Be Friends with (Your) Benefits: Part 3 – Freelancer Edition

Most people look for a full-time gig for the amazing benefit of a steady paycheck and assurance that it will keep coming every month. But there are tons of other benefits that you get from full-time employment that you either need or want … things like health insurance, retirement accounts and reimbursements for work travel. So if you are a freelancer you probably want all those things too, right?

This post is full of tips for those of you that don’t have full-time work and a few ideas for how to still get benefits. I’ve split it up by category of what you’d normally get a full-time job.

Health Care

It is really important to have health care, not only because you might need it and medical bills are crazy expensive.. but also because it’s the law and you’ll get dinged at tax time if you have not been covered.

If you are under 26 years old, score! You can still be on your parent’s health care plan. It gets a tad tricky if your parents are retired or live in another state, so just chat with them and their provider to figure it out.

If you are over 26, check out this article from Time for do’s and don’ts regarding your own plan.


Lot’s of full-time employers set up retirement accounts for you and maybe even a pension plan. But that does not mean you can’t do it yourself if you are a freelancer. Almost all banks will help you set up an IRA account and you can chat with someone about where that money should be invested. Yes, what’s in your retirement account counts.

My husband has his set up through Wealthfront, which is a robo-advisor, and we love the low management fee (you get an extra 5k managed for free when you sign up with my link). With any account you choose, it is super easy to set up auto deposits each month, every little bit helps and the earlier you start the better.

Tax Time

It is hard working from gig to gig and not knowing when you’ll get paid and for how much. My biggest piece of advice is to set yourself up to live on the lowest amount you could be making and save, invest and put away anything extra so that you can use it later when you have a slow period.

Also, keep careful track of your invoices, income, and expenses. I use a google doc to track all of this for my side hustle gigs and at the end of the year, it is easy to tally up what my deductions can be for tax time. Be sure to check the tax documents carefully from your freelance/side hustle employers. I once had a company send me a w-2 saying that I’d been paid $3000 more than I had actually been paid. You really don’t want to be taxed on income you didn’t make! Luckily, I had careful notes of all the checks that had come in and straightened it out before submitting my taxes.

For those of you with full-time gigs, be sure to check out my previous posts about open enrollment (part 1) and navigating your way through your benefits manual (part 2).