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Lawyer to Leader

Lawyer to Leader

著者: Jonathan Cullen
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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.Copyright 2026 Jonathan Cullen 個人的成功 出世 就職活動 経済学 自己啓発
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  • Courage, Entrepreneurship & Boundaries: Building a Law Firm Young (Featuring Sevana Poladian)
    2026/08/07

    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."

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    37 分
  • The High Pain Threshold: Why Lawyers Miss Their Own Warning Signs (Featuring Allison Canton)
    2026/08/04

    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

    Fit to Practice CLE: fittopractice.law

    Practically on Purpose Substack: Allisonalliecanton.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

    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."

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    50 分
  • The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin
    2026/06/05
    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."
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    56 分
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