The Five Year Plan
Looking Down the Road and Then Looking Back at Your Feet
When I was seventeen, I was invited to drive to Boulder, Colorado with my climbing partner / mentor for a weekend of cragging. Specifically, he wanted to try a route in the Flatirons called The Five Year Plan, a steep finger and hand crack that was near the highest end of the grade scale at that time. I remember thinking that it was a stupid name, and told Steve, my mentor, so.
He explained to me that the first ascensionist, Dale Goddard, probably called it that because he had to focus on this climb for five years. Probably trained and toiled for that long. Steve thought it was a great name.
He said, “You’d do well to start thinking five years ahead, kid.”
He was right. I really only looked about five days ahead on most things. When would I get to climb again? What were my friends doing tonight? Was I out of cash?
We spent two days at the climb with Steve’s friend Paul Piana. Steve got close to sending on that weekend, as did Paul, and I got thoroughly walloped. I made a seventeen-year-old-boy resolution to build my own five year plan for this climb, and to send it before I turned 22.
I’ve still not been back.
“The sure sign of an amateur is he has a million plans and they all start tomorrow.” Steven Pressfield, Turning Pro
Even though I failed to follow through there, looking toward doing harder things (more than a week out) had a profound and positive effect on my performance and my life. I started working projects. Doing regular training. Planning to save money. The shit worked.
Of course, I took it too far. Early in my career, I got hooked into the idea of goal setting. I read Napoleon Hill and Brian Tracy, started designing SMART goal frameworks in my notebooks, and started coaching others from a goals-first standpoint. The awesome thing with any goal setting is creating a vision of the future—building a structure around what you want to do.
Often, a goal can be as simple as “I want to climb x route at my local crag.” We think about the climb when we are not there. We make sure to get enough sleep. And we go out and try the thing over and over until we can do it.
Things like relationships, jobs, and overall sports performance get more nuanced, though. It’s not like you can just go to any new job and do a poor or partial job until you finally get it right (…maybe politics?). You need to build the skills first. Likewise, I can’t have unlimited do-overs in a single critical conversation with my wife, Ellen. I need to build skills of organizing my thoughts and feelings, of finding the right time to talk, and of being open to hear what she has to say.
In this way, goal setting is very one dimensional and simplistic. It’s heavy on the strategy, weak on tactics. Which is exactly why I fell into the trap of setting outrageous goals year after year. The notebook time was great…I got to write out all of the hard climbs I wanted to do, all of the PR numbers I would be hitting in the gym, and all the places I’d go climb. The main issue is that getting from here to those goals is the crux. Having them is key, yes, but having what it takes to work toward them day after day is the real skill.
Dr J once said that a professional is a person that does what they love to do on the days they don’t feel like doing them. The hard part about crossing between this moment now and the goal is usually the ingloriousness of everyday tasks. We want to win the lottery instead of grinding out consistent work. Want to go in and have a “Rocky” session at the gym. Want to feel it working. But, as Ice T reminded us, “Shit ain’t like that.”
“To me, the sign of a really excellent routine is one which places great demands on the athlete, yet produces progressive long-term improvement without soreness, injury, or the athlete ever feeling thoroughly depleted. Any fool could create a program that is so demanding that it would virtually kill the toughest marine or hardiest of elite athletes, but not any fool can create a tough program that produces progress without unnecessary pain.” - Mel Siff
A few weeks back I wrote about using the gym as a practice environment to eliminate shortcutting from your daily habits. In the same way, we can use the gym to learn about patient and long-term progress. If my goal is to get to twenty pull-ups, my behavior doesn’t need to be trying twenty pull-ups every single day. It’s actually to do pull-ups at all, progressively, over a long enough period for my body to adapt. It’s about learning what other exercises support that goal. About understanding rest. About recognizing that excellence is never a single-factor event.
If my goal is to be a better communicator, I need to approach my daily conversations with the intent being a little better, not being amazing right away. I can slowly build all of the skills of listening better, responding carefully, and working to assure my message has been heard, but it can’t all happen at once. And I have to accept that I am going to suck at it for a while. Small, regular changes in behavior instead of revolutions. Strategy and tactics.
There is the saying about it not mattering how fast you dig if you’re digging in the wrong place. And so as my pendulum swung from looking exclusively at the horizon with my big dreams to looking at my small, daily changes, I started to realize that the daily habits were their own problem.
I can have a daily habit of exercising, eating right, reading, or whatever, but unless I am doing these things with some sort of intention, I am going to be disappointed in the end. Example: “I exercise every day, and I am still not getting the results I had hoped.”
In my job as a coach, I am usually a person’s last resort. If someone is struggling to get better, they’ll start with the low-hanging fruit: they’ll listen to a podcast, or do what their friend appears to be doing, or maybe find a program for free online. They might download an app or take a class. And when they still are not progressing, they will usually give up and blame something external for their struggle. A few will finally decide to hire a professional.
And why does coaching work? Because a good coach can help the athlete find their way out of their ruts. Keep them from obsessing over good daily habits. Help them find the proper amount of overload and rest. Get them out of the planning and into the doing. Help them see that what they are doing right now matters, and it ties into the Five Year Plan.
The lesson I finally learned is this: If you’re not looking up at the horizon, who knows where all these small steps will take you. And if you’re not willing to grind out all those small steps, it doesn’t matter where you fix your gaze.

