How to Be Self Employed While Working 9-to-5

Going from your full-time job to owning a business can be challenging, but you can do it, like this entrepreneur at his standing desk.

I remember sitting at my desk, tucked in a cubicle, staring blankly at Microsoft Word. The office was quiet, uninspiring, and downright depressing.

Most of the staff members had worked at the company for decades, not because they believed in its mission, but because it was a job—one that paid the bills and was easy to do.

I had to get out.

I began to dream of other career paths. I watched episodes of Sex and the City and fantasized about living out Carrie Bradshaw’s writing career, pitching to all sorts of publications. She had editors she reported to, sure, but she was her own boss. Why couldn’t I write for myself? Wasn’t my work worthy of being published under my own name? And how did Carrie Bradshaw make enough cash to live her fabulous lifestyle? (By the way, I still have no idea.)

The seed was planted, but I didn’t make the leap from 9-to-5 to full-time self-employment until nearly 10 years later! I know, you may be asking yourself why I waited so long. The truth is this: I wasn’t ready, financially or emotionally.

Now, don’t get discouraged. For most people, it doesn’t take that long.

And if you know what to do, it’s easier to start sooner. That’s why I put together a list of steps to help you figure out how to be self-employed. I’ll go over everything from gauging if you’re ready and promoting your business to setting up self-employment business protection and finally taking the leap.

It’s less scary than you think. Let’s go!

How to Be Self-Employed in 5 Steps

1. Figure out if you’re really ready to make the leap.

The truth is, it shouldn’t have taken me 10 years to go self-employed full time. I put it off for longer than I needed to. Deep down, I knew I was ready earlier. Here are some signs you might be ready now:

You’re dreaming of becoming self-employed—during your 9-to-5 job.

As I mentioned, I used to imagine myself pitching to publications. Having an imagination is fine—it certainly comes in handy when writing. But when it comes to daydreaming about being self-employed so much that you ignore your actual work, it’s a glaring clue it may be time to take that leap to self-employment.

If you haven’t already done so, take stock of how you’re spending your time at work. Are you working on your set tasks and daily responsibilities—or are you daydreaming about the life you could be making for yourself in self-employment? If you answered “yes” to this, then it’s one sign you may be ready.

When you’re outside work, you spend free time working on your side business.

Another clue you’re ready to become self-employed is that you spend your highly valued free time doing work for your side business. And you don’t even mind it. In fact, you love spending the free time you have on your side hustle. I used to rush home, only to turn on the computer and design my own logo. Nerdy? Yes. Typical of an entrepreneur? Also, yes.

Think about the last time you had free time. What did you do with it? If you’re looking back on your calendar and seeing that the majority of your free time is spent on your small side business, that’s another clue you need to look into how to be self-employed.

You’ve acquired important skills needed to run your business.

During that 10-year span, I worked under ruthless editors, hired freelancers, and spent time as a marketing manager. That time period gave me invaluable skills that I rely on today: time management, stakeholder relations, and content strategy—to name just a few. These are the same skills that I knew would come in handy one day when I became self-employed.

The people I wanted as clients would be needing my skill set, and I felt confident that I could do the job well for them. When I thought about leaving my job for self-employment, those skills helped me feel like I’d have no problem taking on projects that would be required in my business.

You have your eyes on potential business customers for your side gig.

To make the leap, you don’t have to officially land a customer, but it does help. You may find yourself thinking more about your customer pipeline. Is there interest in your product or service? Is there a need in the market? Who would be best to sell your services or product to? Where would you find them, or how would they find you?

These are the sorts of questions I was asking myself before I became self-employed. When I saw a company advertising that they needed a writer, I wanted to be the one to pitch them and apply for the task. I started daydreaming what kind of posts I could put on social media that would help potential clients find me.

If you’re brainstorming these sorts of questions and scenarios, then you may be ready to take the leap to self-employment.

You feel like the pandemic has made “now” the right time.

Among the effects of the Covid-19 pandemic was an increase in small business starts. A friend of mine was behind one of those new businesses. She was an art director for a company’s in-house creative department. The job stressed her out. However, she liked to bake and found it to be the perfect stress reliever at night. She often made themed cupcakes, and brought them into work. Her colleagues devoured them – and marveled at their design.

Then the pandemic hit and she was forced to work from home. Cupcake co-worker party time was over. Except it wasn’t. Some of her co-workers offered to buy her themed cupcakes for birthday parties and a side-gig was born. Then, boom, she lost her job. Guess what she turned to full time? You got it, a cupcake business.

She admits to this day that she would have been too scared to leave the stability of her job to start her own business had it not been for the pandemic. The pandemic, she said, gave her the opportunity—and the push— to start her own business and do what she loved.

Perhaps you have friends with stories like this. And perhaps these stories have started to make you think that now is the time. If so, keep reading.

2. Know what your manager thinks while planning to become self-employed.

Having a self-employment business on the side of a full-time job is a lot of work. It takes a lot to balance all the responsibilities and still produce good work. While you’re still at your full-time job, it’s important to understand what boundaries your employer has regarding outside work.

For example, when you are hired, some companies require you to sign an agreement that you won’t work on outside work that could be a conflict of interest. Other companies may be OK with your being self-employed, as long as it doesn’t interfere with your work and your self-employment clients aren’t competitors of theirs.

Sometimes this agreement may include rules about the equipment they lend you (like a laptop, extra monitor, company cellphone, etc.) and not using it for personal use.

For example, if you have a work-issued laptop or cellphone, be careful to not use them when doing work for your side business—keep the two jobs and the things relating to them separate.

Finally, will your full-time employer require you to give them a notice within a specific time period before leaving? Many companies have their employees working at-will, but you may have also agreed to give your employer a two-week or 30-day notice before you leave.

Even if you don’t plan on leaving for a while, it’s smart to check those details now. If you’re not clear on what your employer requires, we recommend checking with a lawyer for legal counsel and advice.

3.Make sure you’re protected while becoming self-employed.

One thing that you may not have thought about when it comes to how to be self-employed is preparing to protect and fund your business. When you first become self-employed, you likely won’t be making a profit right away.

It also doesn’t mean that if an accident happens, you’d immediately have the support of a company like the one you’re leaving behind. For example, let’s say you make a mistake while working on a project at your full-time job. Your company’s liability insurance policy could back you up as an employee if a claim was made. Your team could also help to fix things.

But once you’re self-employed, you’re on your own. So it’s important to consider how you’ll stay financially protected and funded while self-employed.

Funding your new business.

Every business is different. As a writer, I just needed a computer. But if you own a landscaping company, barber shop, or you work in farming, for example, you’ll need equipment. For example, my cousin owns a successful maple syrup business in Vermont. I know he’s taken out loans for equipment—those trees don’t tap themselves! Sit down and think about how owning a business will impact your finances

Looking into that impact means looking at how much you estimate each project will cost you and how much money you’ll make from it. Look at your spending budget. What can you cut back on

Consider what is and isn’t necessary for you to run your business. If there’s something that you don’t really need and can cut, consider making the sacrifice. After all, you can always reconsider using that item or service again later on in your business journey

Once you do that, map out how much money you need to get started. This may be a bit different if you’re becoming self-employed by yourself versus if you have a family or any dependents.

If you do have a family, I suggest discussing this with them, because it will impact them, too. Be sure to include any rent, utilities, and other monthly expenses you have (like life insurance or a medical bill payment).

Be detailed about your financing needs and make a plan for obtaining funding if you think you’ll need it. You may think you won’t need funding until later, when your business has grown more. But it’s a good idea to look into funding now. We suggest you consider researching what loan may be best for your business now, because the application process can take some time, depending on the type of loan.

Details of funding you plan to seek should be included in detail on your business plan. If you need a significant amount of cash, you can try

  • Talking to investors. If an investor buys into your idea, you can get a significant amount of money—and fast. An investor doesn’t have to be with a capital firm—they could be a member of your family or even a mentor who believes in the future of your business.

The downside of this strategy is that investors offer funds in exchange for ownership of your company or with specific terms noting interest and repayment deadlines. Depending on how much money they put down, you could lose control of your business and its direction, not to mention have the added stress of interest payments.

  • Taking out a small business loan. A lot of small business owners go this route because it’s simpler and less complicated than dealing with investors. Some banks even have loans specifically tailored for small businesses. People go this route to keep control of their original idea. But loans come with a price, too. You’ll need to pay it back within a certain time frame—plus interest.

The route you take depends on your company, its goals, and your timeline. Either way, there’s a bit of risk, but the reward can be great. One of the benefits you currently have is the luxury of a bit of time to figure this out while you’re at your 9-to-5 position.

Protecting your new business.

Speaking of risk, it would be risky to get farther down your path without doing what you can to protect your business upfront. If you can’t tell already, you’re about to spend a lot of time, energy, and money. And other than the latter, you likely can’t get a lot of that back.

A great way to protect your business and all the work you put into it is to invest in business insurance. It may seem like too much to bother with for a new business, but getting coverage is easier before you need it.

Think about car insurance. Depending on your state, most drivers purchase car insurance when they buy or lease a car, which is typically required by law. Fingers crossed, nothing goes wrong, but chances are that if you have an accident and need repairs to the car, you’ll be glad you’re covered by insurance.

This same line of thinking applies to business insurance. It’s there to protect you in case a client makes an accusation and sues you for a mistake or property damage that occurs during a project. When you start the project, you can’t predict if something like that will happen, so you’ll be glad you have coverage to back you up.

Different self-employed businesses need different policies, depending on what types of risks you’re taking. A general liability policy can help protect you in the event of any third-party injury (e.g., if a customer or vendor gets hurt), property damage, or accidents. A professional liability policy can help protect you in case a client claims you were negligent with the work you did for them.

Each kind of coverage could help protect you if you get in legal hot water, by helping with claim coverage and legal bills. And those can add up FAST

Since each business is different, we can help you find the right self-employment insurance policy that works for you and your business. You can compare quotes from top carriers in the nation by using our free quote comparison tool. But if you’d rather talk to a human, you can call to speak to a licensed insurance agent at 844-654-7658.

Get Insured in Under 10 Minutes

Get an affordable & customized policy in just minutes. So you can get back to what matters: Your business.

4. Begin your self-employment work now, whether it be a service or building a product.

Your business can’t succeed without something to sell. I’ve seen too many startups trying to sell a product that isn’t yet built. You may have, too—a business may promise what a product or service will look like in the future, before it’s been tested or a prototype is created

It doesn’t usually work. You need something to show potential customers, even if it isn’t your final version. In the business world, this is called the Minimum Viable Product (MVP), meaning that it’s what you have that can be sold right now.

For me, while I was thinking of how to be self-employed, this part came pretty easy. I provide a service (writing), and I have years of experience fine-tuning my trade.

If you want to open a store or will be selling a specific type of product, the process may be longer for you. And that’s OK—because you still have your full-time job supporting you financially.

Even though I had years of experience writing, I still thought through exactly what type of writing I would offer and how much it would cost. I created “packages” of my services that potential clients could sign up to hire me for.

Remember, your product doesn’t have to be perfected into its final form—I’ve definitely revised what goes into my writing packages over time. My initial MVP was the first package I offered to potential customers. Later on, once I learned how customers responded to that package and was able to gauge how I felt about it, I was able to make changes to my offering.

It’s a good time to begin thinking about how to get your product up and running quickly, while you’re still working your 9-to-5 job and have a steady paycheck.

You don’t want to spend years building a product before you can get sales. That said, if it will take years before your product is ready at the level you envision, this is an even more compelling reason to seek support from investors or to take out a loan.

You may end up needing investors to help get funding for the tools you need to create the product, or funding to afford specific services you’d need to use to offer the service you’d like to (like a specific software license).

The energy it takes to create your initial product or service can take a toll on you. As business owners, we invest a lot of emotion into what we do—not only is it our livelihood, but it’s usually one of our greatest passions.

I know it’s easier said than done, but be sure to be mindful of your health. Your work will be even more stunted if you become burned out, so there’s no need to rush.

5. Promote your business along the way!

Don’t be afraid of promoting your idea or skill while you still have your 9-to-5 job. Sure, you might risk your manager hearing about your new business venture. If that happens, you can position it as a hobby or explain that you’re developing your professional skills

Be sure to make it clear to your boss that your full-time job is separate from your side business—I’ll give you a tip that can help you separate the two a bit further in this step.

One of the first ways to promote your business is to create a website. It doesn’t need to be fancy right now (kind of like your minimum viable product). You simply need a place to tell potential customers what you do and how to get in touch with you.

You can start with a simple, one-page website with a photo, description of your service or product, and contact information. Later on, when you’ve made enough money to invest into improving your website, you can make changes.

There are website platforms out there like


, WordPress (note that the .com is different from the .org—you want the former), or Wix that make it easy to get started. Each has different templates that you can use to easily build your website, without being a skilled developer or designer. And once you’re up and running, you can use ideas from our FREE 75 Website Tips article to make improvements (hint: bookmark that article now!).

Once you have a website, you can share the link, details about projects you’ve worked on, and expertise about your trade on social media. I know—it’s not what you may want to be doing. I had the same thought

I want to be writing for clients, not working on my website or social media posts. But having an online presence pays off—72% of consumers search for a business online before visiting their store. You can commit to having a presence on one or two social media platforms; you don’t need to do it all.

Finally, promote your business in person. Whether it’s at farmers’ markets, conferences, or other community events, meeting people in person can help kick off word-of-mouth marketing, which is one of the strongest ways out there.

While you’re promoting your business, be sure to stay mindful of your full-time job. Remember how I mentioned earlier that I had a tip about keeping your full-time job and self- employment separate? Here it is!

When it comes to social media, there are tools out there like Sprout Social and Buffer that help you schedule social media posts ahead of time. I suggest taking time on your off hours from your full time job to schedule social media posts for your side business.

This way, you won’t have to take time away from your full-time job and can make sure you’re still promoting your side business

It may be scary putting your work out to the cyberworld, and I get it—it’s a vulnerable place to be. But the truth is, you should be proud of your business venture. Customers want to work with a business owner who is confident about what they do, so don’t be afraid to shout it from the cyber rooftops.

Take the Leap by Becoming Self-Employed—There’s Never a Perfect Time!

Well, this is it: the sixth unofficial step of how to be self-employed. When it’s all said and done, there’s never a perfect time to start self-employment. There will always be an excuse to hold back. Try to ignore your long list of reasons. If it were up to me, my list would be never-ending.

Owning a business isn’t for the faint of heart, and there is risk involved. Eventually, you’ll just have to take the leap.

Remember, taking the leap doesn’t mean you have to start off with a full roster of customers. You can go slow with one project at a time at first—don’t let not having a line out the door hold you back.

As a fellow business owner who struggled thinking of how to be self-employed for far too long, I’ll tell you: I wish I had made the leap earlier. It’s satisfying to develop my own product, choose my customers, and grow my company on my own terms.

I’ve also never worked harder. I’m more motivated, energized, and excited when I go to work. When I wrap a project with a client and am able to deliver work I’m proud of—that feeling is entirely worth it.

So if you’re ready, go for it. What’s the worst that can happen? You may realize you’re not ready and gain an incredible learning experience. The best case? You start your own gig and never look back.

Good luck!

Emily Thompson

I earned a B.A. in Journalism from the University of Wisconsin at Madison (go Bucky). After realizing my first job might involve carrying a police scanner at 2 am in pursuit of “newsworthy” crimes, I decided I was better suited for freelance blogging and marketing writing. Since 2010, I’ve owned my freelance writing business, EST Creative. When I’m not penning, doodling ideas, or chatting with clients, you’ll find me hiking with my husband, baby boy, and 2 mischievous mutts.

Emily writes on a number of topics such as entrepreneurship, small business networking, and budgeting.