Over six years ago, I left the practice of law to pursue my passion for writing and coaching. There were many things I learned along the way that prepared me for the 180-degree shift in my career, as well as things that served as terrific lessons for my continued entrepreneurial path. Over the years, since leaving law and authoring articles about my journey in the HuffPost and CNBC, I’ve had dozens of lawyers reach out and ask about navigating their own entrepreneurial desires. In this week’s piece, I want to take you through the cornerstones of making a transition out of law and mindsets to take with you as you work through your own journey and process.
Know That You Aren’t A Failure If You Leave Law
In the initial months of leaving law, between telling my friends and family about my career leap, to sharing my story on social media, I was met with negativity and backlash. Even in recent times, I’ve had people troll my social media accounts and tell me I couldn’t “cut it as a lawyer” so I became a “career coach” or a “resume writer.”

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The irony of being judged by internet trolls or other Debbie Downers is that I view myself as much more successful now than when I was a lawyer at even the most prestigious law firm or company — I built a widely known brand that’s displayed across major media and page after page on Google, I’ve worked with some of the world’s most respected and regarded attorneys and executives, I created financial security for myself, and most importantly, I created a business where I wake up every day passionate about what I do and love helping clients achieve the next leadership opportunity in their executive career. Those things stand taller in my “eyes of success” than continuing into another decade feeling trapped by a career that just didn’t fulfill me (despite my being good at it).
If you’re on the fence about leaving law and worrying about being considered a “failure” for it, stop and turn that mindset around. Perhaps success for you is trading Biglaw for an in-house counsel job, having a better quality of life, or being able to do what you truly love and finding a way to monetize it. Perhaps success is not having to work for someone else, or creating new opportunity in a different industry. Remember that success means different things to different people and it’s an individual, subjective feeling.
Be Honest With Your Finances
Before I left law, I knew that not having the steadiness of a paycheck every two weeks or guaranteed health insurance would be a heavy weight to carry. I didn’t just wake up one day and leave law without a plan. I spent 18 months building up my writing business on the side and making investments in it that enabled me to create a nest egg and continuously save for it. I also had a plan if things didn’t work out.

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If you’re planning to make the leap out of law, but you still want to ensure a flow of income until things really launch, sign up for contract legal work or commit to part-time or project-based work. There is no shame in taking on something part-time for the short term to have achieve that long-term goal of entrepreneurship.
Focus On Your Best Skills And Interests
As a practicing lawyer, I excelled in legal research and writing, I thrived on taking depositions and being in the courtroom, and I felt energized by writing winning briefs and negotiating cases at mediation that saved thousands of dollars for my clients. These experiences led me to where I am now and formed the basis of what I do daily. My litigation skills built a foundation for me that catapulted my public speaking and led to lucrative speaking engagements. My motion practice centered on rapidly making compelling arguments to judges which then facilitated my ability to make a compelling story for someone’s career to effectively market them as well as condense their career information and effectively summarize it. My best legal skills transformed into my best business assets. Begin to think about your best skills and interests that you can take into your future business and consider ways in which you will market and leverage them.
Think Like A Businessperson, Not A Litigator
One facet of being an entrepreneur that I did not anticipate was how much I would leverage my law degree yet also remove it at times. In business, you will find yourself approaching situations differently. You will hire business counsel on retainer, so you remove the emotion and subjective perspective from challenging business situations. You will sometimes go against the grain to build relationships, increase goodwill, and make decisions based on what’s better for the business long-term and your reputation. Don’t be afraid to embrace it.
Remember that leaving law is not the end. It’s just the beginning of a new life, a new opportunity, and a new journey. I hope these strategies and tips help inspire you if you’re thinking about transitioning out of law or feeling stuck on making the leap. Feel free to reach out and follow along as I share the ups and downs of leaving law on Instagram and my other social media channels.
Wendi Weiner is an attorney, career expert, and founder of The Writing Guru, an award-winning executive resume writing services company. Wendi creates powerful career and personal brands for attorneys, executives, and C-suite/Board leaders for their job search and digital footprint. She also writes for major publications about alternative careers for lawyers, personal branding, LinkedIn storytelling, career strategy, and the job search process. You can reach her by email at [email protected], connect with her on LinkedIn, and follow her on Twitter @thewritingguru.