Find Your Superpower By Identifying Your Biggest Weakness

Why Biglaw requires associates to pay such close attention to detail, and how the flip side of my sloppiness led to success after finding the right environment

When I was a young associate, I struggled with detail oriented work. I’d miss all kinds of typos and mistakes. Which I’d usually realize only after hitting the “send” button. For some reason I never got the memo about proofreading emails before sending out important emails. I’ve always been like this, though. Growing up, I remember constantly being told that I needed to be more careful because mistakes wouldn’t be tolerated in “the real world.”

It’s funny how “the real world” is always used as a boogeyman. Like when teachers would tell me to memorize multiplication tables because “in the real world, you won’t be able to bring a calculator with you everywhere.” Or when they’d warn me to stop playing video games because “in the real world, you can’t make money doing that for a living.”

They were wrong about both

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so after I got older, I should’ve known to take their views on “the real world” with a grain of salt. But old lessons die hard. Even after college, I always viewed my lack of attention to detail as a flaw that needed correcting.

Going to law school certainly didn’t help.

I ended up at the wrong job

I developed a few coping mechanisms during my first year of law school. Like printing out several copies of the same document so I could carefully proofread them multiple times. That’s how I made law review,

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by the way. I printed out a dozen copies of the proofreading exercise and reviewed each of them carefully by hand, before combining my edits into a single document.

My friends thought I was crazy.

“Law review will set me up for life,” I explained. Of course, what I was actually doing was setting myself up for an endless series of jobs that, well, required me to do exactly what I was terrible at: being detail oriented.

That’s how I ended up at a Biglaw job I was ill suited for. My first assignment as a summer associate was a disaster. My memo came back covered in red ink. “Did you even proofread this before sending it to me?” asked the associate tasked with the unenviable job of supervising me.

“You know, I’m not great with details,” I said to him, “I prefer to focus on the big picture.” Which in retrospect probably wasn’t the right response for that situation.

Biglaw didn’t need big picture people. They already have enough of them. They’re called partners. What they need from juniors is the ability to “own” boring assignments and worry about the details so the seniors don’t have to. To keep juniors in line, seniors perpetuate one of the most commonly held misconceptions in Biglaw.

Bullshit tasks won’t help you advance

It goes something like this: Being great at lower level tasks will help you get to the next level of your career. I mean, at some level, it’s kind of true. Like if you’re one day going to be solely responsible for filing an important motion, it does help to first learn how to do basic legal research or draft sections of the argument first.

The lie comes in when they make it seem like everything you do will help take you to the next level. Especially the most bullshit tasks. Like circulating calendar invites for a large team. It’s a shit job for the most junior person on the team. Yes, it’s critical to coordinate and make sure you don’t miss anyone or schedule it at the wrong time. But let’s not kid ourselves. It’s not helping you develop valuable skills.

But instead of admitting that it’s a thankless job that gets you zero career value, you’ll be told that it’s such an important job (so you must make sure to get all the recipients right, and avoid messing up the date and time!) and that doing it well will help prepare you for when you’re a senior lawyer in the real world.

Sound familiar?

Let me be clear. I don’t think experienced lawyers are trying to be assholes. Most of them actually believe what they’re saying.

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Because if you’ve been able to survive long enough in Biglaw to last more than a couple of years, you’ve probably mastered the art of bullshit tasks.

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Which requires a certain level of self delusion about the work you’re doing, and how it’ll help you make it to the next level.

It’s most obvious when you’re on the cusp of making partner. Suddenly you’ll be told that you’re missing a bunch of important skills. They’ll throw phrases at you like business development and client management. Things that never seemed important until they’re used as a way to justify keeping you out of the partnership.

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It’s because of the business model

It took me a long time to realize see through this ruse. After leaving Biglaw it became immediately obvious to me why these lies exist. It’s because the business model requires it.

Biglaw firms make money based on the billable hour. Which means that if you want to maximize revenue, you need lots of people spending as much time as possible doing work. At some point, firms realized that they could have armies of expensive associates do unimportant tasks, and bill that time to the client. The associates would happily do it, since they’re paid handsomely for the privilege.

The Biglaw business model also requires attrition. You can’t make every associate partner without diluting the amount of profit each existing partner earns. That is, unless the newly promoted partner can help “expand the pie” and generate more revenue.

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Otherwise, you make less money.

So the firms incorporate attrition into their HR strategy. This is why so many associates quit a few years in, and why so few associates make partner. It’s by design. It’s why associates are forced to do bullshit tasks for a decade. Those who are crazy enough to hang around long enough to be considered for partnership are told that—surprise, surprise—they don’t have what it takes to make it to the next level.

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Sales: A whole new world

At some point I saw that being a good soldier would not get me to where I wanted to be. I’ve always known that I was a hustler at heart. (I prefer the term rainmaker.) And yet it took a very long time for me to shed the belief that my lack of attention to detail was a problem.

It wasn’t until I ended up in a pure sales role

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that I saw the full picture and began to embrace my weakness.

It turned out that the same part of my personality that made me overlook typos and errors also let me overlook slights and rejections. I was able to brush off setbacks much more easily than my more conscientious colleagues. In business development, you almost have to be bad with details. Otherwise you’ll be paralyzed into inaction.

Sales is hard as it is. You have to find a way to convince someone to do something they hadn’t considered before. Most people don’t want to be convinced. Or even give you a few minutes to hear you out. So when you’re in sales, optimism is a huge asset. Hell, it might even help to be a bit delusional.

Turns out that being sloppy and careless can be a competitive advantage in sales.

Carelessness became an asset

When I switched to sales, I saw some of my more meticulous colleagues struggle. They would spend hours crafting the perfect email to a couple of highly targeted recipients who never responded. “I should’ve done this subject line differently,” they’d say. “Maybe I should’ve switched the order of the sentences.”

Meanwhile, in the same amount of time, I’d cold called a hundred strangers and successfully scheduled a few sales meetings. My pitch was terrible, and I got rejected repeatedly. People were pretty rude. But I’d forget about them quickly and easily move on to the next call. It wasn’t calculated. I really didn’t notice or remember the mean things people were saying to me.

“I had a pretty good day today,” I’d tell my wife after I’d get home, conveniently forgetting the half dozen law firm partners who told me to f*** off. “Everyone’s just so nice!”

My tolerance for rejection and lower threshold for “quality” empowered me to make lots and lots of calls. Which led to fast iteration. My carelessness, my sloppiness, was very helpful. Because it let me put myself out into the world without being self conscious. Over time, my pitch got better. Some of my prospects were even surprised by my confidence and readily agreed to an appointment if only out of curiosity.

In the end, I did well at sales because I just didn’t care.

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Self acceptance

As I’ve gotten older I’ve learned to accept who I am. There’s probably a fine line I’ve got to balance, because I do believe that self improvement is a virtue. The thing I try to remember most is that what seems like a weakness is just the flip side of your strength.

The key takeaway for me is to always be mindful about choosing the right environment. My inability to focus on details made me a bad fit for Biglaw at the junior levels. So I stayed away. When I quit my Biglaw job in 2014, I explicitly ruled out going to another Biglaw firm for this exact reason. The money was tempting, but I just knew it wasn’t right for me.

That’s also why I’ve tried to stay away from cookie cutter jobs or career paths. Traditional law practice probably makes sense for some people, but I’d bet it’s far fewer than actually work there. Too many lawyers are unhappy in their jobs because they are perpetually trying to fit their unique personality to some cookie cutter job. There’s nothing wrong with doing this, as long as you know what you’re doing.

But if you feel like a fish out of water, and you can’t explain why, start with what you’re bad at. That might help you identify your greatest strength and where you ultimately belong.

1. Thank you, smartphones and Twitch.

2. Law review is an invite-only honor reserved for a small group of law students. It’s one of the most important lines on your resume, and will help you get hired at the most prestigious law firms (which pay the highest starting salaries). Invitations are extended based on some combination of your grades and performance on a write-on competition, which has a heavy proofreading component. Which requires strong attention to detail.

3. The whole “wax-on, wax-off” scene in The Karate Kid probably didn’t help. That scene made it seem like doing low level bullshit tasks helps you develop important skills. Maybe it’s true in martial arts. But the real world of work is much more complicated, and usually this mentality is used to keep lower level employees complacent. There’s also a psychological element, where experienced lawyers who were forced to do useless tasks for years, delude themselves into believing that it helped them develop valuable skills.

4. What exactly are bullshit tasks? There are many, but as a litigator, they include: Building privilege logs, document review, managing teams of document reviewers, building chronologies, and cite checking. There are more, but these were the ones that came to mind most quickly.

5. The exception to this general rule, is when you find a politically influential mentor or “sponsor” at the firm. That person helps open doors to valuable skills development opportunities, and protects you from focusing too much on garbage work. The need for this type of mentor/sponsor means that at best, Biglaw firms are selecting for associates who are political savvy ; at worst, it’s keeping first generation lawyers, women, and minorities, out of the partnerships. Mentors typically want to help those who look like them, which would explain the trouble Biglaw firms have in promoting promising associates to the partnership. What looks like a skills gap is in fact something else altogether.

6. This is why business development matters so much. But if it’s so important, why don’t firms teach associates how to do this?

7. The legal profession is full of “hide the ball” rules like this. Getting ahead requires an understanding of “secret” rules that no one ever tells you (unless you have family members who are lawyers, or a mentor who explains the whole system).

8. If you’d like to learn how I found that first sales job, check out my earlier article How I Found My First Legal Tech Job

9. This mentality explains my success on social media. Over the years I’ve posted lots of “bad” content that my more conscientious peers would never be caught dead posting. But being prolific helped me get quick insights and allowed me to iterate more. I got better over time. And guess what? People don’t really care about typos and mistakes. They’ll also forget your terrible, cringey content. Just keep posting, and pay attention to what people like. I’ve been trying to extend this attitude to my long form writing. I try to hit “publish” on my Substack articles before they feel completely ready. Better to post a bad article than keep a perfect one in the drafts.