Career Optimization Is Knowing When to Kiss Ass and When to Kick It
Getting all that “freedom” as a W2 without being a brown-noser
Yes, Chef
People-pleasing is a culturally-induced pathogen according to Millennials. I do tend to agree that some brands of people-pleasing, like those in which we inadvertently try to control how others respond, are unbecoming. I wrote an entire piece on people-pleasing many months ago, which you can read here. My thesis is simple: people-pleasing has little to do with appeasing another person, but is motivated by sheltering ourselves from any reaction we believe we cannot handle. Differently stated: it’s both conflict-avoidant and validation-driven.
My personal version of being a “yes-man”, for the sake of this piece, is thoroughly understanding the motive of the person giving direction and playing directly into their hand---through your body language, your tone, and your choice of language. Mastering the crooked art of understanding human behavior, paired with basic business principles, puts those who have adopted the “Yes, Chef” mentality far above their neurotic, burnt-out co-workers---at least in terms of workplace freedom and compensation.
I suppose this is an argument for, “Work Smarter, Not Harder.” Except most people believe they’re working smarter byworking harder, which can end in the promotion to Company Brown-Noser and further social disapproval. I have a different approach.
To adopt “Yes, Chef” does not assume we tolerate disrespect, excessive irrationality, or utter stupidity. The latter two evils are subjective, and will be entirely up to you to determine what criteria fits those bills. The skills required to analyze and predict human behavior are what will forge a finesse that make you unshakable, unbotherable, and “in-the-know” without the stink of Brown-Noser-Extraordinaire.
To path forward? Be capable and simultaneously not stupid. You will say “yes” to projects, cases, deadlines, or conversations that have been perpetually avoided by your co-workers for reasons largely pertaining to “overwhelm”, “burnout”, or any other emotional trickery.
There’s a subtle but crucial, non-negotiable aspect of taking on your new role of the Fearless ‘Yes, Chef’: you cannot, under any circumstances, demand attention or recognition for it. Remember the validation-seeking “people-pleaser” I described earlier, the type which freakishly complies for reasons almost entirely selfish? The same theory applies to becoming the go-to in your W2.
But Also Learn the Tactical No
People occasionally confuse assertiveness with passive-aggression or flagrant cattiness. Women have long since lamented their “assertiveness” being seen as rude or insensitive in the workplace, while men’s assertiveness being seen as commendable. I do not want to dismiss this as being occasionally legitimate. People who stand up for themselves, whether women or men, are submitting to an invisible target being placed upon their forehead. When women do so, specifically in male-dominated industries, it could mistakenly be taken as snobbery.
But more often than not, behaving like a snob begets being seen as a snob. In other words: you’re perceived as a bitch because maybe you are one. We can reject new projects, cases, or work demands while still being kind and, hell, maybe even apologizing. Here are some examples depending on your mood, who you’re speaking with, and what you hope to gain:
The Professional Straight-Shooter: “I’d really like to give this the quality it needs, and I don’t know that I’m able to do that with what’s on my schedule. Maybe you can help me prioritize what needs to be moved so I can get to it?”
Grateful + Inquisitive: “Thanks for considering me for this! If I do take this on, I’ll be honest, something else will probably slip. Which is most important to you?”
Humor (My Favorite): “If I say yes, you owe me a Xanax. That doesn’t seem sustainable for anybody- can we reschedule this without my refilling a prescription?”
The Deferral: “Oh man, I wish I could! I’m on the cusp of no-can-do. I’ll let you know when I wrap up with [current project], if that works for you?”
Reassuring Boundary: “I can’t do it this week. After X is finished, I’m good to start; so we’re looking at between A-Date and B-Date. How does that sound?”
Competence is the Only “Flex” That Pays
Knowing your audience, learning “crowd work”, and sharpening your skillset is a trifecta I’ve come to refer to as adaptable competence. Your “edge” comes from analyzing information you’re presented with from every angle and only then deciding your stance. There isn’t exactly a formula for how to do this, but I’ve done my best to nail it down into a few steps:
1. Your Boss’s Bottom Line Is Your North Star (TLDR: Get Over Yourself)
2. Be Exceptionally Better Than Everyone Else
3. Explain Boss’s Pain In Their Language
4. Offer Yourself Up As the Only Solution
5. Leverage, Leverage, Leverage
1. Your Boss’ Bottom Line Is Your North Star
a. Forget your own for now. Bosses have their own quirks and “languages,” but strip it down and they’re driven by one thing: reduce pain, maximize profit. Listen for what that is. Memorize their phrasing. Use their words back at them.
2. Be Exceptionally Better Than Everyone Else
a. A downside of hyper-competence is being given more work because your co-workers are probably stupid. I don’t actually mean this the harsh way it sounds; it’s just a fact of working quickly, efficiently, and without turning the workplace into a theater for insecurity. Look to your co-workers’ quality of work and the traits they bring to the workplace; their top-line work ethic is your new beginner-level marker.
3. Explain Boss’ Pain In Their Language
a. You have the skills (professionally and socially) to leverage pain. Now you’re tasked with explaining it back to them by paraphrasing, telling a story, and being careful to use words exactly as they’ve phrased them. It doesn’t matter if you find the phrasing personally repugnant; this isn’t about you, perse. It’s about your boss needing to feel heard so you can move on to step 4, which is one step closer to that freedom you claim to crave.
4. Offer Yourself Up As the Only Solution
a. Because your co-workers are self-centered, stupid, and driven by their own inability to manage their emotions, you’re perhaps now becoming noticeable. You’re spotting inefficiencies and bottlenecks in leadership’s systems, and you’re unknowingly generating ideas to stop the hemorrhaging. Do not share these ideas with your co-workers. Share them with Boss in Boss Language. You are now the only person skilled enough to provide this solution; it’s entirely on you to ensure it stays that way.
5. Leverage, Leverage, Leverage
a. This doesn’t save you from every tyrant boss or office spat, but it ranks you as dependable. Once you’re known for competence and quick wit, you earn trust. Trust = less supervision = more freedom.
Deliver the Results
Because we’re not idiots motivated by emotional reasoning, our work must speak for itself. Delivering results or “making good” on our end of the bargain is a crucial step toward liberation as a W2. Over-committing-and-under-performing, and sheepishly making excuses for biting off more than we can chew because of [insert diagnosis here] is exactly how to become forever micromanaged and watched with hawk-like fervor.
We can deliver results without gloating (see earlier anecdote about “never making a spectacle of your accomplishments”). Delivering the results will depend entirely on what task, project, or demand you’ve taken on, but will include the following factors:
1. Very clear understanding of the problem
a. Example: Instead of saying “The scheduling software is annoying to use”, say “Employees are clocking in late because the software requires multiple log-ins, costing us 40–60 minutes of labor per week across the department.”
2. How the problem is negatively affecting Boss’ bottom line
a. Example: “Because the shipping labels weren’t printing correctly, five orders were delayed last week. That led to two refunds and one negative review, which not only costs money but also affects our ratings--- and most of our referrals come from those ratings.”
3. What you took upon yourself to try to mitigate the damage
a. Example: “I contacted the software vendor directly and tested a workaround that reduces login steps. I trained the morning shift on it so we’re already seeing fewer late punches.”
4. A plan for avoiding these same mistakes in the future
a. Example: “I drafted a quick-start guide with screenshots so future hires don’t waste time on login issues. I also suggested to IT that we set a recurring review of the software to catch these glitches earlier.”
5. Proof
a. Example: “Since we started using the workaround, late punches have dropped from eight per week to zero.”