So You Quit Your Job to Work for Yourself, Now What?

By Sarah null on January 25, 2022Last updated March 15, 2022




So you quit your job to work for yourself, and now you need benefits. Good news—you’re not alone. At least one in four workers quit their jobs in 2021. Even better news—it’s become easier than ever to get set up with personal payroll and benefits. You can get set up with everything you need to be financially secure on this new path. It’s simple to take care of taxes and benefits like health insurance and retirement—even if you don’t have an employer providing them.

Take the stress out of tax time with personal payroll

If you left a traditional 9–5 that withheld your taxes for you, then it’s on you to withhold and make payments at the right time. Don’t stress, you have the tools to handle this on your own like a pro.

Start by figuring out where you earn income from and then set up your own personal payroll. You may have more than one source of income, so using a system that tracks all the places you get paid will make estimating your taxes much more simple. Next, set up withholding so a percentage of each payment automatically gets set aside for taxes, and then you’re ready for tax day without even thinking about it. 

You can also automatically make your payments to the IRS quarterly. If you’re new to independent work, you might be new to quarterly payments. Here’s a little bit more information about how to do your taxes when you’re self-employed

Stay insured and save on premiums

Leaving a job that offers you health insurance can be scary. But just because you’ve quit your 9–5 doesn’t mean you have to or should go uninsured. In fact, thanks to new laws and tools, you have more options and support than ever before to get the best plan at the lowest price. 

Start by shopping around to see which plans fit your budget and lifestyle. Now that you work for yourself, you can find available plans through the Health Insurance Marketplace during the annual Open Enrollment period. If you miss the Open Enrollment period and you’ve experienced a qualifying life event, like losing coverage from a job loss, getting married, or having a baby, you might be able to enroll in a plan during a Special Enrollment period. 


There are also a few other options to consider. For example, if your spouse or domestic partner has insurance through an employer, you might be able to be added to their plan. And depending on your income and/or age, you might be eligible for programs like Medicare or Medicaid. Also, if you were covered under your former employer, you have the option of temporarily keeping the same employer-based health plan—usually for up to 18 months. But keep in mind that the plan will be more expensive since your employer is no longer contributing to the monthly premium. 

Did you know that this year 4 out of 5 people can get a marketplace plan for $10 or less? So as you’re shopping around, make sure you get all the savings you’re qualified for on your monthly premium payments. Just enter a few details and find out how much you can save here. Once you’ve found the right plan for you, click that enroll button! Don’t forget to also enroll in a vision and dental plan, if that’s something you’re looking for. 

Lastly, make sure to automate those premium payments, so you never have to worry about missing one. And if you’re thinking about going uninsured…think again. The average medical bill can be up to $2000, so it is recommended to enroll in a new plan as soon as possible to prevent unexpected medical costs and big bills.

Set future you up for success

No matter where you are in your career, setting yourself up for retirement can seem like a daunting task. But now that you’ve invested in yourself, it’s a good time to make sure you’re investing in your future too. 

Get started by setting up an Individual Retirement Account (IRA). IRAs are an easy and versatile way to put away pre-tax dollars for retirement. And the best part? The account is yours! No matter what you decide to do in the future.

Depending on which provider you choose, the actual steps to open an IRA may vary a little bit, but overall the process is pretty straightforward. First choose which kind of IRA you want to open (Roth or Traditional), and input some standard details like your name, contact information, employment information and social security number. 

Once you’ve set up an IRA, choose a portfolio that you can just “set and forget”. 

Next—and this is key—automatically set aside a portion of your income into your IRA every time you get paid and let your money work for you. 

Avoid burnout and set aside funds for time off

Being self-employed doesn’t mean that you have to work 24/7, 365 days a year. Time off is healthy, and helps prevent burnout. Working for yourself, you have flexibility. lan ahead by automatically setting aside a portion of your income every time you get paid. That way, you know you have enough set aside when those holidays roll around or to cover any sick days or gaps in work.

Future-proof your career with Catch

The way we work is changing and as you take the leap into a new phase of your career, Catch is here to future-proof it for you. We cover taxes, health coverage, retirement, time off and more—all for free—so you can focus on your passion. 

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