“I was unhappy every single day. I was a good lawyer, but I hated it. 

Then I wondered, ‘How good might I be at something I actually liked doing?’”

For Stephanie Wilkins, this question was a wake up call.

After eight years as a litigator with a partnership lined up, Stephanie made the decision to walk away without a clear plan. A “crazy/scary” and necessary move.

In this episode, Stephanie shares why walking away from a potential partnership gave her the space to figure out what she liked doing.  What followed was a year of travel that confirmed her decision to leave.  She found her way onto a more aligned path  in writing, journalism and legal tech.

We talk about:

• What it felt like to walk away from big law without a plan.
• The difference between burnout and misalignment.
• How to reconnect with what you’ve always loved, and turn it into a career.
• Why “quitting” isn’t failure and how to manage expectations - yours and others. 
• How to break into legal tech and why it’s full of opportunity right now.

If you’re wondering what you can do off the “traditional lock-step legal path” out there for you, listen to this conversation! 

About Stephanie

Stephanie Wilkins is the Director of Content at Legaltech Hub, where she helps lead the company in building out its editorial content and thought leadership strategy. Previously, she was the Editor-in-Chief of Legal Technology and Legaltech News at ALM, where she served as a guide for the entire ALM newsroom in tackling the intersection of law, technology, and AI. In a past life, Stephanie was a successful litigator in the New York offices of Clyde &; Co and Dewey & LeBoeuf.

Connect

https://www.legaltechnologyhub.com/

https://www.linkedin.com/in/stephanie-wilkins/ 

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

“I thought people with rich husbands could make career pivots, not me.”

After 20 years as a lawyer and in-house executive, Pam Richardson had the career many attorneys work decades to achieve. But beneath her title, compensation and success, she couldn’t shake the feeling “There has to be something more than this!”

As a single mom of twins, leaving law felt impossible. In this episode, Pam shares how she slowly shifted from feeling trapped in a high-achieving legal career to building a path toward work that feels aligned and meaningful.

We cover:

• Why so many women lawyers struggle to imagine careers outside law.
• The mindset shifts that helped Pam stop seeing herself as “stuck.”
• How coaching, community, and possibility changed the trajectory of her career.
• The financial planning and practical steps behind making a sustainable career transition.
• Why lawyers often stay years longer than they want to.

As a woman lawyer, leaving a legal career is almost unthinkable, especially if you believe you can’t do anything other than be a lawyer or you are accustomed to people-pleasing.

This conversation is a powerful reminder that meaningful change is possible as a woman lawyer, even if it happens one step at a time.

About Pam

After more than 20 years as an attorney and in-house executive advising leaders at Fortune 1000 and Global 500 companies, Pam decided to step away from the practice of law and focus fully on the work she finds most meaningful; partnering directly with people as they navigate growth, change, and leadership challenges.  She founded Waypoint Partners where she works with organizations and individuals at all stages of their careers.

Connect

https://pamrichardsonllc.com/

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

Follow

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw
• Web: https://womeninterestedinleavinglaw.com

References

Alternative Careers Panel Discussion: What Claude/Chat Can’t Tell You”
Watch here: https://alternativecareers.womeninterestedinleavinglaw.com/

“I thought… ‘I’m earning forty thousand dollars a year, working seventy to ninety hours a week… and I’m going to have a heart attack.’”

Before becoming a coach for lawyers, Michelle Thompson practiced as a labor lawyer. Fueled by caffeine and alcohol, the years of overwork and financial stress took a tool.  She faced the real “costs” of how she was lawyering.

In this honest conversation, Michelle shares her journey from lawyer to PhD candidate to coach. She explains why so many women lawyers stay trapped in survival mode for years longer than they want to. 

This episode covers:

• Hidden physical and emotional costs of legal culture.
• How women lawyers lose touch with what they actually want.
• Nervous system impacts from chronic stress, overwork, and perfectionism.
• Burnout, depression, and rebuilding her life.
• How Emotional Freedom Technique (EFT/tapping) can help lawyers regulate stress and reconnect with themselves.

This episode is especially for you if you’re a high-achieving lawyer, conditioned to white knuckle and push through exhaustion, and no longer want to live that way. 

About Michelle

Michelle Thompson, JD, PhD, works with women lawyers to build their book of business and/or hit their billable hours without the burnout. She does this through public speaking at Bar Associations and law firms, as well as through coaching programs in Resistant Vision.

Connect

LinkedIn: https://www.linkedin.com/in/dr-michelle-thompson-esq-b75317403/ 

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

What if your negative thoughts aren’t the problem, but actually clues pointing you toward what you truly want?

In this episode, Elena shares a powerful mindset revelation she recently uncovered while coaching women lawyers through the CPR process: underneath every critical or limiting thought is actually a deeper value, desire, or goal.

Through personal stories and client examples, Elena walks listeners through how to transform self-criticism into clarity, create more empowering thoughts, and generate the energy needed to take meaningful action toward a more aligned life and career.

In this episode, you’ll learn:

• Why negative thoughts are often clues to your deepest desires
• How to reframe self-criticism into empowering beliefs
• The 3 questions that help generate positive energy and action

If you’ve been feeling stuck, uncertain, or trapped in negative self-talk, this episode offers a practical framework to help you uncover the “gold” hidden beneath those thoughts and use it to move forward.

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

“I thought people with rich husbands could make career pivots, not me.”

After 20 years as a lawyer and in-house executive, Pam Richardson had the career many attorneys work decades to achieve. But beneath her title, compensation and success, she couldn’t shake the feeling “There has to be something more than this!”

As a single mom of twins, leaving law felt impossible. In this episode, Pam shares how she slowly shifted from feeling trapped in a high-achieving legal career to building a path toward work that feels aligned and meaningful.

We cover:

• Why so many women lawyers struggle to imagine careers outside law.
• The mindset shifts that helped Pam stop seeing herself as “stuck.”
• How coaching, community, and possibility changed the trajectory of her career.
• The financial planning and practical steps behind making a sustainable career transition.
• Why lawyers often stay years longer than they want to.

As a woman lawyer, leaving a legal career is almost unthinkable, especially if you believe you can’t do anything other than be a lawyer or you are accustomed to people-pleasing.

This conversation is a powerful reminder that meaningful change is possible as a woman lawyer, even if it happens one step at a time.

About Pam

After more than 20 years as an attorney and in-house executive advising leaders at Fortune 1000 and Global 500 companies, Pam decided to step away from the practice of law and focus fully on the work she finds most meaningful; partnering directly with people as they navigate growth, change, and leadership challenges.  She founded Waypoint Partners where she works with organizations and individuals at all stages of their careers.

Connect

• https://pamrichardsonllc.com/
  

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

Follow

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw
• Web: https://womeninterestedinleavinglaw.com

“The world's not gonna fall apart without you for a couple of hours.” It’s the phrase that EVERY woman lawyer needs to hear.

From early career misery to making partner in big law, Heather did everything “right.” Until a life-changing cancer diagnosis forced her to rethink what success actually meant.

In this episode, Heather shares how she rebuilt her career and her life on her own terms. We cover:

• Why you can’t just “think” your way to clarity.
• The identity shift required to leave or redefine your legal career.
• How to build a successful, sustainable career without sacrificing your life.

Learn how to leave law or love your role within law. As a woman lawyer, leaving a legal career is almost unthinkable, especially if you believe you can’t do anything other than be a lawyer or you are accustomed to people-pleasing. 

About Heather

Heather Moulder is a former BigLaw partner turned lawyer business coach and host of Life & Law, a lawyer podcast about achieving success without the sacrifice. After building a multi-million dollar law practice around a full life, she left it all to help other lawyers do the same. 

Connect

• Coaching Website: https://www.coursecorrectioncoaching.com/ 
• Podcast Website: https://www.lifeandlawpodcast.com/ 
• LinkedIn: https://www.linkedin.com/in/heathermoulder/

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. 

As WILL Alumni and guests share their journeys beyond traditional legal careers, you’ll see that you can leave or love law.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation: https://consultation.womeninterestedinleavinglaw.com/2-step-sales-page-page-4160

Follow

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw
• Web: https://womeninterestedinleavinglaw.com

“What if nothing is wrong… but it still doesn’t feel right?”

Jessie Brown didn’t hate being a lawyer. She had a prestigious career, stable income, and was at a “good” firm. But beneath it all, something felt off.

After years of pushing through and ignoring what her body told her, Jessie reached a turning point.

In this episode, Jessie shares her journey from Big Law to coaching and how she left behind a life built on safety to follow something far more aligned.

We talked about:

• How you can outgrow a “good” legal career and what keeps lawyers stuck
• How to listen to your body as a compass for career decisions
• Why curiosity (not clarity) is the first step to career change
• The difference between career coaching and deeper “soul-level” work
• Why not everyone needs to leave law, but everyone needs alignment

About Jessie

Jessie is a former lawyer turned coach, purpose guide, meditation teacher, and breath work facilitator. She also facilitates sound baths and forest bathing. She’s a mom of two boys and married to a lawyer.

Connect

www.linkedin.com/in/jessiebrowncoaching

www.jessiebrown.org

https://substack.com/@returningtosoul

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. As WILL Alumni and guests share their journeys beyond traditional legal practice, you’ll see that change is not just possible, it’s within your reach.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation with Elena: womeninterestedinleavinglaw.com/book-a-call
 

Follow Us:

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw
• Web: https://womeninterestedinleavinglaw.com

Imagine having a simple tool to stop your spiral into doubt, fear, or worst-case scenarios.

Imagine you easily interrupt negative thought loops. 

You are able to intentionally reignite your motivation, clarity, and desire.

In this episode of the [@] WILL podcast, I talk about a powerful mindset tool called "CPR".  

CPR stands for Choose, Positive, and Repeat/Reignite. It was inspired by a coach I study with, Stacey Boehman who teaches “Intentional Thought Creation”.  As part of that I heard her say, “Choose positive thoughts, and then repeat.”  I wrote down CPR.  I am adapting her methodology for you. 

CPR connects you with your heart's desires, and shows you how to break free from doubt and create momentum. 

This episode is especially valuable for women lawyers (and high-achievers in general) stuck in cycles of overthinking, self-doubt, or inertia. 

Listen in to learn:

• How not to “dance” with negative thoughts.
• Focus on positively-framed questions to create momentum. 
• Repeat and rewire your brain and belief in what’s possible.

Are you ready for a practical way to shift your mindset quickly and effectively? 

Listen in now and give yourself CPR!

Show Notes

Stacey Bayman

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. As WILL Alumni and guests share their journeys beyond traditional legal practice, you’ll see that change is not just possible, it’s within your reach.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation with Elena: womeninterestedinleavinglaw.com/book-a-call
 

Follow Us:

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw

Web:https://womeninterestedinleavinglaw.com

“What does your ideal day look like?” 

It was the first time that Hillary Sobel had ever been asked that question.

32 years of feeling unseen, undervalued and “unallowed” to want anything else.

22 years of knowing that law was not for her.

Then in the space of 10 seconds, her world shifted on its axis.

In this episode, WILL Alum Hillary Sobel talks about her life transformation from 32-years as a lawyer to seeing her face on a Times Square Billboard.
 

We discuss openly:

• Why it’s NEVER too late to change careers (and what keeps women lawyers trapped).
• Why investing in yourself isn’t indulgent; it’s transformational
• How mindset work becomes the foundation for real reinvention

Hilary shares her fear, skepticism, identity shifts, and eventual success when she began to live her ‘ideal day’.
 
About Hillary

Hillary began her career in law, grounded in an understanding of business and Corporate America from family entrepreneurs. Her practice focused on corporate-related litigation including securities and antitrust.

After successfully practicing law, Hillary refocused her attention on advising growing, mostly women-founded, businesses. Through her consulting business, Minerva Turning Point Strategies, Hillary combines strategic thinking and curiosity to identify new pathways to growth. She has been published in Forbes Women on the intersection of profits and people, and in Medium on opening hard conversations to expand our understanding of each other. 

Hillary’s passion for storytelling and advocacy finds an outlet in speaking and writing. From her Substack, “The Cowgirl, The Shark, and Stilettos” (and other upcoming publications including a chapter in an anthology and her memoir), Hillary connects current and historical events to the stories of our daily lives.

Connect

• Contact: [email protected]
• Website: www.minervaturningpointstrategies.com
• Substack: The Cowgirl, The Shark, and Stilettos
• LinkedIn: https://www.linkedin.com/in/hillary-sobel

Show Notes

Abby Womack

• Instagram: https://www.instagram.com/abbywambach/ 
• Book: https://www.amazon.com/WOLFPACK-Together-Unleash-Power-Change/dp/1250217709 

WILL Transformhttps://womeninterestedinleavinglaw.com

In this episode Anne Marie Segal and I discuss how your resume isn’t a record of your past, but rather a strategic document designed to answer one question: Why should I hire you?

Anne Marie walks us through the mechanics and mindset of moving beyond Big Law — without losing the gravitas that comes with it. We cover…

• Resumes, cover letters, and LinkedIn optimization.
• Networking strategy, recommendations, and how to “straddle” a transition while still employed.
• How to assess real market demand for your skills.

This conversation is tactical and psychological — because transitioning careers isn’t just about formatting. It’s about translation, positioning, and clarity.

If you’ve ever wondered how to answer the question “Why should I hire you?” — this conversation gives you the framework, the mindset, and the tactics to do it with confidence.

About Anne Marie Segal

ANNE MARIE SEGAL, founder and CEO of Segal Coaching LLC, partners with board candidates, General Counsel and other senior and rising executives to expand their impact and advance their leadership trajectories. She has helped hundreds of candidates prepare for job interviews and is excited to be able to help you today.

Web: segalcoaching.com and segalcoachingacademy.com

LinkedIn: https://www.linkedin.com/in/annemariesegal/

WILL

The WILL- Women Interested in Leaving Law Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen; it’s an invitation to explore new possibilities and shed limiting beliefs. As WILL Alumni and guests share their journeys beyond traditional legal practice, you’ll see that change is not just possible, it’s within your reach.

Feel stuck, unhappy, or ready to explore your own WILL journey?

Book your consultation with Elena: womeninterestedinleavinglaw.com/book-a-call
 

Follow Us:

• LinkedIn: https://www.linkedin.com/in/elena-deutsch/
• Instagram: www.instagram.com/womeninterestedinleavinglaw
• Facebook: https://www.facebook.com/womeninterestedinleavinglaw

Web:https://womeninterestedinleavinglaw.com