Considering self-employment? Things to think about before quitting your day job

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Make a solid financial plan before you do anything drastic.

© Helen Davies/stock.adobe.com, © carballo/stock.adobe.com; Photo composite Encyclopædia Britannica, Inc.

Many people dream of leaving the rat race and working for themselves. After all, you gain the ability to set your own schedule, the ability to charge what you think you’re worth, and the freedom to wear what you like. But consider the things you might give up, such as a predictable, steady paycheck; health insurance; a match to your 401(k) contribution; and even day-to-day watercooler conversations with coworkers.

Is it all worth it? Here are some things you need to consider before turning in that resignation letter.

A good way to prepare yourself for leaving your current employer is to develop a side hustle. With the security of your full-time job and its paycheck, you can take the time to develop your strategy, hone your skills, and build a client base (or a follower base, if you’ve joined the influencer economy). Once you feel that your income is going to be enough to support your financial goals, leaving your current employer might become an option.

If you start selling a product or service on your own without filing any paperwork with the state, you are running a sole proprietorship. You’ll likely buy business supplies with your own money, run your business out of your home, and make all business decisions yourself. If your business grows and you gain a partner or hire employees, you’ll need to file appropriate paperwork with your state and follow rules and regulations.

If you’re performing services rather than selling something, you’re an independent contractor (sometimes called a 1099-NEC contractor) to your customers. The IRS defines an independent contractor as someone whose customers have “the right to control or direct only the result of the work and not what will be done and how it will be done.” So if you’re a writer who submits articles for publication or a landscaper who mows lawns, you are controlling what will be done and how it will be done; your customer only dictates the result of your work.

Self-employment income is sometimes steady. If you perform work for certain clients on a regular basis—such as accounting, a cleaning service, or another job with a predictable monthly work cycle—you may be able to bill the same amount each month so that you can plan your income and time your expenses accordingly. But often the number of items you sell or the amount of work you do is variable and unpredictable, affecting the money that comes in the door.

An emergency fund is crucial. Consider saving enough to cover at least six months’ worth of expenses, if not a full year. What will happen if your current customers or clients stop needing your services or products? Your income depends on your customers’ ability to pay you. So if there is a downturn in the economy, you might lose customers, or some might not pay you on time.

It’s more important than ever to make and stick to a monthly budget if you’re unsure how much money will come in. You may want to look at last year’s income to see if you can predict when you might receive money this year. If your business is new, try to predict income based on cycles in your type of business or jobs you have under contract.

As your business grows, you might have a sudden windfall one month—perhaps a big job or order comes in and the client pays on time. It could be tempting to reward yourself and spend a big chunk of that money. Instead, plan your entire year to decide if this one month needs to pay for the rest of the year’s expenses or if you have other income on the way.

All expenses and income pertaining to a sole proprietorship are reported on Schedule C, flow up to your Form 1040, and are taxed at your personal tax rate. You also owe self-employment tax on your business net income through Schedule SE.

One benefit of owning a small business is the qualified business income deduction (also called the 199A deduction), which will reduce the taxes you owe when you complete your Form 1040. Qualified business income (QBI) is calculated on tax Form 8995. The deduction is calculated as 20% of QBI. The deduction can’t be more than 20% of taxable income minus net capital gain (usually reported on Schedule D). This deduction is currently in effect through December 31, 2025.

If you receive payments from customers for services you performed as a contractor, you may receive a Form 1099-NEC, Nonemployee Compensation. If your customers or clients pay you via PayPal, Zelle, or credit cards, you may receive a Form 1099-K, Payment Card and Third-Party Network Transactions. Use these 1099 forms to help total the income you made for your business.

As a self-employed person, you don’t receive paychecks, so taxes aren’t withheld for you. You’ll need to make estimated tax payments to the IRS, and possibly to your state department of revenue. The IRS supplies Form 1040-ES to help you figure out your estimated taxes. Note that these taxes are due quarterly, and penalties and interest are due if payments are not made.

As a freelancer, even though you won’t get a company match from an employer, you’ll be eligible for Social Security when you retire. You’ll be reporting your wages to the Social Security Administration (SSA) when you file your tax return and paying into Social Security via self-employment tax. When you calculate the savings you’ll need for retirement, you should include your estimated Social Security benefits.

To boost your retirement savings, you can also contribute to other retirement savings plans:

As you begin to develop your home business, you may find that you put in more work and hours than you ever did working for a company. But because it’s your own business, you keep the full benefit of your hard work.

Don’t undervalue other people in your quest to work alone. Reach out to others in your field. Attend conferences. Stay connected so you can keep current with trends and technology and build your business.

After all—at least according to some fortune cookies—if you love what you do, you will never work a day in your life.