but to act through the desire of making the absolute most of this precious and amazing life with my family.

The sayings about how there’s never a “right” time to start a family are mostly true - although nobody would fault you for trying to have your shit together as much as possible before starting one. While I personally was on the roughly the right track when my wife and I had our son, I was by no means the type of man or person I needed to be yet to offer my son and my family unit the safety and support they needed. That’s the journey right there and the process is probably 90% of what makes it all worth it.