The Lawyer's Escape Pod

Megan Smiley

Megan Smiley interviews recovering lawyers, career advisors, and other professionals for advice and inspiration on transitioning out of law practice.

All Episodes

Emily Hirsekorn is a former lawyer turned career confidence coach. After a stint in higher education, she decided to pursue a certification in professional coaching with iPEC. Specifically, Emily now helps lawyers and other ambitious professionals navigate their careers, develop as conscious leaders, and integrate work and life for faster success and greater fulfillment. In this episode, we discuss: Emily followed her long-standing interest in psychology into coaching Emily wanted more control over her work and life, and realized self-employment was the best route for her The progression from thinking about a big jump to committing to it It’s possible to start while you’re still employed and before you’re fully “ready” Get clear on what your bottom line, sufficient income number is The early entrepreneurial experience   You can find Emily at: Accessible Coaching Campaign:   LinkedIn: ~ Connect with Megan!   Private Podcast Waitlist:   Schedule a Catalyst Call:   Instagram:


Nov 16

50 min 34 sec

Seth Bradley is a former big law attorney who decided to follow his passion for real estate and create his own unique career path. He started his own firm, Bradley Law Limited, where he helps his clients with their real estate and asset protection needs. He has also become a real estate entrepreneur and an expert at creating passive income. Seth is also the host of the Passive Income Attorney Podcast, educating attorneys and other professionals on how to stop trading their time for money so that they can practice when they want to, not because they have to. Seth talks to us about his evolution from medical school student to big law associate to independent law firm owner and entrepreneur. His story really shows how you can design a multi-faceted career around your interests if you have the courage to go for it.   You can find Seth at: Free Gift - The Freedom Blueprint: Passive Income Attorney Website: LinkedIn: ~ Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz:

Nov 9

32 min 47 sec

Morgan Thomas Hall is an Account Executive at Twilio Inc. Morgan practiced in both a firm and for the government before realizing that it wasn’t just a job problem, it was a career problem. She went back to the drawing board to explore her interests, and found herself drawn to tech, and then specifically to tech sales. In addition to her day job, Morgan now also helps people transition from other careers into the tech industry. In this episode, we discuss: Morgan had both firm and governmental jobs She considered trying to become a judge After giving it every possible shot, she accepted that it wasn’t just a job problem, it was a career problem Morgan initially considered some JD-preferred jobs as an obvious next step, but quickly realized that none of those appealed to her Morgan went back to the drawing board thinking about her interests She felt drawn to technology and the start-up world, particularly because of how different the mentality is to the legal world Morgan was worried her family would be disappointed, but also knew she had to make a change - she’s the one who has to live her life She told anyone who would listen that she was looking to get into tech, leading to connections and information Morgan kept coming back to tech sales, which leveraged transferable skills and checked a lot of boxes for her She had confidence in her capacity to learn because she was both committed and interested She found a way to effectively communicate her unique story as a positive to potential employers You will be your biggest hindrance, so learn to get out of your own way   You can find Morgan on… ~ Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz:  

Oct 5

39 min 52 sec

Marie Sotelo is a former lawyer turned freelance writer. After leaving the law, she leveraged her legal experience to become a go-to ghostwriter for entrepreneurs and chief executives in the law, compliance, and risk management space. She firmly believes that money is a means to an end—lifestyle freedom; and that you really CAN do anything with a law degree. She now helps other freelancers make smart money moves in their business and teaches other lawyers how to launch a writing side hustle.   In this episode, we discuss: Marie had been hoping to do environmental law in some capacity, but that didn’t pan out She ended up at the Customs & Border Protection Agency for a decade Working within such an entrenched bureaucracy eventually got too stifling  She developed anxiety and depression (it’s not just big law that can impact you in that way) Her family moved and she decided to take time off to focus on raising her son  She got into part-time freelance grant writing, testing it first with some volunteer jobs Marie worried about finances and wanted to do something that could sustain her family, if needed, but also be flexible  She transitioned to content writing for law firms  Freelance writing is a great thing to experiment with on the side, and build up some extra funds She’s built a life and career around her values and priorities   You can find Marie on…  ~ Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz:

Sep 28

45 min 38 sec

Heather Eastwood is a public interest lawyer (with a brief detour into BigLaw) who found her long-term calling teaching public high school.  In today’s episode, we discuss: Heather came out of college feeling adrift without a clear path to follow She went to law school somewhat on a whim, because it was at least an extension of learning Heather ended up working for legal aid in Hawaii Her best professional experience was based on a highly collaborative environment Heather decided to move to the Bay Area and ended up having to take a firm job  She felt deeply misaligned doing big corporate work Heather quit from her honeymoon She went back to the core of what she enjoyed in previous roles and her core values Heather decided to teach high school, and has been happily doing it for a decade The best piece of advice she ever got was “you are never stuck; you always have choices”   Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz:


Sep 21

39 min 27 sec

Rachel Coll is a lawyer turned life coach. Although Rachel actually largely enjoyed practicing, she allowed herself to evolve and follow the threads that interested her. She ultimately felt called to get into coaching. It did require pushing through some discomfort and external judgment around the decision, but she has now built a successful full-time practice. In this episode we discuss: Rachel largely enjoyed her practice first as a public prosecutor, then at the Board of Elections  Rachel came to a place in her personal life where she hired a life coach, and that ended up changing her trajectory  Rachel became a certified life coach on the side  She didn’t leave law because she didn’t enjoy practice, but because she felt drawn more strongly to something else Although other people warned her otherwise, she always felt she could go back to law after coaching Rachel’s practice has evolved from relationship coaching for lawyers to more general practice around embracing your full self and owning it You don’t have to have a huge problem or official diagnosis to justify getting help Trust if you’re called to something that it’s worth pursuing   Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz: ~ You can find Rachel on…  

Sep 15

46 min 3 sec

David Johnson is a lawyer, writer and professor at Stanford Law School. He started his career working in house at tech companies, received a JSM in Law, Science, and Technology and now (among other things) teaches a course on design thinking as applied to negotiations at Stanford Law. Dave talks to us first about how he got into academia outside the tenure-track, and gives us some great tips around finding adjunct professor positions. Then Dave lays out the framework for using Design Thinking to help move you towards a fulfilling career shift. In this episode, we discuss: How David got into academia as non-tenure track professor Tips on getting into adjunct teaching  David started an online course (MOOC) that ended up getting licensed to Microsoft If you want to do something, don’t think too hard about where it’s taking you. Just do it. Specific tips on applying design thinking to career and personal development The importance of enduring, engaging, and embracing ambiguity  Bill Gates’ quote: “People overestimate what they can do in 1 year, but underestimate what they can do in 10 years”   You can find David Johnson on . . . LinkedIn: Blog: ~ Connect with Megan! Instagram: Lawyer’s Escape Call: Lawyer’s Escape Plan Quiz:

Sep 7

47 min 30 sec

Today’s episode is the audio from the webinar I hosted last week, The 5-Step Lawyer’s Escape Plan. It walks you through the roadmap that will take you from stuck and uninspired to having clarity and a plan.   The 8-week Lawyer’s Escape Plan group program begins next week, so if you’re interested in joining us, sign up before doors close on Friday, June 18 at midnight EDT!   8-Week Group Program:   Instagram:     Lawyer’s Escape Plan Quiz:  

Jun 15

50 min 22 sec

On Thursday, June 10th at 7:30pm EDT, I'll be hosting a free live webinar. A replay will also be available.   I'll be walking you through the 5-Step Lawyer's Escape framework that you can follow to go from stuck and uninspired to confident and planning your move.   Sign up for the free webinar here:  

Jun 8

2 min 31 sec

Risa Weaver-Enion is the founder and chief planner at Risa James Events, where she both plans weddings and offers product branding photography services. Risa went to law school thinking she’d get into entertainment law, but after her summer internship, quickly realized that there was a lot about actually working at a firm that she didn’t like. After some time in law and quasi-legal positions, a cross-country move proved to be an inflection point that prompted her to go back to the drawing board. She asked herself what she actually wanted to do, and that’s when she decided to start her wedding planning business. In this episode, we discuss: Risa went to law school 12 years out of college because she was bored She decided she was interested in entertainment law from the IP angle She was counting down the days in her summer associateship, which was the first sign that she didn’t love the work She hated being beholden to other peoples’ timelines and unnecessary fire drills She ultimately took a job in an environmental compliance role in the UC-system When she moved to DC for her husband’s job, she had a hard time finding a legal job Not loving law anyway, she stopped to ask herself what she actually wanted to do She reached out to some local wedding planners and offered to work as an intern She started working as a paralegal part-time to help support her as she built her business Risa has started a product brand photography business as an exit strategy, because weddings can be grueling after a while Challenge Sign-Up: Instagram:   Lawyer’s Escape Type Quiz:


Jun 1

53 min 35 sec

Eimear McCann is the Head of Strategy at Summize, a legal tech company in the UK. Eimear left law school vowing not to practice. But, after a stint of freelance writing, she came back to the law and worked in immigration and human rights. She loved the work, but when her organization lost funding, she decided it was time to move on. She was intrigued by the technology space - it’s innovation, creativity, and flexibility. She followed that interest into legal tech.  In this episode, we discuss: Eimear originally decided not to practice law after school She was a freelance writer for a few years How particular the structure of the US legal education system is in keeping us trapped Eimear ended up circling back to law, working in immigration and human rights  She had to go back to private practice after her organization’s funding was lost, and she realized just how draining it was At the same time, the immigration work had taken an emotional toll, and Eimear felt it was time to move on   She found herself interested in legal tech because of its environment of innovation and flexibility Breaking into a new field may not be easy, but it’s about reframing your experience Eimear emphasizes importance of finding the kind of work that truly motivates you    Get on the VIP List for The Lawyer’s Escape Plan program: Lawyer’s Escape Plan Quiz: Instagram:  

May 25

43 min 17 sec

In today's episode, I talk about how can take an overwhelming project (like eating an elephant or finding a new, fulfilling career) and break it into bite-sized, executable steps.  You can do hard things. It's just about getting started, strategizing, and taking one step after the other.   Get on the VIP Waitlist for The Lawyer’s Escape Plan program: Lawyer’s Escape Plan Quiz: Instagram:


May 21

17 min 28 sec

Jen Berson left civil litigation after she “saw the light”, decided to pursue more creative endeavors, and founded her own business. She is now the President & Founder of Jeneration PR and the creator of the Agency Accelerator, where she teaches entrepreneurs how to launch, grow & scale a profitable PR & marketing agency. Jen talks about listening to and following her inner voice to a career she finds incredibly fulfilling and which allows her to also prioritize being a present parent.  In this episode, we discuss: Jen had a vague intention to get into entertainment law, and ended up in general litigation Went to a smaller firm, which allowed her more time to explore other interests Jen somewhat randomly reached out to help market a small fragrance business she liked Jen realized she enjoyed work with a tangible result, that had an immediate positive impact on a business She started exploring the various routes within PR, starting by working with a solo firm and then going out on her own She did battle with this idea that she left law because she couldn’t hack it, but she realized it was just a complete personality mismatch Jen wanted to build a life where she loved her work, made good money, and had time for family Get on the VIP Waitlist for The Lawyer’s Escape Plan program:   Instagram:     Jeneration PR:   Agency Accelerator:

May 18

42 min 54 sec

I'm letting you in on the top 2 mistakes I see people make when trying to change careers. First, they start by asking what job they think they can get, rather than asking what they want. Second, they don't prioritize themselves and the process of figuring out the next best career step.    Get on the VIP Waitlist for The Lawyer’s Escape Plan program: Instagram:

May 14

12 min 28 sec

Robert Ingalls is a former litigator turned founder of Lawpods, a podcast production company for lawyers. Robert tells us how he tried a variety of practice areas before realizing that law just wasn’t the right fit for him. While he still had a full-time job, Robert experimented with a number of business ideas and followed the path of his interests. That ultimately led Robert to starting the company he runs today. Robert reminds us of the importance of expanding your circle of influence beyond lawyers who will tell you that your ideas aren’t realistic and this path they don’t understand won’t work out. In this episode, we discuss: Robert went to law school to practice criminal law, which he then actually did But, after realizing it wasn’t the right fit, Robert transitioned to civil litigation He enjoyed trial, but the rest of the package was unappealing  The stress of the environment started really weighing on him Robert then moved into estate planning. It was less stressful, but also more boring Listening to a podcast made it click that he could actually do anything he wanted  Robert realized he needed to leave law, but wasn’t sure what the next thing would be Played around with a few different business ideas, and started his own podcast Robert then started helping other lawyers launch podcasts He battled with the thought “who am I to do this random thing?” and found it hard to tell his network he was taking such a different path Robert went to a podcast conference, where he was surrounded by people making a living in this field  It can be transformative to be around people who believe in the possibilities rather than only seeing the pitfalls  When you enjoy what you do, you don’t mind working hard Get on the VIP Waitlist for The Lawyer’s Escape Plan program: Lawyer’s Escape Plan Quiz: Instagram:    Lawpods:


May 11

51 min 2 sec

You know those people who seem to just always have things work out? From career to relationships? They're just "lucky."  Turns out it's not magic. There are some habits these people have that put them in the path of luck more frequently: Putting themselves out there Listening to their gut Having a positive attitude and believing that good things are coming Resilience Get on the VIP Waitlist for The Lawyer’s Escape Plan program: Instagram: 

May 7

13 min

Rob Bertman is a senior consultant at Student Loan Planner, and a CFA and CFP. Rob talks to us about how it’s possible to manage your student loans around your life, rather than have them dictate what your options are. We get into how it’s even possible to have a runway for starting your own business while carrying loans. If there’s one message I hope people get from this is that you aren’t as trapped as you may think, and you do have options. You just have to tackle the issue head-on. In this episode we discuss: Loan repayment options The opportunity cost of your money  The importance of looking at real numbers; you might actually end up better by going the loan forgiveness route Setting a budget can be uncomfortable, but it allows you to execute a plan (something you probably want and are naturally good at) The risks and potential upsides of legislative changes Get on the VIP Waitlist for The Lawyer’s Escape Plan program:   Instagram:     Student Loan Planner:

May 4

42 min

Lisa Rosen is the Chief Operating Officer at SustainCERT. After starting her career in litigation, Lisa followed her interest in environmental issues to an in-house legal position at a non-profit and ultimately transitioned into an operations role there. Lisa’s story shows how your legal experience is seen as valuable for a non-legal position and that by taking that first step, you put yourself on the path for new, more interesting opportunities to present themselves. In this episode, we discuss: Lisa felt that the conflicts of interest inherent in the billable hour system was misaligned with her values and integrity  Lisa followed her interest in environmental issues into carbon credit work  Lisa found work that was intellectually challenging, but wasn’t technically practicing law Eventually, her position evolved into a general counsel role Lisa raised her hand when the Chief Operating Officer role opened up and transitioned to that  The importance of resourcefulness   Failure is part of the path to your goal Lisa has come to realize that what she enjoys is operating a company Lawyer’s Escape Plan Quiz: Instagram:   

Apr 27

49 min 17 sec

Francesca Chang is a lawyer turned marketing professional, tech recruiter, published travel writer, and now life coach for lawyers. Francesca tells us about leaving practice to explore various other career opportunities. It’s a great example of what can evolve when you don’t tie yourself to a preconceived notion of what your career might look like. In this episode, we discuss:  Francesca went to law school because of interest in social justice Coming out of law school, she worked for solo practitioner which she didn’t love Francesca started looking for other jobs, and didn’t limit it to legal positions She was comfortable with change, but was worried about other people’s opinions about leaving practice - particularly lawyers She ended up in a business development and marketing role for legal services  Francesca then moved to tech recruiting and Ediscovery software marketing She was on a journey to find the right match, and wasn’t averse to trying different things Francesca moved to Taiwan when husband was relocated and had to rethink her career yet again She started travel writing and worked as a tour scout Francesca has now also begun a life coach business for lawyers Lawyer’s Escape Plan Quiz: Instagram:     Francesca’s Instagram:

Apr 20

29 min 30 sec

Are you living your life by design or by default? As crazy as the world is right now, it's a great opportunity to move forward more purposefully.

Apr 16

10 min 52 sec

Dr. Aisha is a former practicing physician turned coach specializing in helping high achievers create change in their lives. Her core message is that in order to make meaningful change in our lives, we need to slow down long enough to get off autopilot and connect to our real thoughts and desires. The world can be very loud and distracting and often confuses us with respect to finding our happiest path.  In this episode, we discuss: A lot of family and social pressure around leaving medicine   Leaving her home and her profession meant letting go of a portion of who she was Her passion was coaching people informally when she was still practicing   At 30, Dr. Aisha was working part-time minimum wage jobs in Canada to take the time to figure out her new path Total clarity didn’t come all at once; it came bit by bit The world is very loud, so it’s hard to know what you really want We’re running on autopilot most of the time The problem of feeling misaligned in life is solved by looking inwards, not outwards One way to start reconnecting with yourself is to disrupt your energy at the start of the day before you’re even fully awake (trampoline, hula hoop, dancing, anything that is a pattern interrupt) It may take a while to go through this process, but time is going to pass anyway - may as well be making progress It’s ok to change at any age; we are in constant evolution  “You can only connect the dots looking backwards” - Steve Jobs Lawyer’s Escape Plan Quiz: Instagram:      Dr. Aisha’s LinkedIn: 

Apr 13

47 min 22 sec

Rho Thomas is a trademark lawyer at Kilpatrick Townsend & Stockton LLP, a financial coach for lawyers, and the mom of two young boys. Rho tells us how she has a vision for her life that includes working as a lawyer, pursuing her side business, and being a present mom. Part of that journey has been creating more financial freedom by tackling the substantial school debt she and her husband accrued in becoming a lawyer and doctor, respectively. It has also meant setting boundaries at work and holding to them. Rho’s story is a great example of what it looks like to be purposeful and committed to creating the life you want. In this episode, we discuss: Rho enjoys practicing trademark law, but it isn’t her sole priority  Rho moved to a reduced hour schedule when she became a mom She wanted to work even fewer hours, but had to balance the finances first The school debt between her and her doctor husband was significant The vision of the life they want has kept them motivated to pay it down She found examples of people doing this, which proved to her that it’s possible Rho started a blog about their debt journey, which has evolved into her starting her own financial coaching business The side business organically grew out of her natural interests  Rho has been successful at setting boundaries at work so she doesn’t burn out The pandemic has shown her she can slow down, have her business, be a mom, and still practice Rho’s Website: Lawyer’s Escape Plan Quiz: Instagram:  

Apr 6

34 min 13 sec

In today's episode, I talk about Human Design, hustle & flow, and why it's ok to be more of a sprinter than a marathoner. Lawyer’s Escape Plan Quiz: Instagram: Human Design Chart:

Apr 2

11 min 36 sec

Kat Johnston spent over a decade between BigLaw litigation and being in-house at a Silicon Valley company. The intensity of working in those environments and the stress took their toll. So, Kat started to prioritize taking better care of herself. Ultimately, as her focus and priorities shifted, Kat decided to leave practice and has taken the past 2 years off to give herself time to reset, explore, and find the next right step for her career journey.  In this episode, we discuss: Working hard along the path isn’t the same as working hard at figuring out a path Kat enjoyed the clarity of mission working in-house and the ability to be more herself, have room to innovate and be creative  In-house practice at a Silicon Valley company is still an intense place to work Kat was really burned out physically and emotionally She realized that she had to take self-care more seriously and set real boundaries at work You can start being the person you want to be before you leave your job The more she took care of herself, the more it made her question “what are we all doing?” As she shifted, she was more out of sync with her colleagues For Kat, she came to decide that she didn’t need to have the answers before leaving her job She left with no plan for a year - other than that she’d planned out the money piece with her financial advisor She sold her home, sold most of her things, and traveled for a year The first year was not about figuring it out - it was about allowing herself to reset and live differently She then spent another year traveling the US in an airstream, but more focused on thinking about next steps She’s now in the early stages of building her own wellness & nature retreat Lawyer’s Escape Plan Quiz: Instagram:     Kat’s Instagram:  

Mar 30

50 min 49 sec

We all want to be able to sit in a room, research our career options, and come up with a plan we're 100% confident in before taking action.   But here's the thing: you can't wait for total confidence and clarity to take action because it's the action taking that grows your confidence and clarity.   Lawyer’s Escape Plan Quiz: Instagram:

Mar 26

10 min 46 sec

Vanessa Kuljis is the Founder of BloomRise LLC and a GALLUP Certified Strengths Coach. She works with lawyers and other professionals to discover individual talents, own their unique value proposition, and move toward setting and achieving authentic goals. Vanessa was previously the Director of Professional Development and Leadership Initiatives at the University of Miami Law School and, before that, a litigation associate. In this episode, we discuss: Vanessa went straight through from undergrad to law school into a litigation practice As the child of immigrants, the idea of being a professional working in a big fancy building seemed like the ultimate achievement  Vanessa realized she really wanted more interaction with people, and more emphasis on relationship-building in her work She also started to realize she wanted to build something, she just wasn’t sure what yet Vanessa moved to NY for a year for her husband’s job and decided to explore other interests rather than practice Ultimately, Vanessa went into higher education, working in student services at a law school As part of her job, Vanessa got the Gallup CliftonStrengths certification  She ended up consulting on strengths on the side and realized this was the business she wanted to build In leaving her job to do her new business full-time, Vanessa realized how true it is that courage isn’t absence of fear, it’s taking the leap despite your fear It may look from the outside like a move was sudden and easy, but it’s just because you don’t see all of the the thought and processing going on behind the scenes Strengths coaching walks you through 3 stages: awareness, appreciation, application You often can’t see your strengths because they are so inherent to who you are It’s a much higher return to invest in your strengths than try to improve on your weaknesses Vanessa’s Website:   Lawyer’s Escape Plan Quiz: Instagram:   

Mar 23

58 min 32 sec

Being a lawyer can make you feel very one-dimensional. Finding the time and space to explore your interests will both make you a happier person in the moment, and help you figure out that elusive right next step in your career. Lawyer’s Escape Plan Quiz: Instagram:    

Mar 19

18 min 36 sec

Vicki Huebner is the Director of Online Legal Programs and an Adjunct Professor at Santa Clara University School of law. She is also the founder of Upskilled Canines, a dog training business. Vicki spent a number of years in litigation, from a clerkship, to a big firm, to a smaller firm. She realized that practice did not light her up the way she saw it do for some people she worked with. On somewhat of a whim, she took an opportunity to work in career services at a law school. 25 years later, she’s still working in higher education. But, she has simultaneously pursued her real passion for dog training and started her own business. She figured why wait until retirement to start doing what she really loves. In this episode, we discuss: Vicki’s parents had pushed her towards law as a stable and lucrative career Vicki’s practice ranged from a clerkship, to BigLaw litigation, to small firm litigation Vicki saw the partners at the small firm be so passionate about the work and having fun That’s when she realized law practice was probably just not her thing Somewhat serendipitously, Vicki came across a job in law school career services  Although it was a bit of an impulsive move and Vicki thought she might return to practice in some form, she’s now 25 years into higher education She enjoys the scholarly environment At some point, Vicki felt she was outgrowing career services, but was able to pivot to a more strategic area of the law school in online program development Vicki realized she liked the business strategy and operations, which is what she’d liked from the small firm Higher education can be very slow to evolve and bureaucratic  Vicki followed her passion for dogs and started training them and volunteering at the humane society Her natural talent for dog training came through, and she now has a small side business Lawyer’s Escape Plan Quiz: Instagram:

Mar 16

45 min 18 sec

Working in your zone of excellence can be the enemy of finding true fulfillment at work. I know it can be very hard to even think of what else you'd do besides being a lawyer. Working to uncover your Zone of Genius is one step in that process.   Lawyer’s Escape Plan Quiz: Instagram:   

Mar 12

12 min 40 sec

Elena Deutsch is the founder and CEO of WILL (Women Interested in Leaving Law). With a background in executive and leadership coaching, Elena guides women through the process of discovering what they want, leveraging their strengths, and researching inspiring new possibilities.  In today’s episode, we discuss: Many of Elena’s clients want to do work that’s more meaningful to them Try saying “I do lawyering” versus “I am a lawyer”  We are all creative, we just have to access it The power of the StrengthsFinder test The concept of zone of genius  We often don’t recognize our own strengths because they are so natural to us Lawyer’s Escape Plan Quiz: Instagram:     Elena’s website:

Mar 9

38 min 53 sec

Jay Harrington is the Co-Founder and Chief Strategist at Harrington Communications. Jay went from a big law bankruptcy practice to a portfolio career that spans from marketing & PR to training & coaching to book author. Jay highlights two things I think are so important. First, you can design your life. You can pick the work that supports the life you want to live, rather than live the lifestyle demanded by a certain job. Second, he talks about making yourself your own best client and committing time to pursuing your priorities, whatever you decide they are. Without that, you’re stuck in a reactive mode that makes it very difficult to move forward in a meaningful way. In this episode, we discuss: Jay had a relatively positive experience as a big law associate, but found he had the entrepreneurial bug Jay jumped into a marketing business with his wife, a graphic designer The company provided him with an outlet for more writing, which he enjoyed The benefits of taking a chance before the golden handcuffs and family obligations take full hold During the Great Recession, as a hedge, Jay started doing some bankruptcy work again, which snowballed into a small law firm 3 years into that, he burned out on doing both law and marketing The way Jay decided which route to take was by deciding what he wanted his life to look like  Jay and his wife decided their priority was moving to a small town where they could get outdoors often. So, that led him to lean into the marketing business, but do it remotely Jay now has portfolio career of marketing, consulting, trainings, and writing Find the time to prioritize yourself, or you’ll stay stuck Lawyer’s Escape Plan Quiz: Instagram:  Jay’s Website:

Mar 2

45 min 55 sec

A gratitude practice will not only make you feel happier on a day-to-day basis, but it will help transform you into the kind of person who sees possibilities, rather than limitations.   Lawyers’s Escape Call:  Instagram:

Feb 26

9 min 13 sec

Geoffrey Stein is a litigator turned portrait artist. Geoffrey initially went into the law because it was something reasonably stable to do with a liberal arts degree. Although he wasn’t passionate about it, he found himself at the top of his class and going down the standard firm route. He practiced in a few different arenas, while trying to incorporate more and more of his long-standing love for art. Eventually he decided to go all-in and leave the law to be a full time painter. In this episode we discuss: Art was always a part of Geoffrey’s life Geoffrey knew that big law wasn’t for him Geoffrey tried to combine his practice with his interest in art for many years Eventually Geoffrey went all in on his art career It was a gradual process to identify fully as a painter, not a lawyer Lawyers’s Escape Call:  Instagram:    Geoffrey’s Website:

Feb 23

28 min 47 sec

In today's episode I talk about identifying your unique strengths through the Clifton StrengthsFinder test, and why this will be more useful in helping you identify next steps than just trying to repackage your skills.   Lawyers’s Escape Call:  Instagram:

Feb 19

10 min 21 sec

Alli Elmunzer is the Attorney & Founder of Influencer Legal, a virtual law firm helping entrepreneurs navigate the legal side of online business. Alli started her career in commercial real estate. But after becoming quickly disillusioned, she left to be a wedding photographer. Alli was a photographer for 6 years. During that time, she also helped other creative business owners with legal issues on the side. She found that the legal work, done on her terms, was a good fit. She is now able to run her law practice the way that suits her and still be immersed in the world of entrepreneurship that she loves. Alli was pretty clear from the beginning that she wasn’t happy in firm life In the process of planning a wedding, Alli fell in love with photography Alli initially gained experience by offering to work for photographers for free   She was able to build her business before quitting As life evolved, she didn’t want to work on the weekends and started considering another pivot She was able to jump back into practice helping other creative business owners  Alli considers herself a lawyer-entrepreneur  Working for herself makes all the difference The traditional law industry is so antiquated, it’s become a bad fit for more people   Lawyer’s Escape Call:  Instagram:  Alli’s Website:

Feb 16

34 min 29 sec

In this episode, I talk about how big tech companies know that well-designed spaces can reduce stress, improve cognitive function, and enhance mood, creativity, and productivity. They go to great lengths to incorporate this knowledge into their office space. I also give a few tips on how you can leverage this information to get some of these same benefits, even when you work in a boring gray box.

Feb 12

10 min 4 sec

Stacey Wang is the Director of Product Marketing at Ironclad, Inc. Stacey went from Harvard Law to being a BigLaw litigator, along the traditional path. But a few years in, she started to feel unfulfilled and started assessing what, specifically, wasn’t working for her. She realized that the practice of law was stifling her creativity. She also had an epiphany that you only live once, so she better make it count. So, she pushed past the identity crisis and fear and landed a job at a start-up. From there, she’s been building a career in start-ups that she loves.   In this episode, we discuss:  Stacey reflects on how her experience in the early years of practice were colored by being very young You can be dissatisfied in law even if you don’t have horror stories She felt like her creativity was stifled Her identity as a lawyer and the weight of her loans held her back for a little while Stacey ultimately reframed things and realized she was more concerned about losing time than the financial challenges Stacey used the Designing Your Life book exercises for self-observation and discovery She found a start-up company she liked and then applied to an open job she thought she could fit into The key is knowing you can learn quickly. If so, you’ll be fine in any new position Don’t just jump into the next thing without the reflection on who you are and what you’re really looking for Illegal Design: Leaving Law made Fun Facebook Group:  Instagram: 

Feb 9

39 min 53 sec

In today's episode I talk about the importance of broadening your circle of influence. If you're always surrounded by lawyers sticking to the traditional path, it's going to continue to make it hard to see different perspectives and opportunities. So, spend time with people who expand your world, not limit it.   Leaving Law Made Fun Facebook Group:   Instagram:

Feb 5

10 min 27 sec

Amy Impellizzeri is a former big law corporate litigator who leveraged a sabbatical opportunity to do freelance writing for a  start-up publisher. She then permanently left practice to lean into her interest in writing and is now, as she says, a writer who used to be a lawyer rather than a lawyer who writes. She’s published 5 fiction novels and one non-fiction book, “Lawyer Interrupted”. In 2022, “How to Leave the Law”, her second non-fiction book with co-Author Liz Brown, will be released. We have a great conversation about creativity, limiting beliefs, and prioritizing taking the time for exploration. For anyone who has thought about chucking it all to become a writer, I think you’ll love this interview.   In this episode we discuss: Amy started in a smaller law firm, then moved to big law for a decade thinking that’s what you do if you have the chance Having kids was a respite from a grueling practice Amy was offered a 1 year sabbatical offer during the great recession  Amy used the year to gain clarity on her next step Amy did freelance writing for a start-up publisher Law is basically designed to stamp out your creative and innovative sides Amy reconnected with her interest in writing A legal background helps you in so many business ventures Craft exit plan by spending a year of intentional exploration You have time - you just have to draw boundaries and take it   Illegal Design Facebook Group: Instagram:  Amy’s Website:

Feb 2

43 min 50 sec

In today's episode I talk about 3 reasons why you should prioritize play in your life:  Calms the mind Sparks creativity Connects you to what you enjoy doing I also talk about the 4 main types of play: Physical Ritual Imaginative Discovery Illegal Design Facebook Group: Instagram: 

Jan 29

10 min 49 sec

Vanessa Perlman is a corporate attorney and has mixed freelance legal work with running her own travel business. She gives us a great example of how building a career isn’t an all-or-nothing endeavor. You can mix and match. You can go back and forth. You can do what makes most sense for each season of your life. As lawyers, we often put so much pressure on making a change, and Vanessa shows us that we can lighten up on ourselves a bit and it will still all work out. Vanessa ended up doing freelance legal work Freelance work opened up time and space to start a travel business  Vanessa incorporated her interests by including a global health philanthropic element in her travel business You don’t have to be all or nothing in your approach to exploring your interests Vanessa has balanced exploring different career options with the reality that she’s her own sole breadwinner   It’s ok if something ends up not working - it’s all still a worthwhile experiment  Let go or be dragged Illegal Design Facebook Group: Instagram:

Jan 26

36 min 1 sec

Kim Nicol is a lawyer turned mindfulness and leadership coach. Kim tells us about how she explored her natural interests and that took her into a new field. It was scary, but also enlightening to realize that people actually make money outside of the legal and corporate world. Kim has created a portfolio career for herself. Among other things, she specifically works with lawyers on wellness and mindfulness. It can be an important tool to calm your brain long enough to get clarity on whether you hate practice or just hate your environment. Kim is a great example of someone who’s found work that really aligns with her personality and strengths. And she gives us some hope about managing the stresses of being a lawyer.  In today’s episode we discuss: Being good as a litigator was going to run against Kim’s natural grain Being a lawyer is like becoming a professional pessimist...possibly negative Competition isn’t a natural strength for everyone Kim initially landed in legal publishing  The next career pivot was the scary part for Kim Kim’s interest in mindfulness, yoga, and fitness guided her next steps Kim realized people make money outside the legal/corporate world Kim’s curiosity and confidence combined into courage We have the skill of advocacy, we need to start advocating for ourselves Kim has created a portfolio career of mindfulness, leadership, and life coaching Kim specifically teaches continuing legal education on wellness and mindfulness Illegal Design Facebook Group:  Kim’s upcoming CLE: Kim’s Website:

Jan 19

38 min 39 sec

In today's episode, I give you 5 tips on designing your home office: Quality Chair Lighting Declutter & Organize Plants & Nature Personalize Illegal Design Facebook Group:

Jan 15

16 min 31 sec

Sarah Cottrell is my podcasting soul sister. She is a former big law litigation associate who, after 10 years of practice in various forms and paying off her law school loans, moved into the work she’d been wanting to do for years. She launched the Former Lawyer Podcast in August 2019 (within a week of this podcast’s launch!) and now also runs the Former Lawyer Collaborative. In today’s episode we discuss: Sarah and I geek out on our shared brain So many of us are under-educated on the realities of being a lawyer In applying to smaller firms, Sarah realized she didn’t want those jobs either Sarah’s anxiety disorder made her a great lawyer, in many ways, but also made the law a particularly bad fit  Sarah left big law and took a job making 1/6th what she made Eventually, Sarah went on to become an appellate court staff attorney This was the best legal job she could have had, so it made it extra clear she didn’t want to practice at all Sarah and her husband had a long-term plan for her to leave the law completely, after paying off their loans Sarah explored her interests in the name of figuring out who she was, if not specifically for figuring out her next career Side hustles work for some people, not everyone Sarah left her job to start the podcast and business that had been in her head for years Sarah also runs the Former Lawyer Collaborative, a confidential community supporting lawyers moving into new careers Illegal Design Facebook Group: Former Lawyer Website:

Jan 12

50 min 50 sec

In the Illegal Design mini-episodes, I will go deeper on how we get unstuck and actually design a purposeful and fulfilling life.  Join the Facebook Group:

Jan 8

12 min 2 sec

Annette Choti left a 20 year career at the Department of Labor to start her own legal marketing firm. Annette tells us how she came to make a shift, the moment of serendipity that led her to her new career. She also tells us about all the rewards and challenges of running your own business. Annette worked for Department of Labor for 20 years The stable lifestyle of the job was worth the trade-offs for her  After 20 years, when she started thinking about a shift, she didn’t know what her options would be In a moment of serendipity, Annette heard about legal marketing writing  Annette built a side business, which for her was a reasonable balance between risk and stability  She baby stepped to a new career Going down this road lead Annette to learn all sorts of new skills in digital marketing  There’s still a long time left in your career. Even if you’re 20 years in! Illegal Design Facebook Group: Megan Smiley Interiors:   Law Quill:

Jan 5

37 min 54 sec

Today’s episode is a little different. I don’t have a guest. Instead, I’m filling you in on what has been going on in my life and career. I get into the whole process, what I’m doing now, and what I see on the horizon. I also talk about my thoughts on building a purposeful life and my new free Facebook Group designed to help us do that together. In the episode I talk about: Getting stuck in my second career Having no idea how to start to take the next step Getting help thinking through my confusion Considering ayahuasca on the advice of a career coach Doing all of the things trying to find a clue to my next career step  Identifying my core values Starting and then pivoting a new interior design business My Illegal Design Facebook Group (free)

Dec 2020

27 min 17 sec

Shunta Grant is a former litigator turned business owner. When it became clear that practicing law wasn’t a fit for her, she leaned into her side project making hair bows. She grew that business successfully and leveraged all of her new business experience to launch her current product, The Best Today Guide. Shunta tells us about the power of letting go of the expectations you had for yourself and creating a career around your life, rather than the other way around. In this episode we discuss: Being focused on checking all the boxes Gaining clarity that your goals and priorities may have shifted Letting go of your identity as a lawyer Embracing your new identity Finding a more aligned career felt like a weight lifted It’s an evolution finding what feels right Building your business around your life, not the other way around Shunta Grant’s Website:    Podcast Instagram: Podcast Website:    

Dec 2020

36 min 30 sec

If you ever feel like you’re drawn to something that just isn’t “realistic”, think about Jess’s story. It's hard to make a bigger leap than from international human rights at the Hague to stand-up comedy. In this episode we discuss: The limited view of career options many of us have Jess’s career in international criminal law At the end of the day, practicing law is still practicing law - even in an interesting context Looking down the career path, Jess realized she wasn’t excited to practice forever Watching Jon Stewart inspired Jess to combine her interests in politics and comedy She took a huge risk and went all in on comedy Jess Salomon’s Website:   Podcast Instagram: Podcast Website:

Dec 2020

43 min 1 sec

Jessica Medina is a former big law litigator and SEC investigator who now runs her own financial coaching business. She helps big law attorneys who need a financial plan in place to allow them the freedom to explore new career options. Basically - she helps people avoid or remove those pesky golden handcuffs so many of us get caught in. Jessica tells us about her own journey of 14 years in practice, 5 and 10 year financial plans, and finding the right fit for her next career move. I think her story is very relatable in that she identifies herself as a risk-averse person. But, just because you value security or your timeline may be a bit longer does not mean you can’t be making a plan to open up options for your future self. In today’s episode we discuss: How a big firm career seemed like the only responsible option right out of law school as a single mother of twins  It’s great if a firm supports parents with free, onsite childcare, but there are still always challenges of balancing work and family time When faced with the possibility of partnership, Jessica was forced to admit to herself that she didn’t want to continue down that road Working for the SEC was a big improvement in terms of work/life balance, but also made it clear that practicing law was not Jessica’s forever dream It’s hard to decide what to do when you’ve spent your whole life chasing one career path In thinking through possible alternative careers, intuition told her that financial counseling (a “fun” hobby for her) felt right and aligned It was hard to walk away from practice - both for prestige and financial security Jessica did this on her own timeline, one that made sense to her Entrepreneurship works different muscles, but you can learn new skills Jessica now helps big law associates who are both “underwhelmed and overwhelmed” by their situation Having a financial plan in order allows you to think more broadly about new career path options Talk to people outside of your immediate work environment; include non-lawyers in your friend group Competitive karaoke singers remind you that life doesn’t all have to be so serious Instagram:  Website:   Guest Website:  

Nov 2020

48 min 44 sec