Learning From Mistakes

Over the course of my career, I’ve learned to be okay with getting things wrong.       Not because it feels good (it doesn’t), but because every mistake creates an opportunity to learn and grow. And because it means someone trusted me enough to tell me when I missed the mark. That kind of honesty feels increasingly rare—especially in a world where AI is telling people exactly what they want to hear and where people increasingly gravitate toward information that confirms their beliefs.      That’s why I think one of the most valuable skills you can cultivate is this: Find people who will give you tough feedback.      Across my time at Microsoft, the Gates Foundation, and Pivotal, the moments that shaped me the most weren’t the wins. They were the times when someone I trusted pulled me aside and gave me feedback I needed to hear. These conversations helped me see what I’d missed and rethink how I was showing up, which made me a better leader. But they only happened because the people around me knew they could be honest, and in fact, I expected them to be. You can’t grow—or help your teams grow—if you act like you’re the only one with all the answers.      I’ve seen this in every place I’ve worked. The leaders who made the biggest impact weren’t the ones who got it right all the time. They were the ones who created the conditions for honesty. Their teams felt free to surface new ideas, ask tough questions, and admit their mistakes. And those leaders were humble enough to hear feedback about themselves—and then take the steps to do things differently.       My advice on how to build this skill? Seek out colleagues and mentors you can trust to give you honest feedback. Ask for it often. Be vulnerable—not defensive—and take the opportunity to understand what you didn’t see before. It will transform the way you learn, lead, and build teams that thrive. #SkillsontheRise 

In late 2016, while at Microsoft, I wrote a piece of code that caused severe crashes across 8+ regions, reducing our Service Level Agreements (SLAs) significantly. Within 30 hours, our team had jumped into action and resolved the crisis. This is the story of one of my biggest career mistakes and what it taught me. It all started with a subtle error: a null pointer exception in a rarely used code path. I thought it wasn't urgent and even considered going on vacation. But as life would have it, another team made changes that increased the frequency of this problematic code path, leading to massive crashes in multiple regions and affecting our SLAs badly. I was in shock when I realized the magnitude of what had happened. My heart pounded, but I knew I couldn't freeze. I took ownership and immediately informed leadership. Initially, they thought I was joking, but soon realized the severity of the issue. I involved the Product Management team to communicate with impacted customers while I focused on finding a fix. Within 30-40 minutes, I had a solution. I tested it thoroughly, validated it in a test region, and gathered approvals for a hotfix. Within 30 hours, we rolled out the fix to all regions. This experience taught me: 1. High-Quality Code Is Non-Negotiable: Quality code and thorough testing are critical, especially at scale. 2. Ownership Earns Respect: Taking responsibility rather than deflecting blame is crucial in resolving issues. 3. Communication Is Key: Proactive communication with leadership and customers maintains trust. 4. Learn and Reflect: Reflecting on mistakes and learning from them is what makes us better. I survived one of my worst mistakes by owning, fixing, and growing. Mistakes happen, but it’s how we respond that defines us. What's your biggest mistake, and what did it teach you?

🧵 Ever heard of a “Failure Résumé”? It might be the smartest career exercise you’re not doing. Here’s what it is—and why it can change the way you grow 👇 A failure résumé is exactly what it sounds like: Not a list of wins. Not your greatest hits. But your flops, screw-ups, and bad decisions. It’s uncomfortable—and incredibly useful. The idea comes from Tina Seelig at Stanford. She challenges her students to build a résumé of their failures. Then asks: “What can you learn from each one?” I made my own It wasn’t for the public. Just a long list of personal and professional misfires. Then I reviewed each one and asked: Was there a pattern? Was there a lesson? Turns out—yes. My biggest insights? Mistake #1: Starting projects based on untested assumptions. Assuming I “knew enough” instead of doing the homework. Mistake #2: Saying yes to things I wasn’t fully committed to. Half-hearted effort = half-baked results. Those 2 patterns showed up again and again. But here’s the upside: Once I spotted them, I could fix them. That’s the power of a failure résumé. It turns regret into direction. So try this: List your failures. Big, small, awkward, and ugly. Then ask: Where did I go wrong? What keeps showing up? There’s gold buried under the cringe. You don’t need to share it with anyone. Just be honest. Be curious. And if you don’t do it? Well… you might have to add that to your failure résumé too 😅

Half of the internet was down due to an outage in us-aws-east-1 And Hundreds of on-call engineers got paged.. Amazon.com, Perplexity, Duolingo, Snap Inc., Substack are just a few examples of the many services that were completely offline. Even some features of the TopCoding App were temporarily unavailable. 1. Context on the scale of us-east-1 Many people don’t realize that us-east-1 is the largest and oldest AWS region, hosting a massive portion of the world’s internet services, which makes it critical for the global infrastructure. 2. What happens inside the company (in this case, Amazon) during such an incident 2.1. The on-call engineer for the team gets paged as soon as the anomaly is detected 2.2. They review metrics and dashboards to determine the scope of impact. Percent-based metrics are used because they more accurately show how critical the situation is 2.3. If the impact exceeds a certain threshold, the issue is escalated to the team’s leadership to ensure that the right decisions are made quickly and in a coordinated manner 2.4. The Root Cause Analysis process begins. The most common scenarios include: a recent deployment introduced a regression, an external dependency was affected, a new edge case was triggered by real users in production, etc 2.5. Once the cause is identified, the team looks for the fastest recovery path, such as: rolling back the latest release, scaling up affected services, adding temporary logic to handle or bypass the edge case, etc 2.6. The fix is deployed and the team monitors metrics and logs closely until all systems are fully recovered 2.7. Afterwards, a Postmortem is conducted, detailing what happened, what worked well, what didn’t and what preventive measures will be implemented to avoid recurrence 3. Cross-team coordination In major outages, multiple teams usually respond simultaneously - working in parallel to determine whether the issue is local or global 4. Communication with customers While engineers work on recovery, customer communication is prepared in parallel. Amusingly (and ironically), during this outage, Statuspage - the platform many companies use to report their own service status - was also down, so many companies appeared "all green" simply because there was no way to update the page 5. Key Takeaways There are no perfect systems - every outage is an opportunity to learn and improve. What matters most is reacting quickly, escalating effectively and ensuring that the best possible decisions are made in the shortest possible time. Personally, I’ve learned the most during these high-pressure, critical situations. They shape a mindset and reaction pattern that are invaluable for any project. Getting involved during critical incidents within your team is one of the best ways to learn - it’s hard, stressful and often avoided by many engineers, but it’s exactly how the best technical instincts and skills are built.

You can’t have a high-velocity, high-impact career without screwing up. I had multiple public screwups on my way to Amazon VP. The good news is that mistakes can help your career if you handle them right. Here is a formula: 1) Own it. 2) Fix it. 3) Communicate it. 4) Learn from it. 5) Move on. That really is it, but of course, each of those pieces has steps of its own. To own your mistake, you must be specific and direct. Tell your leadership what went wrong and why to the best of your knowledge. Tell them that it is on you to fix and how you will go about doing that. If you don’t know any of these details, tell them you don’t know and when they can expect an update. To fix the problem, consider what options you have based on new information. If time allows, pressure test these options by running them past one expert and one skeptic. Ask three questions: “What am I missing?” “What breaks first?” “What would have to be true for this to work?” Then, assign clear owners, clear expectations, and call in reinforcements. Get experts from other teams to help you—don’t be proud. Make small adjustments where possible, but don’t be afraid to roll it all back. Don’t be tied to old expectations or original ideas. Give your leadership and team a cadence for your updates, and stick to it. Frequent updates will help buy you time and win back trust piece by piece. When the crisis has been stopped and things have been fixed, reflect on what you have learned and share it. Then, move on. Dwelling on what you did wrong does not help your career, your mental health, or the business. Moving forward, setting new goals, and bouncing back helps all three. If you want a more in-depth lesson on how to mentally prepare to lead through crises, how to manage them, and how to recover, read this week’s newsletter: https://buff.ly/uZWsxLV Readers- what mistakes have you made that you were able to thrive through? How did you bounce back?

Regret your candour with the boss? Made a careless blunder that will cost the company a lot of money? Ignore a minor problem that now puts your credibility at risk? You’re not alone. Everyone I know makes mistakes. Many of them are also leaders, doers, trailblazers and have profit from making mistakes. James Joyce says mistakes are the portals of discovery and the management literature abounds with many articles advocating that mistakes can be a good thing. But there is a caveat - whilst making mistakes is part of working life, learning from them and managing their consequences requires integrity and skills. We all make mistakes and if managed poorly, mistakes will damage our reputation and career. This is especially true when we are at vulnerable points in our career like when we are just at the beginning of our career or starting a new role, or trying to win over a new manager. So how does one respond when one makes a significant mistake? Many wish the mistake would not be noticed, or are gripped by fear that prompts poor decisions. The key is to replace wishful thinking and fear with taking control of the situation. This can be achieved by a four-step approach. 1. Own up. But tread carefully especially if the company has a culture of blame-shifting - it's important to pick your moment and find allies. But whatever you do, own up before your hand is forced. And own up properly - admit the mistake and don't make excuses. 2. Improvement. Shift the focus from blaming people to improving processes by doing an objective assessment to identify root causes and process improvements so the same mistake will not happen again. Also articulate accurately the consequences of the mistake and recommend specific actions to mitigate its impact. 3. Permission. Share how you would implement the mitigation measures and improvements, and get approval to proceed. So from being the person who made the mistake, you become the person who eliminates mistakes. 4. Compassion. Have compassion for yourself. Recognise that A. mistakes likely happen when you strive for growth and push for performance, B. You can learn from this experience and reduce the chances of mistakes, Whilst we can't make an omelette without breaking eggs, we can learn, be better and never make the same mistake. Agree?

Have you ever written a personal Failure Log? It’s a simple but powerful self-improvement technique which builds mental resilience. Setbacks happen in everyone’s career journey. But documenting the decisions and circumstances that lead to failure will let you transform defeats into lessons and strengthen your capacity to bounce back. It’s easy to do too. Here’s how to write a Failure Log: Pick a format (spreadsheet, notebook, or digital journal) and a frequency (weekly is good for reflection). For each entry, answer: - What went wrong? - What did I learn? - How will I change my approach next time?   Use one or two sentences to answer each question. Stay objective. Use a neutral tone (“I didn’t delegate enough tasks”) rather than inflammatory statements (“I’m terrible at managing projects”). Focus on describing events and lessons, rather than beating yourself up. The aim is insight, not self-blame. Review your entries every month or two to spot patterns — maybe you sometimes underestimate timelines or often fail to communicate well enough with stakeholders. Over time, you’ll course-correct with consistent strategies. Celebrating your successes is important, but objectively acknowledging your failures will often yield the most impactful lessons. A Failure Log can be a transformative tool to consistently improve your outcomes. Best of all, over time you’ll develop a more resilient form of confidence — grounded in reality, not wishful thinking. What techniques do you use to learn from your own professional setbacks?

Stop arguing with people about their lived experiences simply because it doesn't match your own. Instead of trying to disprove them, just listen. Ask yourself, 'why has my experience been different?' The discomfort you feel is a mirror, sit with it. Growth doesn’t come from staying comfortable or always being right. It comes from sitting with the uncomfy feelings, wrestling with new perspectives that challenge your own ideals, and letting them change you. Being willing to be uncomfortable is a strength. And being willing to sit with it will be the greatest gift you ever give yourself.

In school, we’re taught that failure is something to avoid at all costs. But failure is actually required to reach your long term goals. Here are 5 ways failure helped me reach mine: 1. Building A Music Blog In 2011, I started a music blog. It never got more than 200 total visits. I eventually shut it down. But it taught me how to set up my own website and the basics of internet marketing, which allowed me to start Cultivated Culture without any funding. 2. Building A Social App In 2014, I had an idea for an app. I spent dozens of hours mocking it up and $1,000+ on prototype. Two weeks later, two other companies launched identical apps with venture funding. But it taught me the basics of developing a piece of software, and allowed me to build our current suite of job search tools. 3. Freelancing I wanted to change industries, so I freelanced to gain experience. I didn’t get any clients from the first 1,000+ emails I sent. But it taught me that “sales” and outreach are volume games, as well as giving me data that I eventually used to optimize, get clients, and leverage in my networking efforts to land referrals. 4. LinkedIn (Take 1) I shared my first piece of LinkedIn content in 2016. I did it for about two weeks before feeling dejected that I wasn’t getting any reactions or views. That eventually led to the realization that, if I wanted to grow, I needed to focus on creating content instead of outcomes at the beginning. 5. LinkedIn (Take 2) About six months later, I starting sharing LinkedIn content again. This time, I kept it up for a month before running out of ideas. I had to stop again, but it eventually taught me that creating content is about building a repeatable system vs. just writing when inspiration strikes. 6. The Outcomes Of Failing Every one of these failures taught me lessons that I eventually leveraged successfully down the road. I was able to start my own business and bootstrap it without needing funding or paid ads because of everything I’d learned from past mistakes and failed ventures. Every one of those experiences is a lesson, if you’re open to seeing it.

The difference between career plateaus and breakthrough moments often comes down to how we process setbacks. 76% accurate recovery prediction. 61% reduced recovery time. 82% renewal rate within 90 days. These aren't just hopeful claims. There's research-backed evidence that failure recovery is a learnable skill. We're not in an era where resilience is optional. We're in a time where your bounce-back ability determines your career trajectory. 💡 Elite performers don't just endure failure differently. They transform it systematically into a future advantage. Here's how research shows they do it: 🔹 𝗡𝗮𝗿𝗿𝗮𝘁𝗶𝘃𝗲 𝗥𝗲𝗰𝗼𝗻𝘀𝘁𝗿𝘂𝗰𝘁𝗶𝗼𝗻 - Reframe setbacks within larger success stories rather than as isolated incidents. Stanford University research found this predicted recovery speed with 76% accuracy and improved subsequent performance in 83% of cases. 🔹 𝗦𝗽𝗲𝗰𝗶𝗳𝗶𝗰𝗶𝘁𝘆 𝗙𝗶𝗹𝘁𝗲𝗿𝗶𝗻𝗴 - Isolate exact failure points through detailed analysis rather than generalizing. Applied Psychology studies show this reduced recovery time by 61% compared to self-criticism approaches. 🔹 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗩𝘂𝗹𝗻𝗲𝗿𝗮𝗯𝗶𝗹𝗶𝘁𝘆 - Share failures with 2-3 carefully selected trusted individuals. Harvard Business School research found this accelerated recovery by 40% and increased learning integration by 57% versus private processing. 🔹 𝗘𝘅𝗽𝗲𝗿𝗶𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 𝗠𝗶𝗻𝗱𝘀𝗲𝘁 - Treat outcomes as data points rather than judgments about your capabilities. MIT Technology Review studies show this approach predicted renewed achievement within 90 days with 82% accuracy. 🔹 𝗥𝗲𝗰𝗼𝘃𝗲𝗿𝘆 𝗥𝗶𝘁𝘂𝗮𝗹𝘀 - Develop specific practices that reset mental and emotional states after setbacks. Research found structured rituals reduced rumination by 34% and accelerated return to productivity by 2.7 days. The world doesn't need more perfectionists afraid to fail. It needs resilient innovators who can extract maximum value from inevitable setbacks. That's the mindset we're helping build - for professionals who see failure not as the end, but as the beginning of their next breakthrough. Coaching can help; let's chat. | Joshua Miller 🚀 Download Your Free E-Book:  “𝟮𝟬 𝗦𝗺𝗮𝗹𝗹 𝗦𝗵𝗶𝗳𝘁𝘀 𝗧𝗵𝗮𝘁 𝗟𝗲𝗮𝗱 𝘁𝗼 𝗕𝗶𝗴 𝗟𝗶𝗳𝗲 𝗖𝗵𝗮𝗻𝗴𝗲𝘀” ↳ https://rb.gy/37y9vi #executivecoaching #mindset #leadership