After hearing episode 73 of "In Beta" and reading the blog post "Your Career is a mess" from Roy Bahat I had to share my thoughts on this perceived and real problem. Gina Trapani talked about the current system not being ready for the modern free-lance multiple job situation. She was frustrated that the mortage broker was confused about her income/employment situation. I was actually surprised to hear this struggles and I felt for her. I thought as the co-founder of ThinkUp and Lifehacker she already followed some basic principles of getting "On your own". I understand that every country/state has a different taxation system which allows individuals to provide free-lance work - but most of those systems are aimed for a temporary solution - student work, the famous in-between jobs. So is the system broken or out of date?
In my opinion no - if you want to stop working for "the man" go for it, but do it in a system friendly way.
Once you are sure you like working on your own and you can make a living out of it - create a business. I mean incorporate a llc, small business, whatever fits you. This way you can "hire" yourself and your records will be cleaned up. This can happen after a couple of months, but should IMO happen after a year.
You will become a "business owner" - something that not only sounds respectable, but also gives confidence to your business partners. It sounds great to have a business for 10 years (most businesses don't live that long), certainly better than being "self-emplyed". You personally have just one income source (on paper) but can have as many as you like in reality for your business. Income sources become clients and all that explaining your family what you do just becomes so easy - "I own a business. A business that offers "service xyz" to websites, businesses, people ..:"
Some people, especially in the mobile app space, tend to create a business for every new app they launch. This makes it easier for them to sell the whole operation if they need to.
So bottom line: Commit to your new career in your own business and incorporate.