Before the start of COVID, I was running a very successful business in the travel, events, and tourism world. Relief programs and existing contracts help us stay afloat for the last two years—but it’s becoming very clear that the nature of my industry has changed and the level of income and stability I was enjoying just won’t be possible anymore. And I’m tired of the fear and extra level of responsibility that being self-employed brings.
I feel really confident applying to decent jobs, and the success of my current work is easy to demonstrate. The problem is that the last “real” job I had—that is, in an office with a boss—ended terribly. I was an executive admin for three years, and my relationship with my boss became quite untenable in the end. He was an insufferable rich guy who had a complaint about every single person he encountered, and spent truly baffling amount of every day complaining to me that his wife was spoiled, his family was ungrateful for his help, and his friends resented his success. I had to hound him to sign papers and write checks, and he blamed me for our budgetary issues even though how we spent money was never my call—just my job to execute. He gave me work to do that I made clear was outside of my job description and abilities (like bookkeeping and taxes!) and was furious when I made mistakes.
I gave a month’s notice when I decided I was ready to start my company, and at first, he said he was pleased for me, but his behavior in that last month was incredibly strange. He stopped coming in to the office, and hired an elderly friend of the family who had not been employed in over 25 years to replace me. They were barely able to operate a computer, and he received my inability to train them as me having one foot out the door and giving up on the transition. At some point he just turned off all my access to our email and software accounts and stopped communicating with me. I never got my last paycheck or was even able to log my last 30 or so hours, so I just never turned in my computer. One of our last conversations was him accusing me of putting personal expenses on my business card (untrue).
It was a messy and vague ending to the only job I’ve ever had that wasn’t waiting tables. So now when I need to list my employment history, I can point to five years of hitting goals, working with high-end clients, developing good systems, managing a small staff, following through with projects, and hundreds of lengthy and glowing google reviews from happy clients. But before that all I’ve got is a few years grinding my teeth under the supervision of a weird and unprofessional boss who probably wouldn’t give me a good reference. Is there a professional way to speak about this experience? I don’t want to sound bitter, or like I’m covering anything up, but for the life of me I can’t figure out how to address it.
— Will They Overlook It?