6 Stupid Mistakes Smart Developers Should Make

6 Stupid Mistakes Developers Should Make


“Keep your head down.”

“If you want to keep your job, work hard, keep your head down and do what’s in front of you. Remember, it’s the squeaky wheel that gets replaced.”

Have you ever gotten this advice? You’re not alone. It’s advice developers often receive when they leave college or start a new job. Sometimes that advice is implicit, other times it’s explicit. But is that the right move for you? If you want recognition as the all-star you are and want to be paid accordingly, the answer is no.

“Keep your head down” is damaging career advice.

So what are you supposed to do instead? How do you navigate office politics, huge workloads and poor management?

You make “stupid” mistakes.

The strategies I’m about to share are typically labeled as stupid, ignorant or foolish by those who don’t understand them. They’re counter-intuitive and bizarre sounding. But they’re career makers for those who understand and apply them.

Wait a minute.

“Why do I have to make mistakes? Can’t I get the career I want without making ”stupid mistakes?” The vast majority of your coworkers don’t get it. Not only will they not understand, many of them will criticize and mock you for it.

A word of caution. If you’re expecting this article to go over details like “coding mistakes” this isn’t for you.

Use these strategies well and you’ll be the one in charge of your own career.

Let’s start with the first mistake you should make.

1. Pick a Fight with Your Boss

When people see the word “fight” they cringe. Their mind goes to violent, abusive or dark places.

That’s absolutely not what this means.

When an employee picks a fight with their boss, there’s always a reason. Employees who do it late express their desires as revenge or slander. Most people choose self serving reasons — I want a raise, a promotion, more hours, better projects, etc. These are great and even necessary things to go for, but they’re focused on the wrong person.


Fighting with your boss over any self-serving topic is employment suicide. It’s the fastest and easiest way to lose your job, client or position.

Here’s the dirty little secret all-stars understand. If you’re fighting or begging for the things you want, you’re less likely to get them.

So what do you fight with your boss about?

You fight with them, for them. You fight for their goals, desires and aspirations. This is the part where many would chime in: “I don’t care about my boss or his lame aspirations.”

That sound about right?

Why should you care at all about their goals, desires, and aspirations? Isn’t that their responsibility? Helping them, helps you. Taking a genuine interest in their “stuff” is better for you in the long run.

  • Looking for a pay raise? It’s easy to get when your boss believes you’re in his corner.
  • Want a promotion? A supportive boss and supportive co-workers makes that inevitable.
  • Want to start your own thing? You can ask your boss for contacts, an introduction and opportunities.**

Amazing careers, all-star recognition, preferential treatment, they’re all based on relationships.

So how do you fight with your boss?

You do it gently.

Here’s an important yet easy to ignore rule that many, many people seem to ignore. Don’t humiliate others. Don’t call your boss out publicly or corner them psychologically. Avoid trolling your boss to look good.

Ask gentle, well-timed questions focusing on what they want. Do it privately where appropriate and publicly with discretion.

Okay, what does that look like?

Your boss wants to launch a new site in 3 weeks.

“I noticed you added some new features to the list. These two features alone will add an extra four weeks to the project. Did you still want to keep those on the list or pick the features that’ll help us hit the deadline?”

I want this to work the same way as…

“I noticed they’re running these applications in this environment. We’ll need to spend an extra $16,000 to $25,000 to get this setup the same way. Do you still want me to look into this for you?”

Can you see what’s happing here? A single, well timed response tells your boss several things.

  1. You know what’s important to them (time and money in our examples)
  2. You’re looking out for his interests first instead of yours.
  3. You speak his language.
  4. You’re fighting his ignorance, rather than his intentions.
  5. You’re willing to extend compassion and respect, sharing your advice in a way that’s free from condescension and contempt.

This attitude is something employees, managers, executives and managers all look for. But they’ll never tell you.

2. Fail, Then Ask to be Punished

Is your career something that just happens to you? Or are you choosing the kind of career, the kind of life you want to have? Many developers go through their careers in a daze. They get a job, learn the rules, then settle in to 90/10.

90% maintenance and 10% development.

They spend most of their time maintaining someone else’s bloated, poorly written code. They’re responsible for fixing bugs and dealing with customer service issues. But they’re not getting the chance to actually create something useful.

Sound familiar?

If it does (and you’d like that to change) failure could be your way out. Let’s pretend…

  • You’re working for an eCommerce retailer.
  • They’re using an out-of-the-box shopping cart.
  • Their inventory system isn’t compatible with their shopping cart software.

Your boss is stressed out; he’s getting chewed out by his boss. Customers visit the site to buy products (good), but those products are almost always out of stock (bad). As a result your boss has seen a 40% drop in sales. He’s got six months to turn things around. If he can’t he’ll be out of a job.

And that’s the problem. He doesn’t know where to start.

You know he’s going to start contacting “vendors” to see if they can do the impossible. But you also know they’re just going to try to squeeze as much as they can out of your boss. They don’t care about his problems.

But you do.

So you create a solution to his problem. You meet with the warehouse guys, you learn about their problems. You talk with your boss about his struggles. You talk with marketing to see how many customers leave. You listen, create specifications, and get to work.

If you’ve solved the problem, you’ve saved the day. You’ve given him peace of mind. But what if you fail? What if you get it wrong?

Easy. You ask to be punished.

And your punishment? Fixing the problem, whether that’s getting more details, changing your requirements, rewriting something, etc. If you’ve planned things well, odds are good you’ll get the chance to make things right.

And that’s important.

Because the first iteration will have problems. It’s pretty unlikely that you’re going to get things right the first time.

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Source: Sitepoint