We live in a world obsessed with friction-less experiences. One-click checkouts. 30-minute grocery deliveries. Algorithmic feeds that spoon-feed us exactly what we already like so we don't have to strain a single brain cell. But in the professional world, this obsession with "easy" is a silent career killer. Honestly, if you aren't regularly saying don't make it easy for me to your mentors, your bosses, or even yourself, you’re likely stagnating.
Growth is a biological and psychological response to resistance. Muscles don't grow by lifting air; neurons don't fire new pathways by solving 2+2 over and over again.
I remember talking to a senior developer at a fintech firm who was miserable. Not because the work was too hard, but because it was too easy. He’d automated himself into a corner where he did maybe twenty minutes of real thinking a day. He was well-paid, comfortable, and absolutely terrified that his skills were becoming obsolete. He had forgotten how to struggle. That’s the danger. When everything is easy, you aren't just comfortable—you're becoming fragile.
The Psychological Trap of the Path of Least Resistance
There is this concept in psychology called "Desirable Difficulty." It was coined by Robert Bjork, a researcher at UCLA. Basically, his research shows that we actually learn better when the process feels harder. If you read a book with a slightly harder-to-read font, you might actually retain more because your brain has to work to decode it.
If you’re constantly looking for the shortcut, you’re bypassing the encoding process.
Think about the last time you followed a GPS blindly. Could you find your way back without it? Probably not. You didn't build a mental map because the technology did the heavy lifting. The same thing happens in business. If a manager gives you a template for every single task, you never learn the "why" behind the structure. You become a technician, not a strategist.
People who say don't make it easy for me are essentially asking for a mental map. They want the struggle because they know the struggle is where the expertise is actually forged. It’s about seeking out the "Goldilocks Zone" of stress—not so much that you burn out, but enough that you’re forced to adapt.
Why High Performers Beg for Friction
Look at the elite. Whether it's sports or high-stakes negotiation, the best of the best intentionally add hurdles to their training.
- The Steph Curry Factor: He doesn't just practice three-pointers. He practices them while being distracted, while tired, or with a literal flashing light system that forces him to process information while shooting. He’s telling his trainers: don't make it easy for me.
- Iron Sharpens Iron: In top-tier law firms or surgical residencies, the "easy" cases are for the juniors. The seniors want the mess. They want the edge cases where the rules don't quite apply.
When you ask for the harder path, you're signaling something huge to the people around you. You're signaling that you're an owner, not a renter. Most employees want the clearest instructions and the least amount of pushback. If you’re the one saying "Actually, let me try to figure out the framework for this from scratch," you’re building a different kind of capital.
How to Apply "Don't Make It Easy For Me" Without Burning Out
You can't just dive into the deep end without knowing how to swim. That’s a recipe for a mental breakdown. The trick is "staged difficulty."
Start by identifying the areas where you are currently on autopilot. Maybe it's your weekly reporting. Maybe it's how you handle client calls. Instead of using the same old script, try a different approach that requires more active listening or complex data synthesis.
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Stop asking for answers. Start asking for resources.
Instead of saying "How do I do this?", try saying "What's the goal, and what are the constraints? I'll come back with three options." This small shift moves the cognitive load from your boss to you. It’s harder. It takes longer. But the next time a real crisis hits, you’ll be the only one in the room who knows how to build a solution from nothing.
The Problem With Modern "Efficiency"
We’ve confused efficiency with effectiveness.
AI is the latest iteration of this. It’s incredible for drafting emails or summarizing long PDFs. But if you use it to do your thinking, you lose the ability to think. If you let an LLM write your strategy, you aren't a strategist. You're a prompt engineer for someone else's logic.
There is a visceral difference between knowing a fact and understanding a concept. Knowledge is cheap. Understanding is expensive. It costs time, frustration, and a lot of "failed" drafts. But that cost is exactly what gives it value in the marketplace. If a task is easy for you, it’s easy for everyone else. And if it’s easy for everyone, the market price for that skill will eventually drop to zero.
The Social Component: Changing Your Reputation
When you start adopting the don't make it easy for me mindset, people treat you differently.
It’s kinda weird at first. Your boss might be confused why you're turning down a "simplified" workflow. But over time, you become the person they go to when things get complicated. You become "anti-fragile," a term popularized by Nassim Taleb. You don't just withstand stress; you actually get better because of it.
Practical Steps to Build Resistance
- Audit your "Easy" tasks: Once a week, pick one thing you do on autopilot and intentionally change the method.
- The 20-Minute Struggle Rule: When you hit a wall, don't ask for help immediately. Set a timer. Struggle with the problem for 20 minutes. Even if you don't solve it, you’ve primed your brain to understand the solution better when you finally do get help.
- Request "High-Level" Feedback: Instead of asking for a proofread, ask for a critique of your logic. It’s much harder to defend a logic chain than to fix a typo.
- Volunteer for the "Mess": Every company has that one project no one wants because it’s a disorganized disaster. That’s your gold mine.
The Long Game of Difficulty
In the end, this isn't about being a martyr. It’s not about working 100-hour weeks or seeking out misery for the sake of it. It’s about long-term survival in a world that is rapidly automating the "easy."
The people who will thrive in the next decade are the ones who can handle ambiguity. Ambiguity is never easy. It’s messy and uncomfortable. But by saying don't make it easy for me today, you are training your "ambiguity muscle" for tomorrow.
You’re choosing the harder path now so that the rest of your life isn't impossibly hard later.
Real growth happens when you stop looking for the exit and start looking for the obstacle. Stop trying to find the "hack." There is no hack for experience. There is no shortcut for wisdom. There is only the work, and the work is supposed to be hard. That’s how you know it’s working.
Actionable Next Steps
- Identify your "Autopilot": Write down three tasks you did this week that required zero mental effort.
- Introduce One Friction Point: On Monday, take one of those tasks and do it differently. If you usually use a template, build it from a blank page. If you usually delegate the "hard part," take it back.
- The "Why" Conversation: Meet with your lead or mentor. Tell them you want to take on a project that is slightly outside your comfort zone. Specifically tell them: "I'm looking to stretch my problem-solving skills, so please give me the objective without the step-by-step instructions."
- Track the Struggle: Keep a simple log of when you felt frustrated this week. Reframe that frustration as "data being uploaded." It sounds cheesy, but it changes your neurochemistry from "threat" to "challenge."