TLDR: the easiest way to be brilliant is to study and avoid mistakes
Your resume is a record of your greatest hits with all the misses erased. Yet the misses often contain the richest learnings. It’s natural to interpret your hits as a sign of your amazing ability, whereas the misses force you to confront what went wrong.
We need more anti-resumes — stories that normalize failures, help us learn from each other, and realize “overnight success” often emerges from years of unseen work. We see people at their peak, not all the versions that came before.
There are two modes of learning: first hand experience, and second hand observation. If you don’t plan on making every mistake yourself, it’s crucial to learn from others.
In that spirit, I wanted to share a few of my memorable misses.
How to manage up
One of my early consulting projects involved Excel modeling. Manually updating numbers for 50+ sheets seemed like a good idea to my naive self, but when the work stretched into 3 AM, I had a sinking feeling I was in deep trouble.
Truth is, I had many opportunities to ask my manager for help. But I was scared of being judged, so I soldiered on in the dark.
The next morning, my manager found an error in my model… then another… and another. I was devastated being exposed as an Excel fraud. But it also marked a valuable turning point. I got the training I desperately needed. I also got my first lesson in managing up.
Your manager’s job is to train you to do your job today, and create opportunities for you tomorrow. Managing up is about making your manager’s job easier. One of the best ways to do this is to ask questions when you’re stumped and seek feedback on where you need to grow.
What about bringing solutions not problems? That’s ideal, but when you’ve tried your best to figure it out, raising your hand earlier will save you so much time, and accelerate your learning. It also shows humility and self-awareness of your limitations.
In short, people want to help. Give them an easy way to do it.
Market trumps individual performance
The problem you choose to work on matters immensely. Hard work helps you reach greater heights within the bounds of what’s possible. That upper bound is determined by what you work on.
When I look back on launches, there’s surprisingly little correlation between success and hard work. Teams generally put in the same amount of effort, maybe even more(!) to get traction for less promising ideas.
I remember iterating tirelessly on an invoicing product, working down the list of customer requests. Eventually, it became clear that even if we reached feature parity, the switching costs were too high. Our big effort had nothing to show for.
Why did this happen? For the first time, we were chasing a problem that was already solved. We needed to make something 10X better in ways that mattered to our customers. Not a clone with some marginal improvements. Habit is a very strong moat, and takes a lot to unseat.
This is why working on overlooked problems is, all else equal, a more promising path. You can succeed working on known problems, but you need to convince the market you have a special angle that matters. What’s your thesis? How will you validate it?
Ask “why” more often
The path of least resistance is executing without thoroughly challenging the assumptions… especially if your manager is asking for it.
Working on top-down initiatives is the norm in many places. The problem is nobody can will a product into success if the market does not want it. When your ultimate judge of success is the market, do yourself a favor by asking “why” until you have a solid grasp of the value you’re creating for the customer and the business.
The more effort it takes to build something, the more worthwhile the investment in upfront research. Slow down at the start so you can move faster in the right direction.
As an example, we created a new installment payment method with the primary goal of reducing our time to get paid. It took months to build into the codebase and endless edge cases to cover. In the end, a comically small number of customers chose to use it.
Given the amount of work we signed up for, you would think we would rigorously validate customer demand before starting. But it was sponsored by an executive, and the mantra was to launch it ASAP. Months later, we had to kill the feature.
Executives may be able to sway people within a company, but your customers don’t care who came up with an idea. They only care if you’ve made their life better. Frankly, the team was not emotionally invested either because we had doubts from the start, and it didn’t feel like our idea. Killing the feature was actually a relief, but my failure was in not voicing our concerns earlier.
Sometimes you may still need to forge ahead if it’s a special someone’s pet project. However, probing the “why” behind your work can save unnecessary work, or at least allow you to set the right expectations.
What are you really solving for?
Think about what you’re working on right now. What is absolutely critical to get right?
It’s very tempting to fall in love with part of the solution and spend all your time there, at the expense of the outcome.
When we personalized our homepage, we fell in love with the glamorous visual mocks. Sadly, our real inventory looked nothing like it. More importantly, the solution hinged on nailing the recommendations. We didn’t have the data density to 1) understand the customers’ taste profile, and 2) map it back to our inventory. By failing to recognize the most important thing, we shipped a product that crumpled in the real world.
As the saying goes, if all you have is a hammer, everything looks like a nail. We tend to apply the same playbook to solving problems, even if the nature of the problem is completely different. Resist the urge to copy paste what worked before. Instead, diagnose the problem first. What are your bottlenecks?
Most of the moments above were lived in dread at the time. It sucks to fall short of expectations, but we are defined by how we respond to them. By learning from what went wrong, we can create more hits.
It’s also a reminder that how often you’re right or wrong does not matter. It’s how much value you can create and capture when you’re right, and how much value you destroy when you’re wrong. Magnitude matters more than ratio.
I have plenty more failures I’m happy to share if there’s interest. And if this resonates with you, I would love to hear your anti-resume!
- The 7 biases of product teams by Shreyas Doshi- guarantee you’ve fallen prey to some of these
- Day 1 vs. Day 2 companies by Jeff Bezos
- Tips to receive 10X more feedback by Nikhyl Singhal
(Photo by Sarah Kilian)