4 Survival Tips – Staying Sane with an Insane Boss

Most of us, at one time or another, have dealt with a difficult boss. Some of us have experience with a boss that is outright insane. The insanity can be the good kind, the bad kind or a mix of both. It may also depend on the day, the hour or the minute.

When my current boss approached me about joining SoapBox as the second employee, I immediately felt her passion and enthusiasm. She is still just as passionate. What I didn’t realize at the time, is that passionate can be seemingly (or realistically) INSANE. Let’s just say, if there was a college degree program based on “how to manage your boss who may be off their rocker at times”, I would have a PhD.  If you have an insane boss, and want to live to tell the tale, definitely read on.

Let me tell you how it all began…

When I think about working with Jacqueline over the last 4 years, it plays out in my mind like a movie montage of a 5-foot tall, blonde Army General threatening to make me do push-ups if I ever even think about chewing gum during a meeting.

When we started the company in 2012, there were less than a handful of us. We put in 12-16 hours a day, 8 days a week. We had to be swift on our feet, ready for whatever came, and manage up, down, and sideways. I had to create a list, that when followed diligently, would save myself and the lives of those around me. I actually titled it “The Boss Lady Survival Guide” and it went something like this:

  • Times New Roman should NEVER EVER ANYWHERE be used. EVER.
  • We never “wanted to follow up”, “wanted to talk” or wanted anything really. You are doing and you did.
  • Everyone has a second chance every day. Just don’t mess up.
  • Double space after a period = death.

Once the dust settled, I had to admit that there is something to be said about the nutty ones. As the years passed, I realized that there is indeed a method to the madness. She might have seemed unreasonable and seemingly inappropriate at times, but she also has a way of earning the respect of others, and knows how to get the seemingly impossible done.

Her type of cray-cray somehow translates into making the company succeed. She is uber passionate. At times, I think she has lost it and we are all doomed. Other times, we are in awe of the genius. Her unpredictability is utterly predictable. And if you aren’t prepared to train with the best, run the other way. Fast.

So, now that I have earned my PhD (feel free to call me Doctor Dan), I decided to lend a helping hand to others who might be in a similar position. Here are my tips…

  1. Some Battles Are Unwinnable

I’m often puzzled by how my boss’ brain works. Build a successful startup from the ground up with almost no funding? Sure, no problem. Remember where you put your keys? That’s a tough one. From working with Jacqueline, I’ve learned that it’s not possible to change a person. So while she’s focusing on ways to revolutionize Market Research, I’ll make sure she has her phone charger, something to eat and a lint roller in her desk.

  1. Learn Your Boss’ Style

Some bosses are prim, proper and polished at all times. My boss is more like the opposite of this. She can, at times, rival a truck driver in her language choices, and I always know when she has to go to the bathroom. Early on I learned to stop wasting mental energy on perfecting “being professional.” Throw the “I-am-at-work persona” out the window – doesn’t fly with her. She is real. And wants everyone around her to be real.

  1. Accept Emotional Meltdowns

Tears are a normal, and acceptable, part of growing a startup. If you, or your boss, doesn’t have an emotional breakdown (the public kind, not the kind when you are alone in your car driving home), you might be doing something wrong. Instead of trying to shield people from your boss’ emotions, use them to your advantage. Next time you’re involved in a high-stakes negotiation, try mentioning that your boss is likely to “freak out” if things don’t go her way. It just might tip things in your favor.

  1. Invest in a Good Pair of Sneakers

So if nothing else works, you can run away. Or, if you have a boss like Jacqueline you can last through the early-morning or late-night “team-building” workouts that she will force you to participate in. I have been subject to mud runs, a 200-mile team running relay (I need to add here the teams were 12 people and I was the only male. We didn’t sleep for 32 hours because we were RUNNING across Nevada), and vomit-inducing workouts in hotel gyms. She doesn’t ever care how “good” I do – she is addicted to people who try.

My final bit of advice. If your boss is actually insane, these tools will not work. You can’t reason with crazy. If your boss is more concerned about themselves than the employees, run the other way. Finally, I may need a new job after this – just kidding. I already tried to quit one time to pursue my “higher calling” and she wouldn’t let me. Best decision someone ever made for me.

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