Most success advice tells you what to do. Today, let’s talk about what not to do.
The secret to winning isn’t always about being brilliant. It’s about avoiding being dumb. And before you get offended, let me clarify what “dumb” means here - it’s not about intelligence. It’s about doing things you’re smart enough to know better than to do.
We all do it. The tech lead who ignores obvious risks because their last project succeeded. The executive who builds what they love instead of what users actually want. The manager who confuses having a vision with having a plan.
Smart people make stupid mistakes all the time. The difference between those who succeed and those who don’t often comes down to who makes fewer of them.
Pride and Bad Decisions
Nothing clouds judgment quite like success. Win a few times, and suddenly you’re invincible. You stop asking hard questions. You ignore the warning signs. You assume that what worked before will work again.
A successful project breeds confidence, confidence breeds complacency, and complacency breeds spectacular failure. To avoid this, you need friends. Specifically, friends who aren’t emotionally invested review your ideas. Smart people need protection from their own egos.
The particularly insidious thing about pride is how it warps risk assessment. You start believing that higher risks mean higher rewards (they don’t - they just mean lower probability of success). You begin expecting profits without proportional effort. You become susceptible to shortcuts and schemes that promise easy wins.
The User Delusion
Nobody cares what you love. They care what solves their problems. Users, as it turns out, only care about themselves.
Don’t work on one of those projects built on your passion as opposed to real user needs. These projects inevitably fail. If you want to have a large impact, find out what your users love - and are willing to pay for with their time or money - then deliver it as quickly as possible.
This extends to a related trap: trying to be everything to everyone. Remember that there are three qualities that make a good product: “Good, Fast, Cheap. Now pick two.” Successful projects and products typically excel in one area (speed, quality, cost), are competitive with other products in another, and basically ignore the third. The ones that try to do all three? They spread themselves too thin and disappear. Pick your lane and own it.
Goals Are Not Plans (And Other Obvious Things We Ignore)
We love setting goals. “Increase clicks by 30%!” “Be the product with the largest user base!” “Transform our feed!”
Inspiring stuff. Also completely useless without a plan.
A goal without a plan is just a wish. You need to identify exactly what obstacles stand between you and that goal (because if nothing was in the way, you’d already be there) and figure out specifically how to overcome them.
The value of a detailed plan isn’t that it’s sacred - plans should change as you learn. The value is that it’s actionable and gives you something to measure against. When you inevitably deviate from it, you’ll know, and can decide whether that deviation is a problem or an opportunity.
The Metrics That Mislead
What gets measured gets done. Choose the wrong metrics, and you’ll optimize for the wrong things.
Track notification clicks? Teams might just send more notifications, potentially sacrificing actual user value as long as the number of clicks increases. Track notification clicks while keeping click-through rates high instead? Now they’re focused on what matters.
Most standard business metrics are lagging indicators - they tell you about problems after they’ve happened. Daily Active Users (DAU) or worse Monthly Active Users (MAU)? That’s measuring the symptom, not the cause. Find the drivers of those results and measure those. Give yourself leading indicators that let you steer toward the results you want, not just document the crashes after they happen.
The Thinking Deficit
Here’s perhaps the most practical insight: We don’t think enough. Actually think. Not worry, not plan, not brainstorm in meetings - but sit quietly and think deeply about important questions.
Try this: Block an hour, twice a week minimum. First 45 minutes: ponder a specific question or problem and write down possibilities. Last 15 minutes: evaluate what you came up with and document anything worth pursuing. No distractions, no devices, just you and the problem.
What should you think about? Start with these:
What’s the real problem here, not just the symptom?
What assumptions am I making that could be wrong?
What are the unintended consequences if this succeeds?
Am I asking the right questions?
The Human Element
One last thing about avoiding stupidity: Remember that humans are fallible by design. When something goes wrong and we find someone to blame, we often stop there. “Human error,” case closed.
But that’s stupid. Human errors are usually predictable results of poorly designed systems. We design processes for hypothetical perfect people, then act surprised when real, fallible humans can’t execute them flawlessly.
Teams want to succeed. Before you blame them for failing, ask: Do they understand the expectations? Do they have the skills and resources to meet them? Is the system set up for normal humans or imaginary perfect ones?
The Bottom Line
Success isn’t just about making brilliant moves. It’s about making fewer stupid ones. And stupid doesn’t mean lacking intelligence - it means ignoring what you know to be true.
Take time to think. Really think. Challenge your assumptions. Check your ego. Focus on what users want, not what you love. Make actual plans, not just goals. Measure what matters. Design systems and processes for humans, not robots.
The road to success isn’t always about finding new shortcuts. Sometimes it’s about taking the road less stupid - the one where you simply stop making the mistakes you’re smart enough to avoid.
After all, you don’t need to be a genius to succeed. You just need to stop doing things that you already know won’t work.
The images in your posts are always so cool. If you don't mind me asking, how do you generate them?
This is an excellent post to remind us that we can succeed if we set aside our egos, state the goal and make a plan. We focus our efforts, but we monitor the process, ready to pivot.
I have seen many companies I have worked with lose market for all of the reasons mentioned in this post. They just get lost in thinking in abstract terms, creating vanity metrics and celebrating fake successes.
Thank you also for highlighting the need to "Think"! This is becoming increasingly problematic, as LLMs (Gemini, ChatGPT) are replacing people's thinking process. The future is for the deep thinkers, and we must not lose that skill!
Grab a Coffee as a takeaway and walk the next 60 minutes, rethinking a problem you are facing. Made such a difference in my life!