Man drinking coffee and working on his laptop.

How to Start Freelancing (Hint: Do It on the Side)

First things first. Where to begin?

Sure, you’ve got a day job, but those martinis and shrimp ceviche cocktails can add up fast. Enter freelance work. Extra dough to spend or save as you please.

Freelancing on the side is a safe– but not always easy– way to start a freelance business while still holding onto that steady source of income. If you’re considering going freelance full-time, try doing some of these things first.

Set some goals.

Do you want to become a self-employed freelancer so you can make your own path in life? Or are you just trying to get some more cash for your weekly massage habit?

Once you know what you want to do, you can make a plan and set a timeline.

Find your niche.

What can you offer that is slightly different or better than anyone else? Do you aspire to be the biggest banner-ad maker in the free world? Do you want to design e-book layouts for pharmaceutical companies? What about writing copy for law firms?

As unromantic as these options may sound, it’s good to figure out what you think you’d be best at and what types of clients you’d like to target. Then, do it better and harder than anyone else.

Bonus: It makes sense to find a niche, because you’ll get referrals from people who run in similar circles, and you’ll start to garner a reputation.

Get the official business stuff done first.

You need to make sure you seem super professional when you go freelance.

Get all your branding, website, and social media stuff up to par. Also, finalize any client materials, like on-boarding documents, legal agreements, and invoicing materials.

That includes making a better business card than anyone you know. (And getting used to handing it out.)

Get Business Insurance
Get Business Insurance

Make a portfolio site that dazzles.

Show your future clients what kind of work you are able to produce. This is one of the single most important things you can do.

Make it official with the government.

If you’re serious, you should register your business. You can enter the big, bright world of freelancing as a sole proprietor or you can start an LLC or S-Corp right from the start.

English, please?

Sole proprietor: This is a business entity that is owned and run by one person. There is no separation between that person and their business. So, if your business fails, your personal assets could be in danger.

LLC: This business entity has its own tax ID and its own assets, completely separate from you. This is great, because it limits exposure of your personal assets.

Subchapter Corporation, or S-Corp for short: With an S-Corp, income and losses can be included on the owner’s or shareholders’ personal tax returns. Not only do you have just one level of federal tax that needs to be paid, but you also have the protection of limited liability. Yay!

If you want your assets protected and easier taxes, it might be a good idea to set up an LLC or S-Corp.

How to handle (freelance) work at your (full-time) job.

Your boss expects you to be fully engaged while you’re on the clock. This can be difficult, especially when your personal email is only a click away. What if a client has emailed? If you don’t respond right away, will you lose the job? To help fight off this temptation, be sure to be upfront with your clients. If you know you won’t be available to connect at certain times, give them a heads-up!

Note: Don’t freelance while you’re on the clock at your job or use your employer’s tools or resources for freelance work. That can get you into trouble. (Also, make sure you’re not breaching your contract by taking on freelance projects.)

Lasso in your first clients.

Rome wasn’t built in a day. The key to winning clients is through WOM. That’s right, word of mouth. Reach out to friends, family, old co-workers, and even random people on LinkedIn if you’re gutsy enough. Let them know your doors are now open for business.

    • People who have hired you in the past might consider you for work again. Shoot them a nice note through the Interweb. and let them know you’re in the market for gig work.
    • Remember cold calling? Give cold emailing a try. Pick a few dream clients and put some feelers out there. You never know when someone might bite!
    • Google’s always your friend. So are LinkedIn and Working Not Working, which is like a dating site for freelancers and those who hire freelancers. (To work. Not date.)
    Ultimately, there are a million ways to find a new gig, so go on, get out there and do your thing. Godspeed!

    Network more than everyone else.

    Keep networking and growing your audience by becoming an authority in your niche.

    Get Business Insurance
    Get Business Insurance

    Don’t get too comfortable.

    We all know that wonderful feeling you get when you realize that people will actually pay you to do what you’re good at. Call it passion or drive or chutzpah if you like. But whatever you call it, there’s a huge ego boost from having people you can call “clients” and going to “meetings” with them to discuss real work in the making.

    But once you get rolling, you need to keep in mind that a big reason freelancers fail is that they start to feel comfortable and don’t secure clients for the future.

    Here are some ways to get a few clients on lock:

    • Freelancing websites like Upwork and Freelancer
    • Cold emailing (or Tweeting)
    • Social media and content marketing
    • Subcontracting through other agencies


    Get the right tools.

    There are a lot of tools on the internet that can really help budding freelancers. Here are a few.

    Eventually, you might need a bookkeeper, too. We recommend Bench.

    Get ready for your friends and family to ask for favors.

    You might suddenly become a lot of people’s new BFF. But unless you’re getting something out of it (like a warm fuzzy feeling or an awesome portfolio piece), you should not work for free.

    Starting your own company?
    Protect your assets with business insurance. Get an online quote.

    Pogo is an online business insurance agency dedicated to helping entrepreneurs and the self-employed get the right insurance, easily.
    Learn more about freelance business insurance