The Tale of the Terrible Boss: For Dreamers, Doers and Overachievers

Warning: this article may cause some discomfort. It caused me great discomfort to write. Read it anyway.

We’ve all had a bad boss (er, maybe a few). And let’s be clear, “bad” can take many forms- unorganized, well-intended but directionless, one who takes credit for others’ work, one who lacks critical leadership qualities like vision and passion, etc. Those types of bosses are irritating, maddening even. But with the support of co-workers and love for your job (hopefully), you push on through, requiring nothing more than monthly vent sessions over drinks. But sometimes we find ourselves under the guidance of those who push the boundaries of what is ethical, acceptable, professional or healthy. Most of us who have experienced these conditions start looking for something else, anything else, immediately. I worked for this particular type of individual for eleven years.

When I was in my early twenties, I lacked career confidence. I was bright and driven, but unsure of where, exactly, I wanted to put all my energy and passion. Then, the skies cleared and I was given the opportunity to move to Washington, D.C. for graduate school. It quelled my lifelong fear of failure and validated that I would, finally, become Somebody(!). I was accepted into a top ten graduate program in my chosen field, during which I made a lot of connections and impressed a lot of people. I soared with the opportunities surrounding me. I became a board member at 25, graduated with near perfect grades, and got my dream job with a salary that made my eyes water. People were seeing me, they were seeing my potential. This was it! I was going to make it!

It was then that I met my future boss. Let’s call her Sophia.

I admired her, and I believed in her. She had vivacious energy, a way with words, and explained ideas that gave me a rush. She made me want to be better. More importantly, she made me believe I could be better. I also thought she was cool. She always looked put together and went to rock shows and traveled the world. I overheard others talk about her like she was going places, and I wanted to go places, too. I decided that, since she clearly saw my potential, she must really like me. She was nice to me. She took me on bike rides through the city, treated me to fancy lunches, and even bought me expensive stuff (with her own money!!) for performing well. There was zero downside to this woman. I was ready to do whatever it took to stick by her, impress her and to eventually reach my ambitious dreams of, well, world domination (ahh, the energy we have at 25).

Looking back, it didn’t take long for Sophia to change her behavior. But, like any relationship that starts off exceptionally, I made excuses for all the red flags. I did not want that bubble to burst. I put all my eggs in one basket, and she was holding my future, my confidence, in her well-manicured hands.

I honestly don’t know the moment things began to change, because like anything, change started small. There were moments Sophia asked me to stay late, which was fine. And then it became an expectation, which I also told myself was fine. I had to put the work in, I was capable and she depended on me heavily. It felt good, she believed in me! I started to run on adrenaline. I frequently worked from 8am until 1 or 2am and I loved it, because she loved it. I was unknowingly forming harmful habits but, even while I was waking up in cold sweats and becoming increasingly reliant on her opinion, I was too close to it all and too excited by it all to notice. Then, over the next ten years, a series of events lead to me finally walking away:

  • I flew through the ranks and quickly earned the respect and trust of those around me. I led teams, improved performance, kept morale high and gained a reputation for my work ethic and intellect. These actions were waved off as expected and not in any way exceptional. A few times she even insinuated that I should be as far along in my accomplishments as professionals 15 years older than I.

  • Those I supervised over the years said things like, “You’re the best boss I’ve ever had” and “I am learning so much from you”. When those comments were made in her presence, she quickly responded with a negative comment about what I could be doing better. Her attitude toward me rapidly evolved from, “You are talented and I believe in you” to “Your worth only shows in our profits, and if you think you can sit at this table with me, you are mistaken.”

  • I was solely responsible for getting the company global attention, on multiple occasions. She never gave me credit, so I told myself that those things were just expected at this level of work and were therefore not worthy of praise or acknowledgement.

  • I took an “idea notebook” everywhere I went and even started waking up to write my ideas on a chalkboard over my bed. In the dark. At 2am. When I came to her with my ideas the next day, she was at her most encouraging. She allowed me to work on all my ideas and projects for her own gain, but never once gave me a team or any type of support or proper resources. Asking for help, I learned, was not acceptable.

  • More times than I care to mention, she sat me down to explain that my energetic personality and love for humor made me appear immature and “very girly”. My whole way of being had to be made small and stoic in order to be believable as a high-performing and bright (female) individual.

  • She accepted my requests for vacation, but did so in a way that made me feel guilty. Prior to leaving the country for my birthday one year, I worked for 23 days in a row to show my dedication and “earn back” her respect. As I was under extreme amounts of stress, I also earned an upper respiratory infection that lasted until the final day of my trip. When I texted her upon my return and asked for a sick day to recover, she replied, “Oh no! I hope you feel better, you can come in at 11 tomorrow".”

  • I put together our business plan and our extended marketing plan, attended networking events on her behalf, and made hundreds of connections that would benefit the company. She frequently feigned praise and encouragement, but nothing was ever enough. Before I could finish a project, she would compare my work to others who had ten times the resources and support I was given. One time, I casually asked if “our expectations” (I had mastered passive by then) were realistic. Her response was that I was being “a little lazy and short-sighted” and then she asked me if I was still dedicated to my work.

  • When I told her of my weekend plans to attend birthday parties, adventure through Mexico or simply relax and read a good book, she questioned me passive aggressively (the worst kind) by saying “Oh. So… you’re not working on ____ ? I mean, I thought you were serious about your career but…have fun this weekend.”

  • Near the end of my relationship with her, my confidence was so low and my thinking was so cloudy that I ended up being taken advantage of through manipulation and intellectual dishonesty by two businessmen she told me I needed to learn from and trust. I had previously been so alert and aware of the people I surrounded myself with and, suddenly, that skill was put in the hands of someone who only valued me for my achievement and potential, not for me as a person, who dedicated so much time and effort to her dreams and endeavors.

As you can imagine, I was suffocating. After all these events (and many, many more) I went back to my values. I grounded down and asked myself all the hard questions: How did I get here? What do I really want for myself? What makes me happy? Is this person healthy for me? Am I growing? Am I learning? Am I living?

I know what you’re thinking…

“This girl sounds super weak, what is wrong with her?”

“She has no backbone, she should’ve stood up for herself.”

“I would never have put up with that".”

I’m here to tell you- yes, you would.

Because the woman in this story, the individual who spoke down to me, who told me I didn’t deserve a life beyond work, who told me that I wasn’t worth anything until I accomplished this and that, who stopped me from doing all the other things that used to sustain me and fulfill me and make me happy- that person is me.

And that person might be you.

The Sophia in us is dangerous, because you never see her coming. Ask anyone close to me what I’m like, and they’ll tell you I’m extremely ballsy, strong and that I don’t take sh*t from anyone. I’m an East Coast Italian with a fierce sense of justice and a penchant for fighting for those who have trouble fighting for themselves. I am not, by any stretch of the imagination, someone who appears vulnerable to this kind of treatment. But even when you do recognize that you’re taking yourself down, you excuse it away. Maybe you blame others, maybe you go home and kick the dog, so to speak. Maybe you tell yourself, “This is how I got where I am, this is necessary.” (guilty).

But let’s be honest, you listen to the worst of you every single day. This is the worst of you, and it’s likely so completely false. If I were in front of you right now, I’d put claps in between those words. So. Completely. False.

It’s also So. Completely. Unfair. (more claps)

How are you supposed to grow? How are you supposed to get up, excited for your day and with the energy to do big things, when you know this jerk is lurking around the corner, ready to hand you a cup of coffee and a punch in the face? How are you supposed to create a life well-lived? You can’t. And for those of you who think I’m just dropping this knowledge for the ladies, think again. I am forever fighting for women, for their ability to dig deep, to find their power and to achieve big things. Sometimes we do need a little more care and compassion (for ourselves as much as each other, as I hope you’ve realized by now). But now that I own a company, I sit next to both genders. I have real discussions with men and they share their struggles with everything from imposter syndrome to feeling unhappy with who they have let themselves become. More often, it’s about who they felt they had to become in order to be successful. So let me tell you, this is a human issue, not a gender issue. This is not about excusing all of your actions, or inaction, so you can naively ride a unicorn to work everyday and avoid all responsibility for a life you’ve created. What I hope to convey to everyone who has read this far is this: you can fire the jerk within you and be kind to yourself. You didn’t get to where you are because you beat yourself up, you got there in spite of it. I struggled with this, but it is by far the most freeing and interesting work I’ve ever done.

Scientists like me rarely write about things like self-love. We like to see things in black and white and ignore all the mushy stuff. But self-love and self-care is a real thing, and it starts from the space we create for ourselves. From our physical space to our physical health, to who we listen to and what we tell ourselves. And it’s hard, it requires time to master. But like learning to walk and drive and cook and understand your taxes (just kidding), it’s 100% possible. Looking for a good place to start? Write about your inner jerk, the worst boss you’ve ever had, and fire them, politely. Then, hire yourself a new boss. Make a list of all the qualities that will help you grow and move forward toward a bigger goal, whatever that is for you- being an amazing parent, a supportive and loving partner, the next startup unicorn, getting into the best shape of your life, whatever.

While I’m being wildly vulnerable, here is the job description for my new boss:

  • Accepting- is open to mistakes, takes a lesson from each one, sees mistakes as successful steps forward, sets performance based on number of failures

  • Truthful- makes statements (internal and external) grounded in observable truth, avoids statements not rooted in reality

  • Realistic- sets expectations based on available time, effort, skills and resources

  • Authentic- appreciates and encourages humor, energy, humility, vulnerability and not always having the answer

  • Kind- maintains 100% jerk-free environment

  • Unapologetic- confidently and happily carries out all of the above in the pursuit of a life well-lived

I started our wellbeing company because I had read the research highlighting how work affects the health of individuals and, consequently, the people around them. I’m proud of what my team and I have started, and there’s nothing in my life I want more than to be a part of changing people’s lives for the better by making work a place where people find health and happiness and connection. We’ve done so much to push our purpose forward, to educate people about the intersections of behavior and business and health, so people can enjoy the rest of life. So that people can go home happy and fulfilled and be good for themselves and others. So that people can have hobbies and chase dreams that have nothing to do with the work they currently do. So that the pie chart of their life is not 80% work and 20% whatever-else-they-have-the-time/energy-to-drag-themselves-through. I am also willing to admit that in all my years of success (and more failure), I missed the boat when it came to preserving, supporting and nourishing myself. And while this article was supremely uncomfortable for me to write, I’m willing to send it out into the world on the bet that I wasn’t the only bad boss out there. If I can speak to just one more over-achiever, one more person who drives their worth by their paychecks or achievement instead of the rest of the person they encompass, one more person who now has a better understanding of self-love, mission accomplished.

By: Gianna Biscontini

Gianna Biscontini