No steady income. This will probably be the case in the beginning, depending on your preparation for this time. You might have prepared the best you could and been working the equivalent of 2 jobs at the same time, your ‘real’ job and your freelance work and have a steady stream of client. You could have done no preparation and jumped right into freelancing. Or like me, you could be somewhere in between. Regardless, it makes a lot of sense to have a financial cushion in order to give yourself peace of mind. I feel fairly comfortable knowing that I have 6 months worth of expenses in the bank, and a fair bit more in savings if needed. The plan is to not have to touch any of that and make it through client work, but in the worst case scenario, I have backup. Other ways of minimizing this risk is to have a strong contract, require a down payment before starting work and walk away from a client if your gut says no, even if there is the promise of good money.
No healthcare coverage. If you were getting health insurance through your employer, then it is a daunting task to figure out how you will keep yourself insured. I am lucky enough to be married to a supportive spouse that happens to be securely employed in a profession that will always provide insurance coverage. Most others will not be that lucky, so this is not something I can help answer. There is no easy way around it, explore your options, whether it’s the AIGA or some other professional organization, independent health insurance or something else- you will need an answer to this before making the switch.
Failure. Yes, you could fail at this freelance thing, but you can reduce the chance of failure if you prepare by making sure you can check all the boxes in the ‘requirements’ department. And remember, failure can happen anytime, whether you work for Bigshot Agency or yourself.