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The Hole Where All The Success Leaks Out

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Each of us has a few professional-level skills—usually ones relating to our jobs, or hobbies we’ve been trained in formally. But when it comes to everything else we do, we’re amateurs.

Being an amateur just means below pro level—you may do some aspects quite well, but you still muck things up that a professional never would. For example, there are dishes I can cook pretty well, but I’m no chef. I chronically overcook vegetables, serve things I haven’t tasted, and who knows what else that would make a proper chef cringe.

There’s a huge upside to being an amateur, however. On the excellent Farnam Street Blog, Shane Parrish dusted off a brilliant insight about effectiveness and expertise, which he found in an old “get better at tennis” book from the 1970s.

Shane isn’t particularly interested in tennis. Neither am I, and chances are you aren’t either. But this insight is so powerful and universally applicable that anyone could use it to drastically improve their performance at virtually anything—any job, any art, any sport, any skill at all. 

The author of the book, Simon Ramo, was very interested in tennis, however. And he watched a lot of it, looking for what makes some players better than others. One thing he noticed is that the pros weren’t simply better than amateurs, but that they won their matches in a completely different way.

When pros meet, matches are decided mostly by a slight edge one player has over the other—in speed, awareness, or some other highly-trained quality. Their rallies go back and forth, both players knowing where they need to be, until one player puts the ball just beyond the other’s stroke. Pro players have all the fundamental elements mastered, and they win by being slightly better than their opponent at one or more of them.

When amateurs meet, they don’t edge each other out by being slightly more skillful. Instead, it’s a contest of who makes the fewest huge, gaping blunders. Amateurs constantly make egregious point- and game-losing mistakes, of the sort that pros no longer make. The outcome is decided by who makes the fewest—or least catastrophic—such mistakes.

And of course it works that way. Getting to the pros is a long, arduous process, one that filters out players with major flaws in their game. Coaches leap on those flaws as soon as they see them and drill them out of their athletes. Amateurs don’t go through this filtering process, so the flaws and bad habits remain, costing them bigtime every single time they play.

Everyone’s strategy, therefore—whether you want to win more amateur matches, or graduate to professional status—should be to identify and eliminate these big, costly rookie blunders, one by one. This is far more effective than getting quicker, hitting harder, or making that one brilliant shot now and then.

The same principle applies across the non-tennis world. Everything has its own list of classic amateur blunders:

Poker: slow-playing every good hand; betting without remembering your position

Frugality: buying lunch instead of packing one; trying to “tighten the belt” without tracking the numbers

Meditation: trying to silence mental chatter; only meditating when you’re in a good mood

Office productivity: leaving email notifications on; switching tasks when you hit a hard part

Just one of these blunders, made consistently, can undermine almost everything you’re doing right. Each is like a hole where your success leaks out. If the hole is big enough, or there are multiple holes, it’s hard to get anywhere beyond “struggling,” no matter how good you are at other parts of the game.

The good news: this also means that fixing even one such hole, or starting to, will make you immediately better, and not by just a little.

The boxer who stops dropping her right hand while throwing a jab becomes immediately and permanently better. The freelancer who quits trying to compete on price suddenly has a much easier time getting decent clients and interesting work.

Think about your best-honed skills, whatever they are: designing websites, selling cars, moving furniture, splitting logs, cooking omelets, forming concrete, tending bar, writing papers. Whenever you observe an amateur doing something you’re really good at, you will always spot major, self-defeating mistakes they are consistently making.

Amateur blunders take one of two forms: a tendency you’re aware of but don’t think is a big deal, or one you don’t even see. In both cases they’re essentially invisible to us until we either stumble across a better way, or (more often) a veteran points out the problem to us.

I’ve been lifting weights for almost three years now, and while I’m certainly fitter and better for it, I haven’t made very consistent progress. A determined beginner could start today and easily surpass me in six months.

I’ve coasted on this trajectory for a while, and only recently sat down with a pencil and paper to diagnose the problem. When I thought about what accomplished lifters do that I don’t, one thing jumped out: they definitely don’t miss as many workouts as I do. When I get busy, tired, or cranky, I frequently cut a workout short, or I “reschedule” it, and then it usually doesn’t happen at all.

This is a classic rookie mistake: trying to train without a consistent standard. I’m probably doing dumb things too but that’s a big one.

So I sketched up a very modest program, less than half of what I “normally” do, and then resolved to complete every rep of it for three months. The idea is to completely eliminate this one gaping blunder, my casual inconsistency, before trying to improve at the “top end” of things—personal bests, big volume, showy numbers.

Three weeks in, I haven’t missed a set, and the whole endeavor feels completely different. There’s no second-guessing, no bargaining with myself. I’m doing less work and advancing more quickly.

Now that I’m watching my consistency closely, I realize I had probably never completed ten consecutive workouts without skipping or shortening at least one of them.

That’s kind of embarrassing, but it’s also a hugely valuable discovery. There was a great big hole in the bathtub the entire time; no wonder it was filling so slowly. Meanwhile, I was fixated on the faucet part of the equation, and how I could crank it open even wider.

What are your chronic amateur mistakes? Think about where you’ve been stagnant, and ask yourself what you do that the pros would never allow themselves to do.

What are the big holes in the tub? If you don’t know, any veteran can surely tell you.

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Photo by Ben Hershey

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{ 34 Comments }

Calen May 15, 2018 at 2:24 am

You have a tendency to post profoundly helpful, insightful things at exactly the time I most need to read them.

More than that, you have the ability to take small truths that seem so self-evident that they’re almost always overlooked, and you drill right down to the core of them and present them in a way that makes them new again to your readers and makes them (or me, at least) wonder why they forgot them for so long. Very much your style, I think – spotting meaning by stopping, and watching, and actually paying attention to the things others rush by.

Anyhow, I don’t want to get too ebullient here. But thank you. This bit made my night. And gives me a pretty big understanding of how to tackle some things tomorrow.

One small helpful bit here: a good way that comes to mind to find the big, obvious holes you’re talking about is through mental inversion. When youre trying to improve at something, instead of asking yourself how best to succeed at it, ask yourself how best to fail at it. Come up with a list of big, obvious ways to fail and ask yourself how many of those things you do. Often, there are a lot. It’s just that they’re obscured by a layer of excuses that hides them from notice until you look for them directly.

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David Cain May 15, 2018 at 9:12 am

Ah, I love this mental inversion idea. I’ll look forward to trying it. I suspect that for a lot of things, the answer to “How best to fail at this” will be close to what I normally do :)

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Kent Fackenthall May 16, 2018 at 8:03 am

Great comment. I dig the inversion idea as well as a compliment to what David wrote. Between the two ‘views’ one could potentially really get a handle on where to focus efforts and what not to repeat. Thanks.

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Aleisha May 18, 2018 at 4:14 pm

Thank YOU. The mental inversion idea bridged a gap for me that will help me actually act on this article’s premise.

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Calen May 22, 2018 at 2:54 am

Hey, guys,

I’m really glad that you found the mental inversion thing useful. Between that and the advice that David provided from this article, I’ve sat down over the last couple days and asked myself some hard questions. They’re mostly variants on the theme that David discussed here, although occasionally I reframe them. So, some of the areas of my life where I really feel like I’m falling apart – productivity, money management, close social relationships. And then I ask myself, is there a simple, basic, easily corrected thing that I’m failing to do that is sabotaging me? Really simple, easy-to-implement stuff that’s like “if you put 10% effort into this it will take you 50% of the way to where you want to be.”

And, of course, for each area of my life I’m struggling in, there’s something like that. A very simple “basic technique” thing that I’m messing up on which undermines any other attempts I make at improving. And with some small tweaks to my behavior I’m noticing some small effects.

An example: I have trouble managing my money, which is very dangerous because I’m a poor graduate student. Some of the most basic skills, I’ve neglected for years – simple things like tracking my spending. So I downloaded a tracking app (simpler for me than a pad of paper) and am logging my purchases. The simple act of being aware of it has curbed impulse purchases substantially.

An interesting side note – I’m a smoker, and I usually smoked half a pack a day until two days ago when (you guessed it) I started logging my money. Apparently, the simple act of logging my purchases and having to look at a $10 expense for a pack of cigarettes is aversive enough that I couldn’t justify buying a new pack. So I’ve been smoke free for the last two days, and I figure, since I’ve broken through the worst of the withdrawals (today was nasty), I’ll ride this wave for a while and see if I can drop this habit permanently.

I did not expect this; it was actually a very impulsive choice, not premeditated at all. I think that a lot of things had to line up to make it happen, though, so it’s not just the “find the hole where the success leaks out” thing that made me quit. And, of course, these types of changes are only made meaningful by sticking to them long-term: I’m not fatalistic, but I’m hesitant to talk about having “quit” until I’ve proven to myself with my own actions that, yes, I’m sticking with this change.

But still, I think that’s a pretty cool ripple effect. I thought you all might appreciate it.

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David Cain May 22, 2018 at 11:33 am

Hey well done. This notion has really changed my life in the last two years or so: that we’re always closer than we think to making substantial changes. Like you say, the simple change from not tracking spending to tracking spending makes an immediate difference to the outcome, and in many ways it is easier to live that way. It’s just a matter of hopping out of our usual groove to a different way, and often that different way is easy to identify if we just reflect on it a bit, or better, consult someone who is good at what we want to be good at. Best of luck with the no-smoking adventure!

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Zoe May 15, 2018 at 2:32 am

What a simple yet powerful way of looking at things. I seem to spend more time thinking about the things I should (or want to) be doing than actually doing them. As a result, I end up resenting myself for not putting those thoughts in motion more often and almost like a form of punishment, maintain myself in this inertia. It’s a vicious cycle :-(

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David Cain May 15, 2018 at 9:15 am

I suppose we can never do everything we think we should do, because doing takes much more time and energy than thinking. So we always need to be giving ourselves a break, for most of it at least.

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Curtis M Michaels May 15, 2018 at 3:16 am

Thank you yet again, David. I recently doubled down on my commitment to my marriage and we are communicating through problems that had scared us both for two years.

Your blog post reminds me that I need to make the same level of commitment to succeeding at my freelance work. I hereby commit myself wholly to the success of my freelance career.

Thank you for inspiring and for witnessing it.

By the way, I have completely stepped away from social media. I do occasionally miss some of my online friends, but we swapped emails so I shoot the occasional message out and get one as well. I’ll go back later, but this is good for me. Thanks again for helping me to rethink that.

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David Cain May 15, 2018 at 9:18 am

That’s great. This way of thinking is new to me but so far it really simplifies things. The biggest difference is that you don’t need to commit to “stepping up” or “sorting things out” in some vague general way, you just commit to identifying and fixing one major hole in your “game” so to speak.

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Accidental FIRE May 15, 2018 at 3:41 am

switching tasks when you hit a hard part

That’s me when writing a blog post or doing a new design. And social media is always the culprit. “I’m stuck at the hard part of explaining what I’m trying to explain, so let’s check Reddit”

Ugh. I know I do it but it’s so hard to change habits like that. This is a reminder that I need more discipline, thanks.

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David Cain May 15, 2018 at 9:20 am

Realizing this mechanism in my writing has been huge. There is zero temptation to take breaks when I’m on a roll, and huge temptations when I’m struggling with something. But it’s really the worst time to take a break. I try to quit for the day while I still have some momentum.

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Wildly Imperfect May 18, 2018 at 11:21 am

switching tasks when you hit a hard part.

This was an Aha! for me as well. Now that I’m aware, I hope to change this. It will be interesting to start paying attention and discover what other holes might be leacking.

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Agustin May 20, 2018 at 10:32 am

Switching parts when hitting a hard part.

You know David, when that hard part of a task gets hard I end up more often than not, going to this blog and reading your latest entry. What a irony lol. But alas, stopping this behavior is critical for fixing the big holes. Great article!

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Ameen May 15, 2018 at 3:57 am

I really like your idea of approaching learning and improving a skill as discovering answers instead of tediously accomplishing goals and reaching targets. School has trained people that learning is a means to an end rather than something to be enjoyed in and of itself. This is why many people like the idea of learning something new instead of actually learning it because it’s painful to see the gap between where you are and where you want to be.

When you view learning as something where you’re behind and you need to catch up as opposed to a process driven by curiosity, learning becomes embarrassing rather than something that could be exciting.

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David Cain May 15, 2018 at 9:25 am

Agreed… two years ago I took a writing course at the local university, not having attended a class for probably ten years. And I was amazed at how different it felt, being there purely to learn, rather than to graduate or gain a credential. I feel like I learned five times as much in every class. I’m not sure what the state of public schooling is these days but I remember just wanting it all to be over.

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Gabriel Rocheleau May 15, 2018 at 7:29 am

I enjoyed reading this post very much. You’ve definitely got this nailed.

This past year, I’ve read a lot about “learning”, and am fascinated by what differentiates excellent performers/achievers from “standard” ones. My main takeaway is that pros consciously focus on eliminating their weaknesses, while amateurs will settle for a relatively satisfactory level of competence.

This is why, for example, people tend to stagnate after a year of learning an instrument. Once they get good enough to play a few pop songs, they get complacent, and stop improving, even after many, many more years of “practice”.

What are you actively trying to improve at the moment? You mention weight lifting, but I’m curious as to what other skills you’re applying this mindset toward.

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David Cain May 17, 2018 at 9:15 am

I am focusing on four areas this year: fitness, meditation, work habits and relationships. In each area I’m trying to identify the most obvious self-defeating rookie mistake, and I have a pretty good idea for each of them now.

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woollyprimate May 20, 2018 at 9:40 am

Ah, now I’m curious. What are they? If you don’t mind sharing. I can’t imagine you’re making rookie mistakes in meditation.

I’m also focusing on relationships and also decluttering/organizing. My mistake in relationships up to now has been to presume the other gender has the same mating psychology as I do.

And I’m making pretty much ALL the mistakes you can make in decluttering: not having a place for everything, not putting things back, assuming unpleasant tasks take a long time and therefore, not doing them, etc.

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Tonya May 15, 2018 at 8:03 am

I feel like this with my website. How is it that I’ve been doing it for 6 years, yet blogger x comes along and in 6 months they are making lots of money off their blog and have thousands of views? I imagine it’s the same thing. I haven’t make the commitment to strengthen those “weaknesses.” Good stuff as usual!

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David Cain May 15, 2018 at 9:26 am

Same here… I’m happy with this blog but I’ve been at this almost a decade, and I remember seeing bloggers fly past my numbers in less than a year. That’s good though — it means there are still big holes to plug that will make a big difference.

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Edith E Esquivel May 21, 2018 at 10:42 pm

Numbers don’t mean anything. Popularity is not always liked to quality. Your blog is amazing.

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Brani Andreev May 15, 2018 at 12:24 pm

Thank you for the insights! Identifying and eliminating weak areas in what we do is essential in getting better. Some say that the path to perfection is never being quite satisfied with your achievements. Perhaps that is what helps us discover what we lack or identify the “hole”. I would think you would agree that even pros have “holes” to overcome and weaknesses to eliminate. I also feel there is something greater that helps us on our path to getting better in something, and I feel it stems from deep inside, from who we are, from how we have grown and developed so far.

And what about faith, passion, excitement? They surely would add that “spice” or boost to our persistence to keep on track, to identify the “holes”, to simply want to be better …

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Max May 15, 2018 at 12:51 pm

> Three weeks in, I haven’t missed a set, and the whole endeavor feels completely different. There’s no second-guessing, no bargaining with myself. I’m doing less work and advancing more quickly.

A wise man once said “rules are good decisions made in batches” :)

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David Cain May 17, 2018 at 8:53 am

Haha I should read that guy’s stuff :)

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Abhijeet Kumar May 15, 2018 at 2:09 pm

This is quality stuff. I read through the entire article, and there was a lot of in depth points you made in every part. But yes “The Hole Where All The Success Leaks Out”, this is real. It took me sometime to realize why I struggled so much at my job. I could do well sometimes, but it was always a bathtub that was not going to fill (other sides of the equation — social life, family, long-term goals).

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Timothy Mills Jr May 15, 2018 at 5:04 pm

David,
Thank you so much for your article. I really enjoyed the ideas that you present here. It is incredibly beneficial for me to think about fixing the glaring mistakes in my endeavors, because I believe there is a whole lot of low-hanging fruit there, rather than my typical tendency to try to fix everything all at once as I wonder why I am not an expert. I really like the way that you presented the information by viewing it through the lens of someone who really wanted to become an expert at tennis.

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David Cain May 17, 2018 at 8:57 am

Low hanging fruit for sure. Every skillset is different but we’re talking about fixing the what’s most glaring and obvious to any veteran of that skillset. And the more glaring/detrimental the hole is, the greater the gain from addressing it.

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Beth May 15, 2018 at 9:34 pm

Oh my gosh, thank you for writing this. This gave me a huge aha. Thinking about all the things I don’t have compared to competitors and things I should be doing is suffocating, but focusing on the blunders to avoid is so much easier to think about. Thank you.

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KG May 18, 2018 at 11:03 am

Great blog and love your insights, as always. Really provoking self awareness. Seeing the unvarnished truth has such a positive effect!

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Steve Markham May 18, 2018 at 2:36 pm

I’ve had that exact insight with respect to chess. Step one of improving your game is to stop making completely horrible blunders that immediately lose you the game. Step two is to notice when your opponent makes blunders so that you actually capitalize on them. Chess is nice, because after a game you can have a computer find your blunders, and your opponents, to see how you are doing. I have many, many games where it was just one blunder after another and neither of us noticed for 5 or 6 moves. If only there was a super-human life coach to review everything else I do looking for the big gaping holes:)

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Réparateur Électroménagers May 19, 2018 at 1:22 am

Totally agree, it’s both easier and more worthwhile to avoid a few big mistakes than to accomplish difficult acts.

I think that in business as in fitness, consistency is the key. Even if it’s obvious, we often get distracting by any new shiny thing.

Great post as always David, you suceeded in going deeper in the topic while keeping everything simple.

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Shane McLean May 19, 2018 at 12:57 pm

David, love this post and I don’t want to add what has already been added to the comments above. I’m interested that you used weight training as an example. I’ve been a personal trainer for 8 years and I’m pretty good at coaching clients but lousy at coaching myself. That’s why I hire a coach to write my programs. Not only do they see the gaps, it exposes me to a different way of doing things.

If you keep showing up and not missing a rep, good things will happen .

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TJ May 21, 2018 at 5:45 pm

The most obvious gap in most people’s life when it comes to most part of their lives is – I think – not getting enough sleep. It’s almost like a sort of meta hole.

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