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  • Writer's pictureTaylor Nakakihara

Stage 5 Mistake Clinger Recovery

Updated: Apr 27, 2022

You know what the proverbial 'They' say - Don’t cling to a mistake just because you spent a long time making it.

Well 'They' are right, but clinging to my painstakingly handcrafted mistakes is also probably my most deeply entrenched detrimental personality trait next to opting to island myself instead of connecting with others because I think they might disappoint me instead of giving them a chance. 🙃

The biggest career mistake I made in the past few years is not stopping between positions to figure out what I really wanted to be doing and jumping blindly to the next step of my Be An Executive Assistant plan that I had been following for a decade. As a result, even when asked point-blank by my former executive if I even wanted to be doing this job at all and tearfully swearing I liked my job, I spent almost two years barely wanting to get out of bed because I refused to even consider that this job and title (the one I had worked to get for ten years) was absolutely not what I wanted to be doing anymore.

Sidebar about Executive Assistants vs. Administrative Assistants - in my experience, I had to work as an Administrative Assistant for a few years before I would be considered “qualified” to apply for Executive Assistant positions based on job posting requirements. The job duties are similar, but an Executive Assistant has a much more direct relationship with their Executive and typically does not do as many basic “office manager” tasks as an Administrative Assistant does. The shortest way I know how to explain it is

  • Administrative Assistant - assists the business (the administration)

  • Executive Assistant - a leveled-up AA that assists one or more Executives in their work functions, rather than the business as a whole. Typically requires a certain number of years of Administrative Assistant experience supporting a manager or executive in their work functions

Don’t get it twisted - I think that a successful Executive Assistant is a force to be reckoned with, and it can be an incredibly rewarding and fun career. I traveled the world and met some really interesting and professionally supportive people during my decade as an assistant. Because of my experience I can manage a calendar like a mf’er, give great gifts on behalf of other people, and boy can I plan a corporate event to dazzle. I was just in it for the wrong emotional reasons and my time had come to move on.

One of the main reasons why I had to be done assisting was that I had come to define so much of my self-worth by how useful I was to other people - I’m still working on not being a people-pleaser just to be essential or feel wanted. If I failed at work, even a small stumble, it affected me deeply and I started to not be able to shake things when they happened. Truthfully it’s been well over 5 years since I was able to trick myself into thinking I was happy if I was making someone else happy... I just figured that out this year because part of being a Stage 5 Mistake Clinger is also owning a houseboat on Denial River. I’m learning now that I find a lot of happiness in graphic design work and especially like project-based work where I am given an end goal and set free to make it happen.

I also think that there are two kinds of people who are Executive Assistants - people who are actually passionate about their role as a key support person, and people who grow out of finding joy in supporting someone else’s career because that's not where their true passion lies. I thought I was the first kind, but I am most definitely the second, and I was for some reason ashamed to admit that after I had done “all this work” to become an EA. Think of how sometimes parents will make you eat something because they/someone else went to all this trouble to make it - I was forcing myself to eat emotional peas and for what?

While my Assistant chapter is over, I am grateful for the experience and think it’s a really fulfilling position for the right person. Even if you don’t plan to make a career out of assisting, it is a great stepping stone to gain experience in a lot of varied fields. I have assisted in accounting, door-to-door cable/satellite sales, public insurance adjuster firms, payroll and hr, hospitality, higher education, and now non-profit offices. IMO - the coolest thing about being an EA/AA is that you get the inside scoop about how so many different industries work and what the different job functions are within that industry. I learned that the industries I actually get excited about are education and hospitality and that regardless of the industry my absolute favorite things to do are to write and create beautiful content. I do also still like some of the less-intense tasks from being an Administrative Assistant like organizing files and doing things in Quickbooks.


I am pleased to announce that this week, I am starting as the Marketing Coordinator at Palm Creek Resort and Residences in addition to my current part-time WFH position as Office Manager for the Arizona Association for the Gifted and Talented! That’s right - I have somehow managed to finagle my way into doing all the things I like, in both the industries I love. How's that for professional growth?

I guess I’m learning my lessons and the Mistake Clinger (Level 9000) Recovery is going really well!

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