Mark: You know that phrase, ‘Go big or go home’? It’s the mantra of every motivational poster and Hollywood movie. But what if that’s the worst career advice you could possibly follow? What if the secret is actually to go small, and go often? Michelle: Okay, that's a bold claim. You're telling me my meticulously color-coded, five-year life plan is basically a work of fiction? I spent a whole weekend on that, Mark. Mark: It might be a beautiful work of fiction! But perhaps a little misguided. This is the core idea in a fascinating book, Choose Possibility: Take Risks and Thrive (Even When You Fail) by Sukhinder Singh Cassidy. Michelle: That name sounds familiar. Where do I know her from? Mark: You definitely know her work. She's not just a theorist; this is a woman who has been at the absolute center of the tech world for decades. She was the President of StubHub, a top executive at Google overseeing their Asia-Pacific and Latin America operations, and is now the CEO of the global accounting software company Xero. Michelle: Wow. Okay, so when she talks about risk, she’s not talking about whether to try a new coffee shop. She’s lived in the high-stakes world of Silicon Valley. Mark: Exactly. And her whole argument is that most of us, especially those of us with our five-year plans, fundamentally misunderstand what risk even is. We see it as this one-time, terrifying leap off a cliff. Michelle: The big promotion, the startup launch, the cross-country move. The decision that feels like it will define everything. The anxiety is real. Mark: It is. And Cassidy calls this the "Myth of the Single Choice." It’s this belief that our lives are a movie, building to one climactic scene where we have to make the perfect decision. This myth is what paralyzes us. It makes the stakes feel so impossibly high that we end up doing nothing at all, just stuck analyzing and re-analyzing. Michelle: I absolutely know that feeling. Analysis paralysis. You get so scared of making the wrong move that you just stay put, even if staying put is making you miserable. How do we break out of that? It sounds great to say "don't be scared," but it's not a switch you can just flip. Mark: This is where her perspective gets really powerful. She argues we need to stop thinking of risk as a single, monumental event and start thinking of it as a muscle. Something you build over time, with small, consistent reps.

Michelle: A risk muscle. I like that analogy. It’s like you wouldn't just walk into a gym for the first time and try to bench press 300 pounds. You’d start with the bar, maybe even just do push-ups. Mark: That is precisely it. And she has this perfect story from her own life that illustrates it. It’s what she calls a ‘near win.’ Michelle: A near win? That sounds like a very polite way of saying ‘failure.’ Mark: It was a failure, by any traditional definition. But it’s what happened because of the failure that matters. So, picture this: it's the early 90s. A young Sukhinder Singh Cassidy is fresh out of business school in Canada. All her friends are getting prestigious jobs at big firms, but she missed the on-campus recruiting season. She’s unemployed, anxious, and feeling left behind. Michelle: Oh, I’ve been there. That’s a uniquely painful kind of stress, watching everyone else get their life started while you're just… waiting. Mark: Exactly. So she’s scanning the job boards and sees an opening at a legendary private equity firm called Claridge Investment. This was a place that hired seasoned MBAs with years of experience. She had neither. On paper, she was completely unqualified. Michelle: So applying was a total long shot. That’s her first small risk. Mark: A tiny one. She sends her resume, leaves a voicemail, and expects nothing. But, to her shock, she gets a call back. They invite her to Montreal for an interview. This kicks off a grueling, six-week vetting process. She’s flying back and forth, doing intense case studies, meeting with partners. She’s the only candidate without an MBA, competing against people who are, by all accounts, far more qualified. Michelle: The pressure must have been immense. She’s the underdog, the imposter. Mark: Completely. And she makes it all the way to the final round. It’s down to her and one other person, an experienced MBA graduate. She’s so close she can taste it. And then… she gets the call. They went with the other candidate. She didn’t get the job. Michelle: Ouch. After all that. So she failed. How does that help her? That just sounds crushing. Mark: It was. But here's the twist. In the book, she describes how, despite the rejection, she walked away from that experience feeling… powerful. For six weeks, she had competed and held her own against the best. She had proven to herself that she belonged in those rooms. The experience didn't land her that specific job, but it fundamentally changed her perception of herself. Michelle: Ah, I see. The outcome of the risk wasn't the job. The outcome was the confidence. It was the proof of capability. Mark: It was the rep! That ‘near win’ gave her the momentum and the self-belief to keep going. A few months later, she lands her actual dream job at Merrill Lynch in New York City, a job she says she might not have had the courage to even go for without the Claridge experience. That ‘failure’ was the most important career step she had taken up to that point. Michelle: That completely reframes it. We're so obsessed with the binary of success or failure. You either get the job or you don't. You either win or you lose. But this suggests there’s a third category of outcome. Mark: The outcome of learning. The outcome of data collection. The outcome of building that muscle. Every small risk you take, whether it "succeeds" or "fails," gives you information and makes the next risk a little bit easier. You’re not trying to win the lottery on a single ticket; you’re just trying to get a little stronger, a little smarter, with every attempt. Michelle: So the goal isn't to avoid getting a wet foot, to use our earlier analogy. The goal is to get used to the feeling of a wobbly stone, so you're not afraid to cross the stream at all. Mark: You’ve got it. You’re building resilience to the small stumbles, so that when a bigger leap is actually required, you’re not starting from a place of fear. You’re starting from a place of experience.

Michelle: Okay, I get the 'small steps' idea. It’s incredibly liberating, actually. But it brings up a new question. Steps toward what? If you don't have a grand, color-coded plan, how do you know which direction to even step in? It feels like you could just wander aimlessly. Mark: That is the perfect question, and it leads directly to the second major idea in the book. If the "Myth of the Single Choice" is what we need to unlearn, the new model is what Cassidy calls "Proximity Beats Planning." Michelle: Proximity beats planning. Tell me more. Mark: The idea is that the most valuable career moves aren't about following a pre-determined path. They're about placing yourself in an environment—a location, a company, a team—where possibility is high. It’s about getting physically and intellectually close to the people and the work that energize you, even if you don’t have a specific goal in mind. Michelle: So it’s less about the ‘what’—the job title, the five-year goal—and more about the ‘who’ and the ‘where.’ Mark: Precisely. And the foreword of the book, which was written by Kim Scott, the author of Radical Candor, tells two stories that illustrate this with breathtaking clarity. They are perfect mirror images of each other. Michelle: Okay, I’m intrigued. Mark: The first story is Kim Scott's own. After college, she decides she wants to work in Moscow. She just shows up, gets a measly-paying job at a Russian think tank, and starts writing letters to the one American company she wants to work for. They don't respond. So what does she do? She just marches into their office and asks for a job. And she gets one. For her, the risk was almost entirely about ego. The worst that could happen was embarrassment. Michelle: That’s a story of privilege, of course. A young American woman in Moscow in the 90s has a certain safety net. Mark: A huge safety net. And Scott is the first to admit it. Which is why she contrasts her story with another one. The story of a man named Shaun Jayachandran. Shaun is an Indian American man who, as a student, wanted an internship at the World Bank. So, just like Kim Scott, he walks into the main office to inquire. Michelle: And what happens? Mark: The security guards draw their guns on him. Michelle: Oh my god. That’s horrifying. For doing the exact same thing. Mark: The exact same action. For him, the risk wasn't ego; it was physical. It was a brutal, discriminatory encounter that could have ended tragically. It’s a stark reminder that the "cost" of taking a risk is not the same for everyone. Michelle: Absolutely. And it’s a critical point to make. The advice to "just take risks" can sound hollow if you don't acknowledge the systemic barriers and real dangers that many people face. Mark: It's essential to acknowledge. But here is the powerful connection between the two stories. What did both Kim Scott and Shaun Jayachandran do? They chose proximity. They physically went to the place where opportunity, in their minds, resided. And while Shaun’s experience was traumatic, it became a defining moment for him. It didn't crush him; it ignited a fire in him to fight for a more just world. Michelle: So what did he do? Mark: He eventually went on to found an incredible organization called Crossover Basketball and Scholars Academy. It’s a program in India that uses basketball to provide educational opportunities for students from all socioeconomic backgrounds. His proximity to a hostile power structure fueled his life's mission to build an inclusive one. Michelle: Wow. So in both cases, the plan wasn't "get job X" or "achieve outcome Y." The plan was simply "get closer." Get into the ecosystem. Mark: Yes! Put yourself in the flow of interesting people and ideas. Serendipity can't find you if you're sitting at home perfecting your five-year plan. It finds you when you're out in the world, in proximity to the action. This is the "Who before What" principle. The people you align with, the environment you immerse yourself in, will shape your opportunities in ways no plan ever could. Michelle: It’s a much more organic, emergent way of thinking about a career. It’s less about architecture and more about gardening. You can’t design the perfect plant, but you can choose the right soil, the right amount of sunlight, and the right companion plants. You create the conditions for growth, and then you see what happens. Mark: That is a perfect analogy. You are cultivating a garden of possibilities, not building a skyscraper from a rigid blueprint.

Michelle: So when you put these two ideas together, a really clear picture emerges. It feels like a formula for getting unstuck. Mark: It really is. It’s a two-part formula for navigating uncertainty. First, you dismantle the paralyzing fear of the giant, single leap by reframing risk. You see it as a muscle you build through small, frequent, low-stakes actions. You make a habit of choosing possibility. Michelle: And second, you guide those small, risky steps not with a rigid map, but with a compass. A compass that points you toward interesting people, dynamic environments, and problems you care about. Mark: Exactly. You're not aiming for a fixed destination on a map. You’re moving toward a vibrant ecosystem where you can thrive. You’re choosing proximity over a plan. You’re choosing people over a position. Michelle: So the practical takeaway for someone listening right now isn't to go home and write a new, better five-year plan. It’s almost the opposite. Mark: The opposite. The takeaway is to identify one small, manageable risk you can take this week. Just one. It doesn't have to be life-changing. It just has to be a step into a slightly unknown space. Michelle: Maybe it’s finally sending that email to someone you admire and asking for a 15-minute virtual coffee, just to learn from them. The risk is they say no or ignore you. The potential upside is a new connection, a new idea. It's a classic proximity play. Mark: A perfect example. Or maybe it’s volunteering for a small project at work that’s outside your comfort zone. Or signing up for a class in a subject you know nothing about. It’s a small rep to build that risk muscle. Michelle: I love that. It makes it feel so much more achievable. You’re not trying to change your whole life tomorrow. You’re just trying to take one interesting step. Mark: And that’s how you build a career, and a life, full of possibility. One small choice at a time. We'd actually love to hear from our listeners about this. What’s one small risk you’re inspired to take after this conversation? Share your stories with the Aibrary community. It’s always powerful to see what we can learn from each other. Michelle: Absolutely. It’s a great way to hold ourselves accountable and get into proximity with other people who are also trying to grow. Mark: This is Aibrary, signing off.