Why we should strive to fail

If failure is never an option, we’ll never reach the heights we are capable of.

As the end of law school approached, a friend invited me to join him on a hike to the top of Granite Peak, the highest point in Montana. It’s 12,807 ft. up. The last serious hike I had been on was a 50-mile backpack trip in Yosemite National Park in 8 years earlier.

The time for the hike arrived. We drove up to the foot of a small dam. We climbed up a few small switch-backs to walk around the lake behind the dam. Then we started the real ascent. It miles of switchbacks. We climbed thousands of feet.

At the top we arrived at a plateau. This plateau stretched to the foot of the peak. On the map, the plateau was mostly flat, so we figured it would be relatively easy. The hard part was behind us!

Turns out the plateau wasn’t a field. It was miles of rocks and boulders. We had to hop from rock to rock. With packs. For miles. And the sun was low in the sky.

By the time we arrived at the base of the peak, I was soaked in sweat and the sun was going down. At 12,000 feet, in the dark, it gets cold fast. I started shivering uncontrollably. I recognized the early symptoms of hypothermia and we quickly set up a tent, I changed, and we had a warm meal. We slept, hoping to feel better in the morning so we could climb to the peak.

Unfortunately, I didn’t feel much better in the morning. The climb to the summit required some rock-climbing and I was not confident that I could handle it. We didn’t want to wait, either. There were clouds and we were worried a storm could begin. Being above the treeline in a storm isn’t a pleasant experience.

So, I backed out. My friend was not happy. He told me, “When I set a goal, I accomplish it.” I told him I wasn’t going to risk my life to summit the peak. Disappointed, we turned around and began the long trek back to the car.

Setting Goals

I’ve often reflect on this experience when setting goals. The way I see it, there are two approaches to setting goals: non-negotiable and stretch.

Non-Negotiable Goals

This same friend sets non-negotiable goals. He currently works for an airline and a year or two ago, set a goal to go on a certain number of flights that year. On New Year’s Eve he was a flight or two short, so he went to the airport (he lives really close) and jumped on a short flight. He never left the airport at his destination, just jumped off one plane and onto another, and welcomed the new year in the air, having met his goal.

There’s a trick to accomplishing non-negotiable goals. Some people use the acronym SMART: specific, measurable, attainable, realistic, and timely. I’d argue attainable and realistic are similar enough in practice to be redundant, but removing one would ruin the acronym. This can be an effective goal-setting strategy. Carefully set goals, make plans to achieve them, and you can feel proud when you check them off at the end of the week, month, year, or whatever time period.

There re obvious benefits to non-negotiable oals. If I had made reaching the top of Granite Peak a non-negotiable goal, I would have taken more steps to achieve it. I would done more to prepare so that the goal would be more realistic and attainable. Mostly actually physically trained, rather than just studying and whatever else I was doing at the time.

Stretch Goals

Regardless, at the end of that hike, I felt pretty good. Just getting to the plateau was a greater accomplishment physically than anything I’d done in 8 years. I never would have gotten there if I hadn’t set the goal to make it to the summit of Granite Peak. It was a stretch goal.

Stretch goals differ from non-negotiable in one main way: the psychological impact of failing to achieve it. The point is to push yourself out of your comfort zone. If we look at the SMART strategy again, stretch goals probably fudge on the attainable-realistic portion. A good stretch goal will still have the other aspects, though.

Which Type of Goal is Better?

Not having any sort of expertise in this, I can only speak for myself: I prefer stretch goals. I like the added flexibility of knowing that I don’t have to achieve the goal. But I will strive for it and do more than I did otherwise.

My wife hates this. She, like my Granite Peak friend, achieves the goals she sets. She often tells me, if you’re not going to do it, why set the goal?

There are two potential drawbacks to the non-negotiable approach. The first is that we might not push ourselves to do more than we feel capable of. We underestimate what is attainable and realistic, so we set mild goals just to check off the box.

The second problem, and this is the trap I’ve fallen into the last few years, is that the non-negotiable approach can lead to discouragement. I often fail to achieve my goals. Now, this has a lot to do with how I set them. I overestimate what is attainable, I mis-estimate the time it takes to accomplish things, I fail to make the goal specific enough. Whatever the reason, as I pushed myself into the non-negotiable approach, I began to get discouraged and largely stopped setting goals for a time.

Obviously, even if the stretch approach is inferior in every way to the non-negotiable approach, either one is better than no approach. Living life without a goal is a good way to end up as a leaf tossed on the wind.

These goal updates are evidence that I’m trying to turn over a new leaf.

So, on that note:

Goal Update

My tracking took a hit this week. No, that makes it sound like I didn’t have a choice. I failed at tracking this week. So I don’t have a clear picture on how I did.

Did that long intro serve as a justification for this failure?


So I suppose the number one goal this week is to track better.

Write daily for 30 minutes. 

I did write most days. But my problem remains not having a plan. So, here’s the plan:

  • Plan what to write each day. I often procrastinate writing because I don’t know what to focus on.
  • Require myself to write in the morning. This will help me get it done earlier so there’s less chance of missing a day.

Habit resolution: Stop eating between meals.

Didn’t do a great job. Snacked a few times during the week. Turns out I’m pretty bad at controlling myself when the fridge is right there all day long. Weigh about the same as I did as of last post, so at least that’s not backward progress. Of course, weight also is impacted heavily by what I eat at mealtime, but one thing at a time.

Project resolution: Have the desk put together.

I have a shopping list and a cut list! Now I just need to get to the store and buy the materials. Slow progress, but it is progress.