Give Yourself Permission to Change Careers featuring Dena Lefkowitz

Dena Lefkowitz practiced law for 25 years, even though she was unhappy with being a litigator and working in BigLaw. After working with a career counselor, Dena decided to change practice areas and found success as the General Counsel at the School District of Philadelphia.


  • How to avoid derailing your career
  • Why Dena wrote the book, Winning In Your Own Court
  • Going in-house after working in a BigLaw office


  • Why identifying your values and interests will improve your job search
  • The adversarial nature (and stress) of litigation
  • How lateral job moves may create more money in the future
  • Why you should hire a career coach BEFORE you get desperate

Advertiser: Journey and Practice offers The Heart-Centered Lawyers Membership, a community of law students, grads, and lawyers who participate in self-care activities to improve their legal journey and practice. Visit and enroll with code "podcast" for a special rate.

Give Yourself Permission to Change Careers featuring Dena Lefkowitz

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Give Yourself Permission to Change Careers featuring Dena LefkowitzGive Yourself Permission to Change Careers featuring Dena Lefkowitz

About This Episode

Dena Lefkowitz’ Background

Dena Lefkowitz had no idea what it meant to be a lawyer; she didn’t watch Perry Mason or any other legal shows. She went to law school because she was encouraged to go; Dena did all the things her professors said she should do. Which meant that Dena ended up working in a Big Law office.

Dena was unhappy working in litigation so she changed firms a few times, before realizing that she needed to get away from this type of practice. Having a more reasonable work life has more of an impact on you than having a ton of money. It took Dena a few years to realize that free time was important and to look towards in-house positions so that she could spend her time how she wanted. 

Why Leave BigLaw

Dena hired a career counselor and that helped her identify her values and move from litigator to being general counsel of a school board and various government organizations. As general counsel, Dena faced labor and employment issues, contract disputes, establishment clause issues, vendor agreements and food service contracts, which allowed Dena to use her legal education and experience in new and exciting ways. 

“It is good to be on the same side,” exclaimed Dena Lefkowitz when discussing how the School Board of Philadelphia was fighting for the students. Litigation is about being assertive and adversarial, which is taxing. 

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Lawyer Side Hustles

Dena was a lawyer by day and a career coach, thought expert at night for six years. Dena was on a great trajectory, where the only way that she could continue to serve her clients was to leave her full time job. 

Dena took her side hustle and transitioned it into a full career and founded a career coaching business called Achievement By Design, LLC. As a coach, Dena helps people find careers that respect their values, preferences, and motives. Dena credits her time attending the Michael Baime Eight Week Mindfulness Retreat and working with a career counselor as showing her that she could work in a field that she enjoyed and be financially stable.

As a business owner, the income takes a change because you are doing everything on your own and there may be a lean period as you are making a career change or transformation. 

Although Dena’s income was different from being a litigator and school board lawyer, Dena has increased her income to match what she made as a litigator. Dena is a walking advertisement that you can enjoy your job, make good money, have free time all while your career aligns with your motives and values. 

What’s important to me? What do I like doing? How do I enjoy spending my time? I hadn’t considered those things when looking for a career.

Dena Lefkowitz is also the author of Winning In Your Own Court, a book that encourages people to create a successful career without burnout or selling out. This book is a valuable resource for anyone who is interested in changing careers, but unable to work with a career coach. With chapters entitled, Curate Your Career and Honing Your Soft Skills, Dena offers her wisdom and experience as a career coach to the reader. 

Don’t Derail Your Career

Even a nice person who is trying their best to do a good job is not always prepared for what they will do when they are representing a client. When professional conduct is out of the course book and law school, what soft skills do you have where you can deal with client management or development.

Understanding yourself and learning how to get along with others will take you way further without investing in your soft skills. Career coaches can help you identify defenses and other issues that could have a negative impact on your career and even derail your career.

To work with Dena Lefkowitz, request a meeting or consultation here.

It is not too late to change your career, explains Dena Lefkowitz in Episode 73 of the You Are A Lawyer podcast.

Contact Dena Lefkowitz

Dena Lefkowitz is licensed to practice law in Pennsylvania. Learn more about Dena Lefkowitz:  

Website: Achievement By Design, LLC 

Links and Notes

As an Amazon Associate, I earn from qualifying purchases. Get your copy of Winning In Your Own Court by Dena Lefkowitz:

Michael Baime - 8 Week Mindfulness Seminar

Advertiser: Journey and Practice offers The Heart-Centered Lawyers Membership, a community of law students, grads, and lawyers who participate in self-care activities to improve their legal journey and practice. Visit and enroll with code "podcast" for a special rate.

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