Money Moves to Make (and Questions to Answer) Before Taking Your Side Hustle Full-Time


You’ve been working on your side hustle for a while now to generate some extra money on the side. It’s always been something fun and enjoyable — and you’ve gotten really good at it.

So good, in fact, for the last 3 months you’ve made more than you make at your day job! And you’re ready to devote yourself to this budding business full-time. Can you make the transition?

First, look back at your side hustle income. How long have you been at it, and how much have you made total? Are you making enough to pay taxes, business expenses, yourself (via retirement savings and investments), bills and living expenses, and have a little left over for discretionary spending or to reinvest in your business?

Were those last 3 months sustainable or was there a reason for a big bump in earnings? Is your income seasonal, meaning you need to plan for slow times by saving more of your income when you’re busy and making more?

These are the kinds of financial questions you need to ask yourself before you hand in your notice at work to leap into a life of self-employment.

There’s not necessarily a right and wrong answer here — but it’s important to think through these things and gather the information and details so you can make the best decision for you when determining if it’s time to go from side hustler to full-time entrepreneur or freelancer.

Here are some other questions to consider and the money moves you need to make before you make a change.

How and When Will You Pay Yourself?

It’s nice to generate an income on your own and be in control of your own salary. But that also requires discipline. Just because you made an extra $2,000 this month doesn’t mean you should transfer it to your personal checking account and enjoy a little shopping spree.

Decide how much you’ll pay yourself each month and stick to it. You can pay yourself weekly, twice a month, or once a month. Anything extra is profit in your business and can go toward investing in your work, savings, or retirement accounts.

Who’s Taking Care of Your Future?

Speaking of, when you go from side hustler with a day job to full-time entrepreneur, you don’t just lose your steady paycheck. You give up access to employer-sponsored retirement accounts too.

That doesn’t mean you’re out of luck when it comes to saving for your future. It just means you’re responsible for funding your retirement accounts on your own. Make sure you set aside a percentage of your earnings to contribute to an appropriate savings vehicle, like a traditional, Roth, or SEP IRA or a Solo 401(k).

Do You Know How to Budget on Variable Income?

Most people who freelance or own their own business don’t make the exact same amount month after month. Not only does your income rise and fall each month, but your expenses might too.

Before you strike out on your own, make sure you can budget on a variable income.

That means knowing the difference between your truly necessary, non-negotiable expenses (like your rent or mortgage, utilities, and groceries) and expenses that you usually pay every month and make your life a little better, but aren’t essential to your wellbeing and survival (everything else).

You also need to be prepared to cut back on anything that’s a want or a discretionary purchase if you experience a month where you make less than usual.

Do You Have an Emergency Fund?

Regardless of the type of work you do, you need a cash reserve set aside to help cover emergencies and unexpected expenses. The general rule of thumb says to put 3 to 6 months’ worth of expenses into an account you can easily access should you need cash immediately.

But when you want to go from side hustle to full-time self-employment, you take on more risk because you leave a steady paycheck behind. That can make your cash flow more volatile, increasing your chance of getting stuck with a hefty bill in a slow period where you made less than expected.

Before you go out on your own, make sure you have at least 6 months’ worth of expenses stashed away in your emergency fund. You may also want to build a cash cushion in your business checking account, since you may experience not just personal emergencies but professional ones, too.

Do You Want to Buy a House in the Next Few Years?

Plenty of people take a side hustle full-time because it’s more lucrative than their day job. They have big goals to hit, like buying a house. But unfortunately, going into full-time self-employment in order to do something like that can backfire.

That’s because mortgage lenders require 2 years’ worth of tax returns as proof of your self-employment income in most cases. Even if you have more in the bank thanks to your side hustle turned full-time business, you may not get approved for a loan until you have those tax returns showing your official self-employment income.

Think through your goals and consider how switching from employment to self-employment may impact your ability to reach them — whether it’s through a technical issue like needing to build a history of tax returns showing self-employment income or through practical ones like the possibility of a cash flow that fluctuates from month to month.

Are You Prepared to Pay Taxes?

Taxes get more complicated when you work for yourself full-time and no longer make any kind of W2 income.

You may need to pay more than you did when you were an employee making 1099-MISC income on the side. And depending on your situation, changing your filing status (from a sole proprietor to an S-corp, for example) may make sense.

Before you head off on your own, make sure you have a good CPA lined up who can help educate you about your business taxes.

What’s Next for Your Financial Plan?

On a similar note, plan to speak with a fee-only financial advisor who understands the ins and outs of self-employment before you make the leap.

Changing up your career path can lead to changes in your financial situation. Talking through the possibilities now will help you leverage your resources and capitalize on any opportunities that might come your way.

It’s all about being proactive to put yourself in the best position possible to enjoy success — both in your new full-time venture and your financial life.

Mary Beth Storjohann, CFP® is an author, speaker, and financial coach who takes a fun, no-nonsense approach in working with individuals and couples across the country, helping them make smart choices with their money.

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