Lawyer to Leader

About Lawyer to Leader

This show is built around a single question: why do technically brilliant lawyers so rarely break through as strategic leaders? The answer is simpler and more uncomfortable than most lawyers expect: technical excellence is the entry ticket, not the destination. The Lawyer to Leader is the podcast for driven attorneys who have mastered the law and are ready to master the room, the strategy, and the career that follows. I'm Jonathan Cullen, award-winning former General Counsel and certified Leadership & Performance coach. I've spent nearly two decades in legal leadership, and I built this show for the lawyer who wants more. More progress. More influence. More life. Start here: grab your free Lawyer to Leader Assessment at jonathancullencoaching.com and find the one thing holding your career back.

Publisher

Jonathan Cullen

Category

business · business · education

Language

en

Explicit

No

First episode

19 May 2026

Latest episode

29 Sept 2026

Latest episodes

9 episodes in the feed.

1. 

   29 Sept 2026

   How to Become General Counsel: 3 Challenges Every In-House Lawyer Must Overcome (Jonathan Live)

   Recording of a live solo event. Most in-house lawyers are excellent at the law. That's not the problem. The problem is that the skills that got you into your first in-house role are not the ones that get you to general counsel. In-house counsel career development rarely covers this gap. That's what this video is for. I spent nearly 20 years leading legal teams at Pfizer across three continents, and was named Canadian General Counsel of the Year. I was the client. I decided where the legal work went, and I watched in-house careers progress and stall up close for two decades. If you're wondering how to become general counsel, what I share here is what I actually noticed. In this 45-minute live session I cover 3 challenges facing every in-house counsel, mapped to my 3S Model, self, systems, and scale, and 9 tactics for working through each one. I also walk through the In-House Counsel Accelerator, my small-group coaching program built around this exact framework, launching this fall. WHAT YOU WILL LEARN Challenge 1: The Value You Haven't Defined Yet (Self). In-house, nobody hands you a scorecard the way a law firm does. 3 tactics for defining your own value on purpose: the fast, cheap, good trade-off conversation, building a personal bank of phrases that shapes how clients read you, and delivering principle-based advice instead of one-off answers. Challenge 2: The System You Haven't Built Yet (Systems). Early on, raw effort and good judgment are enough. Eventually they're not. 3 tactics for building systems instead of solving the same problem for the first time, every time: pre-deciding your response to a crisis before it lands, solving problems at their highest conceptual level instead of managing symptoms, and using a red, yellow, green decision matrix to kill the long memo. Challenge 3: The Bottleneck Is You (Scale). You're good at your job. That's actually the problem. 3 tactics for scaling your impact past your own two hands: treating your legal advice like a product, giving away your best work instead of just your busywork, and building systems you're willing to let go of. TIMESTAMPS 00:00 Welcome and who this session is for 02:00 My background: 20 years as the client at Pfizer, and the 3S Model overview 03:00 Challenge 1: The Value You Haven't Defined Yet (Self) 05:00 Tactic: Fast, Cheap, Good, pick two 07:00 Tactic: Build your bank of phrases ("it's fine, JC") 12:00 Tactic: Deliver principle-based advice 17:00 Challenge 2: The System You Haven't Built Yet (Systems) 22:00 Tactic: Pre-decide before the crisis lands (Admiral McRaven) 25:00 Tactic: Solve at the highest conceptual level (fix the roof, not the bucket) 27:00 Tactic: Use color, kill the memo 29:00 Challenge 3: The Bottleneck Is You (Scale) 31:00 Tactic: Treat your advice like a product 33:00 Tactic: Give away your best Legos 35:00 Tactic: Build it, then let it go 38:00 The In-House Counsel Accelerator: format, pricing, how to join 40:00 Q&A QUOTABLES "There are no solutions. There's only trade-offs." "Every one-off answer you give is a system you're choosing not to build." "Expertise alone fails under complexity." "Fix the roof, not the bucket." "There's no color for 'it depends.'" "You're good. That's the problem." WHO THIS IS FOR Junior, mid-career, and senior in-house counsel. Anyone asking how to become general counsel or how to grow an in-house legal career. GCs and legal leaders looking to develop their teams. Anyone trying to figure out why the skills that got them in-house aren't the ones getting them promoted. ABOUT I spent nearly 20 years leading legal teams at Pfizer across three continents. I was the client. I decided where the legal work went, which lawyers got more responsibility, and which ones stayed transactional no matter how technically strong they were. I now coach lawyers and consult with legal departments on in-house counsel career development and the gap between where people are and where they want to be. I help them go from lawyer to leader. WANT TO BECOME A GENERAL COUNSEL? If you want to work through these 3 challenges directly instead of on your own, book a free discovery call and we'll talk through where you're at and whether the In-House Counsel Accelerator is the right fit: Book a Discovery Call (https://www.jonathancullencoaching.com/service-page/discovery-call) Subscribe to this channel for more on in-house counsel career growth, leadership, and what it actually takes to make general counsel. Website: jonathancullencoaching.com Connect on LinkedIn: linkedin.com/in/jonathanjcullen (linkedin.com/in/jonathanjcullen)

2. 

   16 Sept 2026

   Financial Planning for Lawyers: Why High Income Doesn't Mean Wealth (Featuring Dalia Feldberg)

   Most lawyers spend years mastering the law and almost no time learning how to protect or grow the income it earns them. In this episode of the Lawyer to Leader podcast, financial advisor Dalia Feldberg breaks down financial planning for lawyers: why a high salary doesn't automatically create wealth, what changes financially the moment you make partner, and the accounts most lawyers are using wrong. Dalia also talks about why she's built her practice specifically around wealth building for women in law, and why covering your downside (wills, disability insurance, income protection) has to come before you chase any upside. If you've never had a real conversation about money as a lawyer, this episode is where to start. Guest Bio Dalia Feldberg is a financial advisor with Desjardins based in Ottawa specializing in financial planning for lawyers, with a particular focus on wealth building for women in law. She holds a First Class Honours degree from McGill University and a Master's in Sustainable Business and Innovation from EADA Business School in Barcelona, and is currently working toward her CFP® designation. Dalia works with lawyers navigating student debt, rising income, and partnership decisions, building financial plans around their actual goals instead of just selling products. Timestamps 00:00 Financial planning for lawyers: the gap nobody talks about 00:02 Why being a great lawyer isn't the whole story 00:03 Meet Dalia Feldberg, financial advisor for lawyers 00:07 How she got into financial planning for lawyers 00:13 Why lawyers are financially underserved 00:20 Financial advisor vs. lawyer: the same confidence problem 00:23 The real gap between lawyer income and lawyer wealth 00:25 Lawyers working into their 60s with no retirement plan 00:26 The one habit that builds long-term wealth 00:29 Wealth building for women in law: why the focus 00:34 Managing money from articling student to associate 00:38 Disability insurance and income protection for lawyers 00:42 Financial planning for law firm partners 00:44 The biggest investing mistake lawyers make 00:47 What a financial planning meeting actually looks like 00:57 Planning a career change as a lawyer 01:00 One financial move every lawyer should make this week 01:02 The book that changed how she thinks about money Key Takeaways Financial planning for lawyers isn't optional, it's overdue. Income and wealth are different things, and most lawyers never get taught the difference. The habit matters more than the amount. Financial planning for young lawyers can start at $10 or $100 a month. Once you've started, there's something to build a plan around. Disability insurance and income protection are the financial planning basics lawyers skip. Wills, disability insurance, and income protection are the pieces lawyers treat as a "later" problem. How accounts are used are the most common financial planning error. Most lawyers don't have a pension, so if they're not building retirement savings themselves, nobody is. Every career transition resets your financial plan. Articling to associate, associate to partner, employee to business owner, each one changes your income, your tax exposure, and often your team. Wealth building for women in law is a growing, underserved niche. Financial planning for lawyers is a gap; that gap runs deeper for women in law, where there's often no one in the room having the conversation with them. Links Dalia on LinkedIn (linkedin.com/in/dalia-feldberg) (booking link in her bio) Desjardins Financial Security Independent Network Ottawa (https://www.dfsin.ca/en/get-in-touch/financial-centers/ottawa.html) The Happiness Advantage (https://www.amazon.com/dp/0307591549?lv=shuf&channelId=500&plpRedirect=mhFallback) by Shawn Achor The Psychology of Money (https://www.amazon.com/Psychology-Money-Timeless-lessons-happiness/dp/0857197681/ref=sr_1_1?crid=261W5QOUPZ15F&dib=eyJ2IjoiMSJ9.1Ej9TpPoVuWM_km1joB3isSnYwELjItVV5sshabWX3oTmvKhXEbrymaflRhi2mUPnI4PwtGT1xCTV7es7vGqhcsA2kY64dZP5uEYnVNYTkxMkt-W4fQTL4ji4b-JarVkcN-y5yFrgjSzyoHte5LQZQFd5l1OoyGHV1O63DYwwcGWm7-Iq_Zv4pYQ_Kl-vyRgG0kkzPaB0ucUGwQ21KZiHSay2tsn07rDaqTBumje9pQ.MDgSpuVXHXW1k_u0LE4IApTkV3lQCaIaXwYgBMrPE38&dib_tag=se&keywords=The+Psychology+of+Money&qid=1789581771&s=books&sprefix=the+psychology+of+money%2Cstripbooks-intl-ship%2C123&sr=1-1) by Morgan Housel If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com (https://www.jonathancullencoaching.com/) Shareable Moments "If I don't wake up every day and talk to people about death, I'm doing my clients a major disservice. We all die. That's the one reality." "It doesn't matter how much you're putting away. If you can put something away, we can work with that. Until then, there's not much to work with." "You just went to school for seven years. Surely you'd want to protect your ability to earn that income." "If you were there right now, you wouldn't enjoy the journey as much. The journey is where you see the fruits of your effort." "I can speak their language. We resonate with one another."

3. 

   9 Sept 2026

   AI For Lawyers: Why Your Judgment Matters More Than Ever (featuring Colin Levy)

   Colin Levy has read more legal AI hype than almost anyone, and he thinks most of it is useless. In this episode, Jonathan Cullen sits down with the General Counsel of Malbek and author of the new book Code Switched: A Lawyer's Guide to the Era of AI to cut through the noise around AI for lawyers. Colin explains why he thinks lawyers should stop saying please to ChatGPT, why AI hallucinations are a feature not a bug, and why the real risk in legal AI adoption isn't the technology replacing your judgment, it's you forgetting to use it. They get into tokens, AI agents, the billable hour, and why Colin believes we're only in "chapter one" of what artificial intelligence will do to the legal profession. If you've been putting off learning how AI works in legal practice because you're not sure where to start, this episode is your starting point. Guest Bio Colin Levy is General Counsel at Malbek, and one of the most respected voices in legal technology and AI for lawyers, with a large following on LinkedIn and through his newsletter. He's an adjunct professor at Albany Law School, author of The Legal Tech Ecosystem, and editor of the Handbook of Legal Tech. His new book, Code Switched: A Lawyer's Guide to the Era of AI, is on presale now and releases October 6, 2026. Timestamps 0:00 Intro: AI for Lawyers with Colin Levy 1:00 Code Switched: What the Book Title Means 3:00 Writing an AI Book That Stays Relevant 6:00 Global AI Regulation for Legal Teams 8:00 Why Bjarne Tellmann Wrote the Foreword 9:00 Best Chapter for AI Skeptics 11:00 ChatGPT Mistake: A Real Legal Example 12:00 How to Prompt AI Like a Lawyer 13:00 Why AI Hallucinates: Tokens Explained 15:00 AI as a Thought Partner, Not a Chatbot 16:00 AI for Lawyers: Judgment Over Replacement 19:00 The Chainsaw Analogy: AI and Legal Judgment 20:00 Stop Saying Please to Your AI Tool 23:00 Why AI Tools Are People Pleasers 25:00 AI and the Billable Hour Model 27:00 Legal AI Adoption: We're in Chapter One 28:00 AI for In-House Legal Teams 29:00 Week One of Responsible AI Adoption 31:00 Why AI Rollouts Fail Without Training 34:00 AI Hallucinations: Feature, Not a Bug 37:00 Lateral Thinking and AI Creativity 39:00 The #1 Mistake Lawyers Make With AI 41:00 AI for Solo and Legal Aid Lawyers 42:00 AI Ethics for Lawyers: The Real Question 44:00 AI Fails in Law: Real Examples 46:00 Disclosing AI Use to Legal Clients 47:00 AI Agents Explained for Lawyers 49:00 Fruit of the Poisonous Tree: AI Agents 51:00 Legal AI in 5 Years: Read the Book or Not 52:00 What Writing Code Switched Taught Colin 53:00 Rapid Fire: AI Advice for Lawyers 55:00 Where to Find Colin Levy and Code Switched Links Colin's website: colinslevy.com Colin on LinkedIn: linkedin.com/in/colinslevy Colin on Twitter/X: x.com/Clevy_Law Colin on Instagram: instagram.com/clevy_law Code Switched: A Lawyer's Guide to the Era of AI (releases October 6, on presale now): On Amazon and here: https://amplifypublishinggroup.com/product/nonfiction/industries/technology/code-switched/ (https://amplifypublishinggroup.com/product/nonfiction/industries/technology/code-switched/) The Legal Tech Ecosystem (Colin's first book): amazon.com/Legal-Tech-Ecosystem-Innovation-Advancement/dp/B0CKCZTLWW (http://amazon.com/Legal-Tech-Ecosystem-Innovation-Advancement/dp/B0CKCZTLWW) If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com (http://jonathancullencoaching.com) Key Takeaways Code Switched is about the shift from AI helping lawyers finish work to AI helping lawyers build things, a bigger adaptation than any previous legal tech shift. AI for lawyers means AI amplifies judgment, it doesn't replace it. The more powerful the tool, the more skill you need to wield it. Colin's line: a hammer makes it easier to build a wall, but you still need to know where the nail goes. AI hallucinations are a feature, not a bug. Large language models are predictive, token-based systems. They match patterns, they don't understand your question. That means wrong answers aren't a glitch to patch, they're baked into how the technology works. Stop humanizing AI tools. Don't say please, don't treat "I" and "me" as anything but a marketing choice. AI models are built to be people pleasers, which means the lawyer has to be the skeptic in the room, every time. Responsible AI adoption in legal practice starts small and low-risk. Week one should mean one repetitive, low-stakes task done in a controlled way, not a firm-wide rollout with no training behind it. The real AI ethics question for lawyers isn't "should I use AI." It's "how am I using it." Client confidentiality, data hygiene, and transparency matter more than the yes-or-no debate most people are stuck on. Shareable Moments "Assume it knows nothing, and assume you need to give it a seemingly absurd level of context." "These tools don't understand the way humans understand." "AI doesn't power anything." "We're kind of in chapter one. We finished the prologue." "Hallucinations... are a feature, not a bug." "You shouldn't be worrying about hurting its feelings. It has no feelings." "That old saying, it seems too good to be true, can often be the case." "The number one mistake most lawyers make when using one of these tools is assuming it's just gonna be right."

4. 

   7 Aug 2026

   Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian)

   Most lawyers build a career to check boxes: prestigious firm, litigation wins, a steady climb. Sevana Poladian checked those boxes too, then built something of her own. In this episode, Jonathan Cullen talks with the Montreal litigator about launching a solo practice in the middle of COVID, why she chose to partner up years later instead of staying independent, and how she's learned to say no to the wrong clients. This is a story about building a practice on her own terms, one boundary at a time. If you've ever wondered whether going out on your own is worth the risk, this episode is for you. Guest Bio Sevana Poladian built the kind of legal career most young lawyers dream about. She started at smaller firms then, moved into a larger litigation firm before eventually going out on her own. Today she's co-founder of Rastani Poladian Légal, a Montreal firm she launched with Camaylia Tavakol Rastani, pairing her civil and commercial litigation expertise with Camaylia's criminal law practice to serve clients across Quebec. She's also co-chair of the Armenian Bar Association's Québec chapter, where she supports Armenian lawyers and students. Timestamps 00:00 Show intro 00:55 Meet Sevana 02:41 Starting out in litigation 04:07 How litigation builds confidence under pressure 06:44 The leap to solo practice during COVID 08:01 The entrepreneurial skills law school never teaches 10:52 Wearing every hat in a solo practice 13:33 Should young lawyers start their own firm early? 15:51 Why she decided to partner up 17:45 Building Rastani Poladian Légal 19:57 Two practices, one culture 21:02 Spotting client red flags 25:21 Her ideal client today 25:49 Leading the Armenian Bar Association 27:31 Boundaries and balance 30:49 Defining success on her own terms 31:42 Rapid fire 33:46 Closing thanks and where to find Sevana 35:19 Outro and takeaways Key Takeaways Litigation is training for entrepreneurship. Years of thinking on her feet and staying calm under pressure in court gave Sevana the exact muscles she needed to run a business. The leap doesn't need perfect timing. Sevana launched her solo practice in the middle of COVID, after a personal awakening, not once things felt "ready." Running a firm takes a different skill set than practicing law. Resilience, risk tolerance, empathy, and leadership matter as much as legal knowledge, and none of it gets taught in law school. Wearing every hat is a phase, not a permanent job description. The growth comes from learning to delegate and finding mentors who've done it before you. Partnering up can cure the loneliest part of solo practice. Joining forces with Camaylia in 2026 wasn't about needing legal help. It was about growth, and no longer building alone. Selectivity is a skill you build over time. Sevana has learned to spot client red flags early and has gotten comfortable turning down work that isn't the right fit. Success isn't a title or a verdict. For Sevana, it's inner peace. Links Sevana on LinkedIn: https://www.linkedin.com/in/sevana-poladian-b70b2b128/ Rastani Poladian Légal: info@rplegal.ca Recommended show: The Good Wife If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com Shareable Moments "I don't consider age as a factor anymore. A case can be won solely on the strength of the case, not the person handling it." "I'd already proved to myself I could do it alone. So why not do it with someone else?" "Nobody knows everything in this world, including lawyers." "There must be a point where you draw a line, build a wall between yourself and your clients." "Success to me looks like inner peace. There's a constant inner peace knowing that whatever decisions you make are the right ones." "Nothing is guaranteed in life, not even the judge you get. About 95% of cases settle amicably." "One word young lawyers need more of? Patience. Not just young lawyers, everybody, especially in litigation."

5. 

   4 Aug 2026

   The High Pain Threshold: Why Lawyers Miss Their Own Warning Signs (Featuring Allison Canton)

   Episode Introduction In this episode, Jonathan Cullen talks with Allison Canton about what it actually looked like to unravel while succeeding, why lawyers have such a high tolerance for their own misery, and how she rebuilt her life through small experiments instead of one dramatic exit. They also get into sleep, boundaries, and why "don't overthink it" might be the most useful advice a lawyer can hear. Guest Bio Allison Canton spent years checking every box on the traditional success list. Harvard Law. BigLaw. General Counsel at high-growth startups, where she scaled legal teams through hypergrowth and a multi-billion-dollar acquisition. Then came the uncomfortable realization: the work she excelled at was also making her miserable. She didn't leave the law. She rebuilt her relationship with it. Today, Allison is a Senior Advisor at Markups.ai, where she helps legal teams use AI to move from contract processors to strategic partners. And through her new project Fit to Practice, she teaches entertaining, practical and data-backed CLE programs to help high-achieving lawyers protect their most valuable asset: their wellbeing. She also writes and podcasts about ambition, meaning, and life after chasing gold stars on her Substack, Practically on Purpose. Timestamps [00:00] - Dream job misery [00:45] - The sleep deprivation trap [01:39] - Podcast intro [02:20] - Allison's story, and how she almost became a sociology PhD instead [04:37] - 1L anxiety and not sleeping for days at a time [07:58] - How a sleep meditation search became a 15-year practice [09:24] - BigLaw reality check: they're buying 100% of your time [12:08] - The leap to Flatiron Health as employee number two [16:02] - Hypergrowth and the breaking point [19:29] - Leaving to heal, and getting pregnant three weeks later [22:16] - Rediscovering the self she'd cut off to fit the mold [24:30] - The identity box: why her lawyer friend won't publish her books under her own name [25:20] - The small experiments mindset [26:02] - Testing meditation teaching in her own backyard before building anything bigger [30:01] - The alarm bells lawyers miss: impatience, dread, a tight throat [33:05] - Rebuilding a legal life: advising, investing, and stepping back from GC-level weight [38:39] - Making wellness data-backed for a skeptical audience [43:30] - Redefining success [46:10] - Rapid fire [48:31] - Where to follow Allison Key Takeaways Lawyers have a dangerously high pain threshold. Allison didn't notice she was unraveling until she was snapping at her three-year-old and journaling "I hate this" at 3am. The signs were there long before she acted on them. You don't need 100% of your fulfillment from your job. Allison's advice: find one small thing outside of work, a ceramics class, a walk, whatever it is, before you try to overhaul your whole career. Small experiments beat big plans. Instead of quitting to become a meditation teacher, she offered one free session in her backyard and asked for feedback. Lawyers tend to over-engineer the thing before they even know if they want it. Sleep is non-negotiable, not a nice-to-have. Being chronically underslept is functionally like being drunk, and most lawyers would never practice law drunk. Allison holds a hard boundary now: in bed by 9 or 10, no exceptions. Don't overthink the decision. Lawyers are trained to argue both sides, which means they can talk themselves into staying in something that's making them miserable. Trust your gut first, then use the analytical skills to execute. Links Allison on LinkedIn: linkedin.com/in/allisoncanton (https://www.linkedin.com/in/allisoncanton/) Fit to Practice CLE: fittopractice.law Practically on Purpose Substack: Allisonalliecanton.substack.com (https://alliecanton.substack.com/) Recommended book: Designing Your Life by Bill Burnett and Dave Evans If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com (https://www.jonathancullencoaching.com/) Shareable Moments "I don't want to do this." "We're really good at coming up with plans and following plans." "Don't let analytical reason run rampant." "That's the thing I always compromised on." "This life, even as a lawyer, can be a playground."

6. 

   5 Jun 2026

   The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin

   Episode Introduction Most lawyers are trained to have the answer. To advise, fix, and move on. Rebecca Hockin spent years doing exactly that. She was good at it. But something kept drawing her in a different direction. In this episode, Jonathan Cullen talks with Rebecca about what happened when she started pulling on that thread, how she built a practice that's part lawyer, part coach, entirely on her own, and why curiosity might be the most underrated skill in the legal profession. If you've ever wondered whether there's a version of your career that's both successful and sustainable, this one's for you. Guest Bio Rebecca is a commercial lawyer who is also trained as an executive coach. She's based in Vancouver, British Columbia. Rebecca has worked both in private practice at a national firm and in-house on global legal teams. She currently practices law as a fractional in-house counsel, where she brings her legal, leadership, and coaching experience to legal and business teams. She also coaches and mentors other lawyers to help them create rewarding and sustainable law practices. Timestamps [00:00] - Opening [01:01] - Podcast intro and guest introduction [03:00] - Why Rebecca always wanted to be a lawyer [05:00] - Psychology: how it shaped everything [07:00] - Finding work that felt like being part of something [10:00] - How a broad practice prepared her for in-house work [11:00] - The moment that broke her out: burnout, a friend's loss, and three days of vacation [13:00] - What surprised her most about going in-house: the point of the legal work [14:00] - Working directly with the business and what it unlocked [15:00] - The feedback shift: from "firm lawyer" to "commercial and practical" [17:00] - How she actually learned to be commercial: site visits, questions, and proximity [20:00] - The Center for Creative Leadership, and a new pull [21:00] - "I don't know what this is, but I want to do it": finding coaching [24:00] - The decision to leave in-house and give coaching a real shot [25:00] - Discovering she still loved practicing law, just differently [26:00] - How the fractional model came together [27:00] - Five coaching skills that made her a better lawyer [30:00] - Why more lawyers should learn coaching [33:00] - The identity shift from advisor to coach: "I don't have to be a lawyer here" [36:00] - What creativity actually means for lawyers [39:00] - Greenhousing: letting things grow before you cut them [41:00] - Safe but not always comfortable: how coaching creates growth [43:00] - The relationship with time and what lawyers get wrong [45:00] - Protect your life outside of work [46:00] - Sleep, routines, & why constraints make you more effective [50:00] - Rapid fire [53:00] - Close Key Takeaways Staying broad isn't a weakness. Rebecca resisted over-specializing in private practice, and it's what made her so effective in-house. Adaptability, pattern recognition, and knowing how to figure things out: those compound over time. The signals don't always announce themselves. Rebecca's move toward coaching wasn't a plan, it was a pull. Psychology in undergrad. A leadership course that made her think, "How can I do this?" It all connected later. Burnout rarely announces itself. But back at the office after the kids went to bed, running on empty, a close friend hit with loss, three days of vacation that cracked it open. That's what it looked like. And it led to the best decision she ever made. Coaching and advising pull in opposite directions. Lawyers are trained to have the answer. Coaching asks you to hold back. Rebecca describes it as taking off one hat and putting on another. The relief she felt, discovering she didn't have to advise, tells you everything about how heavy that hat was. Constraints make you more efficient. Having to leave at a certain time to pick up her kids forced Rebecca to use her time better. The boundary wasn't the problem, it was the solution. Links and Material Find Rebecca at recreativecoaching.ca (https://www.recreativecoaching.ca/) and on LinkedIn (https://www.linkedin.com/in/rebeccaehockin/) Tomorrow and Tomorrow and Tomorrow by Gabrielle Zevin Four Thousand Weeks by Oliver Burkeman If this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.com (https://www.jonathancullencoaching.com/) Shareable Moments Lines worth pulling for social: "I stayed very broad and did a lot of different things. That's not usually the recommendation, but it worked out really well for me." "What hit me really early on was the point of the legal work. Oh, we're doing this because we have to sell this. This is how we make money." "I had to create it for myself first. I built a coaching practice to help other lawyers, but really I just needed that for myself." "I remember having this realization: I don't have to be a lawyer here." "Safe but not always comfortable. That's what leads to growth." "Foundational things like sleep, hydration, exercise. I have a lot of energy. I have to get it out so I'm not getting it out every time I talk to a client."

7. 

   19 May 2026

   Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs)

   Episode Introduction Most lawyers are trained to work alone, grind through problems in silence, and figure out their careers by watching the person above them. Dylan Gibbs saw that model up close, from the Supreme Court of Canada to national litigation firms, and decided there had to be a better way. In this episode, Jonathan Cullen sits down with Dylan, founder of Inn Laws, to talk about why lawyers are so isolated, what happens when you give them a real space to compare notes, and why AI is no longer something you can afford to put off. If you've ever felt like you were guessing at how your career actually works, this episode is for you. Guest Bio Dylan Gibbs is the founder of Inn Laws, a private community for Canadian lawyers who want to move the profession forward instead of waiting to see where it goes. Members are building modern firms, rethinking client service in the AI era, and taking an intentional approach to growing their practices. Before Inn Laws, Dylan clerked at the Supreme Court of Canada and litigated at national firms. He started Inn Laws after seeing that the next generation of legal leaders didn't have a place to get together, exchange ideas, and learn the things they don't teach in law school. Timestamps [00:00] - Newsletter to business: the bet most lawyers thought was crazy [00:59] - Podcast intro and guest introduction [02:53] - Dylan's origin story: from software developer to Supreme Court clerk [03:55] - What clerkship and big law actually taught him [08:09] - Burnout, perfectionism, and tech frustration: the breaking point [11:47] - Going all in on the newsletter [14:30] - Finding a writing voice that didn't sound like a law firm blog [17:09] - What was missing in the Canadian legal information space [18:46] - How the peer group concept was born [19:36] - What networking looked like pre and post-COVID [20:35] - Building a community lawyers actually want to be part of [21:52] - How membership works day to day [25:26] - How Dylan matches lawyers into peer groups [27:36] - Trust, confidentiality, and the Chatham House rule [30:43] - What transformation actually looks like in the groups [33:16] - Individual vs. firm buy-in: who gets the most out of it [34:47] - AI challenges in law: the turning point that changed everything [41:35] - Where Inn Laws is going: quality over scale [43:39] - Rapid fire questions [44:44] - Leadership and AI: what today's leaders need to understand [46:14] - Closing and call to action Key Takeaways The peer group model works because it's forced in the best way. Everyone has bought in, the agenda is built from real problems, and the confidentiality holds. That's what creates the space for honest conversation. Lawyers consistently hedge before sharing a problem in a group setting: "This might not be relevant" or "Don't worry about this one." It almost always turns out to be the thing everyone else is dealing with too. The newsletter success formula: people think they want to read about work, but what they actually want is entertainment. If it also happens to be educational, even better. Burnout in law often hits the best people hardest. When you're a perfectionist in a profession that rewards thoroughness, the work expands to fill every available hour. Good work earns more work. AI is no longer an admin tool. Since late 2024, lawyers are asking how to use it for substantive work, not just toning down emails. The lawyers who figure this out first are building a real advantage. The 20-hour problem: Dylan's observation that the bulleted notes from an hour of research were often 90% of the final memo, and the remaining 20 hours were just turning it into something deliverable. That's exactly what AI can compress. Buy-in matters more than firm support. The members who get the most out of Inn Laws are the ones who pay for it themselves, or at least feel personally invested. When it's just another employer-funded benefit, the commitment isn't the same. Today's legal leaders need a concrete answer to: how am I using AI, and how am I helping my team use it? That's not optional anymore. Links Inn Laws (https://innlaws.ca/) - Dylan's community for Canadian lawyers Dylan on (https://www.linkedin.com/in/itsdylangibbs/)LinkedIn (https://www.linkedin.com/in/itsdylangibbs/) Free Lawyer to Leader Assessment (https://www.jonathancullencoaching.com/) If this episode is still on your mind, here's where to go next: Take the free assessment. Find the one thing holding your leadership back at (https://jonathancullencoaching.com/)jonathancullencoaching.com (https://jonathancullencoaching.com/) Follow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content. Share this episode. If you know a lawyer who's grinding through their career alone and wondering why it's so hard, send them this one. Shareable Moments Lines worth pulling for social: "Do good work and your reward is more work. That's the trap." "We're not running a webinar. We're getting lawyers in a room to talk about the problems they can't ask about anywhere else." "The lawyers I was working for, I looked at their jobs and thought: if that's the reward, I'm not sure I want it." "When I say lawyer, I think: tired. But you don't have to be." "Today's leaders know how to use AI. That's not a future skill. It's a now skill."

8. 

   19 May 2026

   Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)

   Episode Introduction Most lawyers are trained to have the right answer. Stephen (Shed) Shedletzky argues that the most powerful thing a leader can do is ask the right question and then actually listen. In this episode, Jonathan Cullen sits down with leadership expert Shed Shedletzky to unpack why speak-up culture isn't a "nice to have, it's the difference between a team that performs and one that quietly fails. If you've ever wondered why smart people in your organization stay silent, this episode will tell you exactly why, and exactly what to do about it. Guest Bio Stephen (Shed) Shedletzky is a leadership expert, keynote speaker, host of the Shed Some Light podcast and author of Speak-Up Culture: When Leaders Truly Listen, People Step Up. A former Head of Brand & Communications at Simon Sinek Inc., Shed has spent his career helping leaders build environments where people feel both psychologically safe and genuinely motivated to speak up. He works with organizations worldwide on the connection between culture, trust, and performance. Timestamps [00:00] - The pickle jar culture metaphor [00:54] - Podcast intro [01:54] - Meet Shed [04:28] - What does "speak up culture" actually mean? [07:21] - Why silence is killing your team [10:14] - Culture is local - your team is your culture [12:24] - Vulnerability with context [17:27] - Soft skills aren't soft - they're career-defining [23:10] - Why work is not family (and what it should be instead) [26:41] - Designing meetings that include introverts [32:27] - Leading from any seat - without formal authority [38:50] - Curiosity and context in client service [45:49] - Rapid fire wrap-up [49:12] - Outro Key Takeaways Culture isn't set at the top of the organization, it's local. Your immediate team is the culture you can actually control and change. The "pickle jar" metaphor: you absorb the environment you're placed in. Leaders set the brine. Speak-up culture requires two conditions: psychological safety and genuine worth. People need to feel safe and believe their voice will matter. Vulnerability without context is just noise. Leaders need to share struggles in ways that inform and build trust, not create anxiety. Soft skills are the hard skills. The technical work gets you hired. The so-called soft skills determine how far you go. Rubber ball vs. glass jar: not all mistakes are equal. Design your learning environments to match the stakes. Inclusive meetings aren't accidental -pre-reads, deliberate silence, and inviting quieter voices are leadership choices. Mandela's lesson: meet in a circle, speak last. Position and posture both signal whether you actually want input. Curiosity is a client service strategy. Lawyers who ask better questions build better relationships. Links Speak-Up Culture: When Leaders Truly Listen, People Step Up (https://www.shedinspires.com/speakupculture) by Stephen Shed on Substack (https://shedinspires.substack.com/) Free Lawyer to Leader Assessment (https://www.jonathancullencoaching.com/) If today's conversation is still rattling around in your head, that's a good sign. Here's where to go next: Take the free assessment. Find the one thing holding your leadership back at jonathancullencoaching.com (https://www.jonathancullencoaching.com/) Follow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content. Share this episode. If you know a lawyer who stays quiet in rooms they should be leading, send them this one. Shareable Moments Lines worth pulling for social: "Soft skills aren't soft. They're the skills that determine how far you go." "Culture isn't set at the top. It's local. Your team is your culture." "People don't speak up when they don't feel safe or when they don't believe it's worth it." "The pickle jar doesn't care what kind of pickle you were before you went in."

9. 

   19 May 2026

   From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)

   Episode Introduction Most lawyers are taught to stay on the path. Build the credentials, climb the ladder, collect the titles. But there’s another way, and sometimes it’s good to look outside the professional for a model. Chris Ito did all of that, and then walked away from every bit of it. In this episode, Jonathan Cullen sits down with his oldest friend, a Stanford and Google engineer turned chef and nonprofit leader, to talk about what it actually feels like to leave a life that looks great on paper but doesn't fit who you are. This isn't a story about quitting. It's a story about listening, about the signals your life keeps sending you, and what happens when you finally decide to follow them. If you've ever looked at the person above you and thought "I'm not sure I want that job," this episode is for you. Guest Bio Chris Ito is a former software engineer, Stanford graduate, and PhD in electrical and computer engineering who spent years at Google and Facebook in Silicon Valley before following a completely different calling. In 2021, he enrolled at the Culinary Institute of America in Napa, left tech, and became a chef. He also served as president of Hope's Corner, a nonprofit providing free meals and services to those in need in Mountain View, California. In 2024, Chris returned to Canada and became a food recovery chef at A Better Life Foundation in Vancouver, where the team recovers unwanted food from grocery stores and produces around 300 meals a day for people in need on the Downtown Eastside. Chris lives in North Vancouver with his wife and their two kids. Timestamps [00:00] - Opening: walking a high wire with no net [01:01] - Podcast intro and guest introduction [03:55] - A prescribed plan: medicine, engineering, & a rejection that opened it all [07:00] - Escaping the rails: how Chris navigated pressure to follow a prestigious track [09:55] - Stanford, Silicon Valley, and pulling on threads [13:20] - How to balance curiosity with focus [15:30] - Life in Silicon Valley: Google, satellites, and the moment Elon Musk walked in [20:45] - The Starlink decision: why Chris said no [23:30] - Google Home, factories in Vietnam, and a growing sense of misalignment [25:00] - "Be the hero of your own life": the David Copperfield moment [26:30] - From Google to Facebook's social impact team: moving toward the feeling [29:00] - Hope's Corner: volunteering with his son and planting a new seed [32:00] - The Culinary Institute of America: an Uber ride & a "why not now?" [36:00] - Going back to school at 44, surrounded by 24-year-olds [37:00] - Terror in a Michelin Star kitchen: the "show up today" post-it note [39:00] - "I don't know where I'm going, but I know exactly how to get there" [40:00] - The Elon Mansion to the Airstream trailer: moments of doubt [43:00] - When it takes too long to decide, you already know the answer [45:00] - Moving back to Canada: a glass of wine, a question, & a 9:34 PM phone call [52:30] - Finding A Better Life Foundation: the dinner that felt like a lightning bolt [57:30] - From dinner guest to volunteer to chef: how it all came together [1:01:00] - Service, mastery, and where real meaning lives [1:02:00] - For people who feel stuck: you don't have to make a dramatic change [1:08:00] - Showing your kids you can reinvent yourself [1:13:00] - Rapid fire questions [1:17:00] - Closing and call to action Key Takeaways Don't think about the safety net. Chris's philosophy is to walk the high wire without one. When you keep a fallback in mind, you're not fully committing, and you're not giving yourself the best shot. Signals are everywhere if you listen. What you read voluntarily, who you admire, how you feel when someone asks what you do. These aren't random. They're pointing somewhere. The path analogy: walk it as far as it goes, and when it ends or forks, turn. Time on one path is never wasted. You bring everything with you. If a decision is taking you weeks to make, you probably already know the answer. Your head is just trying to talk you out of what your heart already knows. You don't have to make a dramatic change. Dip a toe in. Volunteer. Take a class. Move toward the feeling in small steps. The universe tends to open up once you start moving. The body keeps score. It never lies. If something is out of alignment, your body will tell you before your mind catches up. Listen to the whisper before it becomes a pile of bricks. Showing your kids you can reinvent yourself is one of the most powerful things you can do as a parent. Chris's move, and Jonathan's own career shift, both landed with their kids without a single objection. The overlap of service and mastery is where real meaning lives. When you're giving your best skills to something that genuinely matters to you, that's where the magic is. Links Hope's Corner (https://www.hopes-corner.org/) - Where Chris began his non-profit journey A Better Life Foundation (https://www.abetterlifefoundation.ca/) - Chris' current home base in Vancouver The Lion Tracker's Guide to Life by Boyd Varty (https://boydvarty.com/book/the-lion-trackers-guide-to-life/) - Chris' top book recommendation Free Lawyer to Leader Assessment (https://www.jonathancullencoaching.com/) If this episode stuck with you, here's where to go next: Take the free assessment. Find the one thing holding your leadership back at (https://jonathancullencoaching.com/)jonathancullencoaching.com (https://jonathancullencoaching.com/) Follow the show. Apple Podcasts, Spotify, and YouTube. It helps more lawyers find this content. Share this episode. If you know a lawyer who's climbing a ladder leaning against the wrong building, send them this one. Shareable Moments Lines worth pulling for social: "Walk the high wire with no net. If you're thinking about the safety net, you're not fully committing." "I don't know where I'm going, but I know exactly how to get there." "If it takes you that long to decide, you already know the answer." "The body keeps score. It never lies." "I recovered from a life that wasn't aligned with my values." "At the beginning of the night we're always strangers. At the end of the night we're always hugging."

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