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

Happen To Your Career
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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. What Executive Career Change Actually Looks Like at $200K–$500K: Beyond Draining and Unfulfilling Work (Executive Series Part 1)

    16h ago

    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
  2. How Your Strengths Build Career Alignment, Fulfillment, and Meaningful Work You'll Never Want to Retire From

    2d ago

    How Your Strengths Build Career Alignment, Fulfillment, and Meaningful Work You'll Never Want to Retire From

    Most people plan for retirement because it's what you're supposed to do. But the real question almost no one asks first is whether the work they're doing right now is even built around their strengths in the first place. Because if it isn't, retirement won't actually fix the problem. The restlessness most retirees describe inside the first year is the same friction they had been ignoring in the years before they left. This episode walks through why retirement is a relatively new concept, what the Gallup research from Jim Harter actually shows about strengths and engagement at work, and the reframe that turns "when can I retire" into a more useful question about meaningful work and career fulfillment. It also draws on the stories of Dan Ruley, who realized fifteen years of chasing the next promotion had taken him away from the work that actually energized him, and Edna, who left a 19-year career in consumer packaged goods, joined a new organization expecting it to be better, then walked away inside a year because the role couldn't give her the autonomy she needed to do meaningful work. In this episode, we'll unpack: Why retirement is a recent invention and what that reveals about how most people think about modern work The difference between a skill and a strength, and why being exceptional at the wrong thing will still deplete you The Gallup engagement finding that people who use their strengths daily are six times more likely to be engaged at work Three questions that surface your strengths profile based on the patterns your own career has already left you Why high performers feel the strengths gap most acutely, and what designing a career around your strengths actually looks like at any stage   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) An Overthinker's Guide To Making Better Career Decisions (Spotify /Apple Podcasts)   Mentioned Episode: The Power of Fitting Strengths to Role with Gallup's Jim Harter (Spotify /Apple Podcasts)

    11 min
  3. From Law Enforcement to Tech Sales Engineer: How A Mid-Career Change Translated 24 Years Behind the Badge into a $35K Pay Increase

    6d ago

    From Law Enforcement to Tech Sales Engineer: How A Mid-Career Change Translated 24 Years Behind the Badge into a $35K Pay Increase

    After twenty-four years in law enforcement as a Captain, Tavis made a mid-career change into tech that translated his public sector experience into a $35K pay increase. The story of how he made the jump from a long-tenure law enforcement role into a Sales Engineer position is the kind of executive career change most people in his position assume isn't possible. He had to work through the fear that his background would be a strike against him, the doubt about whether his transferable skills would carry into the private sector, and the years of quietly considering the move before he actually did it. What he found on the other side was that the skills he'd spent two decades building were exactly what tech hiring managers were looking for, once he knew how to talk about them. In this episode: What Tavis was telling himself to stay in law enforcement, and when he stopped believing it The Clifton Strengths work that gave him clarity on what he actually wanted next The negotiation that landed a $35K pay increase on top of an already-strong offer   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 Designing Career Experiments and Testing New Careers (Spotify / Apple Podcasts) Executive Burnout: Making A Midlife Career Change (Spotify / Apple Podcasts)

    23 min
  4. Still Marketable After 10+ Years at One Company? Career Experiments That Give You the Real Answer

    May 27

    Still Marketable After 10+ Years at One Company? Career Experiments That Give You the Real Answer

    After 10+ years at the same company, a specific kind of doubt creeps in. You start to wonder if you're still marketable, whether the skills you've spent the last decade building are still relevant to anyone outside the building you've been showing up to, and whether anyone would actually want to hire you if you had to leave tomorrow. In this special Q&A episode, we walk through a specific framework for testing your marketability without putting your current job at risk. You'll hear why the same expertise that built your career is also what's keeping you from seeing your real options, how to use career experiments and test-drive conversations to gather real data on your skills, and the often-overlooked difference between marketable skills and signature strengths. You'll learn: Why the longer you stay in one place, the harder it gets to honestly assess your marketability The concept of "systematic exposure" and why it's the missing piece for most people in your situation How to use career experiments and test-drive conversations to gather real data on your transferable skills The difference between marketable skills and signature strengths, and why most people are looking at the wrong layer How to start running small, low-risk experiments today that build your career clarity over time   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)

    14 min
  5. Should I Quit My Job or Stay for the Benefits and Job Security? The Hidden Cost of Staying in a Career You've Outgrown

    May 25

    Should I Quit My Job or Stay for the Benefits and Job Security? The Hidden Cost of Staying in a Career You've Outgrown

    You've thought about quitting your job more than once. But every time, the same things pull you back: the salary, the benefits, the 401k match, the job security, the predictability of a paycheck that shows up every month no matter what. On paper, staying in a career you've outgrown sounds like the safe call. But the real math of staying tells a different story. In this episode, we break down the three hidden costs of staying in a job that no longer fits, and why the financial case for staying is built on incomplete math.   What you'll learn: Why staying for the benefits and job security often costs more than leaving ever would The three hidden costs of staying in a career you've outgrown that never show up on a pay stub How "opportunity cost" quietly erodes your career trajectory while you stay in a role that doesn't fit Why staying in a draining job makes you a worse negotiator in every future job offer (and how that costs you in real dollars) The "compounding drain tax" you pay every month you stay in work that drains you, and how it shows up in your sleep, your relationships, and your future earning potential Real stories from Dan, Kristen, and Charity about what actually changed when they finally made the move   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)

    9 min
  6. Career Change Advice That Actually Works: 6 Real Career Change Stories From People Who Found Their Ideal Role

    May 23

    Career Change Advice That Actually Works: 6 Real Career Change Stories From People Who Found Their Ideal Role

    Most people trying to figure out how to change careers think they're stuck because of the job market, the timing, or not knowing what they want. But after thousands of conversations with people who've made successful career changes, we've found the real reason and it has nothing to do with any of those things. In this episode, we're sharing six real career change success stories from people who found meaningful work, discovered their ideal career, and made the move without starting over from scratch.   What you'll learn Why most career changers stay stuck and the critical mindset shift that finally gets them moving toward something instead of just away from something How a VP of Marketing discovered her ideal career was in a field she didn't even know existed and why your next role might be the same Why the people closest to you aren't always the best support system during a career change and how to protect your momentum How knowing your core values becomes a decision-making system when you're facing multiple offers or competing opportunities Why saying no is one of the most powerful career change tools high achievers consistently underuse   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 Six Career Experiments To Help You Discover Your Ideal New Role (Spotify / Apple Podcasts) Changing Careers (When You Don't Know Your Next Job Title) (Spotify / Apple Podcasts)

    16 min
  7. How to Make a Career Change in Your 40s: Midlife Crisis or Midlife Clarity?

    May 22

    How to Make a Career Change in Your 40s: Midlife Crisis or Midlife Clarity?

    Making a career change in your 40s can feel like a midlife crisis. After two decades in a career that no longer fits, the temptation is to assume something is wrong with you. What looks like a midlife crisis from the inside is often something different. It's the start of a successful midlife career change, the moment of clarity that comes from twenty years of doing the work and finally knowing what you want next. This episode breaks down how to make a career change at 40 without starting over, what's quietly keeping high performers stuck for another decade, and how to use your twenty years of experience as the asset it actually is. What you'll learn: Why most career change advice for people in their 40s misses the actual obstacles entirely The Identity Trap that makes midlife career change feel impossible after twenty years in one industry The Responsibility Myth that keeps high performers stuck in their 40s for another decade Why your twenty years of experience makes career change at 40 an asset, not an obstacle Real stories from four people who made successful career changes in their 40s and what it actually took The three-step framework for making a career change in your 40s without starting over or throwing away what you've already built   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 Six Career Experiments To Help You Discover Your Ideal New Role (Spotify / Apple Podcasts) Designing Career Experiments and Testing New Careers (Spotify / Apple Podcasts)

    20 min
  8. Why You Don't Actually Want Early Retirement: How to Make a Career Change at 40, 50, or 60 That Brings Real Career Alignment

    May 21

    Why You Don't Actually Want Early Retirement: How to Make a Career Change at 40, 50, or 60 That Brings Real Career Alignment

    Susan came to us with one goal: find something she could tolerate for the next seven years before she could finally retire and start living. Two weeks later, she wasn't retiring anymore, because she had finally found work that fit. In this episode, we break down why so many high performers in their 40s, 50s, and 60s mistake "I want to retire" for "I want to stop doing this." There's a specific psychological reason it happens, and there's a way to fix it that doesn't require waiting for retirement at all.    What you'll learn: Why most people counting down to retirement aren't done with work, they just can't picture what else is possible The availability heuristic and how it traps high performers in jobs they've outgrown Three "systematic exposure" experiments that rewire what feels possible: the Goldilocks Conversation, the small side experiment, and the targeted course immersion Why being over 40 is the best time to change careers, and how the experience you've built becomes the asset that makes it work How Susan went from planning to retire in seven years to finding work she didn't want to retire from at all   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 Should I Quit My Job? How to Know It's Time (Spotify / Apple Podcasts) Discover Your Strengths to Find Your Ideal Career (Spotify / Apple Podcasts)

    9 min
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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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