Robert A. Di Ieso, Jr.

Q: I have a question about how to best list freelance experience on my resume. Would it make sense to list all five years of my freelance work under one title with start and end dates for that period of time? If so, can I also list my overall accomplishments beneath this one title?

I was a freelance designer and design assistant for five years after I graduated college (everyone in my field worked on a freelance basis, in case that matters). After five years, I decided I wanted more structure and work-life balance, so I moved into an administrative role at a large company in a completely different industry. I’ve now been in this role for three years and am looking to pursue other administrative opportunities in a more creative environment.

I’m concerned about future employers thinking I’m flighty or a job hopper based on my prior freelance experience (most of these gigs lasted anywhere from two months to two years). All of my freelance projects generally followed the same process and required the same skills.

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A: Grouping them all under one overall freelance heading is the perfect way to do, and then you can list all your accomplishments from that time period there. You don’t need to list every specific freelance job you held during that period or individual dates for them — but if it strengthens your resume (it may or may not), you could include one bullet point that says something like this:

* Clients included Teapots International, Texas Rice Sculpture Tournament, Northwest Llama-gram Society, and more

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Q: Does the order of names in an email matter?

This might seem like a minor question but it’s something I’ve wondered about in passing from time to time. When sending an email, does it matter the order in which you have people’s names in the “to” section? Like should it be based off order of title importance or relevancy to the topic at hand, or does that not matter at all? For example, if I’m emailing the president of my company along with my boss and then an entry-level person (all who are directly affected by my email, so wouldn’t necessarily go in the cc section), would it be strange to list my president last?

A: In general, it doesn’t really matter. That said, there are some companies where this kind of thing does matter and people do pay attention. In case you’re at one, I’d just pay attention to how other people at your company do it — particular your boss and other people senior to you — and if you notice that they seem to list names in order of hierarchy, it’s smart to do the same. (But know for the record that this is a weird thing for a company culture to care about.)

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These questions are adapted from ones that originally appeared on Ask a Manager. Some have been edited for length.