The Skill of Trying Your Best

“As long as you tried your best,” was a phrase I’d hear as a kid. It was supposed to console you in the event of failure. Reminding you that, as long as you put your best effort in, then it didn’t matter if you lost.

Hearing that phrase as an adult, I wonder how often it really applies. How many times do we fail, even though it was impossible for us to try any harder? When do we lose, despite genuinely trying our best?

“I Could Have Tried Harder”

At least in my life, I’ve noticed that during most of my failures I wasn’t really trying my “best”. It’s rare when I can’t pinpoint a moment where I couldn’t have put in more effort, showed up more consistently or worked harder. The times when I went all-in and still fall flat on my face are greatly outnumbered by the occasions when I lost, but still had some chips at the table.

I took a finance class with a friend who had failed the previous three exams. He needed the class to graduate and wanted it badly. Yet, he still skipped many of the classes. When he failed the exam again, he blamed the difficulty of the course.

It’s hard to judge the relative effort of other people, but I don’t feel my friend is unique. Had he tried his hardest, he could still have failed, but it’s far more common to fail while there is still effort unspent.

The expression, “as long as you tried your best,” takes effort for granted. It assumes that the hard part was winning, and that everyone tries their hardest. Instead, the hardest part appears to be trying your hardest.

The Difficulty in Trying Your Best

When I’ll hear from other advice-writers, they often get frustrated with the apparent laziness of their audience. After all, they are giving them perfect advice that will surely solve their problem—but most people never do any of it!

But if the biggest obstacle is summoning the effort to try your best, then doesn’t this advice have it backwards? It’s telling people the second step—what to eat, where to invest, how to study—while ignoring the much harder first step of building the self-motivation to execute on all those things.

This means that the skill of self-motivation matters more than a lot of specific advice. Knowing how to flip on the switch that causes you to “try your best” is critical; the rest are just details.

Triggering Effort

If I tell people that I write about motivation, they tend to imagine me telling dramatic stories for inspiration. While inspiration is great, that’s not what I mean by motivation at all. Inspiring is giving someone a temporary push. Self-motivation is knowing how to push yourself.

Writing about motivation, for me, isn’t about sharing inspiring stories. It’s about looking deeply into the psychology of why we act or don’t act. Understanding what triggers effort is worth hundreds of stories about climbing a mountaintop.

Motivation isn’t only emotions either. Although getting excited about something will encourage effort, a lot of motivation is coldly rational.

Through hundreds of hours of self-experimentation, I’ve discovered that performing a habit daily makes it far more likely you’ll keep up the effort than doing it four times per week. That isn’t immediately intuitive or emotional, yet it works.

The design of your project can also affect effort. If you eliminate the need to make routine decisions, effort goes up. Studies have shown that making prenatal HIV testing in Sub-Saharan Africa opt-out instead of opt-in greatly increased results—no inspiring speeches required.

Effort is a Skill

If someone fails a race because they lack the skill of running, we aren’t too hard on them. After all, running takes a lot of practice, and some people are better than others.

But, if someone fails a project because of a lack of effort, most people are ruthless in their judgment. Laziness is treated as a sin, not an inability.

I want to flip that understanding. Not one that chastises people for failing to try their best (how often does nagging work?) but by deciphering the code for improving effort.

Guilt is an unproductive emotion. Yet a lot of people guilt themselves constantly for lacking the discipline or self-motivation to succeed at a particular goal. A far better use of energy would be trying to uncover what tactics successful people used to stay motivated.

Effort Isn’t Universal

Another common assumption is that effort is a character trait, irrespective of context. Lazy people are always lazy, and industrious people are always hard-working. This is nonsense.

I’m great at summoning up my effort for particular types of goals. I generally finish projects well ahead of time and I’m highly focused doing my work for the day. While I don’t embrace workaholism, I can summon the effort to work without interruption for 12 hours in a pinch.

Yet I’m a disaster when it comes to summoning effort for other types of goals. When searching for an apartment for August, I procrastinated terribly. Now that I have the apartment, I’ve also been procrastinating a lot on searching for furniture.

Now I could rationalize this to myself by saying that my work is more important, and that I procrastinate on the second tasks to focus on the first. But, if I’m honest with myself, that’s not the real reason. The reason is that I’ve carefully trained the skill of self-motivation with certain types of work and projects, but not in others.

Learning Context-Specific Self-Motivation

Hunting for furniture may be a fairly trivial task. But we all have strengths and weaknesses of self-motivation that are far larger. Certain goals that we always show up for and try hard, and others where we fail miserably to put in the effort.

It could be that we simply have less intrinsic motivation for some goals, but that can’t be the full explanation. My self-motivation skills work better for my work life than my social life, even though I care about both.

But the two goals are also completely different in structure, which means certain self-motivation tactics will work well on one but not on the other. Habits and endurance are critical to summoning the effort to work, but flexibility and boldness matter a lot more for meeting people.

How Do You Learn to Try Harder?

Just as it’s okay to be a lousy runner, it’s okay to lack certain self-motivation skills. You can learn to run, most of the time, and you can learn effort too.

The two ways I’ve learned effort are by experiment and modeling.

By experimenting, you pay great attention to how you do things when you are motivated, and how you do things when you aren’t. Most people try the same approach of emotional force of will, and so they tend to fail repeatedly at the same goals. It’s smarter to observe carefully the differences between sticking and slipping, so you can engineer them from scratch.

Modeling is simply looking for people who have achieved in the area you want to build effort in. People reveal their heuristics for self-motivation when they talk. It doesn’t take too many success stories of entrepreneurs to observe how they tackle fear of uncertainty, or successful dieters revealing how they avoid temptation.

When I listen to inspiring stories, what interests me most are uncovering the mental heuristics the person used to commit themselves to effort. I’m currently reading the memoirs of Richard Feynman, Nobel laureate and physicist, and what interests me most aren’t his accomplishments, but the mental heuristics he applied to motivate himself in science.

Trying Your Best

Do failures still happen when you’re trying your best? Of course they do. But 100% self-motivation, where not a single opportunity is wasted and effort is at a maximum is rare. Reaching the point of “trying your best” is the limiting constraint for most people.

If you recognize that effort is a skill, then you can also try to figure out how it works. Learn the skills of self-motivation, instead of wasting years of effort on guilt over opportunities lost.