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.

  • Ken Wert

    You’ve hit on something very important, here, Scott.

    As I’ve said elsewhere, as a high school teacher, there are students who can be motivated to excel. Others who don’t care and can’t be budged. It is at the level of giving them a reason to care about how well they do that a greater effort has to be made if improvement is to be had.

    Still, I think which buttons are pushed is much more than simply “the details.” There are so many buttons available in life to push. Many of them, however, are quite self-defeating. Some of them are self-destructive. Both, I think, are critically important. “Why should I push any buttons at all?” has to be answered to start any kind of process to begin with. But, “Which buttons should I now push?” is equally important.

    What’s nice about the blogging community is that those who come to our sites to read what we have to say have actually sought out that advice. So maybe selling the point is less critical than in a captive audience.

  • Nick

    I think there’s also an element of not killing yourself- ie, conserving your energy. If you went 100% in on all projects, you’d be dead by Tuesday.

    Good post.

  • Nicky Spur

    Modeling and experimenting are great for progress, especially if the motivation is already there. I’ve found that the fine balance between the two becomes a catalyst for progress whereas if you spend too long modeling someone you lack identity. If you spend too long experimenting you also lose sight of your past simply because you don’t know where you’re going.

    Interesting post.

  • Bruce

    I think the problem with the concept of trying one’s best is that the term feels like an absolute (nothing better is possible) that cannot be defined. My best in terms of what I have done before? what I am capable of of? when I am at my peak? when I feel low? When I have a cheering section? In spite overwhelming odds? When the going is smooth? Add into that the complexity of constantly changing environments, both internal and external, and even defining “best” seems impossible.

    In my opinion “Did I try my best?” really means “Did I do better at accomplishing this task in at least one way?” (Faster, more effectively, more correctly, …) or “Did I apply more effort than the established norms for accomplishing this, given these circumstances.” Answering those questions rather then “did I do my best?” allows me to more clearly analyse the expended effort and the reward that came from it, with out all the baggage of self doubt that an absolute like best entails.

    For me, motivation is the result of an “estimated effort to estimated reward” calculation, either with conscious contemplation or subconsciously. The reward portion does not just have to be the result of the task at hand either. It can be enjoyment of the process, pride in overcoming obstacles, enjoyment of the company that I do the task with…… you get the idea. I have found that if I am lacking in motivation to do something, it is because I have either weighted the effort too high or some aspect of the reward too low.

    Anyway, just my 2 bits

  • n.roberts

    Hi Scott
    Good reminder of what i could have done with your learning reasoning.Behind it all is another story….mine was over – sensitivity,and not seeing the wood for trees.Luckily somehow books was in my being,and nutured that part alone.Frightening how things dont connect,would you say,and moved on with relative love of the job,and not the studying synonymous with your great stuff!

  • Kieran

    Hey Scott

    Could you share a small list of some of the thought leaders (and relevant books/vids/articles from them) on motivation that you’ve found most enlightening to date. (eg. Dan Ariely, Daniel Pink)


  • Scott Young


    Of course energy management matters. But there are plenty of times where we want to work harder on a goal, but fail to summon the effort. Those are the situations I’m talking about.


    “Best” is a vaguely-defined absolute. Perhaps it’s better to talk about times where we fail, but there was still significant effort unspent. My point still applies even if we aren’t talking about extremes.

  • Jonathan

    Great post, Scott. Learning to try harder has got to be the key to life, and it is absolutely context specific. There are countless lives who would have flourished in one direction, but fell into another without ever growing that self-awareness. It takes a lot of energy to improve in uncomfortable areas. You have to accept a kind blindness for a while. Man, it’s tough. Most people don’t see effortfulness as an improvable skill in itself. Instead of thinking of learning to play the piano, I like to think of learning how to learn to play the piano. It gives me leverage on myself when I see a drift occur. It is worth considering also that no one can be all things in all seasons. We are social animals and solitary beings at points and intersections. I’m sure, as your career expands, you will find socializing with your readerbase easier and more rewarding than interacting cold at clubs of interest. When the party comes to you, you’re habitually the life of it. And that’s motivating! – Jonathan

  • Elizabeth

    So, will you tell us about Feynman’s heuristics?

  • Clingspiration

    I completely agree. Effort, self-discipline and self-motivation are skills. It’s reassuring to hear – because like playing an instrument, the skill of self-discipline can be learned, one small habit at a time.

  • Monish

    I don’t agree with this article.

    The focus should not be on self-motivation. Rather, the relationship one has to one’s word. It’s simple, when you say you’re going to do something, do it. Ask yourself: what is your relationship to your word. Is it Gold, Silver, or Bronze. Not wanting to do something because you FEEL like not doing it, isn’t an issue of motivation. it’s an issue of your commitment to your word. People get up in the morning and go to work, DESPITE, not feeling like they need to go to work.

    Of course, you cant be 100% on the dime about your word, but u can work at following through as much as possible.

    A lot of the above thoughts come from Landmark Education. If you are familiar with the work, they do not go into self-motivation or effort or self-disipline — until they have taught people how to honor their word and how important that is to making your life work for you.

  • Vipul Shah

    I think having a clear action plan which is unambigous matters a lot. I have been able to build a consistent exercise schedule because it is dead clear at what time I need to work out and what I need to work out. But I havent been able to do the same with some other goals I had like self study because there are lot of occassions where I need to think and decide which actually takes away the motivation.

  • MBVV

    What an excellent article, I really enjoyed this. Took my own previous thoughts and built upon them. Excellent work.

  • MBVV

    What an excellent article, I really enjoyed this. Took my own previous thoughts and built upon them. Excellent work.

  • richard coughlan

    Good article. I think we first have to accept that it is impossible to ‘try your hardest’. In the same way that perfection is impossible. You can try very very hard, but it will never be your best. Your ‘best’ is unacheivable. If you do a task 1000 times, trying your hardest, one time you will have done the task slightly better than the other 999 times but you could still do it better if you did it another 10,000 times. I think all we can do is try hard, focus on the job at hand, finish it, and realize this is the best we can do. In other words, be at peace with the fact that it is impossible to do your best. Focus on finishing a job. If you can finish something using your skills well, then that is your best.

  • mlaclave

    Your article was wonderful. I so appreciate how you spoke to the fact that effort is something we can all get better at. The desire to change can happen and putting forth your best is something we should always strive for. Thanks again.