Hi Jesse,
Freelance is tough - but it does help you gain broad experience, build portfolio and retain a pro-active mindset.
Overall I recommend joining an existing company. You can also do freelance to grow into an independent entrepreneur but if you present yourself that way I found that companies are less willing to hire you.
Design firms especially look for people who can develop bright ideas and execute them as well, with a good approach to work planning and specific expertise areas that makes them stand out.