Chere Estrin on Life, Lessons & Legacy

We’re looking forward to introducing you to Chere Estrin. Check out our conversation below.

Hi Chere, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: Have you stood up for someone when it cost you something?
Absolutely. I stood up and expected to stand with others but instead, I found myself standing alone.
Not long ago, I came across a statistic that stopped me in my tracks: women paralegals are paid 14% less than their male counterparts. That’s not a typo. A decade ago, that gap was 3%. In what world is that progress?

As someone who’s been in legal staffing for over 25 years, I was stunned and frankly, embarrassed. This is my business. This is my lane. And yet, I hadn’t seen the warning signs. So, I did what I do best: I spoke up.

I wrote a bold, solutions-driven piece on my blog. I sent it to a major legal association and urged them to make it a central discussion topic. I shared it with my 75,000+ subscribers. I knew I was taking a risk. As a recruiter, I advocate for both law firms and candidates. Calling out pay inequity could have easily ruffled feathers or lost me business. My reputation was on the line.

And what happened? Crickets. The association did publish the article… at the very back of the publication, behind tips on résumé writing. I received exactly two responses from tens of thousands of readers. Two.

I expected pushbacks, maybe applause. Instead, I got apathy. That silence was louder than any backlash. Did it cost me? In a literal sense, no. But it was a gut punch. It showed me just how deeply ingrained this issue is. People didn’t get mad: they just didn’t care. And that, to me, is even more alarming.

So yes, I stood up. And I’ll keep standing. Because silence may be easier…..but change doesn’t come from silence.

Can you briefly introduce yourself and share what makes you or your brand unique?
I am the owner and CEO of a nationwide legal staffing organization, Estrin Legal Staffing where we find lawyers and legal professionals great jobs. Our clientele consists of some of the top revenue producing law firms in the world. I am also the Co-Founding member of The Organization of Legal Professionals (OLP), an online legal technology training company. What a fun and interesting career ride I have had! From Administrator in a major law firm, to opening my first staffing company, selling it, become a Sr. VP in a $5billion public company, hating it, and back to being an entrepreneur. I love to write and have authored 11 books on legal careers and have an award winning blog, The Estrin Report. At this stage in my career, I am amazed that the American Bar Association is publishing my next book, due Winter 2026.

I have been on CBS News, interviewed by The Wall St. Journal, Fortune magazine, Forbes.com and lots of legal media. It seems like folks think I have lots to say! (And I do. Can’t keep quiet.) I am also a co-founding member of the International Practice Management Association, and recipient of Women of Achievement recognition from Century City/Los Angeles Chamber of Commerce.

I can’t seem to stop. My mantra is “You have to get up in the morning and love it. Otherwise, don’t do it.” I can’t wait to see what the future holds. I’m definitely ready for the next chapter!

Great, so let’s dive into your journey a bit more. Who were you before the world told you who you had to be?
Oh, gosh. I really thought I was going to be a famous Broadway singer and actress. I took voice and acting lessons like crazy. My mother wanted me to be a teacher because then I would “always have something to fall back on!” I didn’t quite see it that way. Well, it was $50,000 worth of voice lessons right out the window. Apparently, you have to sing on key. Who knew?

I opened a traveling theatre company, The New York City Theatre Company – West.” We traveled around the country and while it was great fun, there was very little money. But somehow, we made it. One day, we were in Seattle during the Christmas season. I was driving down the street seeing Christmas trees all lit up in the windows and I suddenly knew I had to get off the road and settle down. So, I opened the paper and saw a position for a Paralegal. I had no experience but I figured, “Heck. It’s like a time step. Go home and learn it.” I interviewed, and it turns out the Administrator just happened to have seen one of my shows, so he hired me. I don’t think it was based on anything else. I had no experience in this arena which just goes to prove people hire because they like you.

That opened a whole host of doors for me. I went from Paralegal to Paralegal Manager in a prestigious entertainment firm in Beverly Hills (I knew my way around that one!) and the rest is career history. No one told me who I had to be. It’s always been a self-finding experience. Frankly, I don’t think I would have listened anyway!
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Was there ever a time you almost gave up?
I can’t remember thinking I had to give up. During the 2008 recession, we went down, hard, like almost everyone else. It was horrific. We lost just about everything. We had a Paralegal SuperConference business at that time that provided professional development conferences all over the country. (There I go, traveling again!). However, during a recession, one of the first things cut from budgets is professional development, not to mention travel. Boy, did they cut us!

While I was devastated, something inside of me said, “Don’t give up.” My attitude has always been, “Don’t give up. Change the way you are doing things.” So, I did a crazy thing. I opened up my second staffing agency right in the middle of a recession – and succeeded. I had sold my first company to that $5billion company and ran their legal division. I reported directly to the CEO and was in charge of millions of dollars in revenue. I hated it. But my attitude has been: “I did it once. What prevents me from doing it again.” I like to think I was right.

Next, maybe we can discuss some of your foundational philosophies and views? What are the biggest lies your industry tells itself?
In my field (the legal field), women legal professionals are paid significantly less than men. The lie? That women are less intelligent, less capable, can spend less time on the career, and peak earlier than men. After 15 years in the career, women lawyers earn 61–63% of what men are paid, and paralegals are paid 14% less than men. Ten years ago, women paralegals were paid 3% less than men. Get this: the paralegal field is a female dominated field. Clearly, we’re riding the horse backwards.

And let’s not forget ageism as a lie the industry tells itself. Gender related and age-related discrimination is called genderized ageism and boy, does the legal field tell itself lies about that! Why should women (and men for that matter), have to only go back 10-15 years of experience on their resume? Wouldn’t you think that all the years of experience culminates into a highly knowledgeable worker? Of course. Yet, the lie is that the older you get, the less productive, accurate and up to date you must be. Not so. Lie, lie, lie! It’s these lies that lead to blatant discrimination.

Instead of fighting ageism, we lie to cover up how old we are. Women in particular, believe the lies. I just wrote an eBook, Hot Flashes, Cool Resume: Still Billable. Still Brilliant. Not Done Yet and here I am giving advice how to get around it. I would much prefer to give advice as to how to just get out there, be who you are, and the heck with the rest of the world. Unfortunately, no one person has that power. It’s got to be fought back by everyone. Simply everyone.

Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. If you knew you had 10 years left, what would you stop doing immediately?
If I knew I had 10 years left, I’d stop hitting ‘Reply All.’ No one needs that kind of legacy.

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