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Chelsea, and special guest Stephanie Georgopulos, teach you how to earn extra money with a proper side hustle. Want to start a side hustle, but not sure what to do? This video will give you lots of ideas:

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Hi, I'm Chelsea from The Financial Diet and with me is friend, former colleague, writer, editor, curator, copywriter and everything extraordinaire Stephanie Georgopulos.

Stephanie: Hi!

Chelsea: Hi, and today we're going to talk about something that Lauren and I already mentioned was one of the big steps to having the freedom to quit your day job, follow your dreams, and really create your own financial life and that is having side hustles. So for us that means anything from having side jobs outside of your 9-5 or having, you know, a whole freelance career where everything is just a little side job. And I've known Stephanie a long time and the entire time I've known her she's had about 75 side jobs at any given time. And now she's freelance full time after leaving her job in copy writing earlier this year, so I thought that she would be the perfect person to ask about kind of how to make it happen in your own career. So how did you first get into writing/editing?

Stephanie: I was working at a hair salon and my roommate was working for this woman who owned her own PR company. Then she got pregnant and she couldn't come into the office anymore and she needed a job that she could do in between puking and do it from bed, so she started a blog! And it was a lifestyle blog. So after a couple of months I asked if I could start contributing for free and they allowed me to and I got just a ton of beauty products, a ton of alcohol, I got trips to Las Vegas and Atlantic City. So, I wasn't making money, but I was having this sort of double life that afforded me a lot of things that I would have never been able to pay for with my hair salon job.

Chelsea: So since that time, you've obviously gotten jobs as a professional, full time writer copywriter. Have you always had side jobs since then? 

Stephanie: When I first graduated from college I was working at a thrift store, the hair salon, and I was a shop girl a couple times. I also got another little blog gig for this sex and relationships site. I got to get on a lot of press lists and got free vibrators and stuff like that so... *laughing* But I found a job doing tech freelance writing for The Next Web. And I had no idea what I was doing, but I just pretended I did and I went and interviewed people and wrote pieces about who sucked at Twitter... I was submitting articles for free to Thought Catalog and I eventually got hired there part time. So at that time I had no real hustle and then I got hired full time by Thought Catalog and then I wasn't really allowed to freelance anywhere else. And during that time I ended doing social media for my friend who owned restaurants and I also started doing copy writing for Chevy and that was the first that I realized you could make- Can we curse?

Chelsea: Hell yeah!

Stephanie: You can make a shitload of money doing copy writing! 

Chelsea: I think we should clarify- we should pause to clarify that I got her that job.

Stephanie: Yes! *laughing* She did!

Chelsea: I am the hustle in that story- the hustle fairy. 

Stephanie: Once I realized that I was kind of like "where else can I do this for? I'm just going to do this all the time." I talked to my friend who worked at Gawker in advertising and I met with his head of content and she hired me. I worked at Gawker for 2 years. So at the same time, I had reached out to just submitting one article when the site was still invite only and they wrote back and were like "Do you actually want to edit a collection?" and I was like "Yes, I do!" I basically am just living off of side hustles at this point. There's a million side hustles that I'm working on right now.

Chelsea: What's interesting to me is that I think that a lot of people look at it as like you get your job in the field and then stop pursuing any side projects, but I know that for you it's always been something that you've done. Like even when you had like a "dream job" in a field you were still working on still other projects.

Stephanie: Yeah, I mean I don't believe that you should just be using your skills in one way for 8 hours a day and then you don't do anything else, because I think that it's really limiting. And if anything happens to that job, you don't have any connections. You've just been sitting at your desk for like 3 years, not meeting people, not getting your name out there, not expanding your skills. You can take one skill that you have, like writing for example, and parlay that into a million different directions. You can learn how to edit, you can learn how to copy write, you can do a lot of different things, but not if you're just doing your one job all the time. I don't feel comfortable if I have one job because what if that job goes away? What if the company folds? What if I just hate it? And I haven't set something up, so I always try to have 2 or 3 things set up that I can invest more time in. 

Chelsea: Hey, that's a good point you make too because you say like just because you do one job and you're really good at it doesn't mean you might not get laid off, the company might not have financial problems... like it's very scary to have all your eggs in one basket. So you kind of have a time line where it's like you have one job that overlaps with another job and then that job kinda comes in more focus and then another job- it's very interesting in that way and you said that you found some of your jobs just by like trolling the shady parts of Craigslist? 

Stephanie: Yeah, I always go down to the bottom of the page. I don't want a job that's listed under the regular jobs. I don't want PR marketing, hospitality, whatever. I want like a gig. Like I want something that I can do that doesn't involve me going into an office. 

Chelsea: I haven't gone in for a staff job in years now, but I remember when I did, I did have other things going on and I was way too nervous to make that clear, up front and I feel like you owe it to yourself to at least ask. Like "is it okay that I have these side projects?" or just to tell them "I have this going on" and I feel like some employers like it to a degree. It shows that you're passionate, you have interests that are kind of diverse and you're really motivated, so...

Stephanie: Yeah, and especially if they're not paying you what you requested, that's a good way to negotiate. 

Chelsea: So what kind of unexpected landmines or obstacles are there to look out for when you have all these different jobs? 

Stephanie: Two things. You don't want to over schedule yourself. Don't be afraid to say no if something is not paying enough for your time, but something else could or is. It sucks to freelance if you don't ever get to enjoy the flexibility of that. Financially, tax-wise, you really want to be careful, you know, at least- at the very least make sure that you have enough to pay your freelance taxes because when that bomb drops on you, like you get audited for something you messed up a couple years ago or whatever happens, at least you don't have to worry about paying all of your freelance taxes plus, you know, whatever nightmare scenario is. One thing you should definitely do is just get an accountant. I know it seems like it's going to cost a million dollars and only like 50 year old people have accountants, it's not true! They're going to save you money, they're going to write off all your stuff as a freelancer. It doesn't matter if you have a full time job and you're barely making anything as a freelancer, just get one! They will help you and save you money, it's worth the costs. 

Chelsea: So what advice would you give to someone either, well a) looking to find more work in their own field or b) looking to find work in a new field?

Stephanie: My advice for someone who is trying to get more work in their own field is to just let people know that you're looking first. If you see something that can be done, if you have a friend who is building a website let them know that you can code it, or you can write the copy for it. Try to solve people's problems. If you're trying to do something in another field, so say you're trying to make a hobby into something that you can monetize, just start doing it. There's Etsy now, you can sell things. Anything can become a hustle, anything can be monetized. You just have to want it and I would advise that you keep something for yourself that you don't monetize because that's kinda depressing too. Like, everything you do is like a dollar sign, that sucks. No one wants that. You need to keep something for yourself, so always keep that in mind too. 

Chelsea: So, I feel like the big take away is when you're looking to have a side job or a, you know, have multiple streams of income, maybe change careers, whatever you're looking to do by expanding outside of the box of your regular 9-5 is that you have to be, uh..., brave. You have to be willing to look into places other people won't look, you have to go to the weird, janky bottom of Craigslist. If you're just sitting there everyday 9-5 at your same job and you're not working on anything else, you're going to stagnate. And the professional world is going to keep moving and the financial world is going to keep moving  and you're going to be sitting there typing at your computer thinking you have, you know, no options. But you always have options! You just have to be brave, you have to ask questions. Keep your mind open and keep your options open and don't limit yourself to one job. Remember to hit the subscribe button or go to for more. We'll see you soon, bye!