Lawyer to Leader

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 BioDalia 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.Timestamps00:00 Financial planning for lawyers: the gap nobody talks about00:02 Why being a great lawyer isn't the whole story00:03 Meet Dalia Feldberg, financial advisor for lawyers00:07 How she got into financial planning for lawyers00:13 Why lawyers are financially underserved00:20 Financial advisor vs. lawyer: the same confidence problem00:23 The real gap between lawyer income and lawyer wealth00:25 Lawyers working into their 60s with no retirement plan00:26 The one habit that builds long-term wealth00:29 Wealth building for women in law: why the focus00:34 Managing money from articling student to associate00:38 Disability insurance and income protection for lawyers00:42 Financial planning for law firm partners00:44 The biggest investing mistake lawyers make00:47 What a financial planning meeting actually looks like00:57 Planning a career change as a lawyer01:00 One financial move every lawyer should make this week01:02 The book that changed how she thinks about moneyKey TakeawaysFinancial 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.LinksDalia on LinkedIn (booking link in her bio)Desjardins Financial Security Independent Network OttawaThe Happiness Advantage by Shawn AchorThe Psychology of Money by Morgan HouselIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable 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."

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 BioColin 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. Timestamps0:00 Intro: AI for Lawyers with Colin Levy1:00 Code Switched: What the Book Title Means3:00 Writing an AI Book That Stays Relevant6:00 Global AI Regulation for Legal Teams8:00 Why Bjarne Tellmann Wrote the Foreword9:00 Best Chapter for AI Skeptics11:00 ChatGPT Mistake: A Real Legal Example12:00 How to Prompt AI Like a Lawyer13:00 Why AI Hallucinates: Tokens Explained15:00 AI as a Thought Partner, Not a Chatbot16:00 AI for Lawyers: Judgment Over Replacement19:00 The Chainsaw Analogy: AI and Legal Judgment20:00 Stop Saying Please to Your AI Tool23:00 Why AI Tools Are People Pleasers25:00 AI and the Billable Hour Model27:00 Legal AI Adoption: We're in Chapter One28:00 AI for In-House Legal Teams29:00 Week One of Responsible AI Adoption31:00 Why AI Rollouts Fail Without Training34:00 AI Hallucinations: Feature, Not a Bug37:00 Lateral Thinking and AI Creativity39:00 The #1 Mistake Lawyers Make With AI41:00 AI for Solo and Legal Aid Lawyers42:00 AI Ethics for Lawyers: The Real Question44:00 AI Fails in Law: Real Examples46:00 Disclosing AI Use to Legal Clients47:00 AI Agents Explained for Lawyers49:00 Fruit of the Poisonous Tree: AI Agents51:00 Legal AI in 5 Years: Read the Book or Not52:00 What Writing Code Switched Taught Colin53:00 Rapid Fire: AI Advice for Lawyers55:00 Where to Find Colin Levy and Code Switched LinksColin's website: colinslevy.comColin on LinkedIn: linkedin.com/in/colinslevyColin on Twitter/X: x.com/Clevy_LawColin on Instagram: instagram.com/clevy_lawCode 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/The Legal Tech Ecosystem (Colin's first book): amazon.com/Legal-Tech-Ecosystem-Innovation-Advancement/dp/B0CKCZTLWWIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comKey TakeawaysCode 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."

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 BioSevana 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.Timestamps00:00 Show intro00:55 Meet Sevana02:41 Starting out in litigation04:07 How litigation builds confidence under pressure06:44 The leap to solo practice during COVID08:01 The entrepreneurial skills law school never teaches10:52 Wearing every hat in a solo practice13:33 Should young lawyers start their own firm early?15:51 Why she decided to partner up17:45 Building Rastani Poladian Légal19:57 Two practices, one culture21:02 Spotting client red flags25:21 Her ideal client today25:49 Leading the Armenian Bar Association27:31 Boundaries and balance30:49 Defining success on her own terms31:42 Rapid fire33:46 Closing thanks and where to find Sevana35:19 Outro and takeawaysKey TakeawaysLitigation 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.LinksSevana on LinkedIn: https://www.linkedin.com/in/sevana-poladian-b70b2b128/Rastani Poladian Légal: [email protected] show: The Good WifeIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable 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."

Episode IntroductionIn 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 BioAllison 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 AllisonKey TakeawaysLawyers 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.LinksAllison on LinkedIn: linkedin.com/in/allisoncantonFit to Practice CLE: fittopractice.lawPractically on Purpose Substack: Allisonalliecanton.substack.comRecommended book: Designing Your Life by Bill Burnett and Dave EvansIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable 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."

Episode IntroductionMost 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 BioRebecca 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] - CloseKey TakeawaysStaying 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 MaterialFind Rebecca at recreativecoaching.ca and on LinkedInTomorrow and Tomorrow and Tomorrow by Gabrielle ZevinFour Thousand Weeks by Oliver BurkemanIf this episode stuck with you, take the Free Lawyer to Leader Assessment at jonathancullencoaching.comShareable MomentsLines 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."