Are Dads Allowed to Ski?

I grew up in Colorado, but I didn’t ski as a child. If I had to guess why, I’d blame money. Skiing is expensive. The gear is expensive, the lift tickets are expensive, and I grew up out on the plains – so the gas to get there was also expensive.

Around the time I was 15, I got it into my head that I was really going to like skiing. Pretty abruptly, I went from not skiing at all to skiing a few times a month. Nearly all my money went to gear, gas, and passes. I was in love. My group of friends rallied around skiing, going up together whenever we could.

After high school, I slowly fell out of touch with my old friends, but my love for skiing intensified. So I skied alone. By the time I was 21, I was skiing every week, at least. Some weeks I managed 2 or 3 days. I became a skier – not in the sense that I was a person who could ski, or happened to choose skiing over snowboarding, but that my sense of self was hopelessly intertwined with the mountains, the snow, the cold air, the speed, the exploration, and solitude. I defined myself as a skier, in the way a priest defines himself through his religion. I couldn’t imagine a life where skiing didn’t play a central role.

And then I grew up. I got married. I started a business. I became a dad. And I stopped skiing.

To some extent my love for the sport had faded, but mostly life got in the way. Things that were previously unimportant became important. Work. Stability. Family time. Things that were important before became trivial. It’s tough to enjoy a powder day if your family doesn’t have money for food.

Becoming a dad represents a shift in priorities. We’re all out to be the best parents we can be. We love our children, and we want them to succeed, so we do the most obvious thing we know how to do: help. Get involved. Give attention. Protect.

Parenting becomes who we are: our greatest purpose, and the only ambition we see as truly worthwhile.

Something about this has always felt off to me. Before I had kids, I watched it happen to others: people sacrificing who they were completely to fill their new role as parents. It’s a goal too noble to question – a martyrdom of self in the name of the most sacred ideal of our generation: “the children”. No one dares question the lengths a parent goes to help their child succeed.

I love my kids, and I want them to succeed, of course – but what is the endgame? Does “success” mean “growing up with the sole purpose of giving my life to a child, just the way my parents have”? If I, through example, show that my life and happiness is secondary to my children’s, will I be satisfied when I watch them do the same with children of their own?

I believe that the strongest influence on my kids will be who I am. My actions represent what my children will understand “normal adulthood” to be. The things that are important to me are likely to seem important to them, even if they end up on a vastly different path.

So what are the things I want my kids to pick up? Of course, I want my kids to know that I love them, and that their happiness and success is central to my happiness. I want them to see how important family is, and how fulfilling it is to give your love, attention, time, and money to a child.

But that’s not everything I want them to learn from my actions.

I want them to learn how important it is to have a strong marriage – one in which the parents care about each other as much as they care about the children. I want them to learn that nature is a powerful and important part of life. I want them to see that spending some time alone is an acceptable and healthy goal. I want them to see that doing things for yourself – just for your own happiness and enjoyment – is more than just a luxury, it’s important. I want them to know that their own happiness is a valuable resource requiring attention, regardless of what else is happening in their lives.

And if I’m totally honest with myself, I want my kids to be raised by a dad they could find interesting.

Some people just seem to “get” this: effortlessly finding the right place for them on the spectrum between children and self, and between adventure and stability. Maintaining who they were before kids, with a new perspective – a life fundamentally unchanged, but now lived through a new perspective, seen through a new lens.

Specifically where I end up on that spectrum isn’t important. What is important is that it’s a conscious decision rather than one defaulted to because it felt the safest or the most socially acceptable.

I’m going to try to make a point of skiing a little more this winter. Not a lot — maybe a few days a month. We’ll ski as a family some of those days, and that will be great — but dad will have a few days on the mountain to himself as well.

I think we’ll all be better for it.

The Treachery of Optimism

I used to own a business. It was successful, and I’m very proud of it – but it wasn’t a home run. Most of the time it was just successful enough to not be a failure. I paid enough of my bills every month to avoid serious discomfort. When things were good, we caught up. When life was expensive, we fell behind.

The service I offered – a backup and security product for WordPress websites called CodeGarage – came with stress. The code didn’t always work right, and when it went bad, people were occasionally left hanging. If customers got hacked, or new customers needed help cleaning up the mess left by hackers, they were impatient to see results and have things get back to normal. I worked a lot of late nights, cleaning up problems and helping customers. I enjoyed the work, but the stresses it created were not trivial.

Over time I grew tired of the endless financial stress, and felt like I was stagnating professionally. I wasn’t growing as a developer or a business owner, I was just keeping my head above water. In an effort to figure out how to keep moving forward, I applied to, and eventually sold CodeGarage to Automattic (the company behind, joining them as a developer. Personally and professionally, this was a huge victory; vindication that the hard work of the prior years was worthwhile. To top it off, Automattic was (and continues to be) a dream job — a company I had watched and admired for years, which turned out to be even better on the inside than it appeared on the outside.

Overnight, my lifestyle changed significantly. I had gone from a struggling small business owner to an employee. I knew exactly how much money I’d make every month. It was enough money, every time. I knew when it would hit my bank account. I even had health insurance. Real health insurance.

Not all the change was financial. I slept more, and I slept better. I was easier to be around. I could take time off. I lost weight. I could go an entire weekend without working. The release of stress and the accompanying benefits was not slow and gradual – it was abrupt, and obvious.

But somehow, things felt off. I was restless. Uncomfortable. In spite of the fact that I was making enough money to live comfortably, my work/life balance was better, and my stress was way down, I couldn’t shake the idea that something was missing.

My entire adult life had been about hustle: after eeking out a high school diploma, I floundered at community college. Soon after, I found myself working in a factory. I was unhappy, and I knew I could do better. So, in those long nights on the factory floor, I convinced myself that things could get better. Hard work could create a better career, a better life.

Struggle became my life, my mantra. Each step along the way was a victory – the first time I convinced someone to let me build a website for them. The first time I won a job on The first paying customers for my SAAS business. The most crucial piece though — the thing that made it all tolerable, even exciting — was the dream. Owning a big, self-sustaining business. Thousands of customers. Financial freedom. The big payout.

Struggling to get by, and to convince myself (and those around me) that owning a business is a good idea, I felt like I had to dream big. Working long hours and dealing with constant stress (financial and otherwise) didn’t feel worth it if the payout was just an unstable income, and less flexibility than a normal employee has.

As a business owner, it’s easy to believe that you’re just one big deal, one solid marketing campaign, one killer feature away from massive growth. This optimism isn’t necessarily irrational. CodeGarage saw at least 2 occasions that worked exactly like this: events, ideas, or sales that singularly propelled the business to a new level. Without the continuous belief that things will continue working out, and continue growing, I’d have quit or failed long before any money was made. This was the required mindset in order to keep going. However: it came with side effects.

Since I was convinced that I was just a few good decisions, ideas, or turns of fate away from greater success, I knew that these things would come to me. They’d happen, and probably soon. Success was not a question of if, but when, and more than that, it was “how soon”.

In practice, that meant I knew that within some period of time, the business would be successful enough that any of my current problems — work/life balance, money, stress — would disappear. So why bother worrying about them?

Assuming that impending success will solve all of your problems is a bit like praying instead of going to the doctor. It gave me the acute ability to ignore, or at least postpone dealing with problems. Financial problems (say, the massive expense of childbirth without maternity coverage, or poorly calculated tax liabilities) in particular were easy to ignore, as I was convinced greater success would soon solve them.

Of course, living like this is precarious. I slowly realized that while it did just take a few events to massively change a business, I might not have the requisite skills to facilitate those events, or I might not be able to learn them as quickly as circumstance demanded. Most terrifying, they might come too late. I was fortunate to land at Automattic, where I can continue to learn and grow. Maybe someday I’ll end up running a business again – this time with a new array of skills and tools to find success.

This brings me back to the vaguely unsettled feeling I developed after a time in my new, stable job. I had grown to believe massive (and most importantly, financial) success was just around the corner, all the time. In many ways, moving to my current job is that success I sought. However, it’s not “buy a yacht” success. Or “Own a second home at a ski resort” success. It is “Improve your skills working on interesting projects with smart people while not having to worry about whether your child can go to the doctor next month” success.

Having a job with a stable income, and compensation not tied directly to performance (at least, not in the way it is as a business owner) has meant accepting that I’m not going to buy a yacht next year. Conversely, it meant that I could buy a comfortable house this year. Much more importantly, it means that any financial problems I run into actually have to be dealt with, and not put off until the next theoretical deal can erase them. It’s a bit like losing touch with an old, fun loving, terribly irresponsible friend.

I’ll miss you, buddy.