Interview with Jay Harrington, Author of "The Essential Associate" Part 1


This is Part One of our Interview with Jay Harrington, the author of "The Essential Associate".  The Essential Associate, helps young lawyers not just survive, but thrive in today’s competitive law firm environment. It is a step-by-step guide for mastering both the practice and business of law, and includes the insights of dozens of successful lawyer, general counsel at Fortune 500 companies, and leading consultants to the legal industry.  

Jay Harrington is an attorney, author, public speaker, executive coach, and marketing consultant.  The Essential Associate is his third book.  Previously, he was a commercial litigator and corporate bankruptcy attorney at Skadden, Arps, Slate, Meagher & Flom  and Foley & Lardner.  Jay also co-founded a boutique corporate bankruptcy firm in 2009.  He earned his law degree from the University of Michigan in 2001 and his undergraduate degree from Bowling Green State University, where he played baseball.

You can read more of his writing at

Jay Harrington was interviewed by me, Jeff Barlow.  Jay and I have known each other for a long time and we touch on that in the interview.  To recap, Jay has written 3 books.  Jeff, on the other hand, has written 0 books.  Here's Part One of the our interview with Jay:


Jeff:  Give some more detail on your career arc.  Why law school?  Why litigation and bankruptcy?  Why move from Skadden in Chicago to Foley in Detroit?  Why did you decide to launch the boutique firm and how have you ended up where you are now?  I think readers will really want understand the choices and courage.

Jay:  Author Daniel Pink recently appeared on Tim Ferriss’ podcast and discussed how he kind of stumbled his way into law school, having never visited a law school nor spoken to a lawyer about what the profession is really like. That’s my story too! I had a theoretical vision of what it meant to be a lawyer, but not a practical or realistic one. Fortunately, I really enjoyed my law school experience and did well, which put me in a position to start my career at a great firm in a great city—Skadden’s Chicago office in its corporate restructuring group.

The beginning of my career was marked by trial by fire. I joined the firm less than a week after the terrorist attacks of 9/11, and the corporate restructuring group (which primarily represented large companies as debtor’s counsel in Chapter 11 bankruptcy proceedings) was insanely busy. I was overwhelmed, working ALL of the time, and was handling work way above my pay grade (hence the stress and sleepless nights at the office). It was really difficult, but in retrospect I could not have asked for better training, and things eventually settled down into a somewhat normal cadence as planes started flying again and financial markets settled down. I had a great run at Skadden, enjoyed the challenging work, and worked with many great colleagues, a number of whom I still keep in close touch with, including a few who are featured in my new book.

My move back to Detroit, which is where I grew up, was driven by a desire to settle down a little bit and start a family with my wife Heather. Foley & Lardner was a great place to work, too, as its Detroit office has a robust debtor-side corporate bankruptcy practice focused in the automotive sector. I spent about a year and a half there before getting the entrepreneurial bug and started the legal marketing and business development agency that I still run today, which is called Harrington Communications. That was nearly 12 years ago.

In 2009, I made one quick detour back into the practice of law and founded a boutique law firm with one of my best friends, who is a former Foley colleague. I figured that if I was ever going to practice again, that was the time, as the financial crisis was in full effect, and the automakers were on the brink of bankruptcy. It was a crazy stretch, as the law firm was extremely busy and I continued to run the marketing agency with my wife and a team of employees. After three years of juggling both businesses, my wife became pregnant with twins (or second and third kids), and it became clear that it was either going to be me or the law firm, so I transitioned the firm to my partner and have solely focused on the agency ever since.

Jeff:  It takes a LOT of COURAGE to give up the true lawyer career.  I think a lot of people would like to do something else but they are afraid to try something different.  How did you arrive at that decision and how did you make peace with it?

Jay: I’ve never been one to be wedded to a long-term vision for my career. I try to create flexibility to go where passion takes me. What I learned through building my own law firm is that I am passionate about the business of law (marketing, business development, professional development), but less so about the practice of law. What I’m doing now allows me to blend my entrepreneurial nature with my interest In the legal industry in a way that gives me the best of both worlds. The “through-line” that has allowed me to have flexibility in my career has been a vigilant focus on making sure that I leave myself capacity (both in terms of time and financial commitments) to bounce to something new when I want to. I’ve never really looked back on my decision to stop practicing law with regret—the skills I learned while doing so have been invaluable, and having Skadden on my resume has, deservedly or not, helped open lots of doors.

Jeff:  I think that whole backstory sums up why you’re the right person to write this kind of book.  The credibility you bring to having been in trenches at big firms and a boutique.  You took your lumps and learned from all of it.  Speaking of backstory, I think we should mention that we’ve known each other since about 3rd or 4th grade (I can’t remember now).  It’s awesome that we’ve gotten back in touch and are trying to collaborate on a number of opportunities.

Jay: Yes, I agree. It’s funny how things circle back. I’m not a huge social media user, but I love the fact that it creates opportunities to connect with people from one’s past, such as how you and I reconnected. I’m really excited and interested in all of the great things you’re doing at Nimble, and glad that we’re having the opportunity to collaborate! People who know you and Nimble should know that you contributed a great essay to the book, which appears at the end of chapter 2, that shares your thoughts on what makes an associate valuable from a general counsel’s perspective.


Jeff:  Jay, I loved your book.  And I think I mentioned to you that I had an idea for a somewhat similar book way back in 2008 as the economy was crumbling and lawyers we’re being laid off like we had never seen before but like many people with book ideas, I never got around to actually sitting down and writing it.  How have you had the self-discipline to actually write 3 books? 

Jay: I’m not smart enough to know any better! Writing books is painful and frustrating. Book projects, like almost all projects, adhere to Hofstadter's Law, which stands for the proposition that things always takes longer than you expect, even when you take into account Hofstadter's Law.

The truth is, though, that writing a book simple in the sense that you just need to write a few hundred words each day, and if you can do that, you’ll have a 200-page book draft done in a few months. But as you recognized, it’s not easy to have the discipline to do anything habitually for long periods of time. If it was, we’d all write books and have six-pack abs. Accordingly, before setting out to write a book, I make sure that I’m really passionate about the idea that I know I’ll be living with for a year or more, because while it might only take a few months to write a draft, by the end of the process of editing and re-editing, proofreading and production, it’s more like a 12-month process. For me, I need to block time from 5 a.m. to 7 a.m., Monday through Friday, to focus on whatever book I’m working on. Otherwise, if I wait until the workday starts, or try to write at night, the day’s events take priority or my brain is too fried to write. I recently wrote a post about 10 things anyone who is thinking about writing a book should consider.

Jeff:  Your advice on writing is great.  I’m surprised lawyers and law firms don’t take advantage of LinkedIn more and they’re still more focused on writing for legal journals or bar association publications.  I don’t know a client out there that is reading legal journals or bar association publications.  Go where the potential clients are.  Where are the best places for lawyers to publish their writing?

Jay: If you have a niche—meaning a narrow target market that you focus on—it’s far easier to have a big impact with your writing. If you don’t have a niche, then you’ll be forced to write about topics of general interest, rather than of intense interest to a particular audience. So, understand your audience. Then do research and find out what publications and websites members of your audience read. Reach out and form relationships with the editors of these publications and websites—most are starved for good content and welcome the work of thoughtful contributors. You don’t need to a have a big audience of readers. You just need the right audience.

Jeff:  I don’t know about you, Jay, but I still break out into a full sweat when I publish a new piece of original content on either on our blog or social media.  Just like I will be with this one...what do you recommend for hand-wringers like me?  And how did you handle the stress of a book launch?

Jay: I find that most of the stress related to writing stems from lack of preparation. If you just sit down at the keyboard to get started with no plan in place, then you’ll almost certainly be stressed. At the keyboard is the worst time to be brainstorming ideas about what to write about. Collect ideas throughout the week. Think about the questions clients are asking you, and what issues are coming up as you research and work on client matters. Are there common issues popping up? Have you unearthed any new insights? Jot these ideas down and revisit them. Once you pick an idea to write about, outline it first. Write from the client’s perspective—tell a story and answer a specific question and/or provide a specific solution. Have a plan.

In terms of the book launch, it’s not really any different than writing the book. I just chip away at the marketing and awareness campaign one day at a time. Too many authors go into the book writing process with the idea that once they finish the writing their job is over. It is over if you don’t care about selling any books. If you do want sales, you need to treat the launch, and more importantly the ongoing marketing, just as strategically and intensely as you do the book writing process.

Jeff:  Jay, where are all of the places that lawyers, law firms, law students, and law schools can purchase The Essential Associate?

Jay: Thanks for asking! The book is available at and Amazon.

Jeff:  And for those of us that are parents with young children, where can we purchase your children’s book?

Jay: My wife and I wrote an illustrated a children’s picture book called The Magical Tale of the Fairy Trails. It’s available on Amazon and at Life and Whim.

Magical Tale of the Fairy Trails.jpg


In Part Two, we dive into how to excel as a lawyer, the business of law (like it or not, it's a business), and personal branding.  


Jay Harrington, author of "The Essential Associate"

Jay Harrington, author of "The Essential Associate"