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Hello smallbusiness! I've got a bit of a situation and plenty of conflicting advice from well-meaning friends and family and was hoping maybe someone on here with experience could help sort me out. Here's my situation: I live in the United States but spend most of my time traveling internationally. I don't have any job or income reported. My parents claim me as a dependent on their tax returns (I'm pretty young). About a year and a half ago, when I was still in school, I started doing some freelance writing. At the time it was just a bit of a hobby and I was only doing it for people I knew personally. It's something I've always enjoyed, and I have way too much free time anyway, so I ended up doing it quite a bit, taking payment in cash and keeping no records. Fast forward to the present: I still have a lot of free time, and I've increased the amount of writing I'm doing by a ton after I started advertising online. I take payments through PayPal and I'm getting a little bit worried about potential tax problems. When I was making less than $1000ish a month it wasn't a concern but now I'm getting 2-5 times that most months.
Basically, I've got two questions. First (and easiest) is there any good free or inexpensive software for tracking assignment due dates and billing amounts? Ideally I'd like something that allows me to easily track A) when I made the contract, B) when I sent the invoice, C) when I received payment, and D) the name of the client. I've been using Excel to track some of this over the past few months but it's clunky and frankly I've never liked Excel. Is there something with a nicer and more intuitive UI I could use? Ideally it would run on OS X and Windows - IOS and Android apps would also be a plus but unnecessary.
Second question - how do I start reporting taxes? I'd rather not deal with an accountant or anyone else. I'm going to start researching the most efficient way to start a legal small business. I'm not opposed to paying a fair share but I would like to avoid back taxes for the past year and a half - especially because I don't have any records going back past the last three months, aside from PayPal records. If I were to start a business now and pay taxes on 3-4k a month would it look suspicious and would I be at a significant risk of getting audited or something for the past year?
Anyway, thanks for any input. I know I should probably be more proactive and just Google it myself - and I will do that - but it would be great if anyone had any information to start me in the right direction. This is all fairly new to me and seems big and imposing so any help is appreciated.
EDIT: Ooh, one more bonus question I forgot. Most of the money I make is made when I'm out of the country. Should I look into the Foreign Earned Income Exclusion? I'd say something like 60% of my revenue is made while I'm out of the USA, but paid by USA-based clients, another 20% I make from UK/Canada/Norway-based clients while I'm out of the USA, and the rest is made while I'm in the USA. Would any of that even be eligible for the FEIE? If it would make matters cheaper or easier (I'm sure it probably wouldn't) I also have a UK address/residence I could use.
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