The Journey of Turning Your Side Gig Into a Lucrative Career


A lot of us are in the position of having side gigs that we could make more money at, but it seems too challenging and risky to try and take a step toward that. After all, financial security is important — bills need to be paid, families need to be provided for, and there needs to be some safety nets for the future!

But the great thing about a lot of side gigs is that they often start as hobbies that have simply proven to be a little bit more lucrative than we ever thought. It seems a shame to not at least inspect the possibility of making something we love into our careers, doesn’t it? I want to explore this with you, as I’m in the same boat. When it’s done, feel free to leave a comment with your opinions or advice. Maybe we can learn from each other!

Complete Legality

The last person you want on your back is a government official, and a way to avoid that is to simply make sure you’re within the law by registering your business and ensuring that your operations are being done legally. The U.S. and the U.K. are similar in the kinds of registered businesses they recognize.

  • Sole traders (U.K.) and sole proprietorships (U.S.)
  • Limited companies (U.K.) and LLCs (U.S.)
  • Partnerships (U.K. and U.S.)
  • Corporations (U.S. only)

Read more about U.K. business types here.

Additionally, in the United States it’s important to make your intentions clear to the IRS when pursuing a more serious career with your side gig. Even more importantly, make sure you’ve met all of their requirements for you — or else they may be knocking on your door. That is, they need to know that a full-time career is your ultimate goal in mind, not just a side-money making hobby, because they’ll be more willing to write certain expenses off. In the U.K., establishing a new business seems a bit more straightforward, even in the legal department.

Office Space or Make Yourself at Home?

When starting a self-run business or upscaling an existing one, establishing a headquarters is always a topic of conversation. Before you say “obviously making your business at home is the better option,” hold on for a second. It makes sense — in your mind, no extra rental costs and no new landlords mean saving money that other businesses are forced to spend. There’s also the misconception that running a business from home is the same as simply working from home, and they are not always the same thing.

Before you write off a headquarters location separate from your home, answer two questions:

Do You Have Peace and Quiet at Home?

Sometimes there’s too much going on from your home to run a business from it. Children and pets are often big distractions from work and are important to attend to if you’re in the physical vicinity to do so. Leisure is also a distraction, and if you don’t have the discipline to avoid it, running a business from home may not be for you.

Do You Have The Room and Abilities For All Operations To Be Completed?

Take into stock how big your home is. If this next step brings you employees, they’ll either have to work from their own homes or have space at yours, which will have other legal ramifications such as accessibility concerns and OSHA regulations. Similarly, make sure your Wi-Fi is fast enough and you’re able to store information and inventory in house. If you’re taking this thing to a more official or professional level, there’s a chance you’ll be investing in more stock which will require more space.

If you do decide that you must export your place of business to a new location, make sure the cost and room make sense. All of your operations need to be done under the spaces you occupy, and those spaces often cost money. Luckily, there are write-offs for overhead costs such as these that you can often take advantage of in order to get your money back, which you can read about here.

Setting Up Your Operations

The kinds of things you take for granted in your day job are the kinds of things you have to set up and think about now. Aside from legalities, the next level of your business may require things such as a clock-in procedure for employees, intercompany communication programs like Slack or Google Hangouts, and websites/storefront reboots. Desks, chairs, and office equipment could be an important part of operations as well.

If you need a website reboot and have never worked in web design, you’ll need a designer and probably some kind of help desk software (this is more for those turning a freelance side gig into a public-facing business). You may need to update your payment and accounting methods as well, especially if you’re bringing people onto payroll. A payment method update may also lead to getting a company credit card. Once you have your work set up for these operations, though, you may be able to start getting other people involved and turn this side gig into a full-time thing!

What’s been your experience with turning a side gig into a full-time job? Feel free to leave a comment in the links below, or reach out to me on Twitter @Robolitious. I’d love to hear from you and share ideas with you. Thanks!

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Tuesday, 24 September 2019
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