Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search

You're not totally happy with your career (obviously!) You also know that there "has to be something out there that's better." That hope that you can find meaningful and fulfilling work, that also pays you well, has led you here! This is the show that provides the inspiration, tools, and roadmaps to move from where you are to work that matters to you and uniquely fits your strengths and talents.

  1. (3 of 8) Career Clarity: How to Use the 5 Whys to Find What You Actually Want from Work (And Don't Want) | What Fits You

    14h ago

    (3 of 8) Career Clarity: How to Use the 5 Whys to Find What You Actually Want from Work (And Don't Want) | What Fits You

    "What do you want?" sounds like a simple question. Try answering it about your career right now and you'll probably find it's harder than it sounds. Most people don't draw a blank, they tell you everything they don't want with precision and freeze the moment the question gets flipped forward. That's not because the answer doesn't exist. It's because nobody has ever given you the right tool to find it. In Day 3 of the What Fits You 8-Day Mini Course, you'll learn The 5 Whys exercise, the same problem-solving framework we've adapted for career change and used with thousands of clients to surface what you actually want underneath what you don't. Every "don't want" is pointing at something. The 5 Whys helps you see what. What you'll learn: Why naming what you don't want feels easy but naming what you do want feels impossible How what you want shifts over time, and why the dream role of your 30s often isn't the right fit by your 40s or 50s The 5 Whys exercise, how it works, why it cuts through complaint to clarity, and exactly how to use it on your biggest career frustration The real reason high performers stay stuck even after years of self-reflection How Jerrad went from "I don't want technical work" to "I want work that helps me be a better parent" in five questions   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes How to Figure Out What You Really Want (Spotify / Apple Podcasts) Figuring Out Your Perfect Career Match (Spotify / Apple Podcasts)   Mentioned Episode: What Fits You - Introduction (Spotify / Apple Podcasts) What Fits You - Day 1 (Spotify / Apple Podcasts) What Fits You - Day 2 (Spotify / Apple Podcasts)

    9 min
  2. (2 of 8) Career Reflection: Use Your Past to Find What Career Actually Fits You with These 10 Questions | What Fits You

    1d ago

    (2 of 8) Career Reflection: Use Your Past to Find What Career Actually Fits You with These 10 Questions | What Fits You

    You could spend the next decade reflecting on your career and still end up exactly where you are right now. Not because reflection doesn't work, but because directionless reflection won't get you to the forward question. You can probably name what you don't want with real precision, but you still can't tell anyone what you actually do want.   That gap is where most career changes stall for years. Sometimes decades.   In Day 2 of the What Fits You 8-Day Mini Course, you'll work through 10 specific reflection questions designed to use your past intentionally, the same questions our team uses with clients to surface the patterns and themes that point to what actually fits.   The work that genuinely fits you almost always feels familiar, like coming home after a long time away. The pieces are usually already in your history. You just need a framework to see them clearly.   What you'll learn: Why reflection alone leaves most high performers exactly where they started The forward question most people can't answer, and how to actually answer it Why careers that fit feel familiar, not foreign, and what that means for where to look The 10 specific reflection questions our team uses with clients to surface what actually energizes you The bonus question that often surfaces what every other question missed   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes An Overthinker's Guide To Making Better Career Decisions (Spotify /Apple Podcasts) Should I Quit My Job? How to Know It's Time (Spotify / Apple Podcasts)   Mentioned Episode: What Fits You - Introduction (Spotify / Apple Podcasts) What Fits You - Day 1 (Spotify / Apple Podcasts) Episode 222 - (Spotify / Apple Podcasts)

    12 min
  3. (1 of 8) How to Find Your Signature Strengths: The Foundation of Career Fit and Fulfilling Work | What Fits You

    2d ago

    (1 of 8) How to Find Your Signature Strengths: The Foundation of Career Fit and Fulfilling Work | What Fits You

    The thing that's exceptional about you is probably the thing you've stopped noticing. After enough years of high performance, the things you do better than almost anyone get filed away as "obvious" or "easy" or "everyone can do that." Even when they're genuinely rare. That's the Signature Strengths problem most high performers walk into a career change with. They're great at things they don't even count as strengths, and they can't tell you what they're truly built for because they've never named it. In Day 1 of the What Fits You 8-Day Mini Course, you'll start separating what you're great at from what you actually want to keep doing. Because being excellent at something isn't the same as it being a fit, and the gap between those two is where most career changes go wrong. What you'll learn: Why "I'm a good leader" and "I'm great with people" aren't actually Signature Strengths The specific definition of a Signature Strength, and why it's the foundation for every career change that actually fits Why the things that come most naturally to you are usually the things you've stopped noticing The Strengths Reflection Exercise that surfaces patterns years of self-assessment tools missed Why even high performers who've done this work for years often don't know their Signature Strengths until someone helps them dig deeper   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes Discover Your Strengths to Find Your Ideal Career (Spotify / Apple Podcasts) Changing Careers (When You Don't Know Your Next Job Title) (Spotify / Apple Podcasts)   Mentioned Episode: What Fits You - Introduction (Spotify / Apple Podcasts)

    10 min
  4. (Introduction) How to Find Career Fit in 8 Days: A Step-by-Step Process | What Fits You

    2d ago

    (Introduction) How to Find Career Fit in 8 Days: A Step-by-Step Process | What Fits You

    The people who find this course usually aren't here because something obvious is broken. They're here because their career looks fine from the outside and still doesn't feel right from the inside. They can name what they don't want with precision but freeze when asked what they actually do want.    That gap is what this course was built to close. Over the next eight days, you'll walk through the same process Scott built from scratch after his own career fell apart. The same process that's now taken nearly 100,000 people from "I know something's off" to "I know what fits me." In this Introduction, you'll hear what each day delivers, why finding the right career isn't usually about reinvention, and how to set yourself up to get the most out of the next eight days. What you'll learn: Why most career advice falls short for high performers who've already done years of self-reflection The reason nobody has ever taught you how to find work that actually fits, and what to do about it What Signature Strengths are and why they're the foundation of every career change that works What each of the 8 days covers and the simple exercise that pairs with each episode How to get the most out of the course whether you finish with a decision or a clearer next step   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes How to Figure Out What You Really Want (Spotify / Apple Podcasts) Figuring Out Your Perfect Career Match (Spotify / Apple Podcasts)

    10 min
  5. The $300,000 Trap: What It Really Costs to Stay in a Career That No Longer Fits (Identity Loss) | Executive Series Part 3

    5d ago

    The $300,000 Trap: What It Really Costs to Stay in a Career That No Longer Fits (Identity Loss) | Executive Series Part 3

    Most executives never run the math on what it really costs to stay in a career that no longer fits. They calculate what leaving would cost them, the income, the title, the security they've spent fifteen or twenty years building, but they almost never run the numbers on what staying is already taking from them.   In Part 3 of our Executive Career Change series, you'll see what the math actually looks like, including the four real costs of staying that compound year after year, the data on what really happens to income after a structured executive career change, and the three questions that surface the truth for almost every executive we've worked with.   The salary you've been protecting becomes something you've been paying for. And once you see what staying actually costs you, the math of leaving looks completely different.   What you'll learn: The four real costs of staying in a career that no longer fits, including the identity loss that almost no executive sees coming until it's too late What the Wharton data actually shows about income recovery after an executive career change, and why "leaving will cost you forever" is almost always wrong Why the income math of staying isn't safe, it's a slow leak most people never count The three questions our team uses to surface what's actually going on for executives stuck in the trap Why the first real move isn't the resignation or the announcement, it's something simpler and more important   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes Stuck in a Career You're Unhappy With? Fear Of Taking Risks Could Be Keeping You There (Spotify / Apple Podcasts) Should I Quit My Job? How to Know It's Time (Spotify / Apple Podcasts)   Mentioned Episodes: Executive Career Change Series Part 1 of 3 (Spotify / Apple Podcasts) Executive Career Change Series Part 2 of 3 (Spotify / Apple Podcasts) Katie's Career Transition Story (Spotify / Apple Podcasts)

    19 min
  6. Behind the Decision: Real Stories of Executives Who Left $200K–$500K Careers to Do Work That Actually Fits (Escaping Corporate Burnout and Golden Handcuffs) | Executive Series Part 2

    6d ago

    Behind the Decision: Real Stories of Executives Who Left $200K–$500K Careers to Do Work That Actually Fits (Escaping Corporate Burnout and Golden Handcuffs) | Executive Series Part 2

    Most executives know something is wrong years before they do anything about it. They have the title, the income, the team, and still feel stuck inside the corporate burnout and golden handcuffs that come with high-performing careers. Drained, distracted, and quietly miserable for 40 to 60 hours a week. In Part 2 of our Executive Career Change series, you'll hear from two real executives, Hayley and Katie, who finally made the move they'd been putting off for years, without blowing up their income or their lives. The question isn't whether to leave. It's how to stop rationalizing your way into roles that look great on paper but feel wrong in practice. What you'll learn: Why high-performing executives tolerate the wrong situation longer than everyone else, and what finally forces the breaking point The hidden cost of staying that most people never see until they're already on the other side of it Why generating activity like updating your resume, calling recruiters, and jumping into interviews is not the same as making progress How Hayley co-created a role built around her strengths instead of just finding the next available job What Katie had to figure out before she could move forward, and why it changed everything about how she searched   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes Executive Burnout: Making A Midlife Career Change (Spotify / Apple Podcasts) An Overthinker's Guide To Making Better Career Decisions (Spotify /Apple Podcasts)   Mentioned Episodes What Executive Career Change Actually Looks Like at $200K–$500K: Beyond Draining and Unfulfilling Work (Executive Series Part 1) (Spotify /Apple Podcasts)

    15 min
  7. What Executive Career Change Actually Looks Like at $200K–$500K: Beyond Draining and Unfulfilling Work | Executive Series Part 1

    Jun 3

    What Executive Career Change Actually Looks Like at $200K–$500K: Beyond Draining and Unfulfilling Work | Executive Series Part 1

    If you're earning between $200K and $500K and quietly wondering why every career change strategy you've tried hasn't worked, the answer probably isn't more effort. It's that almost none of the advice you've been given was built for executives at your level. The trap is different. The math is different. The way out is different. And almost every executive in this income range falls into the same hidden patterns without ever recognizing what they are. This is Part 1 of our three-part Executive Career Change series. We walk through the five specific reasons career change is fundamentally different at the $200K to $500K level, the trap most executives sit inside without naming, and the three lies that keep high performers stuck for years longer than they should be. Clips from Katie Hyskell, Paul Ichilcik, and Hayley Lowe — three real executives who lived this exact pattern — anchor the diagnosis. In this episode: Why most career change advice was never built for executives earning $200K to $500K The five specific things that make career change fundamentally different at the executive level The expertise trap and why the better you are at work you don't love, the harder it becomes to leave The three lies almost every high earner tells themselves on a loop ("I feel like I should just be grateful," "I just need a better solution," "I'll do it after one more year") Why your income, your title, and your network all quietly work against you when you try to change careers at this level   Our book, Happen To Your Career: An Unconventional Approach To Career Change and Meaningful Work, is now available on audiobook! Visit  happentoyourcareer.com/audible to order it now! Visit happentoyourcareer.com/book for more information or buy the print or ebook here! Want to chat with our team about your unique situation? Schedule a conversation   Free Resources What career fits you? Join our free 8 Day Mini Course to figure it out! Career Change Guide - Learn how high-performers discover their ideal career and find meaningful, well-paid work without starting over.   Related Episodes Executive Burnout: Making A Midlife Career Change (Spotify / Apple Podcasts) An Overthinker's Guide To Making Better Career Decisions (Spotify /Apple Podcasts)

    15 min

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About

You're not totally happy with your career (obviously!) You also know that there "has to be something out there that's better." That hope that you can find meaningful and fulfilling work, that also pays you well, has led you here! This is the show that provides the inspiration, tools, and roadmaps to move from where you are to work that matters to you and uniquely fits your strengths and talents.

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