Here's a question from a Twitter follower who's striking out on his own:
I usually avoid tax questions, and for good reason: I'm not a CPA or tax preparer, so anything dealing with the specifics of a return, etc. is more than I'm qualified to answer. This, though, is a general question and important to answer since so many people are going through career transitions and need to make similar decisions.
Your employment status shouldn't necessarily dictate whether you do your taxes on your own or hire someone. You need to consider the complexity of your return and how confident you are that you can do it without errors that might hold up a potential refund or trigger an audit.
Even though I held only one full time job in most years, for example, I still used a CPA to file my taxes. It cost more than just using Turbo Tax, but I've never been comfortable enough with the dizzying tax forms to want to do even a basic return myself.
If you're uncomfortable with filing taxes on your own, hire a qualified CPA or tax preparer. It will save you headaches, and possibly money down the road. Thanks for the question.