Do I need a PA or a boss?
February 5, 2014 9:38 AM   Subscribe

I need to pay someone to keep me organized and contact other people for me and sort of, well, bully me into staying on task. But I don't know what sort of person that is. Who am I trying to hire? Details below.

Right now, I'm trying to balance a stressful day job with a side career as an author/illustrator (and, of course, my personal life at home with my boyfriend!). Eventually, I plan to leave my day job and transition into the side career full time, but I'm not prepared to make that switch just yet. In the mean time, I can't keep myself organized *at all*. I get requests to do lectures at schools and the occasional interview for small publications and blogs. I have deadlines for books and promotional stuff I have to prepare. It's kind of pathetic because it's not like I'm JK Rowling over here - but I get easily overwhelmed and find myself just sort of shoving these things off to the side until it's too late. That's not good. I need someone to help me stay organized and to occasionally bully me into doing what I need to do. But I don't know what kind of help I need! Is that what a personal assistant does? Is there something like a personal project manager you can hire? I don't even know what to look for. What type of person fits that job description, and how do you find them?
posted by Gee, June! to Work & Money (12 answers total) 6 users marked this as a favorite
That is EXACTLY what a good assistant does.

I would post an ad for an assistant on criagslist or something like that if you don't know anybody. Otherwise I'd ask around my network, does anyone know of someone who needs a part-time position as an assistant?
posted by magnetsphere at 9:41 AM on February 5, 2014 [1 favorite]

You might need a TaskRabbit.

I'd hire someone for a couple of hours a week. You can forward things to him/her via email, and you can share your calendar with that person. Perhaps you have a discussion for 30 minutes, outlining what's available, what you'd prefer to do or not do, and then the scheduler can get down to scheduling you for those things.

You can also hire someone to do your mundane tasks that you'd prefer not to do.
posted by Ruthless Bunny at 9:42 AM on February 5, 2014 [1 favorite]

I've hired a personal assistant before--a former student of mine who needed a summer job. If you'll be paying them much per year, you should look into any tax obligations you may have as an employer, and if they'll be driving around for you (even in their own car), you might consider your liability in view of the principle of respondeat superior. I doubt either of those will really be issues for you, but hiring through some sort of agency where you're just paying for a service and the agency handles the other stuff might be easiest, though more expensive.
posted by Monsieur Caution at 9:59 AM on February 5, 2014

This is what a personal assistant would do, yes.

I would caution you against relying on anyone you hire to "bully" you. A person you employ is your subordinate and, as such, can't push back too hard against anything you decide to do. They can remind you of stuff, but if you are cultivating bad habits they can only do so much about that.
posted by tel3path at 10:00 AM on February 5, 2014 [1 favorite]

Yup, you need a PA.

But beware: just about anyone can do the most basic parts of being an assistant (managing your schedule, contacting other people on your behalf, etc.), but only the best assistants can do that well and effectively keep their boss(es) organized and on task. You need someone who "gets" your personality, how you work, and can quickly pick up on your preferences and needs. So, be sure to interview several candidates thoroughly before making your selection.

I think TaskRabbit is a great resource, but Craigslist and even something like Monster could be useful tools, too.

And as someone in an assistant-like position who was just promoted, I don't think there is anything wrong with having your PA "bully" (I assume you basically mean "nudge" or "politely nag") you into getting things done. Part of my job is to make my bosses' lives easier, and reminding them to take care of Task A now rather than at the 11th hour helps accomplish that. Just make sure he/she knows to take your answer/way of doing Task A as final rather than up for extended debate.
posted by schroedingersgirl at 10:05 AM on February 5, 2014 [1 favorite]

Response by poster: Thanks so much for the advice so far, everyone! And, yes, I didn't literally mean "bully" me. I meant that I may need frequent reminders and polite nagging. ;)
posted by Gee, June! at 10:07 AM on February 5, 2014

Look into a part time/freelance assistant if you have a lot of bookkeeping type tasks that you can pass to him or her which will free you up to do the actual creative stuff.

Things like appointment setting, dealing with email, all the little micro-negotiations that need to happen with conferences and book signings and the like, and those sorts of things.

Unfortunately, I don't think TaskRabbit is going to be a good resource here. For one thing, most people on there are looking to do odd-jobs on a one-time-only basis. I once did a task on TaskRabbit that evolved into sort of an assistant thing, but even then it was mostly task-based (organize my life in X way for a few weeks while I deal with Project Y). The setup also isn't conducive to someone who could "bully you into staying on task". That sort of thing isn't really part of the job description.

A TaskRabbit would be good for things like grocery shopping, picking up your dry cleaning, dealing with minor personal life stuff, etc. so that you can concentrate on your two jobs. You could probably also hire a TaskRabbit to help you get organized in one big push, with an eye toward hiring them as your assistant if you got on well.

I will say a thing about the "I need someone to bully me into [foo]" phenomenon. I have been hired as an assistant a few times with that as part of the job description. Sometimes it works, sometimes it doesn't.

The time it worked, I was working for a filmmaker with ADHD who needed to be reminded to stay on task and needed help focusing. That was pretty easy, because I could just nag him about things, or say "remember you have a casting session in 20 minutes", or "but what about the park location?" and it worked pretty well.

Another time, it was for somebody who wanted to be nagged about eating healthy and working out (on top of more typical assistant tasks). This did not work out well, because I would make appointments with her trainer and then she'd just cancel them.

In my opinion it's really a two-way street and depends a lot on your capacity for being pushed in that way. A film director is used to being shepherded around. A small business owning stay at home mom is not. Which of those categories do you fall into, and how hard is somebody going to have to bully you into doing these tasks?

A thought completely out of left field: if you need to be motivated on creative tasks, what about hiring an editor?
posted by Sara C. at 10:11 AM on February 5, 2014 [1 favorite]

Response by poster: I guess I should add that I'm pretty easy to push into keeping appointments. I just can't seem to be my own motivator. If there's someone saying to me, "Remember, you need to respond to X by this time" I'm going to be embarrassed if I have to say "Uh... yeah... I just... sort of... didn't." Even if I hired that person. So, please, everyone, forget that I said anything about "bullying." Really. I meant that I need a human being to remind me of things. :)
posted by Gee, June! at 10:24 AM on February 5, 2014 [1 favorite]

See, if I were you I'd hire someone to respond to the thing.

They will "bully" you by saying, "I'm emailing Jane Doe over at the Children's Book Event. Which timeslot works for your panel?" Then they will send the email, and you will be booked for your panel at the Children's Book Event.

This type of thing really works, and it also takes a lot of admin work off your plate.

What doesn't really work is when it gets down to the actual nitty gritty of "Do you want to start breaking story for the teddy bear book this week?" every single goddamn week, and you ALWAYS say yes, but then you always find a reason not to do it in the end.

Look at hiring someone as a way to free up time to do the stuff you actually enjoy. Don't look at it as someone who's going to force you to do the stuff you supposedly enjoy.
posted by Sara C. at 10:49 AM on February 5, 2014 [2 favorites]

I was a personal assistant to A-list Hollywood-type people for years. This is exactly what I did. Yeah, what I did wasn't bullying, it was about being firm and organized and knowing how to deal with creatives, whose brains may be wired to make their creative output genius while the rest of their lives fall to shit. I was great at it.

So yeah, start looking around for a personal assistant. Look for someone who has some experience in this area already, who can come in and get you going.
posted by BlahLaLa at 11:22 AM on February 5, 2014 [2 favorites]

Not an exact answer to your question but related.. there's some good stuff on avoiding procrastinating at
posted by tanktop at 11:50 AM on February 5, 2014

You might consider a two-part solution: an assistant plus an accountability partner.

I have a virtual assistant. One of the cool side effects of hiring someone to help is that you have to get somewhat organized in order for them to be *able* to help. They can help you organize and set up processes that will then make it easy for you to assign them stuff.

I have my VA do the stuff I would otherwise procrastinate, like the back-and-forth emails required to finalize a date and venue for a presentation.

The accountability partner could be a paid coach (different from the assistant) or a fellow business owner / disorganized person. You set up a schedule to check in with each other and prod each other. I hired a coach for that; we meet once a week.
posted by ceiba at 7:05 PM on February 5, 2014

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