How We Smuggled a Husky Home (And Why You Should Too)

A couple years ago, we went to Colorado and came back with a Siberian Husky. You know, as one does.

My daughter who was 16 years old at the time was getting a tattoo (that's a different story), and the artist just happened to also run a husky training program for service dogs. Because, of course.

One of the dogs was a sweet, four-year-old, battle-scarred Husky named Nyx who was "unofficially trained" and needed a home. She'd been attacked by another dog but survived. The place said, "She's not certified, but she's just as good. You won't have any trouble getting her on the plane."

We said, "...okay."

So they gave us the paperwork. They gave us the service vest. They even had a vet who signed off on everything. And as luck would have it, we were flying home first class. Not because we splurged, but because tickets were weirdly cheap. Extra legroom, more space for the dog. The whole setup was almost suspiciously easy.

She slept the whole flight. Quiet. Calm. Sweet as ever. A perfect service dog performance from a dog who, it turns out, can't even sit on command.

We were all part of one of those unspoken social contracts where everyone agrees to go along with a mutually beneficial fiction. We were pretty sure she wasn't really a trained service dog. The people giving her to us knew we knew. The airline staff probably had their suspicions. But everyone played along because the alternative made no sense. Leaving a sweet dog behind or stuffing her in cargo served nobody's interests.

Two years later, she's still with us. She doesn't follow a single command, but she's the sweetest member of our pack (we have four dogs total. It’s... a situation). And we never would've gotten her home if we'd waited for official permission or tried to navigate the system "properly."

This whole experience reminds me of what Jeffrey Pfeffer talks about in his 7 Rules of Power. Specifically Rule #2: Break the rules. Not recklessly. Not carelessly. But on purpose. Because power and progress usually go to the people willing to step a little outside the lines while everyone else is still coloring carefully inside them.

So this week, let's talk about strategic rule-bending, why rigid compliance can leave everyone worse off, and how you can ask for forgiveness without being a jerk about it.

When Following the Rules Perfectly Is Perfectly Wrong

Most systems aren't built for nuance. They're built for efficiency, predictability, and the lowest common denominator. But real life is full of messy, human, unpredictable edge cases. And when we prioritize rigid rule-following over real-world situations, we often end up with systems that reward compliance and punish competence.

The people who get stuff done get when rules serve the goal versus when they get in the way. They know the difference between rules that exist for safety and rules that exist because someone needed to write something down in a manual five years ago.

For example, in 2022, my daughter (her again!) was invited to her first concert. Conan Gray at the Moore Theatre in Seattle. I dropped her off at the show with her friend's family, found a nearby pub, and got ready to be on standby. Minutes later, she called me in tears, having a mild panic attack. It was all too much: the noise, the crowd, the chaos.

I rushed back. She stood outside the venue, crying. We started walking to the car. Then a security guard chased us down. He'd seen what was happening and offered us a quiet spot in the open balcony seats near the stage. I didn't have a ticket, but they waved me in. They brought us waters and checked on us during the show.

I'm almost certain that wasn't in the rulebook. But it was absolutely the right move.

That's what it looks like when someone uses discretion instead of deferring to the script. No one got hurt. No rule truly mattered. And a teenage girl got to remember her first concert as something amazing, not something scary.

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First, Do No Harm

Breaking rules does actually come with rules. The first of which is understanding why they exist in the first place. Some rules are there to keep you safe. Buckle up when you drive. Don't skip the safety goggles when welding. Don't drink and drive. Some guardrails are in place to prevent catastrophe.

Other rules exist to keep things fair. You can't just decide your situation is more important than everyone else's. Don't cut the line because you think your time matters more than other people's. Don't use the carpool lane when you're driving alone because traffic is annoying. Don't park in an accessible parking spot because you'll "just be a minute." Being in a hurry doesn't make you special.

Before you go on a rule-breaking bender, ask yourself this: Are you solving a problem or creating one?

And this line of thinking does come with a caveat: you have to be prepared for your rule-breaking to backfire. Have backup plans. Know what to do if things go sideways. Take full responsibility if your shortcut blows up in your face. Don't leave other people to clean up your mess because you decided to wing it.

As I write this, I am at a hotel in San Francisco. My room is being cleaned and I needed a quiet spot for a meeting and to finish this newsletter. There is a big conference going on so many of the meeting rooms are filled. But I’ve worked enough conferences to know that not every room gets used all the time. So I found a room with no one in it and a big gap in the schedule. I squatted there for my meeting. BUT, I sat right by the exit and warned the people in my meeting I might have to skedaddle if I got kicked out.

Was I supposed to use this room? No. Did it hurt anyone that I did? No. Did I have a plan in case I got the boot? You betcha!

Good rule-breakers don't just hope for the best. They prepare for the worst and make sure they can fix whatever breaks. That's what separates strategic flexibility from just being reckless and hoping nobody notices.

Your Strategic Rule-Bending Playbook

Okay, now that we've covered the guardrails, here's how you can actually put this in motion.

Notice the rules. The first step is developing awareness. Start paying attention to the unwritten rules we all follow without thinking. Social contracts that exist mostly out of habit. Train your brain to recognize when rules are actually in place and ask yourself whether they're serving anyone.

Keep the stakes low. Practice with situations where the worst-case scenario is mild embarrassment. Getting politely asked to leave an empty meeting room won't ruin your day or anyone else's.

Start small. Cut through the empty parking lot instead of driving around the block. Ask about room upgrades when you check into hotels. Refill your fountain drink at restaurants that don't explicitly prohibit it. These aren't life-changing moves, but they're practice rounds for reading situations and trusting your judgment.

Watch the pros. Pay attention to people who consistently get better service, find great parking spots, or somehow get into sold-out events. They've mastered the art of spotting which rules are flexible and which ones aren't. They're the Jedi masters of navigating social systems.

Build relationships. The barista who knows your name is more likely to let you use your expired coupon. The receptionist who knows you're genuinely nice to work with will squeeze you into the schedule when there's a last-minute cancellation. A friendly smile and brief explanation might land you a better table. People are more inclined to go along with creative solutions when they trust you're a decent and reasonable person.

Stay quiet when it works. Don't brag about your clever workarounds. The goal isn't to be known as someone who games the system. Just enjoy the victory and move on.

The goal isn't to become a troublemaker. It's to become someone who can navigate the gap between how things are supposed to work and how they actually need to work.

Bring That Dog Home

Often rules are just someone's attempt to organize chaos, but sometimes the chaos has better ideas. Most people spend their lives waiting for permission that's never gonna come, wondering why others seem to navigate the same systems with completely different results.

The people who get things done, who bring home the dog, who find the quiet spot for a panicking teenager, who somehow always seem to make things work, have developed a different operating system. They see rules as starting points for negotiation, not ending points for possibility.

The shift isn't about becoming a troublemaker or a rebel without a cause. It's about developing the confidence to ask "What if we just made this work?"

That's how you end up with a perfectly imperfect Husky sleeping on your couch. And sometimes, that's exactly what the world needs more of.

As always, thanks for reading,
— Derek
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