Welcome to my LinkedIn archive.
Categories: Dear 1L, Dear 2L, Legal Writing
By Year: 2026, 2025, 2024, 2023, 2022, 2021
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Search by word to find what I’ve written on the topic of your choosing!
Dear Legal Writer, The No. 1 mistake associates make in their drafts has nothing to do with legal writing.
It also has nothing to do with English:
-grammar
-punctuation
-usage
-syntax
(Although many associates get those wrong, too.)
I awoke to amazing news: 𝟭,𝟱𝟬𝟭 copies sold for *𝗗𝗲𝗮𝗿 𝟭𝗟*!
I owe ALL of my happy news to YOUR consistent support, and I am so, so grateful. 🙏🏻
My dream is to make Dear 1L the book that EVERY law student reads:
Dear Legal Writer: Clarity is more important than brevity, so please stop mindlessly cutting the word “that” to save space.
True, “I think you should go” = “I think 𝙩𝙝𝙖𝙩 you should go,” and each version is correct.
So there, you can cut the “that” to save space—no problem.
Dear Legal Writer, Is it “myriad” or “a myriad of”? I did a deep dive. Here’s my take, and don’t miss the 3 big caveats. ⤵️
🔷 DEFINITION:
The word “myriad” means “a countless number of specified things,” (Oxford English Dictionary), or “an uncountable number.”
I’m celebrating Dear 1L’s birthday today. And while I missed my sales goal by 50 books, I am feeling good:
▪️ I reached 1,450 books for the year—a HUGE jump of 47 copies since 6 days ago, when I posted an offer to send a free book to 3 incoming 1Ls.
At first, I was embarrassed when only two incoming 1Ls took me up on my free book offer.
Dear Legal Writer, “As regards,” “Regarding,” and “In regard to” are the ultimate life-suckers of legal writing. In fact, you can lose the word “regard” altogether.
—> “Regard” creates clauses that are long, clunky, and awkward.
Instead, try using “On” or “As to.”
❌ “Regarding the first claim, plaintiff cites no support.”
“How are book sales coming, anyway?”
At first, I hesitated when I got that question—was it even appropriate? (It’s kind of a sensitive topic to me—like asking my weight or salary.)
I also felt embarrassed: “Dear 1L” is never going to be some New York Times bestseller.
Legal Writer, We’ve been there: The brief is finally done, but it’s several pages too long. You’ve got a few hours to try to cut it before the filing deadline, and you can’t afford to lose substance.
What’s your first move?
Try my P-E-N-C-I-L approach. It systematically roots out the 6 worst sins in legal writing:
Legal writing has changed since the 1990s when I started.
Here’s my run down of the big changes I see:
🔹 1990’s:
-Use complex words nobody knows.
-Use no charts, timelines, or photographs.
-Use boldface & italics, for emphasis.
-Stick to Times New Roman font.
-Use acronyms for party names.
-Use footnotes to save space.
-Maximize use of legalese.
Over the past 4 years, I’ve reviewed over 100 resumes written by law students, and I always see the same handful of mistakes.
This is AFTER both the student and their school’s Career Office have signed off and think the resume is “final.”
➡️ Please do not rely on Career Services to proofread your resume. That is not their job. The job is yours alone.
So I created this checklist for you. It targets the 10 mistakes I see the most often.
I’ve always felt a bit uncomfortable around law professors.
They’re an exclusive club, and I’ve definitely never been “in” it.
In fact, before doing what I do now, I failed to get the 3 professor jobs I applied to.
👉 That made me feel like the entire law-school universe disapproved of me.
I talk regularly to law-firm owners, and I get an earful about their associates’ legal writing deficiencies.
You might think the greatest gripe I get has to do with the depth of analysis or lack of sophistication in advocacy style.
You’d think the gripe at least had SOMETHING to do with the LEGAL part of legal writing.
But no.
It’s their grammar.
Dear Legal Writer: Before you give that brief to the partner, make sure you’re not using any of these BAD ways to say “because”:
I made this staircase for you, so you can see all of the 10 common ways we express causation:
🔺 As
🔺 For
🔺 Since
➖ Because
🔻 Based on
🔻 As a result of
🔻 For the reason that
Dear Legal Writer, The best legal writers use a 3-pillar approach. Try it in your next brief or business letter:
🔹 1: The first pillar is clarity. That’s the holy grail.
If your writing isn’t clear, it will not persuade.
No judge will take time to decipher what you mean to say.
A client may throw up their hands in dismay.
Hello from Matt and me in RI, where we’ll be spending this summer near my Mom and other family.
Today’s story starts in Nov 2021—when I was NOT ready to be a podcast guest.
I’d never appeared on one before; I didn’t know what to expect; and I got a bit blindsided.
And after that first one, although I thought I did “okay,” I knew equally well that I could get much, much better. So I worked hard at it!