Welcome to The Accidental Assistant

Jennifer Donovan
The Accidental Assistant
4 min readNov 21, 2022
Photo from istockphoto.com

I have been on a mission and personal quest to get my sh*t together for quite a few years now. I joke, but I have spent years doing a lot of introspection in order to shorten the distance between who I have been versus who I want to be, with the goal of eventually eliminating any space between the two, and just becoming me — my true, authentic self. My last year of therapy has been particularly helpful in this endeavor.

Part of this personal journey has been aided and abetted by writing. In 2016, I began very sporadically writing a blog. I followed that by joining Medium in 2020, and I started a newsletter on Substack earlier this year. I have a miniscule (but mightily supportive) following on all of these platforms, and I do hope to change that, but for now, my personal growth has been my priority.

But as I advance personally, I also want to advance professionally, and that means I am making a huge shift in how I view my work life and career. I’ve written before about how I never wanted to be an assistant, and I’ve shared some things I don’t like about the position itself. I stand by what I’ve written in the past. This is my truth. What I have done my entire career, I never wanted to do… ever. For years, stating that I hate what I do became a key component of my identity. I repeated it like a mantra, as if saying it over and over again would somehow manifest me into a different position. That’s not exactly how things work.

Not wanting to be an assistant, as well as actually being an assistant do not need to be my only truths or the crux (cruxes?) of my identity. I never wanted my job to define me, but I’ve allowed it to define me in the worst way possible: I have lived wholeheartedly believing I am a failure. Since I never wanted to be an assistant, and I continued to be an assistant, I am therefore, a failure.

It has taken me years — decades, and I am happy to report I no longer feel like I am a failure. I also LOVE my current job, and no longer hate being an assistant. But we do spend an awful lot of our years on earth, and so much of our precious little time at our jobs. If you hate what you do, that is going to take a terrible toll on your mental health and outlook on life.

I am so glad there are so many voices out there praising and uplifting assistants; showing us how to succeed, thrive and grow. Had I had the courage years ago, I might have joined you. Sadly, I didn’t.

Even now, I don’t feel like… no, I know I am not a part of those folks who are super excited about being an assistant and want to share all of their tips and tricks. I learn valuable things from them every day but having had such a difficult journey to get to the happy little emotional space I am in now, it makes sense that I am coming from a very different place, and I have different goals in sharing what I plan to share here.

While I plan to document my own journey and experience and share my own thoughts and feelings (internalized hatred, misconceptions, and preconceived notions), what I am truly hoping to do is to create a space and a voice for those of us who didn’t plan on walking this path in life, but nevertheless have. A space for people who have doubt; who have felt “less than”; who want to question things. A place for the hopeful, but the lost.

There are so many resources out there for high performers and so few for folks who are average or status quo; folks who are successful, but maybe want more or different, but don’t know where to turn. I don’t know if I can help with your actual advancement, but I know I can create the emotional space for you to examine who you are; where you’ve been; where you might want to go, and to at least let you know there are others out there. At least I am here, and I can’t be the only one who feels this way (I hope)!

So, I invite you to subscribe to this newsletter (and any of my other writing arenas) and come on this journey with me. I invite you whether you are an assistant or not. I especially invite you if you have an assistant. But I also invite anyone who is working in any job who wonders whether or not they are on the right path. I am not a self-help person or a mentor, but I care, and I think when folks share themselves with others, great things can happen.