Career Advice / Career Change
Stability pays the bills. Risk changes your life. The hard part is knowing which one you need right now.
These articles are about the decision itself: when to stay, when to go, and how to start over without burning it all down.
Scott published his book on August 24th and sold 11 copies, 3 of them to himself. On doing the damn thing anyway, and why validation was never the point.
Read Article →Thirty years ago your parents told you to get a job. Scott on why the kids bucking conventional wisdom are learning to build, sell, and fail while everyone else waits in line.
Read Article →Twenty years of experience and still asking where the bathroom is. Scott on why the discomfort of a first week is not regret, and why feeling new usually means you are still growing.
Read Article →A scene from Vicky Cristina Barcelona got Scott thinking about how guarded we are when something spontaneous shows up. Scott on recognizing your version of Oviedo and getting on the plane.
Read Article →Nearly every great career decision sounds a little insane before it works. Scott on why the evidence usually arrives after the commitment, and why other people cannot validate your boldest moves.
Read Article →Scott followed a stranger into a shady Dubai apartment and walked out with a story about risk. A reminder that the best career moves almost always feel like bad ideas at first.
Read Article →Seattle tore down a highway Scott loved to make room for a better waterfront, and he couldn’t see the vision at the time. The opportunities you want are usually hiding on the other side of something you’re refusing to tear down.
Read Article →Three Twilio rejections, a hotel room, and a frozen moment on the Amazon campus. Scott built a product with a 2.3 GPA and no engineering background, and the lesson is for you, not him.
Read Article →If a decision makes you nervous and excited at the same time, it is probably worth exploring. Scott on why the biggest career and business moves are supposed to feel uncomfortable, and how fear mixed with excitement is the signal you are standing at the edge of growth.
Read Article →When Scott was a kid he believed the dome light would crash the car and quicksand was everywhere, because a confident adult said so. That same habit follows us into our careers. We inherit beliefs about money, risk, and success and operate under them for years without checking if they are true. The people who get ahead are usually the ones who question conventional wisdom and have the courage to unlearn.
Read Article →Guest writer Z Zorrilla cuts through the AI noise with three tactics that actually move you forward: understand the landscape, build something real, and measure the impact.
Read Article →Annual raises are designed to reward stability, not ambition. If you want flexibility, leverage, and real choice in your future, you'll need more than incremental gains.
Read Article →Death by misadventure is how they describe Bon Scott's end. Career by misadventure? That's the goal. Why playing it safe is the riskiest move you can make.
Read Article →Someone yesterday quit the job, sent the email, took the step. The difference between them and you isn't talent, it's tolerance for discomfort.
Read Article →My local casino has a slogan: the more you play, the more you win. At first I laughed. Then I realized it's exactly how careers work. The people who win aren't
Read Article →Starting over gets painted as failure by people who've never had the courage to walk away from something that wasn't working. But starting over doesn't mean goi
Read Article →Lindsey Parsons joins to talk career risk, grief, staying too long in the wrong role, and what it really means to take a chance when the stakes are real.
Read Article →Risk tolerance is the great separator nobody talks about. There are people less thoughtful and less prepared than you who are winning simply because they were w
Read Article →I once left a pre-IPO company. Two years later they hit a $2B valuation. And I still don't regret it. Knowing when to walk away is its own kind of intelligence.
Read Article →The breakthrough rarely announces itself ahead of time. Too many people surrender right before the result is ready to appear. Here's why staying one more round
Read Article →Talent matters, but it's not enough. The workplace is full of talented people who never get noticed. Boldness is the real currency, the willingness to speak up
Read Article →A side hustle isn't just extra income, it's optionality. Learn why multiple income streams create freedom and leverage in your career.
Read Article →Bold decisions rarely feel like the right decision when you're making them. The safer option always looks smarter in the moment. But safety is the trap that con
Read Article →Somewhere over the Barents Sea on a one-way flight to Dubai, Scott found himself spiraling about everything that could go wrong. Then he saw it on TikTok: 'What
Read Article →A ship is safe in harbor, but that's not what ships are for. A lot of people spend their entire careers tied to the dock. They pick the safe route, the predicta
Read Article →The world moves fast. Industries shift. The version of you that got here may not be the version that gets you where you're going. Scott Bond on why reinvention isn't optional, it's survival.
Read Article →Nobody talks about career grief. Walking away from something, even when it's no longer right for you, still hurts. Grief doesn't mean regret. It means you cared.
Read Article →Your manager isn't your career planner. There's no bonus for being miserable. And you should have bet on yourself sooner. Three truths that change everything.
Read Article →Pragmatism is a seatbelt. It might save your life, but it was never meant to drive the car. The biggest breakthroughs in history came from people who ignored the practical voice.
Read Article →Writing from Las Vegas on Thanksgiving. A casino floor is the best metaphor for your career I've ever found. You'll never win the jackpot if you never step foot inside.
Read Article →I've been uncomfortable with my content journey since day one. But I've realized: comfort is a trap. The life I want is on the other side of the discomfort I keep trying to avoid.
Read Article →Leaving a job is never simple, even when you're unhappy. Familiarity, fear of failure, emotional ties, this is why people stay stuck, and how to break free.
Read Article →People say they want an extraordinary career, then make decisions every day that protect an average one. Scott on why mediocrity is comfortable and how it arrives through hundreds of reasonable choices.
Read Article →Three months after his role was eliminated, Scott starts a new chapter as VP of Sales and Marketing at a Seattle SaaS company. Scott on the wild job search and three takeaways from the process.
Read Article →Guest post by Hussein Sleiman. He walked out of a meeting one Friday in June 2024 and sent a resignation email from his car after nine years at the same company. What followed was the identity unraveling, the inner work, and the framework he built from the rubble.
Read Article →There isn't a single decision you get to make about your life and career that isn't somewhat of a gamble. Inaction is one of the riskiest bets of all. Are you b
Read Article →Every career decision is a gamble - yes, no, or delay. Learn why inaction is the riskiest bet and how to gamble on yourself for career success.
Read Article →The difference between highly successful people and everyone else? Successful people are slightly delusional. They don't overthink pragmatically, don't worry ab
Read Article →In gambling, there are only winners and quitters. Nobody texts you when they lost, only when they won. The same mindset applies to your career. You either win
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