Surviving the Bad Boss

A Comedic Guide to Working in a Cubical/Zoom Wilderness

Ah, the workplace—the den of dreams, the source of livelihood, and occasionally, the battleground where bad bosses roam like free-range chickens creating chaos, confusion, and much clucking and pooping on everything. If you’ve ever found yourself trapped under the reign of a terrible boss, fear not! Today, we embark on a journey filled with laughter, tears (of joy), and the occasional urge to throw office supplies. Join me as we navigate the treacherous waters of working for a bad boss, armed with a smile and a sarcastic sense of humor.

The “Micromanager” Extraordinaire – Imagine a helicopter parent, except they’ve swapped out their adorable child for a team of adults who want to do their jobs. The micromanager boss has an uncanny ability to hover over your shoulder, pointing out every microscopic detail you missed while stifling your creativity with a fervor usually reserved for art thieves. Remember, no idea is too small for their scrutiny, and no task is complete until you’ve over-analyzed it to the point of existential crisis.

The “Queen/King of Inefficiency” – Picture this: You’ve just spent hours meticulously crafting a report, only to have your boss nonchalantly dismiss it with a wave, claiming they’re “too busy” to read it. Yes, we’re talking about the champion of inefficiency—the boss who devotes more time to color-coding their Post-it notes than making informed decisions. Embrace the chaos, my friend, and take solace in the fact that your boss’s attention span is shorter than a goldfish’s memory.

The “Master of Awkwardness” – If life were a sitcom, this boss would be the star, renowned for their impeccable ability to create awkward situations at every turn. From mistaking a water cooler for an impromptu dance floor to sharing their deepest secrets in a team meeting, your boss can transform any mundane day into a cringe-worthy carnival ride. Remember to keep your poker face strong, my friend, and prepare for impromptu acting sessions worthy of an Oscar.

The “Email Deluge Dynamo” – In a world where email inboxes never sleep, the Email Deluge Dynamo boss takes it to a whole new level. Their superpower? Sending emails at an alarming rate, flooding your inbox with requests, updates, and the occasional cat meme. Brace yourself for a never-ending game of whack-a-mole as you attempt to prioritize tasks while dodging the onslaught of emails. Pro tip: Consider investing in a professional email filtering service or developing telepathic powers to survive this boss’s onslaught.

The “Master of Miscommunication” – Communication is key, they say. This boss misplaced the key under a pile of nonsensical jargon. The Master of Miscommunication boss excels at providing vague instructions, delivering contradictory feedback, and making you question your grasp of the English language. Embrace the art of reading between the lines, my friend, and become fluent in the secret language of boss-speak, where “interesting” translates to “I have no idea what you just said.”

But, all you forlorn minions suffering a bad boss, take note:

A bad boss can test your patience; humor can be your secret weapon in this wild, untamed wilderness of cubicles and Zoom rooms. Remember to:

  • Find joy in the absurd.
  • Laugh at the chaos.
  • Take solace that even the worst bosses provide excellent material for happy hour conversations.

So, sharpen your wit, and face your terrible boss armed with laughter and an unyielding spirit. After all, comedy is tragedy with the benefit of time—so why not shorten that time by finding the humor in your daily struggles? By embracing the absurdity of working for a bad boss, you can transform frustration into amusement and turn your work world into a stage for your comedic genius.

Remember, laughter is contagious, and when faced with a bad boss, it can be a powerful antidote to stress. Share your hilarious tales with your colleagues during lunch breaks, organize an “Awkward Boss Bingo” game, or start a secret club where you exchange survival tips in the form of witty one-liners.

While we can’t change our bosses, we can change our perspective and choose to find joy amidst the chaos. So, chin up, my fellow office warriors, and let the laughter be your shield and the comedy your sword. Together, we shall survive and thrive in the face of even the most atrocious bosses.

And who knows? Maybe someday, armed with your sharp wit and infectious humor, you’ll rise through the ranks, leading by example, transforming the workplace into a comedy club where good bosses prevail, and laughter drives success.

In the meantime, remember that this too shall pass, and the experiences gained from surviving a bad boss will shape you into a resilient professional ready to take on any challenge. So, raise your imaginary glasses, toast to the absurdity, and embrace the comedic rollercoaster that is working for a bad boss—it’s a journey you’ll look back on with laughter and appreciation. Cheers to survival, my friends!


Rich Jones is the Founder/Principal of Leading2Leadership LLC. Before starting his strategic planning agency, he spent over 20 years in leadership roles in the financial services sector. Before becoming an executive in the financial services sector, Rich was an entrepreneur, building and selling two businesses and working for early-stage start-up companies in executive roles in marketing, business development, and seeking investment partners. With more than three decades of experience, he brings innovative thought to companies and executives. Rich published “Leading2Leadership, a Situational Primer to Leadership Excellence.” The book is available on and was designed to be used as a book study for leadership development programs; it breaks leadership skills into manageable situations for discussion and reflection. Rich works with credit unions, CUSOs, and vendors, designing digital, data, culture, marketing, and branding transformation strategies. In 2014, Chosen as a Credit Union Rock Star by CU Magazine, and in 2018, Rich received the Lifetime Achievement Award from CUNA Marketing and Business Development Council. A Marine and graduate of Colorado State University, Jones shares his expertise at

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