When you set a challenging goal, you need to plan multiple ways to motivate yourself to ensure you follow through. There will be days you are distracted or have low energy. There will be unforeseen difficulties. Some of the necessary steps will seem like drudgery. You can’t just rely on your desire for the end state to spur you to follow through.

To ensure you always have enough motivation to follow through, I recommend (and teach) that you consciously seek to develop your own knowledge, values, and skills as a backup means to motivate action toward your goal. Improving your capabilities is your backup plan if you have setbacks or failures along the way. It is how you turn lemons into lemonade.

But you cannot improve your capabilities if you don’t know what they are. Self-understanding is the critical missing link for many people who struggle to achieve ambitious goals.

The role of self-understanding in committing to goals

By self-understanding, I mean your objective grasp of your own present psychology, including three kinds of stored content: your knowledge, your motivation, and your skills. Self-understanding is absolutely critical to setting goals.

A goal starts as an “I want” or an “I wish.” You imagine a future result and how wonderful it would be for you. But the commitment to a goal requires a clear-sighted look at the means needed to achieve that end, so that you can decide whether or not the result is worth the totality of effort it will take to get the outcome that looks so wonderful.

If you expect a goal will be easy to achieve, it can be a no-brainer to commit to it. If a goal has a low cost-benefit ratio, why not reap those benefits with a little effort? On the other hand, if it’s hard, then the pursuit of those benefits will take much time and energy, necessarily pulling resources away from pursuing other values.

Whether a result is hard or easy to achieve depends very much on your own capabilities at the moment, i.e., your knowledge, values, and skills.

Suppose you want to write a bestselling novel. That would be wonderful! If you have never written fiction longer than a short story, you will need to develop a number of plotting and writing skills. If you’re ignorant of how a novel gets published, you will need to learn something about that process to get your novel into print. And if you want it to be a bestselling novel, but you don’t like selling things, you will need to challenge that motivation and develop a love for rational self-promotion.

I never discourage people from setting ambitious goals just because they lack the necessary knowledge, values, and skills at the moment. These capabilities can and will be developed over the course of pursuing the ambitious goal. In fact, that’s the main way they get developed! People who pursue ambitious goals grow their minds and become more capable.

But you need to face the fact that if you will need to grow your own capabilities to achieve a goal, this significantly increases the total effort. The goal needs to be highly meaningful to make it worth that effort.

So, as part of a rational goal-setting process, you need to take advantage of whatever self-understanding you have to help you decide whether or not to commit to the goal and to help you make a doable plan for achieving it. You need to factor in what you already know about your own knowledge, values, and skills.

How self-understanding grows as you pursue an ambitious goal

As you pursue your goal, you will get many opportunities for furthering your self-understanding. Sometimes you will discover that a task was easier than you thought, or that a value was stronger than you thought, or that “you know more than you think you know.” (Oscar Wilde) That’s always nice.

But sometimes you discover that “you know less than you want to know” (also Oscar Wilde) — you’re ignorant. Or you discover the values you hold are weaker than you thought — they don’t stoke your determination to overcome old baggage or self-defeating beliefs. Or you discover the task is harder than you thought. You’re less competent than you expected.

You get this bad news through setbacks and failures. If you aren’t careful, you may wallow in self-criticism rather than use these incidents as opportunities to grow. That’s why you need to consciously pursue self-understanding as a value.

Elsewhere I explain at length the role of self-understanding in happiness. A key point from that discussion is that you need to constantly re-orient to values when you run into problems. Negativity kills creativity. Self-criticism shuts down productive problem-solving. A focus on failure breeds depression and makes it harder to pursue any goal.

Re-orienting to values is also the key to growing your capabilities. You can always reframe a discovery about any ignorance, old baggage, or incompetence into an awareness of:

• What you do know and want to learn
• What you rationally value and any old baggage you will untangle
• What you can do and skills you want to develop

This reflects a desire for self-understanding and a commitment to grow your capabilities. It is this value-oriented attitude toward embracing the facts that then unleashes creative problem-solving. When you see that you want and need to develop knowledge, values, or skill, you are then motivated to find another path toward the goal that gains them.

In other words, failure and setbacks are an opportunity to discover more about what it will take to achieve the goal. That knowledge is priceless. It is exactly what you need to know in order to succeed. If you value the goal, then you can see the value in this information. By growing your self-understanding, you improve your ability to achieve the goal. When you see what you can learn about yourself from a setback, you turn the sting of failure into the satisfaction of discovering important facts about yourself.

Self-understanding as critical to making it through the hard parts

When you commit to a challenging goal, you are committing to all of the actions that will be needed to achieve it, including any self-development. For example, I wanted to be able to teach new ideas, but my first forays into public speaking revealed that my presentations were subjective. This was discouraging at first, but it was clear that however my career developed, I needed better speaking skills.

So I joined Toastmasters — and stayed for 20 years. The traditional Toastmasters program was brilliantly designed by Ralph Smedley to ensure that you could see your own progress with every speech, and indeed in every meeting in which you participated. When I was in Toastmasters, I observed that literally eveyone who worked through the old basic program of 10 speeches got much, much better. I too got much, much better with the help of fellow club members who happily gave me feedback and shared a similar goal.

But if your goal is challenging, there will be difficulties that are unique to you.

In my case, I learned pretty quickly how to give great speeches on topics of general interest. But when I tried explaining my new ideas in psychology, I still put my audiences to sleep. None of the generic public-speaking advice helped much. Nobody was able to explain to me how to implement communication truisms such as “put yourself in the audience’s shoes” or “tell a story that concretizes the point in a dramatic way” for my ideas. I could do it for other people’s ideas, but not for my own.

This is where my commitment to self-understanding made the difference. I analyzed every failed speech in great detail to see what I needed to learn from it about where my knowledge broke down, in comparison to my successful speeches, which I found easy. When I got discouraged preparing a speech — which was often — I used it as an opportunity to understand my own motivation. I figured out why it was such a slog and what was different when I could just speak off the cuff. When I had trouble concretizing my points with stories, I thought more about how to describe what goes on in my mind in an interesting way. In other words, I used my difficulties as springboards to develop new thinking and motivational skills for myself.

Eventually I wound up teaching these skills to the Thinking Lab. But I developed them for myself to get better at explaining my ideas to club members in the standard Toastmasters 5–7 minute increments. If you want to know whether I eventually got good at it, you can judge from my talk at last summer’s OCON. That talk was given semi-extemporaneously, by breaking the topic down into seventeen 5–7 minute segments, and delivering each segment as its own “speech” using just a few lines of notes, just as I had done in Toastmasters meetings for many years.

It’s the experimental method

How did I do it? By the experimental method, which I learned as an engineer.

Whenever you set a goal that is unique to you, you will need to learn as you go. When you come up against a step you don’t know how to do, or you face some uncertainty about whether you are going to be successful, you then need to design the next task as an experimental step. You make your best judgment about what you think might work given the limits of time and skill, plus you identify how you will know if it works. Then you execute on that experimental step. Either you succeed (great! you have more capabilities than you thought!) or you fail (great! you have more information than you had before!).

An experimental step is always win-win — whether you succeed or fail, you advance toward achieving your goal.

You can’t just observe facts about your psychology; you need to infer them from results. It is because I was committed to self-understanding that I was able to run the trials and motivate myself over the long haul even when I failed. Experimentation is self-motivating because it is win-win. You always can get new information when you run an experiment — in this case, about your capabilities — so you will always get a bit of a payoff from doing it.

Consistent payoffs are the key to motivating work over the long haul. Committing to self-understanding — and self-development — is the means of ensuring you can keep getting payoffs from every step, even when the going gets tough.