Playing by the Rules Until the Rules Don’t Apply to You

How competence and charm can break the corporate mold.

Policies, procedures, company by-laws, clocking in and out—these exist to keep the masses in check, to keep everyone compliant with the company’s rules. Worst-case scenario? They get used against you when you fuck around and find out, and then the big bad HR guy (that’s me) has to come in and fire your ass for breaking those rules.

But you know who those rules don’t apply to? The guy who’s charming and competent. That guy gets a pass on—almost—anything.

Let me give you an example. Typically, I wake up at 5 AM to be in the office by 6 AM, sometimes even earlier, just to set the tone for the day. But there are days when I don’t feel like waking up at 5 AM. So, I’ll show up around 8 AM, stroll in a couple hours late, and guess what? No one bats an eye. Not even as a joke.

If anything, they ask if I need to take the rest of the day off because they’re too afraid to lose me. Why? Because they want me to be happy and comfortable, knowing full well what I bring to the table. They don’t want to risk me walking out of that door.

Here’s the thing—this kind of leeway doesn’t happen overnight. It’s not like I woke up one day, decided I didn’t want to follow the rules, and suddenly got away with it. It takes time and strategy to get there.

First, I had to build a reputation. That meant coming in early, being the first one to dive into work, and establishing myself as someone people can count on. I built rapport with everyone—talking to employees, getting to know them personally, and making sure they knew I had their backs. And most importantly, I consistently got shit done in ways that blew people’s minds. Deliver results that no one can question, and suddenly the rules don’t seem as rigid anymore.

Playing the Game Early On

When you first start working in any place, especially early in your career, you’ve got to play by the rules. Why? Because you need to show that you understand the system and can work within it. To become a leader, you first need to learn how to be led.

No matter how smart or competent you think you are, trust me, there’s someone smarter and more experienced higher up in the hierarchy. Your job at this stage is to learn from them and, most importantly, to get them to like you.

The corporate game isn’t just about competence—it’s about knowing when and how to play by the rules while building the relationships that matter.

With time, if you play your cards right—by being competent, reliable, and making sure your superiors know it—you’ll find that the rules start bending for you. It’s not that you’re deliberately breaking them; it’s that your value becomes so obvious that the company starts making exceptions to keep you around.

It’s important to remember that you can’t make too many enemies along the way. You will have people who don’t like you for whatever reason, and that’s fine. But avoid stepping on your own dick by creating unnecessary tension or burning bridges. Keep your relationships intact, especially with those who hold power.

Eventually, you’ll notice that the things that once seemed rigid no longer apply to you. The company sees you as more than just an employee—you become someone they don’t want to lose. And when that happens, the rules? They’re just suggestions.

Learn the Rules Before You Break Them

Here’s the reality: in any company, especially when you’re starting out, the rules exist to keep you in line. They’re there to ensure everyone is playing the game the same way—clocking in on time, following procedures, and maintaining compliance. But the secret to real success isn’t just following the rules—it’s knowing when you’ve earned the right to bend them.

When you’re new, your reputation is zero. You’re an unknown entity. So, your first task is to learn the rules inside and out. Show up on time, do what’s asked of you, and prove that you can play the game like everyone else. It’s only once you’ve mastered this that you can start to navigate beyond those rules.

Why? Because when you prove that you can operate within the system, people start to trust you. They know that if you’re bending a rule here or there, it’s not because you’re lazy or incompetent—it’s because you’ve earned the flexibility. You’ve already proven you can deliver, and that’s what really matters.

You need to remember that breaking the rules too early in your career is a death sentence. You don’t have the track record yet to back it up, and you’ll quickly be seen as a problem. There’s a reason why, early in my career, I was waking up at 5 AM, making sure I was in the office by 6 AM every day. I didn’t have the leverage to do otherwise yet.

But as you build credibility and prove yourself time and time again, the company starts to see you as more than just another employee. You become someone they rely on to deliver consistently, someone they need to keep around. When you reach that point, the rules are no longer constraints—they become guidelines, flexible based on your value to the organization.

Competence earns you flexibility. Charm earns you influence. Together, they buy you the freedom to operate on your own terms.

It’s not about disrespecting the rules. It’s about outgrowing them. The rules are there to maintain order among the masses, but once you’ve proven your worth, the company doesn’t want to lose you over petty adherence to a clock-in time or minor procedural details. They want results, and if you’re the person consistently delivering, they’ll give you the space to do things your way.

So, learn the rules before you break them. Understand how to navigate the system, how to win people over, and how to make yourself indispensable. When you’ve done that, the rules will no longer apply in the same way—they’ll apply to everyone else. And that’s when you’ll know you’ve truly made it.