How to Learn from Risky Decisions

Some of my “worst” investments aren’t the ones that went to zero––they’re the investments where the real cost was saying no. Airbnb, Stripe, and Square: examples that were each a lesson in overestimating risks, underestimating potential, or not doubling down on conviction. These weren’t easy “no” decisions; they were shaped by what I knew at the time, but they revealed something critical about how we weigh opportunity and risk. For Airbnb, I passed on doubling down because I had already led an earlier round of investment and convinced myself I didn’t need to lead the next. Although I had more conviction as time went on, I didn’t press the advantage. For Stripe and Square, my deep knowledge of payments—gained from my time at PayPal—ironically became a blind spot. I knew how challenging the payments space was and let that knowledge overshadow the potential these companies offered. Reflecting on these––and many other misses––I find it’s important to continually challenge the narratives we build for ourselves as founders and investors. Sometimes, those narratives are grounded in logic, and other times they’re too heavily weighing past experiences that don’t necessarily predict future outcomes. No investor can win every bet; But the best outcomes come from a willingness to evolve, to revisit our decision-making frameworks, and to apply what we learn to the next opportunity.

𝗧𝗵𝗲 𝗣𝗼𝘄𝗲𝗿 𝗼𝗳 𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝗼𝗻: 𝗛𝗼𝘄 𝗟𝗲𝗮𝗿𝗻𝗶𝗻𝗴 𝗳𝗿𝗼𝗺 𝘁𝗵𝗲 𝗣𝗮𝘀𝘁 𝗦𝗵𝗮𝗿𝗽𝗲𝗻𝘀 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 . . . 🔷As a manager and leader, whether you're just starting out or you’ve been in the game for years, you know that the decisions you make every day can have lasting effects. But how often do you stop to reflect on how those decisions are made—especially when they don’t go as planned? 👇Before diving into your next big decision, ask yourself: ❓What past decisions didn’t turn out the way I expected? ❓Am I repeating the same approach, hoping for different results? ❓How can I use past experiences to improve my current decision-making? 💡In our rush for efficiency, we often move quickly, believing that speed will bring results. But true efficiency comes from intentional reflection—slowing down to mine the lessons hidden in past decisions, even when those decisions didn’t work out. 👉Here are some key steps you can take to improve your decision-making by learning from past experiences: 1️⃣ 𝗖𝗹𝗲𝗮𝗿𝗹𝘆 𝗱𝗲𝗳𝗶𝗻𝗲 𝘁𝗵𝗲 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗽𝗿𝗼𝗯𝗹𝗲𝗺. Before jumping to solutions, make sure you're addressing the right issue. Don’t let assumptions or desired outcomes cloud your understanding of what’s actually at stake. 2️⃣ 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝘆 𝘄𝗵𝗮𝘁’𝘀 𝗰𝗮𝘂𝘀𝗶𝗻𝗴 𝘀𝘁𝗿𝗲𝘀𝘀 𝗶𝗻 𝘆𝗼𝘂𝗿 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻. Stress can cloud judgment and reinforce biases. By understanding what’s triggering your stress, you can prevent it from skewing your decision-making process. 3️⃣ 𝗔𝗻𝗮𝗹𝘆𝘇𝗲 𝗽𝗮𝘀𝘁 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀 𝘁𝗵𝗮𝘁 𝗱𝗶𝗱𝗻’𝘁 𝘄𝗼𝗿𝗸 𝗼𝘂𝘁. Choose a few decisions that didn’t go as planned. What went wrong? Were there warning signs you ignored? This reflection will help you avoid similar mistakes. 4️⃣ 𝗔𝗰𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 𝘁𝗵𝗲 𝗮𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀 𝘆𝗼𝘂 𝗺𝗮𝗱𝗲. Every decision comes with assumptions. Looking back, what assumptions led to poor outcomes? Did you rely on incomplete information, or overlook key factors? 5️⃣ 𝗔𝗽𝗽𝗹𝘆 𝘁𝗵𝗲 𝗹𝗲𝘀𝘀𝗼𝗻𝘀 𝗹𝗲𝗮𝗿𝗻𝗲𝗱 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝘀𝗶𝘁𝘂𝗮𝘁𝗶𝗼𝗻. Use what you’ve learned from past mistakes to make adjustments to your current decision. What new approaches can you take to get a better outcome? 6️⃣ 𝗗𝗲𝘃𝗲𝗹𝗼𝗽 𝗮 𝗰𝗹𝗲𝗮𝗿 𝗮𝗰𝘁𝗶𝗼𝗻 𝗽𝗹𝗮𝗻. After reflecting on your past and current decision, create a strategy that addresses the lessons learned. Ensure your approach incorporates new insights to avoid repeating mistakes. 🪴Mistakes are not failures—they’re opportunities for growth. By taking the time to reflect on past decisions, you gain the insight needed to make more informed and confident choices in the future. 💫Remember, slowing down and reflecting is not a sign of inefficiency, but a strategy for long-term success. Ask yourself: 𝘈𝘮 𝘐 𝘮𝘰𝘷𝘪𝘯𝘨 𝘲𝘶𝘪𝘤𝘬𝘭𝘺 𝘫𝘶𝘴𝘵 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘴𝘢𝘬𝘦 𝘰𝘧 𝘪𝘵, 𝘰𝘳 𝘢𝘮 𝘐 𝘮𝘢𝘬𝘪𝘯𝘨 𝘵𝘩𝘰𝘶𝘨𝘩𝘵𝘧𝘶𝘭, 𝘥𝘦𝘭𝘪𝘣𝘦𝘳𝘢𝘵𝘦 𝘤𝘩𝘰𝘪𝘤𝘦𝘴?

When I went bankrupt, it wasn’t because of one bad decision, it was because of the assumptions behind it. I assumed the bank would always lend against my equity. I assumed access to capital would always be there. I assumed things would keep working the way they always had. They didn’t. That experience taught me something I carry into every business conversation today: decisions fail less often than the assumptions that create them. Before you double down on a deal, a hire, or a forecast, pause and test your assumptions. Ask why they feel certain. Ask what happens if they’re wrong. That’s how you build real awareness, and avoid learning the hard way.

An employee lost a $15M contract and I refused to fire him. Here’s why. A number of years ago, we landed a large project, led by Chris, a star on our team. He proposed a high-risk resourcing model, focusing on one key individual for delivery. Our leadership debated whether to intervene due to the high risk but decided to trust Chris's judgment, allowing him full autonomy. Everything that could go wrong, did. The key team member underperformed, and we lost the project. The client called me and immediately terminated our contract. Post-blow up, Chris offered to resign. It seemed like a natural response to such a setback. I refused to accept his resignation and told him: "You’re now the most valuable person on our team — you learned a $15M lesson. No way would I let you go.” This experience taught the team to see the value in our failures. Chris’s experience became a lesson for the entire team, transforming our approach to risk and altering the fundamentals of how we manage resourcing, bench, and talent rotation. How we handled this internally showed everyone that we stand behind learning from failure. Fear of failure = no innovation. Testing and failing quickly is good when you use those learnings to avoid future mistakes. We all became better for it. I share this story with every new team member I interact with to emphasize the importance of learning from our failures, regardless of how painful they might be. Consulting at high levels is stressful. It can feel like you’re walking on a knife’s edge — especially for product managers and engagement leads who have to balance internal organizational realities while still pleasing the client. We’ve made it clear that justified risks are genuinely encouraged and failures are dissected for learning. Experience transcends projects and retainers, which fluctuate frequently. Team members with real battle experience are a growth company’s most valuable asset. What is your stance on risk tolerance and failure? Where do you draw the line on mistakes? Are managers treated differently than individual contributors?

More mistakes = more lessons The more mistakes you make, the more lessons you gain. 

It's important not to rely solely on theory or focus only on your successes. 

Embrace your failures and view them as valuable learning opportunities. 

Each mistake provides practical insights that theory alone cannot offer and helps you grow both personally and professionally. 

By analysing and understanding your missteps, you can develop better strategies, avoid repeating the same errors, and ultimately achieve greater success. 

Expanding your focus beyond successes ensures a well-rounded approach to growth and continuous improvement. 1. Reflect on Mistakes: - Daily or Weekly Reviews: Set aside time to review your actions and decisions regularly. Reflect on what went wrong and why. - Journaling: Keep a journal of your mistakes and the lessons learned from each one.
 2. Seek Feedback: - Peer Reviews: Ask colleagues or mentors for constructive feedback on your work and decisions. - Open Communication: Create an environment where team members feel comfortable discussing their mistakes and what they learned.
 3. Analyse and Document: - Root Cause Analysis: Use techniques like the "5 Whys" or fishbone diagrams to understand the root causes of mistakes. - Documentation: Document mistakes and their causes in a shared repository for future reference and team learning.
 4. Create a Learning Culture: - Celebrate Learning: Recognise and reward employees who identify mistakes and share their lessons. - Encourage Experimentation: Foster an environment where calculated risks and experimentation are encouraged, even if they result in

In 2021, I lost $200k trading options. I thought I could quit my consulting roles and make 10x more... oof. It was a painful experience that nearly cost me everything. But it taught me invaluable lessons about risk management and financial decision-making that I now use to help online entrepreneurs avoid similar mistakes. Here are a few things to watch for: 1. Beware of false signals - one big win doesn’t guarantee future success 2. Don’t let FOMO drive your financial decisions 3. Understand the risks before diving into complex financial instruments 4. Be transparent with your team and loved ones about financial challenges 5. Have a solid backup plan and diverse income streams My mistake led me to develop strategies that have since helped hundreds of businesses secure over $20M in funding and optimize their finances. What’s the biggest financial lesson you’ve learned the hard way?

I became a VP at Amazon because I made some risky bets and got them right. I also had some go wrong. But because I generally made good decisions quickly and minimized the risks, I won enough to move up. Here is how you can learn this essential executive skill: The first piece is understanding that the idea of making the “right decision” is a fallacy. Choices in business are not between right and wrong or good and bad options. In fact, they are usually between multiple potentially good options. This truth becomes an obstacle for leaders because they often wait for one option to present itself as superior, but this clarity never comes (or it comes far too late). This is why Jeff Bezos says that you should make your decisions with 70% of the desired data or information. If you wait for 100%, you will either never make a decision or you will make it too late to benefit from it. As a leader, you must become comfortable with making decisions that you don’t *know* are correct. Second, so that your quick decisions aren’t reckless, you must understand the pieces of making an uncertain decision. There are three pieces of every decision to consider: 1) How confident you are in your choice. Remember, this will almost never be 100%. 2) How costly it would be to be wrong. 3) The cost of delaying your decision. Weighing these three factors together will give you a matrix of how to decide—the higher the consequences, the more confidence you need; the higher the cost of delay, the faster you need to move. Finally, you must understand the cost and time commitment of undoing your choice. This should be part of your cost analysis in question two above, and it is also the root of Jeff Bezos’s “One-way and Two-way Doors” theory. Basically, if you know that each decision you make will potentially need to be undone, you must think through that process. For things that are easily rolled back or fixed, move quickly. For actions that are difficult to undo or erase, take more time to build confidence and mitigate risk. If you use these three ideas to build a personal decision-making system, you will be able to quickly make impactful decisions with a high percentage of accuracy, and you will be able to clean up the mess left when you get it wrong. Being right a lot (an Amazon LP), iterating quickly, and being able to do damage control will get you very far as a leader. On the other hand, waiting to make perfect decisions will keep you stuck. If you want to learn more about high speed decision-making systems, read this week’s newsletter: https://buff.ly/mevN6RJ I will be writing more about this topic in the coming weeks, so make sure to subscribe if you are interested.

𝙄 𝙩𝙪𝙧𝙣𝙚𝙙 𝙙𝙤𝙬𝙣 𝙖 “𝙙𝙧𝙚𝙖𝙢” 𝙘𝙡𝙞𝙚𝙣𝙩 𝙬𝙤𝙧𝙩𝙝 $300𝙆. Here's the decision playbook that made it easy. If that sounds wild, read Emma McQueen’s story first... she walked away from a $300K client because it no longer aligned with her values. That line hit me hard... clarity reduces complexity. Her post - https://lnkd.in/guxsvsiN Over the years leading growth and marketing teams, I’ve learned that tough calls aren’t a willpower problem, they’re a systems problem. When the stakes are high (budget, brand, people), I run this 5-step 𝗧𝗼𝘂𝗴𝗵 𝗗𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸: 1) Start with values -> write the "non-negotiables" When values are explicit, trade-offs get simpler. If a decision conflicts with a non-negotiable (e.g., data privacy, fair pricing, team wellbeing), it’s an automatic “no,” even when short-term revenue tempts a “yes.” 2) Run a 10/10/10 check (emotion out, perspective in) Ask: How will this feel in 10 days, 10 months, 10 years? This reframes urgency bias. Pair it with Jeff Bezos’s 𝗥𝗲𝗴𝗿𝗲𝘁 𝗠𝗶𝗻𝗶𝗺𝗶𝘇𝗮𝘁𝗶𝗼𝗻, will saying yes/no reduce long term regret when I’m 80? These time horizons nudge us away from fear based choices. 3) Take the "outside view" (base rates > gut feel) Most of us are overconfident about unique outcomes. Before committing, I look at base rates:  • What happened to similar campaigns, partnerships, or launches?  • What’s the statistical likelihood of success given constraints? Quick ways to apply:  • Pull success/attrition rates from past projects  • Benchmark channel performance vs. industry reports, not anecdotes Write a brief “outside view” paragraph before approving the plan 4) Do a 20-minute pre-mortem Instead of asking “Why might this work?”, I ask the team: Assume it failed badly... what went wrong? List risks, assign owners, add kill-switch metrics. Pre-mortems surface blind spots early and increase follow-through on mitigations. 𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝘄𝗼𝗿𝗸𝘀  • Less noise, more signal. Values and base rates strip away narrative bias.  • Fewer unforced errors. Pre-mortems reduce “I didn’t think of that” failures.  • Speed where it’s safe. Splitting reversible vs. irreversible decisions preserves momentum. Sources & further reading:  • Gary Klein, Performing a Project Premortem - https://lnkd.in/g2NfcnEB   • McKinsey & Company, Decision making in organizations - https://lnkd.in/giG87skX   • Regret Minimization Framework - https://lnkd.in/gaStT2M5   • PMI, Reference Class Forecasting & Outside View - https://lnkd.in/gTU9yYxq If you’d like my 1-page worksheet version of this playbook, say “Checklist” and I’ll share it. LinkedIn for Marketing | Digital Marketing | LinkedIn for Learning

Ever notice how we talk about career moves like they're permanent life sentences? "I'm taking the plunge..." "I'm making the leap..." "I'm burning the bridges..." (Spoiler alert 🚨 Those bridges? They're probably more flame-retardant than you think.) We've got it all backwards. We're treating our careers like a high-stakes game of Jenga, where one wrong move sends everything crashing down. But what if – hear me out – we treated them more like a science experiment? You know, the kind where even the explosions teach you something valuable (and hopefully don't involve actual explosions...usually). The Great Career Experiment 🌀 Remember back in science class when getting the "wrong" result wasn't actually wrong – it was just data? Mind-blowing, right? Now apply that same thinking to your career moves: That side project that "failed"? Data point. That job that wasn't what you expected? Hypothesis tested. That presentation that went sideways? Field research. Ready to run your own experiments? Here's how: 1. Start with a Hypothesis Instead of "I need to nail this new role or my life is over," try: "I believe this role will let me use my creativity more. Let's test that." 2. Collect Data (AKA Live Your Life) Track these three things: What energizes vs. drains you Projects that make you lose track of time When you procrastinate (and why) 3. Analyze & Iterate The magic isn't in getting it right. It's in getting it less wrong over time. Each "failure" is just redirecting you toward what actually works. When you stop trying to get everything perfect and start treating your career as a series of experiments, you actually end up making better decisions. Why? Because you're no longer paralyzed by the fear of making the "wrong" choice. Consider this your official permission to: ✓ Take that "risky" move ✓ Try something that might not work ✓ Be gloriously wrong about something The only real failure is letting fear keep you from experimenting at all. Dig this? There's lots more in the Generalist World 🌀 newsletter: https://lnkd.in/drCxd-58

Most "safe" decisions cost more than risky ones. I've watched hundreds of professionals over the years. The pattern is clear: Some are paralyzed by "what if it fails?" Others are energized by "let's see what happens" The difference in their lives and careers? Staggering. Here's the truth no one talks about: The experiments we DON'T run are more expensive than the ones that fail. When fear of failure stops us from trying at all, we pay with: → Stagnant careers → Missed opportunities → Regret that compounds over time So what separates the paralyzed from the energized? 1️⃣ They start with absurdly small experiments Not every experiment needs to be revolutionary. → Test one assumption → Adjust one variable → Run one conversation you've been avoiding The goal isn't perfection. It's learning. Small steps create momentum. Momentum creates confidence. 2️⃣ They treat resistance as data When you resist experimenting, you're not being difficult. Your resistance is telling you something valuable about: • What you're afraid of losing • What uncertainty means to you • Where you need more safety Honor that signal. Reflect on it. Then design the smallest possible experiment that addresses it. 3️⃣ They build safety nets, not certainty The most innovative people I know share one thing: psychological safety. They know a failed experiment won't: ❌ End their career ❌ Destroy their reputation ❌ Ruin their relationships It will: ✅ Start a conversation ✅ Generate new data ✅ Inform the next move They don't wait for certainty. They create conditions where failure is survivable. 💡 The breakthrough moments? They come from "let's try this and see what happens." Not from "let's wait until we're absolutely certain." Because absolute certainty is a myth. And waiting for it is the most expensive decision you'll ever make. So here's my question for you: Are you paralyzed or energized right now? What's ONE small experiment you could run this week? Drop it in the comments. Sometimes naming it out loud is the first step to actually running it. #Risk #PersonalDevelopment #CareerDevelopment