Ask Jack: Bug a Freelance Boss, Online Dating, Job of the Week

Two colleagues having lunch
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I know what you're thinking: "My question is better than these questions!" Hey, it's not a competition. (And wagering on "Ask Jack" is illegal in most states.) I want to answer your work questions too -- so ask away! You can do so in the comments below, or Tweet your question @AOLJobs with the hashtag #AskJack. Before you know it, someone will be saying "My question is better than that!" about your submission!

An AOL Jobs reader wants to know....

What to do when you get "hired" for a freelance assignment and then, despite the "email handshake," your contact just doesn't get in touch again or return your emails? When to follow up and when to just let it go?

You know, I'm a freelancer, and this is one of my top pet peeves (along with "not having work," "no benefits," "waiting a really long time to get paid," and "getting paid a very small amount"). The non-reply is a great frustration, and seems to happen time and again. Why won't they write back? It feels a little like dating, doesn't it?

First, try not to take it personally. (I know, it's hard not to.) Maybe the money dried up. Maybe another project took precedence. Maybe your contact got canned. There are so many reasons that have nothing to do with you. So all you can do is follow up.

Timing-wise, you just have to find that balance that feels right for you: Not contacting them so often that you seem like a pain, but not so infrequently that you're forgotten. Every three months maybe? Every six months? I hate, hate, hate sending the "Just checking in...." email -- it feels desperate to me -- but it can certainly be effective. As an assigner of work, I've received "checking in" messages on the same day that I needed to hand out some project.

Perfect! Who knows, someone might give you an assignment just to shut you up.

Another reader asks:

I saw a co-worker who I like on an online dating site. Can I...?

You cannot. Don't even think about it. OK, you can think about it -- but don't click anything. Maybe your place of work doesn't have rules against office relationships. But your co-worker may have his or her own rules. Or -- are you sitting down? -- they may not be attracted to you. And now you've intruded on their personal life. That will make it uncomfortable in the workplace. And we don't like an uncomfortable workplace, do we? No we do not.

I don't mean to be completely negative. Be charming in real life. Don't be creepy. Dress a little bit nicer. And maybe, just maybe, this person will be charmed. But wait, that person turns out to be a total jerk -- and it's that shy, clumsy person in accounting who was perfect for you all along! I smell a blockbuster rom-com....

Click here for last week's questions

Do you have a work-related question for Jack? Write it in the comments below (better answers to this week's questions are also welcome!) or tweet it @AOLJobs with the hashtag #AskJack.

Jack's Job of the Week

Dating seems to be our topic of the week, so it seems like our job of the week should be... dating specialist! The dating service It's Just Lunch has 41 available jobs, from coast-to-coast, currently listed on AOL Jobs. Or type in a keyword for any interest or skill you might have, do a search, and see what listings come up in your area. It could be the perfect match!
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