Dena Lefkowitz 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. 


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.


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. 


You May Watch this Interview on YouTube: https://youtu.be/x-c2PdgE1Lg


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How To Increase Your Value with Non-Linear Career Moves featuring Jaya Saxena:

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Links and Notes

As an Amazon Associate, I earn from qualifying purchases. Get your copy of Winning In Your Own Court by Dena Lefkowitz: https://amzn.to/3iLuZCg

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Episode Timestamps

00:00 - PODCAST INTRO

01:03 - WELCOME TO YOU ARE A LAWYER 

00:33 - DENA’S BACKGROUND 

04:01 - LITIGATORS ARE ASSERTIVE

04:57 - ACHIEVEMENT BY DESIGN

05:27 - LEARN DIRECTNESS FROM LAW SCHOOL?

06:46 - TYPICAL DAY AS GENERAL COUNSEL

08:17 - UNDERPAID BUT HAPPY

09:22 - BIG LAW VS IN-HOUSE

10:54 - HIRED A CAREER COACH

11:30 - JOURNEY & PRACTICE AD

12:04 - PERMISSION TO CHANGE CAREERS

14:16 - ORIGIN STORY OF YOU ARE A LAWYER

16:27 - DESPERATION LED TO HIRING CAREER COACH

16:43 - ENJOYED WORKING WITH COACH

18:34 - LAWYER SIDE HUSTLE

19:13 - SALARY CHANGES

20:27 - MOTIVES & VALUES

21:55 - WINNING IN YOUR OWN COURT

25:00 - AVOID DERAILING YOUR CAREER

26:28 - NEVER TOO LATE TO CHANGE CAREERS

27:19 - OUTRO