Setting and Achieving Goals (Summer Challenge Update #1)

Month one of the Summer Challenge is done!  Participants have collectively posted over a thousand completed challenge points so far, and there’s still three months to go—plenty of time to join in on the fun.     

Summer Challenge Point: Climb a Tree

Summer Challenge Point: Climb a Tree

Since the first month of the Summer Challenge is officially complete, I figured that it’s a good time to brag.  See, I hold the current record for most challenges ever completed in one summer: I finished 99 challenges in the summer of 2013.  

Yes, it’s a silly accomplishment.  But to do it, I developed an entire system—because I’m that competitive. 

What I didn’t know at that time was that I’d cracked some kind of Goal Setting Code. It worked fantastically, and now I use this system for all of my goals.


The first year I competed in the summer challenge, I noticed that everyone was trying to do “as many challenges as possible.” 

“As many as possible” is a terrifying number.  Isn’t it always possible to do one more?  Even if you just completed one, shouldn’t you immediately start trying for the next?  Maybe I’m just inherently lazy or unmotivated, but that sounds pretty terrible to me.  

It’s like going to the gym.  If I try to do “as many reps as possible,” my arms are burning by the second pull-up.  I’m full of self-doubt.  I constantly wonder: did I do enough?  Can I quit yet?  

If I try for a specific number—even if it’s a really hard number—it feels like I can make it.

But if I try for a specific number—even if it’s a really hard number—it feels like I can make it.  At the very least, I push past a lot more discomfort.  I don’t worry about self-doubt, because the answer to whether I did enough or not is already defined.  And it’s always a smaller number than “always one more." 

I figured the Summer Challenge was like the gym.  But, you know, fun.  So I consciously set a specific number of challenges as my goal.


The second thing I did was the most useful, and happened practically by accident.

I didn’t know how hard the summer challenges would be to complete.  So I chose a goal number practically at random.  But I also chose a number well below it, in case the challenges were harder than I expected.

Previously, I would just give up entirely if I couldn’t complete a goal.  I had an all-or-nothing mentality: either I succeeded, or I didn’t.  How close I got didn’t matter.  Failure was still failure, so I might as well quit.

Even if I think I can’t succeed, I still show up.

But with a lower goal, I have something else to strive for.  I’m less likely to quit outright.  Even if I think I can’t succeed, I still show up.  And I end up accomplishing far more than if I had quit outright—even if I didn’t meet my original metrics.  

Which leads me to the most important lesson the Summer Challenge taught me . . .


When people talk about accomplishing goals, they usually frame it in terms of motivation.  They ask how to get more done, or how to achieve bigger things.  

In case it’s not obvious: I am one of these people.  I constantly worry about not doing “enough” (whatever that is).  Even when I’m successful, I want to be doing “more.” 

I think in the end I spend more time worrying than I do working.  First I worry that my goals aren’t big enough.  And then when I make them bigger, I worry about how I can accomplish such a huge task.  It’s the opposite of motivating.  Goals are a constant struggle—frankly, it’s a miracle I get anything done at all.

But the Summer Challenge was different.  It was easy to meet my goals.  And what’s more, it was fun.   

So what was different? When I was aiming “as high as possible,” I was creating all of this extra work for myself. Because I wasn’t clear on what was “enough,” I didn’t know how to focus my efforts. 

The most motivating systems actually make the problem smaller.

I was too motivated: I always wanted to do more.  I created goals that were so big they were unachievable, and then I got stuck.

Working on the Summer Challenge showed me that the most motivating systems actually make the problem smaller.  They’re ways to define “enough.”  And once your problem sounds achievable, it’s a lot easier to actually go out and do it.