Aligned

Jessie Brown, JD, PCC
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Conversations on career, purpose, and authentic success for lawyers and other high achievers. Hosted by Jessie Brown, JD, PCC, former Big Law litigator executive coach and retreat facilitator. Inspirational and practical, Aligned (formerly Returning to Soul) explores how to build an authentic career and life that foster joy, fulfillment, and impact. Tune in for solo episodes and thoughtful interviews.

  1. 14 hr ago

    Can Law Firm Partners Be Successful AND Happy? The Six Pillars of a Happy Rainmaker with Jennifer Gillman

    What if you could be a successful law firm partner without sacrificing your health, relationships, and happiness along the way? For many lawyers, success comes with a steep price: long hours, high stress, missed family moments, lack of sleep and exercise, and little time for many of the things that make life meaningful. But does it have to be this way? In this episode of Aligned, I sit down with Jennifer Gillman, former practicing attorney, founder of Gilman Strategic Group, and the "Law Firm Matchmaker," to explore how law firm partners can build successful, sustainable careers that align with their values, strengths, and personal priorities. Jennifer shares her own journey from practicing labor and employment law to becoming a legal recruiter, and why she ultimately created a different approach to helping partners find the right firm for them. We explore why so many accomplished lawyers feel trapped in careers that no longer fulfill them and how perfectionism and the relentless pursuit of achievement can undermine our well-being. Jennifer also introduces her Six Pillars to Becoming a Happy Rainmaker, a practical framework for creating a fulfilling legal career without sacrificing everything else that matters. In this conversation, we explore: Why professional success doesn't always translate into personal fulfillment. How to recognize when your law firm is no longer the right fit for your values, strengths, and goals. Why lawyers often sacrifice their health and relationships in pursuit of an elusive A+. How small, intentional actions—even six minutes at a time—can create meaningful changes in our well-being and careers. The six pillars of a happy rainmaker. Why developing your own clients can create greater autonomy and freedom in your law career. How to evaluate both the tangible and intangible aspects of career satisfaction, including compensation, resources, trust, respect, and belonging. Why creating a meaningful life outside of work is essential to successful succession planning and retirement. Jennifer also shares a powerful personal story about a routine medical appointment that revealed an early-stage cancer diagnosis—a reminder of why our health cannot always wait until work slows down. Whether you're a law firm partner, an aspiring rainmaker, or a lawyer questioning whether there's a more fulfilling way to practice law, this conversation offers practical insights and a hopeful reminder that a different kind of success is possible. Connect with Jennifer Gillman: Website: https://gilmanstrategicgroup.com LinkedIn: Search for Jennifer Gillman, Law Firm Matchmaker Jennifer's book, The Six Pillars to Becoming a Happy Rainmaker, is available on Amazon in print, Kindle, and audiobook formats. Additional resources include a companion workbook and a Six Pillars assessment. About Aligned Hosted by Jessie Brown, JD, PCC, former Big Law attorney turned career coach, Aligned explores how lawyers can create careers and lives that reflect who they truly are and what matters most to them. If this episode resonates with you, please follow Aligned, leave a rating, and share it with another lawyer who might benefit from this conversation.

  2. 6 days ago

    What If Success Isn't What You Thought It Would Be? With Erin Gerner

    What happens when we follow the path we were taught would lead to success, only to discover that the life we've worked so hard to create isn't the life we actually want? For many lawyers, we've spent years chasing the next achievement: getting into a great law school, landing the prestigious job, making partner, earning more money. But what happens when our priorities change? When the career that once made sense no longer fits who we've become? In this episode of Aligned, I'm joined by attorney, entrepreneur, coach, and founder of Powerhouse Lawyers, Erin Gerner, for an honest, heartfelt, and sometimes hilarious conversation about redefining success, navigating life's transitions, and finding the courage to create a career and life that truly align with who we are. Erin shares her journey from Big Law to an in-house legal role, stepping away from practicing law after becoming a mother, building businesses, coaching lawyers, and eventually finding her way back to legal work on her own terms. We explore what happens when our identity becomes wrapped up in being a lawyer, why it's so difficult to let go of the expectations we've internalized, and how we can begin trusting ourselves enough to pursue what we truly want. We also talk about the unique challenges of midlife, including changing priorities, perimenopause, and the realization that what worked in one season of life may no longer work in another. In this conversation, we explore: Why a successful legal career doesn't always translate into a fulfilling life. The difference between what we've been conditioned to want and what we authentically desire. How becoming a mother or entering a new season of life can fundamentally shift our priorities and capacity. Why career paths don't have to be linear, and how we can give ourselves permission to pivot, experiment, and evolve. The power of community and surrounding ourselves with people who remind us of what's possible. How small acts of courage, including simply saying no, help us develop self-trust. Why fear, perfectionism, and the pressure to always get things right can keep lawyers stuck. How taking imperfect action builds confidence and helps us move toward meaningful change. One of my favorite reminders from our conversation is that we don't need to have the entire path figured out. We can simply take the next best step. And sometimes, the greatest growth comes not from achieving another goal, but from who we become when we're willing to feel the fear and move forward anyway. Whether you're questioning your career, navigating a transition, or simply feeling called toward something different, I hope this conversation reminds you that you're not alone, that there are many ways to define success, and that it's never too late to create a life that feels authentic to you. Connect with Erin Gerner: Website: ErinGerner.com Podcast: Powerhouse Lawyers Find Erin on LinkedIn, Instagram, and Facebook. If this episode resonates with you, I'd love for you to share it with another lawyer who might need to hear this conversation. And please follow Aligned for more honest conversations about creating meaningful careers and lives.

  3. 6 Oct

    Mindset Shifts for a Successful Career Pivot, Side Hustle, or Job Change

    What does it take to make a successful career pivot, job change, or turn a passion project into something more? In this solo episode of Aligned, Jessie shares the mindset shifts and mental habits that helped her gradually transition from practicing law into building her coaching, consulting, and retreat business. One of the biggest challenges for lawyers considering a change is the desire to have the entire path figured out before taking the first step. But career transitions rarely work that way. They require experimentation, a willingness to change direction and try new things, and the ability to let go of time or money you've already invested in a path that no longer feels right. Jessie shares some of the practices that helped her navigate that uncertainty, including: • Creating a compelling vision for what you want—not simply focusing on what you want to escape• Committing to that vision while staying flexible about exactly how you get there• Recognizing sunk cost bias and giving yourself permission to change course• Letting go of other people's opinions and focusing your energy on what you can control• Protecting your attention and eliminating distractions• Surrounding yourself with people and stories that expand your sense of what's possible• Taking consistent action, even when the steps feel small Jessie also shares how, while she was still practicing law, she created a vision board filled with women who had once been lawyers and had gone on to create entirely different careers. Those women became evidence for her brain that another path was possible. You don't need to know exactly where the path will lead before you begin walking it. Clarity often follows action. If you're contemplating a career change, building a side business, or wondering what your own "Act Two" might look like, this episode offers practical encouragement for navigating the uncertainty that comes with creating something new. Connect with Jessie on LinkedIn or through jessiebrown.org

  4. 30 Sept

    From the Grind to Aliveness: The Transformative Power of Retreat

    What happens when we spend so much of our lives thinking, producing, achieving, and caring for others that we lose touch with ourselves? In this solo episode of Aligned, Jessie explores the transformative power of retreat—especially for women lawyers whose demanding careers and full lives can leave little room for creativity, embodiment, play, or feeling fully alive. Drawing from her own experience as a Big Law attorney, working mother, and now retreat facilitator, Jessie shares how stepping away from ordinary life helped her reconnect with parts of herself that had gone dormant. Retreat wasn't about becoming someone new. It was about remembering who she had always been. Jessie explores how nature-based and mind-body practices can help us move beyond the analytical, productivity-focused mode that dominates so much of legal life and reconnect with our bodies, creativity, intuition, joy, and the "wild woman" within. In this episode, Jessie discusses: • Why high-achieving women can become disconnected from themselves while caring for everyone else• The difference between simply being outdoors and mindfully immersing yourself in nature• Forest bathing and the restorative power of slowing down in the natural world• Why movement, music, breathwork, sound healing, and other embodied practices can offer something thinking alone cannot• Jessie's own experience of rediscovering parts of herself through transformational retreats• The "wild woman" archetype and reconnecting with our instinctual, creative, embodied selves• Why taking time for yourself can ultimately benefit your family, colleagues, clients, and community• Simple practices you can try at home to cultivate more presence, freedom, joy, and aliveness Jessie also recommends The Wild Woman's Way by Michaela Boehm for women interested in simple practices for reconnecting with their bodies, sensuality, freedom, and aliveness. If you've ever felt that life has become more of a grind than an adventure—or wondered whether some essential part of you has gotten buried beneath your responsibilities—this episode is an invitation to reconnect. Connect with Jessie:Jessie Brown, JD, PCC, is a former Big Law attorney and coach for lawyers. She also facilitates transformational retreats for women lawyers and workshops for law firms and legal organizations. If you're interested in Jessie's coaching, workshops, or future retreats, visit jessiebrown.org If this episode resonated with you, please follow Aligned, leave a rating or review, and share the episode with someone who might benefit.

  5. 20 Sept

    What Makes You Come Alive? Rethinking Purpose

    What if discovering your purpose isn’t about finding one perfect calling but about noticing what makes you come alive? In this episode of Aligned, Jessie explores one of the questions at the heart of her work with lawyers: How do we create lives and careers that feel meaningful, purposeful, and true to who we are? Drawing from her own journey from Big Law to coaching and retreat facilitation, as well as her training as a Purpose Guide, Jessie shares some of the common beliefs and “shoulds” that can keep us stuck when we’re trying to discover our purpose. She explores: • Why purpose may be less about asking “What does the world need?” and more about asking “What makes me come alive?” (inspired by Howard Thurman) • What chronic stress and burnout can do to our ability to hear our intuition and recognize what energizes us • The powerful message Jessie received to “create a clearing in the dense forest of your life” (Martha Postlethwaite) and how creating space allowed her to hear her inner guidance • How your sense of purpose can evolve as your circumstances and priorities change • How to recognize clues to your purpose by paying attention to moments of joy, flow, aliveness, contribution, and meaningful connection • How you can curate your legal career around your values, strengths, and the kind of contribution you want to make • When it might make sense to stay in work that isn’t deeply meaningful because of financial or family priorities—and how to do that consciously • How a creative practice, side business, volunteer work, or other form of contribution can reconnect you with a sense of aliveness • The “default purposes” and inherited “shoulds” we absorb from our families, culture, and other people—and how to begin questioning whether they’re actually ours Ultimately, Jessie sees purpose discovery as a journey of coming home to ourselves—letting go of what no longer fits and becoming more fully who we are. And perhaps the question isn’t “What am I supposed to do with my life?” Perhaps it’s simply: What makes me come alive—and how can I create more space for that? If you’re a lawyer—or anyone navigating a period of career or life transition—this episode invites you to pause, listen inward, and consider what your life might be telling you. Learn more about Jessie and her work with lawyers at jessiebrown.org.

  6. 12 Sept

    How Contemplating Mortality Helps Us Make Brave Choices

    What if thinking about death could help you live — and work — more fully? In this solo episode of Aligned, Jessie shares one of the most powerful tools she's found for cutting through fear and getting clear on what truly matters: contemplating mortality. Drawing on her own story of losing both parents during college, her training as a death doula with former lawyer Alua Arthur, and her time volunteering with hospice patients, Jessie explores how facing impermanence can dissolve the limiting beliefs that keep many of us stuck. Jessie walks through two exercises you can try yourself: a hospice chaplain's post-it note exercise, and the "two jars" practice for visualizing how much time we really have.She also unpacks the two most common regrets from Bronnie Ware's The Top 5 Regrets of the Dying — and why fear of disappointing parents, chasing approval, and financial scarcity often keep people from making the courageous choices they long to make. In this episode: Jessie's personal story of loss and how it shaped her early career choicesWhat she learned training as a death doula with Alua ArthurThe post-it note exercise from her hospice volunteer trainingThe "two jars" exercise for visualizing your remaining timeThe top two regrets of the dying, from Bronnie Ware's researchHow Internal Family Systems (IFS) work helps unpack the fears that can impact our work habits and job choicesResources mentioned: Alua Arthur's TED Talk The Five Invitations by Frank OstaseskiThe Top Five Regrets of the Dying by Bronnie WareConnect with Jessie: Website: jessiebrown.org LinkedIn If this episode resonated, please rate, subscribe, and share it with someone who might benefit.

  7. 7 Sept

    Awakening Your Intuition with Evidential Medium Eliza Rey

    Aligned: Conversations on Career, Purpose & Authentic Success In this episode of Aligned, host Jessie Brown sits down with Eliza Rey — an intuition expert, occupational therapist, and evidential psychic medium affiliated with the research-based Winbridge Institute and Forever Family Foundation. Eliza grew up around lawyers, helping out in her dad's law firm, and has had significant relationships with lawyers throughout her life. She knows the demands of the profession and the way most lawyers are driven to serve and make a difference. She also knows how the typical lawyer brain— analytical, logical, skeptical, and rational — can impede a lawyer's ability to readily access their intuition. Eliza has spent decades helping people reconnect with their inner guidance. Jessie and Eliza explore what intuition actually is, why so many high-achievers — especially lawyers — feel disconnected from it, and simple, practical ways to start listening to it again. What intuition means, and why the "rational mind" and "intuitive mind" aren't at oddsWhy lawyers' analytical training can make it harder to trust a gut feeling — and how to find balance instead of overthinkingSimple daily practices to "awaken" intuition: short meditations, breathwork practices, and time in natureThe power of journaling insights, ideas, or "downloads" before they slip awaySigns and synchronicities — how loved ones who've passed may still send messages (including Eliza's own profoundly moving stories of receiving signs from her late father and brother)Trusting the pull toward an unconventional path, even when it doesn't look logical on paperWhy fatigue and overstimulation dull our intuitive signals, and how to protect our energyEliza's definition of intuition: the ability to gain knowledge and make decisions without needing to reason it out step by stepThe "two roads" story — a simple illustration of what happens when we overthink versus when we trust our inner knowingJessie's own journey from a hectic litigation schedule to a daily meditation practice, starting with just one minute a dayConnect with Eliza: elizarey.comLearn more about Jessie's coaching, workshops, and retreats, and download the free Career Alignment Map and 7 Keys to Succeed Without Burnout at jessiebrown.org If this episode resonated with you, please like, rate, and subscribe to Aligned, and share it with someone who might benefit.

  8. 28 Aug

    From Government Lawyer to Legacy Builder: Sarah Horowitz on Pivoting Into Estate Planning

    In this episode of Aligned, Jessie sits down with Sarah Horowitz — lawyer, mom of four, and founder of the Sarah Horowitz Law Group, Adulting Docs, and the Legacy Collective — to talk about what it really takes to build a law practice around your life instead of the other way around. Sarah shares how a missed school event while sitting idle at her government desk became the turning point that pushed her to leave a stable job at the FDA and start her own estate planning and adoption practice. She and Jessie talk about the fear that comes with giving up a steady paycheck, why estate planning is one of the most learnable and accessible practice areas in law, and how Sarah has built three interconnected ventures — her law firm, Adulting Docs (documents for young adults turning 18), and the Legacy Collective (a mentorship program for women building estate planning practices) — all rooted in her strengths as a connector and a mentor. They also get into something more personal: what it means to think through legacy, values, and how we want to be remembered, and why having these conversations with the people we love is one of the greatest gifts we can give them. How a government law job led Sarah to start her own law practiceFacing the fear of leaving a secure paycheck to go out on her ownCreating a career you enjoy that works for your whole life as a lawyer-momThe power of female mentoring in lawWhy estate planning is one of the most learnable, in-demand practice areas in lawBuilding Adulting Docs to help young adults (and their parents) get essential legal documents in placeLaunching the Legacy Collective, a mentorship community for women growing estate planning practicesWhy there's an abundance of clients — and no need to see other estate planning attorneys as competitionSarah Horowitz Law Group: https://www.sarahhorowitzlawgroup.com/Adulting Docs: https://adultingdocs.com/The Legacy Collective mentorship program (next cohort starts in September!) — linked from the Sarah Horowitz Law Group site aboveEmail Sarah directly: sarah@sarahhorowitzlaw.com If you enjoyed this episode, please rate, review, and subscribe to Aligned — and share it with a friend.

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About

Conversations on career, purpose, and authentic success for lawyers and other high achievers. Hosted by Jessie Brown, JD, PCC, former Big Law litigator executive coach and retreat facilitator. Inspirational and practical, Aligned (formerly Returning to Soul) explores how to build an authentic career and life that foster joy, fulfillment, and impact. Tune in for solo episodes and thoughtful interviews.

Information

  • Creator
    Jessie Brown, JD, PCC
  • Years Active
    2026
  • Episodes
    30
  • Rating
    Clean
  • Copyright
    © Jessie Brown, JD, PCC
  • Show Website
    Aligned

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