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For the past 4 years, Chere Estrin has been an e-mail away from me, the fearless TPS founder. Whether I wanted to chat with her about a particular topic, seek her brilliant advice about the legal field or a writing endeavor, share a laugh or ask a question, I’d send a message her way. But I’ve always found myself wanting to know more about Chere on a personal level. You probably have, too. So I decided to do what any good blogger would do and sent her a list of questions. When I received her responses (which are fabulous), I darn near fell out of my chair. You are about to read the most personal interview Mrs. Estrin has ever given publicly. Yes, ever.

Without further ado, we present to you Chere Estrin – the Editor in Chief of KNOW: The Magazine for Paralegals, Co-Founder of the Organization of Legal Professionals (OLP), owner of The Estrin Report, a leader in paralegal education, my personal mentor, and one of the greatest paralegal thought leaders of our time.

Are you an introvert or an extrovert?

Interestingly, despite my so-called outgoing reputation, I come up in all the personality tests as an introvert. I recall my third grade teacher writing on my report card, “Chere has worked very hard to overcome her shyness.” Who knew? I certainly have no problem standing up and speaking in front of several hundred people. I have a theatre background and feel outgoing with a great appreciation for people all over the world. I will admit, however, that I’m definitely the one blending in with the wallpaper at any party. That’s me over there…….flat against the wall, holding my Perrier so I look like I fit in, Meanwhile, I’m hoping I don’t have to make small talk…..worrying that someone might think I don’t have much to say.

One of my most life-defining moments has been… (I’m looking for something that goes to the heart of who you are or how you ended up where you are in your impressive career.  If you could only share one personal or professional story with me, what would it be?

If truth be known, my most life-defining moments came when I was sixteen years old and found out that a) I was pregnant (in those days, that was the most horrible thing that could happen to a girl) and b) I had cancer at the same time. The girls Vice Principal threw me out of high school.d To get my high school degree, I had to attend a school for handicapped children – my “handicap” was being pregnant. After the birth, I had to take my classes at home over the telephone – unheard of in those days. This was prior to the Internet, mind you. A visiting teacher came once a week. Then, I had to have several operations and radiology to cure cancer. All while I was sixteen and seventeen. It wasn’t that at that point I decided to be a paralegal. That’s like saying, “When I grow up, I’m going to be an actuary.” Instead, what that period in my life did for me was to make me realize that any choices I had in life were mine and mine alone to make. I was the one responsible for my choices. No one else. It defined how I went through the rest of my life.

If I could pick my final meal, it would be:

All my meals are my final meals. How the heck could I have lost 115 lbs. any other way? Every restaurant is my favorite restaurant; every desert is my favorite, mouth-watering, I-promise-never-to-eat-this-again-this-is-my-last-supper-one-time-only-desert. Once I bargain with God to get clear that this is definitely, definitely my final meal if only she would let me have this one, I am immediately on to what’s for dinner.

What is your favorite vacation spot?

Oh, that has to be Hawaii. I have been all over the world except for Asia. Maui, by far, is my absolute paradise. There I am, by the pool, trashy magazine in hand, huge sunglasses on so no one knows who it is reading that trashy magazine, a beach boy nearby to spritz me while I’m  lying in the hot, delicious sun and slathered up in suntan lotion #89. Who could ask for more?

What is one of your biggest pet peeves?

I have several. Big one: I absolutely hate to be lied to. Tell me the truth and we’ll deal with the consequences but don’t lie to me. Once that happens, you’re dead to me.

The best career advice I could give to another person is:

Don’t for one moment think you’re going to be a success without working harder than you ever experienced in your entire life. There are no excuses. Don’t have time? Get up an hour earlier. Don’t have the money to get the training you need because your firm won’t pay for it? Give up the Starbucks. Whatever you want in life, you and you alone have to earn it. No one is going to hand you anything. Not now. Not ever.

When did you actually become a writer?  Tell us about it.

I always took creative writing classes in school. Writing and music was my way to deal with a difficult childhood. Problem was, when I grew up I couldn’t find anyone who didn’t have a difficult childhood. It was a shock to learn that all families are dysfunctional and just about everyone had some kind of release.

I became a professional writer when I was asked to write a career column for what was then, “Legal Assistant Today” magazine. My mentor was a guy who was a former AP reporter and journalist for major newspapers. He put me through the mill. He made me think about every single word – and not just once. I would come out of those sessions just drained. I questioned myself as to whether I could do it but I just knew I could. Then one day, I got a call from Jim Pawell, CEO of James Publishing who asked me to write a book. “What would I write about?” I asked. There was a silence as though he was thinking, “Are you crazy?” “ The paralegal career, of course,” he said. Thus, the Paralegal Career Guide was born, now coming out in its 5th edition followed by 10 books and hundreds and hundreds of articles plus The Estrin Report, my blog since 2005.

The feeling of being a “real” writer happened several times. One, I was on the cover of Legal Assistant Today as the Career Guru. Then I was interviewed by Newsweek, the Los Angeles Times, Chicago Trib, my blog mentioned in the Wall Street Journal and other prestigious publications. There were radio appearances, national speaking engagements, cable TV and lots of other exciting events. All of this started with writing one column in a specialty magazine.

Is there a moment you remember feeling like a failure?  If so, tell us about it. 

Anyone who tells you that there was no time in their life when they ever felt like a failure is lying. There have to be several times for a successful person to feel as though they failed. That’s because successful people always expect to succeed, they do not expect to fail and that’s not reality. They are geared for success, so failure is doubly hard to deal with.

I think I felt most like a failure in the recent great recession. I had a very successful paralegal training company that did big paralegal conferences across the country. I loved it. I remember being in the pool in 2007 with my husband and having a conversation where I expressed my fear that a recession was looming. We talked about changing over to providing training strictly online. At that time, online education wasn’t too well accepted in the legal community. Instead of heeding my gut (which is not magical, it’s experience telling you what’s happening), we continued on. Of course, one of the first slashes in law firm budgets was travel and training. Down we went a year later. Not only did we have to face the community, we lost everything. I mean everything. It didn’t matter to me that millions of businesses and people were facing the same scenario. What mattered to me was how could I have done things better? What more could I have done to safeguard us? It was a hard, hard lesson.

My husband and I had an agreement: If he was depressed, I couldn’t be. If I was depressed, he couldn’t be. However, the reality was that the light at the end of the tunnel was a train coming at us. Fortunately, even though I was in my fifties, we were able to reinvent ourselves, stay in the paralegal community and come back with two very successful businesses. I think the failure does make you much wiser. Certainly much, much more cautious.

What is your biggest career moment?  When did you feel like you had “made it” as a professional?  Why?

When I sold my first paralegal business for over $2 million in the late ‘80’s. It was a culmination of years of hard work, recognition and reward. I could tell you it was when I helped someone become a success or saw a prodigy make it or help win an important case or something like that. But I’m telling you. When you leave a secure job as a paralegal administrator in a major firm that had a regular paycheck to start a new paralegal business with nothing but $2,000 (all the money you had in the whole world), a couple of “go get’em’s  and a short few years later, a CEO of a $5 billion company stands in front of your desk, holds up a check for $2 million dollars and says, “This is yours,” it most definitely represents at least some modicum of personal and career achievement.

What advice would your current self give your formerly 20-year-old self?

Go do exactly what you did when you are done with your life. Keep doin’ what you’re doin’. Don’t change a thing.

What do you hope your lasting legacy in the profession will be?

I really hope that people will remember me as a trail blazer, a pioneer, a thought leader. Someone who was known to have no fear to stand up for what’s right while continuously pushing for advancement. It would be nice to be 95, Botoxed up, wearing Cobby Cuddler shoes and a Victoria Secrets push-up bra, sitting on my porch with the grandkids, be able to look back and say, “I made a difference. I really did.”


A special thank you to Chere Estrin, for sharing this incredibly candid interview with us at The Paralegal Society. We thoroughly enjoyed reading and sharing it.

We look forward to seeing you later this week, TPS readers. Until then, go get ‘em (the esquires, the deadlines, and the caffeine). Ready, go…