Challenging oneself

In my last post, I talked about instigating unhappiness as a way to spur change at organizations. I’ve also been thinking about it in a personal context of challenging myself, and when I should be satisfied and happy with where I am vs. stretching myself for the next goal.

One of the reasons for the introspection is that I am thinking of signing up for the Death Ride next year. The Death Ride, for those that don’t know, is a bike ride that is 130 miles, and climbs 15,000 vertical feet through 5 mountain passes in Tahoe. When I first heard about it 13 years ago, I thought it was completely insane – I had a couple coworkers who did it every year, but it was inconceivable to me, as I had never ridden more than 40 flat miles at that point. But here I am, thinking about signing up, and believing I can do it. So what changed?

Well, this year has been a year of leveling up in bicycling. I started the year in April with an Old La Honda ride with some other Googlers (40 miles – one hill: Strava), where I went all out and was still left in the dust, and bonked so hard that I was late to work. But I trained hard for the rest of the spring, and got in shape for my week-long mountain bike tour from Durango to Moab in July. I had already decided to cap the summer off by doing my first century bike ride (100 miles), but my friend said that I would be in such good shape after the tour that I should do the climbing century (8000 feet of climbing) up and over Mt. Tam in August. So I did (Strava) and it was actually pretty easy. So I signed up for Levi’s Gran Fondo in October, and went all out in that (averaging 20 mph for the first 30 flat miles) and still felt good (Strava).

So I figured if I can do 100 miles and 8,000 feet of climbing in 8 hours (including breaks), I should be able to do 130 miles and 15,000 feet of climbing in 12 hours, right? Right? Okay, it’s a stretch, but it seems like a good goal to aim for next July.

And this is where I wonder about myself. There are many who would be impressed and satisfied with where I got this year, from struggling to ride 40 miles, to being able to ride a climbing century. And I’m happy with that progress, but my first thought is “If I can do that, what else can I do?” and immediately move onto the next challenge rather than taking time to savor what I’ve accomplished.

I see this tendency among many of my friends as well – we end up continuing to push the limits of what we can do when we could easily rest satisfied with what we’ve accomplished. In the Steven Kotler book on extreme athletes, he describes communities as social triggers that help push us to try things beyond what we might on our own, so it is perhaps not surprising that my MIT friends tend to share this limit-pushing tendency and that such a community helps normalize such behavior.

What I find interesting about this is that I change which communities I associate myself with as I get better at an activity. The first time I did the SF to Google 40 mile flat ride in 2012 was the longest I had ever ridden to that point in my life, and I was really proud of myself. Now I’ve done that ride on a fixie, and am using people who do double centuries as a comparison point. Or in volleyball, I used to be content just being able to keep the ball in play at doubles, but after playing a bunch this past year, I compare myself to the A-level players, who can consistently put points away and regularly get incredible digs. I keep moving the goalposts on myself so I’m never satisfied.

Sometimes I wonder if I’d be happier if I let myself be content and happy with what I’ve accomplished, rather than continually striving for more. I do enjoy the continued challenges and the fact that I can do so much more than I thought was possible even last year. And in other areas, I don’t challenge myself as much – I’ve gotten better at being content at work over the years, rather than beating myself up about why I haven’t accomplished more. Chorus is another example where I hit my limits, felt I had done all I could, and accepted that. So maybe it’s just in areas where I feel I still have considerable upside that I keep challenging myself?

Another aspect is that it is only possible to have a couple challenge areas at a time. If I wasn’t secure in my job with a comfortable income, I wouldn’t be able to challenge myself in other areas, as I would be too focused on basic needs. But because I’m in a good situation, I can afford to focus on other challenges such as sports (biking, skiing, volleyball) and socializing (especially in 2013). I’m fortunate to have that freedom to take on those challenges.

As the year winds down, I’ll be thinking ahead to next year and deciding where my next challenges lie – if I do sign up for the Death Ride, biking will definitely be one :).

6 thoughts on “Challenging oneself

  1. Yeah, it’s weird. A few years ago, if you’d have told me what I’d have accomplished in the last six years, I’d have laughed and told you that such an outcome was *inconceivable*. I remember clearly what I felt like the upper possible bound of our success might be, and we did a hell of a lot better than that.

    I think the big thing is that every step of the way, the next incremental step seems like something you have to do. I did this thing, but dammit, that other thing isn’t as good as it could be. I’ve gotta go do that. Enough of those steps, and without even really realizing it, your whole perception of where you are has changed, since you can only really see things from where you are, not where you were. All you see is the difference between where you are and where you might be, and it’s infuriating to not be there now.

    I think with things like chorus for you, and a lot of random shit for me is that there’s some point where there isn’t that infuriating next step. My experience with art, for instance – I hit a wall, and found that I either needed significant instruction (which at the time, I didn’t even understand was something you could get) or I’d hit the limit of my “talent”. I’d worked and worked at it but wasn’t getting any better, and as a result, I didn’t see the next step forward. I knew there was a *possible* step, but after a significant amount of time realized *I* couldn’t see it.

    There have also been things where a realization that the “itch” to move forward is overwhelmed by other constraints – mostly time pressure, these days, and the realization that I just can’t do everything I want to do to the degree I want to do it. If I invest time in work, developing games, building my skills there, I can’t also do the same with music. I can’t also machine things in the garage. I can’t also ride my bike or swim as much as I’d like. So a lot of the stuff gets cut as more time is consumed by parenthood, and that’s fine – it works out well in terms of cost vs. reward of doing all those different things. It still sucks to have let some of that stuff go, and in a universe of infinite time, I’d love to do everything, but in the end, I think I’m doing a good job of maintaining a general sense of happiness and satisfaction (even if that completely breaks down every so often), and feeling like my life is making good forward progress.

    I think in part the MIT connection may be causally backwards. It’s not MIT and the community around it that normalizes the behavior, it’s the behavior that drove those people to end up institutionalized.

  2. Seppo, good point on just looking at the next step. We look at things that are way off from our current level and don’t see how to get there, but it’s just one step after another. Somebody posted to the Google biking list asking how one could get to the point of biking up Page Mill Road (2200 vertical feet) – it seemed inconceivable to them as they struggled with even a couple hundred feet of climbing. And I responded that you go and try it, go as far as you can, then try again the next weekend, and keep trying until you get to the top. That’s what I did, and now I consider that climb a warmup.

    On the other constraints, that’s what I was trying to get at in the second-to-last paragraph – we can’t do everything, so we have to pick the areas where we are stretching at any given time.

    And on the MIT point, I did not intend to imply causality – I agree that it’s the behavior that got those people to MIT, but couldn’t figure out a way to clear that language up without sidetracking.

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