I've been doing freelance work for nearly 30 years, sometimes with a regular job and sometimes without. Freelancing can be a fun way to go, especially if you want more control over your personal time. But it also means having to handle all aspects of your business, such as marketing yourself for your next gigs, taking care of your taxes (in Sitka contract workers have to pay sales tax while there is no similar wage tax burden on staff employees), etc. 

You also can end up at the mercy of your technology infrastructure. Last week we had a citywide Internet outage in Sitka for most of the day, and I had a grant due at 5 p.m. with the only way to submit the grant being online. As 4 p.m. rolled around and still no Internet, I frantically tried calling the contact person for the grant to explain the situation (hitting voicemail). Luckily, the Internet reconnected in time for me to get the application in, but this is the fourth major outage since this spring.