Bet on Yourself: The Expected Value Is Higher Than You Think

You’re not risk-averse. You’re math-averse. The reason you haven’t started that business, published that work, or made that career move isn’t because you’re scared. It’s because you’re running the wrong calculation. Most people think about risk like accountants. They see a potential move - start a podcast, launch a product, quit their job - and immediately calculate what they could lose. Time. Money. Reputation. Stability. The numbers add up to “too risky.” So they don’t move. They stay in jobs they’ve outgrown. They sit on ideas that could change their lives. They watch other people - often less talented, less prepared people - build the things they dreamed about building. And they tell themselves they’re being smart. Being prudent. Being realistic. But here’s what nobody tells you: the math you’re using to justify staying stuck is fundamentally wrong. the math you’re using to justify staying stuck is fundamentally wrong. You’re optimizing for the wrong variable. You’re calculating downside while ignoring asymmetry. You’re treating all risks as equal when they’re not even in the same universe. And that miscalculation is costing you everything. This isn’t one of those letters about “following your dreams” or “just believe in yourself.” This is about the actual mathematics of asymmetric upside. Why the downside of trying and failing is almost always survivable. Why the downside of never trying is guaranteed regret. And why betting on yourself has a higher expected value than you think. Let’s begin. I - The Risk Calculation That Keeps Smart People Stuck I spent two years hesitating on my podcast. I knew I wanted to do it. I had the ideas. I knew what I would talk about. I’d written out episode concepts. I’d even recorded test episodes that nobody would ever hear. But I kept finding reasons not to launch. “I need better equipment first.” “I should have more of a following before I start.” “I need to be more of an expert in my topics.” “I should wait until I have a clear monetization strategy.” Every reason sounded rational. Every excuse felt legitimate. And I was very good at performing preparation. I researched microphones for weeks. I studied successful podcast formats. I planned out 20 episodes in detail. I told people at parties “I’m thinking about starting a podcast” and enjoyed the validation of being someone with ambitious plans. But preparation became my drug of choice. The dopamine hit of planning without the risk of failing. But preparation became my drug of choice. You know exactly what I’m talking about. Because you do this too. You’ve been “thinking about” starting that thing for how long now? Six months? Two years? You have the Notion doc with the perfect structure. The bookmarks folder labeled “Research.” The screenshot folder of inspiration. Maybe you’ve even bought a course or two. Told yourself you’re building a foundation. But here’s what was actually happening in my brain - and yours: My brain was running a calculation. “What if I invest six months and it doesn’t work?” “What if I look stupid?” “What if I fail and prove I’m not capable?” “What if I lose the money on equipment?” The potential losses felt massive. Concrete. Guaranteed. Guaranteed. The potential gains felt distant. Uncertain. Unlikely. So I waited. I told myself I needed more preparation, more certainty, more proof that it would work. What I didn’t realize then - but understand clearly now - is that I wasn’t being careful. I was being mathematically illiterate. I wasn’t being careful. I was being mathematically illiterate. Because the calculation I was running - “What could I lose?” - is only half the equation. The complete equation is: “What could I lose?” versus “What could I gain?” versus “What’s the probability of each outcome?” versus “What’s the cost of never finding out?” And when you run the complete calculation, the math changes entirely. You want to know what actually happened when I finally launched the podcast? Nothing catastrophic. No embarrassment. No public failure. I published the first episode. Twenty-three people listened in the first week. Most of them were friends. The audio quality was mediocre. I stumbled over words. I said “um” too much. And... that was it. No one mocked me. No one called me out for not being an expert. The world didn’t end. Within three months, I had 200 regular listeners. Within six months, one of those listeners introduced me to someone who became a client. Within a year, the podcast became a primary way I connected with my audience and developed ideas that became newsletter content. All of the disaster scenarios I’d imagined for two years? None of them happened. The worst case was so much less bad than I’d feared. The upside was so much better than I’d imagined. That’s the pattern. The fear is always worse than the reality. Let me show you with real numbers. Starting a newsletter (same principle applies to podcasts, YouTube, any content): Starting a newsletter The Actual Downside: The Actual Downside: You invest 3-6 months writing consistently. Maybe 100 hours total over that period. That’s about 30 minutes per day, 5 days a week. You promote it to your existing network and on social platforms. Nobody reads it. Your first few posts get 3 views. Your mom and your two best friends. You feel embarrassed. You imagine people seeing you try and fail. You experience the discomfort of being visible while not being validated. That’s the downside. Let’s assess: Is it survivable? You’re out 100 hours spread over six months. In exchange for those hours, you: Developed clarity on what you think about important topics Built a skill (writing for an audience) Created a portfolio of work that demonstrates your thinking Learned what doesn’t resonate (valuable market research) Proved to yourself that you can finish what you start Made progress while others stayed stuck in planning mode Developed clarity on what you think about important topics Built a skill (writing for an audience) Created a portfolio of work that demonstrates your thinking Learned what doesn’t resonate (valuable market research) Proved to yourself that you can finish what you start Made progress while others stayed stuck in planning mode Your ego takes a hit for maybe a week. Then life moves on. Nobody actually cares that much. Everyone’s too busy thinking about their own lives. Downside: Survivable. The Actual Upside: The Actual Upside: Now let’s say it works. Not perfectly. Not viral-level success. Just... it works. The newsletter connects with 1,000 people over a year. That’s less than 3 new subscribers per day. Completely achievable. Those 1,000 people care about what you think. They read what you write. They respond with their own thoughts. They remember your name. That audience of 1,000 becomes: A distribution channel for anything you want to create A testing ground for new ideas and products A network of people who can introduce you to opportunities Social proof that you can build something from scratch A source of income if you ever want to monetize Conversations you couldn’t have had otherwise Relationships that wouldn’t have formed A distribution channel for anything you want to create A testing ground for new ideas and products A network of people who can introduce you to opportunities Social proof that you can build something from scratch A source of income if you ever want to monetize Conversations you couldn’t have had otherwise Relationships that wouldn’t have formed One of those 1,000 people sends your newsletter to someone influential in your field. That person reaches out. One conversation leads to an opportunity you never would have encountered. Or: Ten of those 1,000 people buy a product you create. $100 each. That’s $1,000. For a first attempt at monetization. Which validates that you can create value people will pay for. Which gives you confidence to build more. Or: Your writing clarifies your thinking so much that you become better at your day job. You get promoted. The writing skills transfer. The audience gives you leverage. These aren’t hypotheticals. This is the actual, documented pattern that happens to people who start creating and stick with it. But here’s what nobody tells you about the year you spend “preparing” instead of starting: But here’s what nobody tells you about the year you spend “preparing” instead of starting: You don’t spend that year in neutral. You spend it moving backwards. Every month you wait to start, someone else publishes their first post. Someone else sends their first email. Someone else builds their first 10 subscribers. You’re not standing still while you prepare. You’re watching a gap open up between you and the people who started before they felt ready. You’re watching a gap open up between you and the people who started before they felt ready. And that gap isn’t just about audience size. It’s about confidence, skill, resilience, and the compounding knowledge that comes from actually doing the thing. By the time you finally start - if you ever do - you’re not competing with who you are now. You’re competing with a version of yourself who started a year ago and has been improving ever since. That’s asymmetry. That’s asymmetry. Same effort. Same time investment. But the upside and downside aren’t even in the same galaxy. The downside is capped (100 hours of learning, temporary ego hit, valuable skills developed). The upside is uncapped (career transformation, financial freedom, opportunities you can’t predict). Most of the bets you’re not taking have a capped, survivable downside and an uncapped, transformative upside. That’s not risk in the traditional sense. That’s asymmetry. And asymmetry is mathematically smart. Yet smart people don’t take these bets. Why? Because they’re running the wrong calculation. They see the downside clearly - the time, the money, the potential embarrassment. They discount the upside heavily - “That probably won’t happen to me.” And they completely ignore the fourth variable: the cost of never trying. Here’s what the miscalculation reveals: You’re not actually trying to make a smart decision. You’re trying to find a reason to stay comfortable. Here’s what the miscalculation reveals: You’re not actually trying to make a smart decision. You’re trying to find a reason to stay comfortable. The math is just cover. The spreadsheet is just permission to avoid risk while feeling rational about it. If you actually cared about making the optimal choice, you’d run the complete equation. You’d see the asymmetry. You’d move. But you don’t want to see it. Because seeing it would mean you have no more excuses. So why does your brain work this way? Why do smart people systematically miscalculate risk? Because your brain isn’t running math. It’s running something far more primitive. II - Why Your Brain Gets The Math Wrong “We suffer more often in imagination than in reality.” “We suffer more often in imagination than in reality.” — Seneca Your brain isn’t doing math. It’s running ancient survival software that was calibrated for a world that no longer exists. The Mismatch Between Ancestral Risk and Modern Opportunity The Mismatch Between Ancestral Risk and Modern Opportunity Ten thousand years ago, risk assessment was brutally simple: Will this kill me? Yes or no. Trying a new hunting ground: Might encounter predators. Risk of death: High. Challenging the tribe leader for status: Might get exiled or killed. Risk of death: High. Eating unknown berries: Might be poisonous. Risk of death: High. In that environment, loss aversion made perfect evolutionary sense. The cost of being wrong once was death. The benefit of being right ten times was... not being dead. once Natural selection strongly favored caution. The humans who took too many risks didn’t survive to pass on their genes. The ones who avoided uncertainty, who stuck with what was known and safe, lived long enough to reproduce. Your brain is descended from those cautious survivors. It’s running their software. And that software has one primary directive: avoid anything that feels like it might threaten your survival. avoid anything that feels like it might threaten your survival. The problem? Your amygdala - the almond-shaped cluster of neurons responsible for processing threats - can’t tell the difference between “there’s a predator in the grass” and “someone might not like my business idea.” Both trigger the same neurological response. Both flood your system with the same stress hormones. Both generate the same behavioral impulse: avoid, retreat, stay safe. But the actual stakes are completely different. But the actual stakes are completely different. Starting a podcast won’t kill you. It can’t. The worst-case scenario is temporary embarrassment. Launching a product won’t exile you from the tribe. Modern society doesn’t work that way. The worst-case scenario is you learn what customers don’t want. Publishing your writing won’t poison you. It’s not possible. The worst-case scenario is some people don’t resonate with your ideas. All survivable. All recoverable. All ultimately beneficial in terms of learning and growth. But your brain can’t process that distinction. When you consider making a bold move - starting a business, publishing creative work, changing careers - your threat detection system treats it like mortal danger. The anxiety you feel isn’t proportional to the actual risk. It’s proportional to how your ancient brain categorizes the situation. And it categorizes all uncertainty as potential death. The Loss Aversion Trap The Loss Aversion Trap This gets amplified by a well-documented cognitive bias called loss aversion. Psychological research consistently shows that humans feel losses approximately 2-2.5x more intensely than equivalent gains. Losing $100 feels much worse than gaining $100 feels good. The pain of rejection hits harder than the pleasure of acceptance. The fear of failure weighs more heavily than the excitement of potential success. This made sense for survival. Missing one meal was more immediately dangerous than finding extra food was beneficial. Losing social status in a small tribe had severe consequences. Avoiding threats was more critical than pursuing opportunities. But in the modern world, where most risks are survivable and most losses are recoverable, loss aversion becomes a systematic source of bad decisions. It causes you to: Overweight small, temporary losses (time, money, ego) Underweight large, lasting gains (career transformation, financial freedom, personal growth) Avoid actions with asymmetric upside because you can’t stop fixating on the downside Stay in situations that are “okay” because changing feels like risking a loss Overweight small, temporary losses (time, money, ego) Underweight large, lasting gains (career transformation, financial freedom, personal growth) Avoid actions with asymmetric upside because you can’t stop fixating on the downside Stay in situations that are “okay” because changing feels like risking a loss Your brain is optimized for surviving threats, not capitalizing on opportunities. Your brain is optimized for surviving threats, not capitalizing on opportunities. And in a world where threats are mostly non-fatal and opportunities are abundant, that optimization makes you systematically worse at assessing risk. Here’s where it gets insidious. You don’t just feel the fear. You rationalize it. You’re smart. You’re analytical. So your brain provides you with sophisticated-sounding reasons for why you shouldn’t try: “I need to be more prepared first.” “I should wait for better market conditions.” “I don’t have the resources yet.” “I need to research more before I commit.” These sound like rational calculations. They feel like smart risk management. But they’re not. They’re your threat detection system generating cover stories for the fear you don’t want to admit you’re feeling. But they’re not. They’re your threat detection system generating cover stories for the fear you don’t want to admit you’re feeling. You’re not being careful. You’re being scared and dressing it up in the language of prudence. And because you’re smart, you’re very good at this. You can build an entire intellectual framework around why now isn’t the right time. You can create spreadsheets that “prove” the risk is too high. You can cite examples of people who failed to validate your caution. But strip away the sophistication and here’s what’s actually happening: Your amygdala sees uncertainty. It generates fear. Your prefrontal cortex - the part that handles reasoning - works backwards to justify that fear with logic. You’re using math to rationalize emotion, not to make optimal decisions. You’re using math to rationalize emotion, not to make optimal decisions. And you know this is true because of what happens when you see other people take the exact bet you’re avoiding: You don’t think “Good, they confirmed my analysis was correct.” You think “Damn, I should have done that.” The Illusion of Safety The Illusion of Safety Here’s where it gets really insidious. Not only does your brain overestimate the risk of action, it also creates an illusion that inaction is safe. Staying at your job feels safe because it’s familiar. The pattern is established. You know what to expect. Not starting the business feels safe because you’re not exposing yourself to potential failure. You’re not risking embarrassment. Keeping your ideas private feels safe because you’re not subjecting them to judgment or rejection. But that feeling of safety is an illusion. Your job can disappear tomorrow. Companies restructure. Industries shift. The “stability” of employment is often just the absence of immediate threat, not actual security. You think you’re safe because you’re on payroll, but you’re actually maximally exposed - your entire income depends on one decision-maker who doesn’t owe you anything. Your job can disappear tomorrow. Not starting the business means you’re entirely dependent on someone else’s decisions about your income. That’s not safe. That’s vulnerable. That’s putting all your risk into one basket labeled “employment” and hoping nobody drops it. Keeping your ideas private means you never develop them, never test them, never build anything of your own. That’s not safe. That’s guaranteeing you’ll never have the resources or leverage that come from building in public. The safe path isn’t actually safe. It’s just familiar. The safe path isn’t actually safe. It’s just familiar. And your brain confuses familiarity with security. Here’s the thought that should haunt you: The riskiest thing you can do is to spend your entire life avoiding risk. The riskiest thing you can do is to spend your entire life avoiding risk. Because while you’re busy playing it safe, the world is changing around you. The job you think is secure becomes obsolete. The industry you thought was stable gets disrupted. The career path you thought was guaranteed disappears. And when that happens - when the “safe” choice reveals itself as an illusion - you have nothing. No skills from attempting bold things. No network from building in public. No track record of betting on yourself. No resilience from failing and recovering. You optimized for safety and ended up with fragility. The people who took the “risky” bets? They built anti-fragility. They developed the capacity to survive failure. They created options. They’re not dependent on one income source, one employer, one path. You’ve been calculating risk backwards your entire life. You’ve been calculating risk backwards your entire life. This is why people stay in jobs they hate for decades. Why they remain in relationships that aren’t working. Why they never pursue the things they claim they want to do. Not because they’re lazy or stupid. Because their threat detection system is wired to prefer the familiar danger over the unfamiliar opportunity. The devil you know feels safer than the devil you don’t - even when the devil you know is slowly destroying your potential and the devil you don’t is actually just an opportunity in disguise. You’re not playing it safe. You’re playing not to lose. And playing not to lose is the only guaranteed way to lose. You’re not playing it safe. You’re playing not to lose. And playing not to lose is the only guaranteed way to lose. When you make that calculation conscious and explicit, you can see past the emotional response to the underlying reality: In a world where failure isn’t fatal, the asymmetry favors action. The biggest risk isn’t trying and failing. It’s letting an outdated survival mechanism dictate your entire life trajectory. The people who win aren’t smarter than you. They’re not more talented. They’re not luckier. They just have a higher tolerance for feeling scared while doing the thing anyway. The people who win aren’t smarter than you. They’re not more talented. They’re not luckier. They just have a higher tolerance for feeling scared while doing the thing anyway. That’s it. That’s the only difference. Now let’s talk about what that faulty calculation is actually costing you. III - The Guaranteed Cost of Never Trying “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did.” “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did.” — Mark Twain But let’s say you don’t take the bet. You decide the risk is too high. You stay where you are. You keep preparing, keep planning, keep waiting for certainty. What’s the cost? Most people think the cost is zero. They think “no decision” means “no risk.” They’re catastrophically wrong. The cost of not trying isn’t zero. It’s regret. And regret isn’t survivable. It’s permanent. The cost of not trying isn’t zero. It’s regret. And regret isn’t survivable. It’s permanent. I need to be very direct about this because it’s the part of the equation that people systematically ignore until it’s too late. When you try something and fail, here’s what actually happens: You feel disappointed for a period of time. Days, maybe weeks. Then you process it. You extract the lessons. You identify what didn’t work. You develop skills from the attempt. You have concrete data about what to avoid next time. You move forward with more information, more experience, and more resilience than you had before the attempt. The failure resolves. It becomes a data point. Eventually, it becomes a story you tell about your journey. I’ve failed at multiple business ideas. A clothing brand that never sold a single item. A software product that took six months to build and zero people wanted. Content projects that went nowhere. Do those failures haunt me? No. They taught me what markets don’t want. They showed me what approaches don’t work. They built my tolerance for rejection and uncertainty. They’re now just part of the path that led to the things that did work. Failure is temporary data collection. Failure is temporary data collection. But when you don’t try - when you stay in the safe lane, when you keep preparing indefinitely, when you wait for certainty that will never come - here’s what happens: Nothing. And that nothing compounds. compounds. You’re 30. You have an idea for a business. You don’t start because you’re “not ready.” You tell yourself you’ll do it when you have more savings, more skills, more certainty. You’re 35. The idea is still there. So is the hesitation. You’re busier now. The excuse shifts to “I don’t have time.” You watch someone else launch something similar. It hurts, but you convince yourself they probably got lucky or had advantages you don’t have. Here’s what you don’t say out loud: You spend 10 hours a week on Netflix, social media, and activities that don’t matter. You “don’t have time” the same way people “can’t afford” the gym membership but can afford daily coffee. Time isn’t the constraint. Courage is. You’re 40. The idea has been with you for a decade. You’ve refined it in your head. You know exactly how you’d do it. But now the excuse is “I’m too old to start over” or “I have too many responsibilities.” The truth you won’t admit: You’re more afraid now than you were at 30. Because now you have a decade of evidence that you’re someone who doesn’t follow through. And starting would mean confronting that identity. You’re 50. You don’t think about the idea as much. It’s been relegated to the “could have been” section of your mind. But every time you see someone doing what you wanted to do, something twists in your chest. And you tell yourself a story: “I had too many obligations.” “The timing was never right.” “I couldn’t afford to take the risk.” But the real story is simpler: You were scared. And you let that fear make your decisions for you for 20 years. You’re 60. The idea is a ghost. You tell younger people “I always wanted to do something like that” with a wistful tone that carries two decades of accumulated regret. You’re 70. You’re talking to your grandkids. They ask about your life. You have the job history, the stability, the safety. But there’s an absence. A path not taken. A version of yourself that never got to exist. I’ve had this exact conversation with dozens of people in their 40s, 50s, 60s. The details change but the pattern is always the same: an idea they saw clearly, a move they knew they should make, years of rational-sounding excuses, and now a quiet weight they carry everywhere. Here’s the truth that should shatter your entire risk calculation: You’re not avoiding the bet. You’re already taking it. Here’s the truth that should shatter your entire risk calculation: You’re not avoiding the bet. You’re already taking it. Every day you don’t try is a bet. A bet that staying the same is better than trying and failing. A bet that comfort today is worth regret tomorrow. A bet that your fear is giving you accurate information about the future. You’re betting on yourself either way. The only question is what version of yourself you’re betting on. You’re betting on yourself either way. The only question is what version of yourself you’re betting on. The one who tries and maybe fails? Or the one who never tries and definitely wonders? That’s the real cost. That’s the real cost. Not failure. Not embarrassment. Not lost time or money. Permanent uncertainty about who you could have become. A life spent wondering “what if?” And unlike a failed business or a rejected pitch or a product that didn’t sell, you can’t recover from that. You can’t A/B test it. You can’t iterate. You can’t go back and try. The opportunity window closes. The market shifts. Your energy changes. Your circumstances evolve. And the version of your life where you found out what was possible disappears forever. They all say the same thing, in different words: “I had this idea when I was younger. I knew what I wanted to build. I saw the opportunity clearly. But I was scared. I told myself it was too risky. I convinced myself I needed to be more prepared. Now I watch other people - often less capable people - doing exactly what I wanted to do. And I can’t stop thinking about what my life would look like if I had just tried.” The regret isn’t just about the missed opportunity. It’s about not knowing who they could have been. It’s about a door that’s now permanently closed. Here’s the mathematical truth nobody wants to confront: Here’s the mathematical truth nobody wants to confront: The probability of regret from not trying approaches 100% over a sufficient time horizon. The probability of catastrophic, unrecoverable failure from trying approaches 0%. Let me unpack that. If you don’t try: You will never know if it could have worked (100% certainty of permanent uncertainty) You will watch others succeed in spaces you wanted to enter (compounds regret) You will accumulate “what if” thoughts that become more painful over time You will reach a point where the opportunity is no longer available You will face the reality that you let fear dictate your choices You will never know if it could have worked (100% certainty of permanent uncertainty) You will watch others succeed in spaces you wanted to enter (compounds regret) You will accumulate “what if” thoughts that become more painful over time You will reach a point where the opportunity is no longer available You will face the reality that you let fear dictate your choices All of those outcomes are guaranteed. That’s not risk. That’s certainty. If you do try and it fails: You learn what doesn’t work (valuable) You develop skills from the attempt (transferable) You build resilience and reduce future fear (compounds capability) You have data for your next attempt (actionable) You move forward without the weight of wondering You learn what doesn’t work (valuable) You develop skills from the attempt (transferable) You build resilience and reduce future fear (compounds capability) You have data for your next attempt (actionable) You move forward without the weight of wondering The “catastrophic failure” scenarios people imagine - complete financial ruin, total social ostracism, permanent career damage - almost never happen in reality. What actually happens: You’re out some time and money. Your ego bruises. You feel disappointed. Then you recover and try something else. That’s it. You’re not avoiding risk by staying where you are. You’re just choosing a different, more painful, more permanent form of risk. You’re not avoiding risk by staying where you are. You’re just choosing a different, more painful, more permanent form of risk. The risk of action: Temporary discomfort, recoverable losses, valuable learning. The risk of inaction: Permanent regret, compounding opportunity cost, lifelong wondering. When you frame it correctly, the choice is obvious. This is what people mean when they say “the greatest risk is no risk at all.” Not because safety is impossible. But because the risk of a life unlived - the risk of reaching the end and realizing you never let yourself try - is worse than any survivable failure you could experience along the way. And here’s the cruel irony: the people who take the calculated bets, who try and sometimes fail, who build the tolerance for uncertainty - they’re the ones who end up with fewer regrets. Not because everything they try works. But because they know. They have data. They don’t wonder. They tried, they learned, they moved forward. The people who spend their lives avoiding risk? They’re the ones carrying the heaviest burden. The weight of all the unlived possibilities. All the versions of themselves they never let exist. That’s not safety. That’s a different kind of prison. IV - How To Actually Bet On Yourself (And Why You Won’t) But before I give you the steps, let me tell you what’s about to happen. You’re going to read these steps. You’re going to think “This is useful.” You might even screenshot them. And then you’re going to close this newsletter and do exactly what you were doing before you opened it. You’ll tell yourself “I’ll come back to this later.” You’ll save it in a folder labeled “Important.” You’ll add it to your ever-growing list of things you’re going to do “when you have time.” But later never comes. And you know it. But later never comes. And you know it. Because this isn’t the first article you’ve read about taking action. This isn’t the first framework you’ve saved. This isn’t the first time you’ve felt motivated to start. It’s just the latest iteration of a pattern you’ve been running for years: consume information about change, feel inspired, do nothing. So let me be very clear about something: These steps only work if you actually do them. And you’re not going to do them unless you admit something uncomfortable first. These steps only work if you actually do them. And you’re not going to do them unless you admit something uncomfortable first. You don’t have an information problem. You have a courage problem. You don’t need more frameworks. You need to stop pretending that one more system will be the thing that finally makes you feel ready. You’re not going to feel ready. Ever. The only way forward is to act before you feel ready. So here’s what to actually do - not because you need it, but because if you’re going to ignore it like you’ve ignored every other framework, I want you to at least be conscious about what you’re choosing. Start With The Smallest Asymmetric Bet Start With The Smallest Asymmetric Bet You don’t have to quit your job tomorrow. You don’t have to bet everything on one idea. You don’t have to make a dramatic, all-or-nothing move. Start with the smallest bet that still has asymmetric upside. The kind of bet where the downside is so small it’s almost negligible, but the upside could be transformative. Publish one piece of writing online. Publish one piece of writing online. Downside: 2 hours to write and edit. Maybe nobody reads it. You feel slightly vulnerable. Upside: It resonates with someone. They share it. It reaches people you don’t know. It opens a conversation. It demonstrates your thinking. It’s the first step toward building an audience. Reach out to one person you admire. Reach out to one person you admire. Downside: 10 minutes to write a thoughtful email. They don’t respond. Your ego feels a small sting. Upside: They respond. You have a conversation. They share an insight that shifts your entire approach. They introduce you to someone in their network. They become a mentor. They hire you. Ship one small product or service. Ship one small product or service. Downside: 20-40 hours to build something simple. You put a landing page up. Nobody buys. You feel disappointed. Upside: 10 people buy. You make $500. You prove you can create value people will pay for. You validate an idea. You have a foundation to build on. You gain confidence to create more. Record one video or podcast episode. Record one video or podcast episode. Downside: 3 hours to plan, record, and publish. It gets 20 views. You cringe at the sound of your own voice. Upside: 100 people watch. Some of them subscribe. One person shares it. It starts a conversation. You develop the skill. You realize you enjoy the medium. It becomes a weekly practice that builds into something meaningful over time. Do you see the pattern? The downside is so small - a few hours, temporary discomfort, maybe $100 - that it barely matters. The upside is completely disproportionate - skills, connections, opportunities, proof of concept, momentum. That’s asymmetry at the micro level. Before you take any of these bets, run this exercise. Tim Ferriss calls it “fear-setting” - a systematic way to define your fears instead of letting them define you. Take the bet you’re considering. Write it at the top of a page. Then create three columns: Column 1: Define - What’s the worst that could realistically happen? Be specific. Not vague anxiety, but concrete outcomes. “I waste 3 months and $500.” “Nobody reads it and I feel stupid.” Write down every fear. Column 1: Define Column 2: Prevent - For each fear, what could you do to reduce the likelihood? “Start with a smaller version - 1 month and $100.” “Share with a small group first.” Most fears can be mitigated with basic precautions. Column 2: Prevent Column 3: Repair - If the worst case happens, how would you recover? “I could save $500 in two months.” “I could use what I learned to try a different approach.” Be specific about the recovery path. Column 3: Repair What you’ll discover when you write it out is that the worst case is: unlikely to happen, not that bad, and recoverable. Most of your fears dissolve when you define them specifically. Most of your fears dissolve when you define them specifically. The vague anxiety of “what if it doesn’t work” feels insurmountable. But “I’ll be out $500 and some time, and I can recover both in two months” is manageable. That’s the difference between imagined catastrophe and actual risk. Pick one small bet. The smallest one that scares you just enough to matter. And do it in the next 7 days. Not eventually. Not when you’re ready. In the next 7 days. Do the thing. Ship the thing. Hit publish. Send the email. Launch the offer. Then take another bet. Then another. Build the pattern. Each bet de-risks the next one because you’re developing skills, building resilience, and accumulating proof that you can survive uncertainty. Let me tell you what’s really happening right now. You’re reading this newsletter. You’re nodding along. You’re thinking “This makes sense. The math is clear. I should take more asymmetric bets.” And tomorrow, you’ll do nothing. You’ll go back to your job. You’ll scroll social media. You’ll think about starting that project. You’ll tell yourself “soon.” You’ll make the same calculation you’ve been making for years: The risk is too high. I’m not ready. I need more time. The risk is too high. I’m not ready. I need more time. And the days will stack into weeks. The weeks into months. The months into years. And five years from now, you’ll be reading another article about asymmetric upside and thinking “This makes sense” and doing nothing. Because here’s what you haven’t realized yet: understanding the math changes nothing. Because here’s what you haven’t realized yet: understanding the math changes nothing. You already knew most of this before you started reading. You already knew that the downside of trying is survivable. You already knew that regret is worse than failure. You already knew that smart people stay stuck not because they’re stupid but because they’re scared. You didn’t need me to explain asymmetric upside. You needed me to give you permission to keep waiting. And I’m not giving you that permission. The asymmetry of upside makes bold moves mathematically smart. That’s not inspiration. That’s fact. The asymmetry of upside makes bold moves mathematically smart. The downside of trying and failing is usually survivable. You recover. You learn. You move forward. That’s data. The downside of never trying is guaranteed regret. You never know. You never build. You spend decades wondering what could have been. That’s certainty. Bet on yourself more often. The expected value is higher than you think. That’s math. But none of that matters if you don’t actually do the thing. And you know what the thing is. You’ve known for months. Maybe years. It’s the project you keep planning but never starting. It’s the email you keep drafting but never sending. It’s the business idea you keep refining but never launching. It’s the content you keep researching but never creating. It’s the bet you keep calculating but never taking. You know exactly what it is. The thing that would change everything if you just did it. The thing that scares you precisely because it matters. Here’s the uncomfortable truth you’ve been avoiding: You’re not actually trying to make a smart decision. You’re trying to find a mathematical justification for your fear. You’re not actually trying to make a smart decision. You’re trying to find a mathematical justification for your fear. The spreadsheet is cover. The research is procrastination. The “one more course” is avoidance. You don’t need more information. You don’t need better tools. You don’t need perfect conditions. You need to stop lying to yourself about why you haven’t started. And the biggest lie you tell yourself? “I’ll do it when I’m ready.” But here’s what “ready” actually means in your internal calculus: “When it doesn’t feel scary anymore. When I’m guaranteed not to fail. When I’m certain it will work.” That moment never comes. That moment never comes. You will never feel ready. The fear will never fully go away. The uncertainty will never completely resolve. The people who succeed at the things you want to do aren’t more ready than you. They’re not more talented. They’re not more prepared. They just started before they felt ready. They took the bet while it still scared them. They understood that the feeling of readiness comes AFTER you start, not before. So here’s the only question that matters: Are you going to make the same excuses next year? Because that’s the actual decision you’re making right now. Not “should I start this thing.” You already know you should. The decision is: Am I the kind of person who lets fear make my decisions? Or am I the kind of person who runs the math and makes the bet? You can’t be both. The math is clear. The asymmetry is obvious. The only question is: what are you going to do about it? The math is clear. The asymmetry is obvious. The only question is: what are you going to do about it? Thanks for reading, — Scott