Interview: Meet the Blogger Behind ‘To My Assistant’

Ever wondered what the people on the other side of the desk think of you? To My Assistant is a clever blog where an assistant chronicles all the things he or she will never ask their assistant to do – whenever they get one, that is. The Hollywood blogger behind TMA reveals the site’s inspiration, explains why it’s not always a good idea to be BFF with your boss, and doles out advice for future bigshots.

What inspired you to start the To My Assistant blog? I’m going to assume it’s because you or someone you know is/was a mistreated assistant, right?

I’ve spent about 3 years working as an assistant in Hollywood, in more than one job at more than one company. While I wouldn’t categorize myself as “mistreated” (well, maybe on a few specific occasions), I certainly know more than a few people who are or have been. The whole idea came about as I was wondering what I would be like as a boss, and if we assistants would keep all the promises we constantly make, i.e. “When I have an assistant I will never blah blah blah.” So I guess it started as a way to keep track of all those things I said I would never do, while also good-naturedly making fun of all the ridiculous things that are asked of us.

Have you been an assistant? Have you had an assistant?

Still an assistant! Haven’t had one yet, but when I do, I’m sure they will carry around a printed copy of the blog and shove it in my face at every possible occasion.

Thanks to books and movies like The Devil Wears Prada, a lot of people think it would be glamorous to be a celebrity or successful person’s assistant. What do you think of some of the pop culture portrayals of assistants (Ugly Betty, Jennifer Hudson’s character in Sex and the City, Entourage, etc)? Are there some you find more realistic than others?

That’s a tough question, because everyone’s experience as an assistant really depends on their relationship with their boss, so there’s no single accurate reality. I would say that Jennifer Hudson’s character in Sex and the City is a complete fantasy, while The Devil Wears Prada is a nightmare situation, but also totally possible. As for Entourage, in the episodes I’ve seen (not many, to be honest), Lloyd enjoys witty repartee with his boss and then pouts – the witty repartee is enviable; the pouting is inevitable.

In this article, I documented how many people take to Twitter to tweet at celebrities and ask to be their assistants. Why do you think people want to work as assistants? What are some differences in the way people within an industry and people outside of an industry view assistants?

I wanted to work as an assistant in Hollywood because I wanted to make movies, but wasn’t quite sure how the industry worked or what part of it I should work in. So for me, the past 3 years have been something like entertainment industry grad school. However, I suspect the people on Twitter have different motivations and see being a celebrity assistant as a chance to hang out with their favorite celebrity while getting paid to fetch coffee and then quickly become their BFFs or get married to them and live happily ever after in the mansion of their dreams.

But, within the entertainment industry, the position of assistant really has no glamour whatsoever. Even if you get to go to a premiere or wrap party with a bunch of famous and important people, it’s second-hand glamour, and you’ll still feel awkward and out of place. Whereas outside of the film industry, I think people see the job of assistant as a position that is inherently glamorous without requiring any kind of skill beyond the desire to be around celebrities. Sadly, this is not the case.

What kind of feedback have you been getting about TMA?

Overall, positive feedback, beyond my expectations. Event though I started the blog from the perspective of a Hollywood assistant, it really ended up having a broader appeal than I first envisioned. I thought that only the assistants in my industry were treated poorly, but it turns out that assistants everywhere are unhappy!

Do you blog on the job? If so, how do you keep from being found out?

I do, but I’m fortunate to currently have a boss who would probably find the site pretty funny. As for not getting found out, it’s basically a matter of not telling people that I write the blog and being really good at switching between websites quickly when someone walks behind me.

What are some strategies you’d recommend to people getting promoted into jobs where they’re getting their first assistant?

In terms of strategies for working with your own assistant for the first time, be kind, be patient, and realize that it’s going to take you as much time to adjust to your assistant as it does for them to adjust to you. And, of course, don’t do anything that has been written about on tomyassistant.com.

According to a recent study, many women in the workplace said that they want their assistant to like them and, in some cases, even be their friend. Do you think it’s healthy for bosses and assistants to be friends with each other outside of the office? Do you think assistants need to like their bosses personally in order to work for them?

I think it’s great for bosses and assistants to be friendly outside of the office. The more you like your boss, the more likely you are to actually care about your job. But I’ve also seen both assistants and bosses embarrass themselves by trying to hard to be “friends!” so I’d say if you’re an assistant, follow your boss’ lead, and if you’re a boss, well, wanting desperately to be cool and young is probably the biggest hint that you’re no longer either of those things. I don’t think it’s necessary for an assistant to like their boss in order to work for them, but I know for a fact that it makes everything easier and more enjoyable for both parties.

One common complaint among managers is that younger employees (aka millennials, although I hate that term) have a sense of entitlement about working and think they’re too good to be assistants. Have you observed this trend, or do you think it’s an exaggeration?

Not to sell out my own generation, but I’ve definitely seen that trend. However, the people who come into internships or mailroom jobs or assistant positions with that sense of entitlement don’t tend to last long, since they’re not willing to give up their excess pride in order to do their job well. I’m not really sure where they go after that – probably law school, if I had to guess.

If you had to be a celebrity’s assistant, who would you choose and why?

Do directors count as celebrities? If so, I’d work for Chris Nolan, because I hear he’s wonderful to work with, plus he makes amazing movies all over the world.

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