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Ultimate motivation: The Attainable Challenge

8 min readDec 1, 2020


Possibly the most motivating dynamic in the human condition.

“Desi” looks out her window to the partly cloudy sky. She’s standing in her bedroom, trying to decide what to do first: check her phone, start a load of laundry, or chip away at a project. Some of these are wants and some are “shoulds”. The “shoulds” weigh in her mind while the wants swirl and multiply: looking for gift ideas, swiping some profiles, crushing some candy, or maybe going out to throw a few poke balls. Ugh. Desi flops down on her bed to think. Her phone buzzes. Several minutes later she wakes up from a cat video haze to remember she should to get a head start on something for work. Double-ugh. She needs to brighten her mood before opening her work laptop. Ten minutes of game should do it.

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Desi’s situation isn’t too far from anyone else’s. She’s navigating motivation. We all do this. However easy or difficult our lives are, we make our decisions. But why is Desi even struggling here? Why did she lie down and play on her phone instead of doing what she knew she should? Why did she choose one activity over another? For that matter, why do even the most “motivated” people struggle with making these choices?

I think something dictates a lot of this behavior. I think it fuels many addictions and sends us down the online rabbit-hole. Why play games, gamble, or shop for discounts? Why seek out a difficult job or relationship? How are targets for crime chosen? Why choose crime? Why do we seem helpless to keep procrastinating or persisting in a pointless struggle? What urge could be so strong? What kind of motivation could feel like the ultimate de-motivator?

Hint: it’s the title of this article

When people speak of motivation I think it’s most often put in terms of virtue: that a person’s choices are dictated by the measure of their morality and self-discipline. While that plays a part, I think it’s smaller than you’d guess. I think the most powerful kind motivator has nothing to do with virtue. I think it has to do with challenge — a particular kind, actually. An attainable challenge.

The Attainable Challenge is a situation that strikes a very particular balance between difficulty and success.

Think about desirable things, situations, and people. What makes you keep coming back for more? It’s hard to name, right? I bet I can describe it though: it’s fun, exciting, rewarding, or satisfying. It’s something that feels a little bit uncertain or difficult and yet you have some confidence in getting it.

I can also describe what it’s not. It’s not too easy and it’s not impossible. Too easy, where’s the fun in that? No story to tell or satisfaction in winning it. Too easy can even make us feel worse about ourselves. At the other end, impossible isn’t fun either. It can be terrible and demoralizing, even considering the bleak future of certain failure — much less living it.

So we keep desiring things that appear to be a mix of difficulty and success, while avoiding things that seem easy or impossible. If it’s in that middle-ground then boom! You’re all about it.

How this plays out: relationships

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Think back a moment on the people you’ve really wanted to either date, have a fling with, or rope into a long term relationship. Are these people that you’d consider in your league? Not usually. How about below your league? Hardly ever I’d say. Most often these are people who are out of our league in some way: more attractive, wealthy, prestigious, funny, smart, etc. than we think we are. We want them. We want to win them over.

Why don’t we want the other people as much? In your league or below, they’re too easy to get. They either seem downright undesirable or just that really, you should be able to “do better” than that. It’s easy to think that if you don’t have to try harder for someone, what does that say about you?

But there’s a limit of course. All of us give up at some point. Maybe it’s the most popular guy in school or the Hollywood starlet. Somewhere we think, “No, they’d never notice me.” and we set our sights a little lower.

For the people in this middle challenge area, we do things — sometimes crazy and even self-destructive things — to try to snare them and keep them. We tolerate disinterest, drama, rejection, neglect, character flaws, disrespect, and abuse to keep trying. What is so powerful that we accept domestic abuse? The Attainable Challenge (AC) is that powerful. Changing this person to make them not flawed is the challenge and it’s totally possible, right? Sometimes only in hindsight can we see that yeah, well, not so much. We over-shot on what we thought was attainable—and the results can sometimes be the worst things to happen in our entire lives.

Shopping and collecting

Getting deals is a great attainable challenge. It’s not easy or impossible but it certainly takes effort and time. Possibly experience and luck. In the case of bargaining, it takes skill. As a reward, you get both the thing you’re after and the satisfaction of attaining it in a special way.

Buying things that others can’t? Great. Finding something your friends are getting too? Add a social reward to the mix. There’s always more stuff to buy and sales happen often, so it’s there as an AC whenever you have the desire and ability. It’s no wonder people ruin their futures with credit card debt.


You’ve heard of the term “workaholic”? Think of the ones who keep at it, regardless of necessity. They see little cycles of success that fuel them into maniacal levels of dedication. Longer hours, tougher assignments, and dwindling personal life become the thing to do. Slackers and moonshots aside, this is what people think of when saying someone is motivated at work.


Video games, board games, card games, role playing games, and mind games. All are compelling and all can be addictive. People have actually died from video game addiction.

They’re so addictive because they’re basically the Attainable Challenge on repeat. An infinite loop. You fail? You try again. You succeed? You keep going. You can even tune it: If it’s too great of a challenge then you can lower the difficulty. Too easy, play at higher difficulty. It’s a never-ending cycle of AC and focus that time just pours into like a rushing waterfall. Lost touch with some friends for a few weeks? It was probably that game they just started playing.


Now watching a tv show or movie might not seem like a challenge per se but finding escape in a good stream of entertainment can be more difficult than we’d like. Shows, movies, songs, theater, books, and likewise are all finite. There are only so many made from each creator or story, they take time to make, and you never really know if the contents are going to be engaging until you experience it. So it’s this great balance of seeking escape which certainly seems attainable and the challenge of finding the next source.

Hence, we get into frequent cycles of seeking and experiencing, trying to stretch together moments of entertainment delight—ever more motivated to reach a sustained bliss of displacing our mental states into the stories and sounds of others’ imagination.


Gambling is an AC depending on how you think about risk. If you see risk as a challenge, then you’re all in. People wanting less risk seek out the slots and computer card games. People seeking more risk sit at the card and roulette tables.

People regularly lose when gambling. They have to, otherwise there would be no profitable casinos. But most gamblers are able to win just often enough to convince themselves that yes, winning is attainable. And whenever they do win, the payoff is that much sweeter knowing they’re beating the odds. The AC just smooths over that little chunk of cognitive dissidence.


Physical activity has the advantage of hormones getting released during various levels of exertion and relaxation. If you can get over the initial hurdle of starting and discomfort, you’ve attained something right there. If you do a little bit better each session—which is natural—now you’ve got a cycle.

If you have any success winning at a sport and you don’t set your sights too high—you get prizes! Do well enough and you even get money or fame. Sports are organized with rules, so attaining success has clear paths of challenge. Keeping at it is what every prizewinner has done.


I don’t know the odds of successful crimes but some portion of them every year come out of desperation. They know no other option. But another portion happen either casually, carefully, or violently because the person committing them feels like there’s a reasonable chance they won’t get caught.

For the casual ones like a rich person driving in the commuter lane, the fact that they could get caught is really the only challenge, since they consider the punishment to be pittance. For felonies, getting caught is more the end of the game and succeeding in your crime is often challenge enough in itself. Whether you start small and build to more difficult crimes or surprise yourself with a big heist right away — every successful crime bolsters a criminal mind for the next potential success. Motivation enough for crimes that aren’t even necessary.

To our success or detriment

Many times the AC works in activities that makes us more successful, like our jobs or our health. But it can also ruin us. It’s easy to see that addiction is a common theme. Obsession to the neglect of other aspects of your life will certainly lead to those parts of your life collapsing.

The important thing to remember is that attainable challenges really are powerful enough motivators to make or break your life. Recognize them where they appear and use them wisely—both for yourselves and for those you love. That doesn’t seem too hard or too easy, right? 😉