I've been freelancing full-time since August, both online marketing/PR & comic book work. Here are some things I have learned about being a freelancer:
1. Your paycheck may be bigger overall. But remember, you have to put away money for taxes. I knew a guy who'd do freelance work all year and then be shocked that he had to pay so much in taxes, like it was this magical, unfair sum tacked on to life.
2. On the subject of taxes: deductions deductions deductions. Keep your receipts. And an accountant may be worth every penny.
3. You will most likely have to cover your own medical insurance, but don't let that discourage you if freelancing is something you really want to do. There are options: cheaper emergency medical insurance that just covers hospital visits, freelancer union insurance, etc.
4. Line up your gigs at least several weeks in advance, if not a month. Think long-term strategy.
5. Don't depend on any one assignment as being your sole and regular bread-winner. Develop multiple streams of income. I not only have multiple freelance jobs, but I maintain a regular sale of stuff on eBay. The eBay stuff is not a lot, but it's something. Keep revenue coming in.
6. A comic book freelancer told me this once: save your money. Develop a cushion. Because there might be times when you can't find anything, or are down to just one part-time thing and you need some help.
7. Maintain your relationships with your bosses, business prospects, everyone. You are your own PR agency. Network.
8. Don't take every job that is offered to you. Some jobs, after some consideration, might be more trouble than they're worth.
9. Don't be surprised if you end up working more hours as a freelancer than you ever did when you had a nine-to-five.
10. Take a walk outside every once in a while. Set up activities "after work" where you completely leave your work station. Do this every day.
11. Don't let people tell you that you aren't really working just because you work from home. But by the same token, admit when you're slacking off (at least to yourself).
12. Keep detailed documentation on the hours worked and what specific tasks you accomplished.
13. I find that getting ready in the morning and doing my hair/wearing a suit really helps get me in the right mindset to work -- especially for the marketing/PR work. I can't work in pajamas, I can't talk to clients in pajamas. Your mileage might vary on this point.
14. Especially if you're a woman: don't get sucked into doing lots of housework during your freelance workday. Yes, you are working on Internet marketing all day on your laptop in your living room. It's still work. You're not lazy. Scrub the floors another time.
15. Freelance work makes you realize that every hour of your time has a price tag on it. For my marketing/PR work, that starts at $25/hr. Knowing this, you might ask yourself if certain tasks might be outsourced to other places as to better make use of your time. Take laundry. Two weeks' worth of laundry costs me, total, almost six hours at the laundromat and $15. I can take it to be done by other people at the laundromat across the street and it will cost me $25. And they fold way better than I do. But I feel guilty about it; that I really should be doing my own laundry. But then, can I justify spending that big a chunk of my time doing the laundry when I could be working or researching? I still haven't quite figured this one out. I'm very tempted today to just take the laundry in and do it myself. Also, I get skeeved out at the thought of strangers washing my dirty underwear.
16. Just because you are now a freelancer does not mean you automatically have time for dozens of new hobbies and projects that make no money. It's not a holiday.
17. Diversify your skill set. Have at least two types of skills that you can use to get work. Make sure that one of those skills is really basic and elemental and might survive a recession.
18. Freelancing is awesome because I have my cat with me all the time. :-)
19. Sometimes you have to lock down your Internet and just focus on the one site you're using for work, because the Internet is your biggest potential time-waster. The Internet is That Which Eats Your Brain. Because I work with social media with clients, this becomes even more of a challenge. If I'm Twittering for a client on their account, what's the harm in checking my own account? Now I'm flipping between Twitters and have literally 16 tabs open. So all the personal stuff has to be minimized on my computer, or even better, completely clicked off -- at least for the duration of my assignment.
20. Time management -- it will make or break you. This has been the most important lesson.
