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5 Reality Checks to Make Before Starting a Side Gig

By June 24, 2021No Comments

A brilliant idea springs to mind on your drive home one day. That night, you write it down, hoping to tackle it first thing the next morning. Or the next chance you get. You’ve always wanted to start a side hustle—you were just waiting for the right idea.

But before you start, think through all of the things that go into starting a freelance side gig. While you can enjoy some extra income, a side hustle doesn’t come without risks.

If you’ve already jotted down your brilliant idea (or two) recently,  then congrats! Coming up with a business idea isn’t easy. But before you jump right in with little research, reflection or planning, here are 5 questions to ask yourself as a reality check before starting your side gig.

5 Reality Checks to Make Before Starting a Side Gig

1. Will this side gig conflict with my main job?

Starting a side gig is invigorating, but it might not be worth it if the trade-offs include its effects on your main job. On paper, the idea of getting paid an extra 5-20 hours per week might sound great. But we’re humans—not machines. Instead of jumping right in, be sure to consider:

  • Time allocation. How much time am I ready to commit to my sig gig, realistically? If you put in 40 hours at your main job, you might want to squeeze in no more than 10 hours of additional work a week. Why? You want to make time for things like spending time with family and friends, exercise, and hobbies.
  • Work productivity. When in the day are you the most productive? If you plan to spend your evenings (e.g. 7 to 9 pm) on your side gig, you want to make sure that you can focus during that time of day. In fact, many of us use the evenings to relax and unwind. Operating at your own schedule is great, but there’s also an unglamorous side to freelancing—the ability to switch off, for example, is one. Consider which hours suit your side gig the most, and keep it consistent.

2. Does this side gig match my values and goals?

A job is what you do for work, but a career is a compilation of many jobs that make up your lifetime (before retirement, at least). So, just like we work a job that meets our personal and financial goals, we also choose to start side gigs that meet those goals, too.

If you value ambition, dedication, and impact, then starting a non-profit side-gig to help a certain cause would be right up your alley.

If you’re passionate about creating ethical, sustainably sourced materials to counter fast fashion, then starting a new clothing line using ethical sources would make a lot of sense.

Whatever side gig you choose, check your own values (and goals) before you dive right in. It’s easy to get swept up in brilliant ideas that are driven by a heated moment of passion.

3. Am I okay with failing in my side gig? (a lot)

Businesses fail—a lot. In fact, approximately 20 percent of small businesses fail within the first year of operating. By the end of the second year, 30 percent of businesses will have failed.

When you fail at your main job, often, you can fall back on your own boss or team and suffer the impact together. It feels a lot safer knowing that you’re in it together, whether it’s a minor mistake or a costly one.

Failing at your sig gig is different though. You’re your own boss, operations manager, project manager, branding specialist, accountant, and revenue-maker. Though you wear multiple hats, chances are, you’re not going to excel at all of them, which leads to the potential of failure.

Failure is simply the opportunity to begin again, but this time more intelligently.
— Henry Ford, Ford Motor Company

4. Do I have the tools I need?

Being a freelancer means you’ve got to manage it all. From pitch-perfect presentations and project management mastery to accounting automation, having the right tools to succeed matters. The right tools can get you a whole lot farther than without them when it comes to working effectively. For example, if you intend to run an eCommerce store on Etsy or Shopify, you might want to check that you have the digital tools necessary to succeed long term.

Here are some digital tools to consider for different aspects of running your sig gig:


TrulySmall Accounting‘s double-entry accounting software automates your accounting workflow, ensuring that the numbers are always up-to-date and stored safely in the cloud. Sign-up is quick and the interface is easy to use. You can re-focus your hours spent on accounting and invoicing tasks to improving your pitch!

Project Management Workflow

When you start a side gig, the goal is to grow your passion project into something much larger. Whether you start off as a one-person show or expand to a team, you want to get those big gigs that eventually enable you to contract out team members. That means you have got to be able to hold your own as a project manager. Agile-focused and hybrid project management tools are available online. Asana, Trello, Notion, and Hubstaff Tasks Premium are all great tools to use. In fact, many of them offer free tools for personal plans—perfect for your side gig!

Team Collaboration

The onset of the global pandemic has forced us all to be okay with working remotely. The distance keeps us safe from transmission, but it has made us feel further and further apart from our colleagues. That’s why the right digital collaboration tools you invest in—even if your small business consists of 2 individuals—are so important.

Relevant: Remote Working Tips to Surviving COVID-19 as a Small Business

5. Is my personal life organized and tidy?

Chances are, if you’re organized in your personal life, you’ll be organized in your work—and your side gig.

Staying focused and productive can be tough for newbie freelancers. Sure, you’ve set your schedule and those deadlines seem way off in the distant future, but working from home can be a gauntlet of distractions. The best way to keep yourself on task and productive throughout the day is with a streamlined focus management tool that turns your to-do list into an organized schedule. That’s where Focuster Productivity App comes into play. This organizing assistant helps you work more efficiently by prioritizing tasks and auto-scheduling them in your calendar, tracking your progress, and utilizing smart reminders so you work more efficiently and stay focused on the tasks at hand.

Ready to get started?

It’s okay to realize a side gig isn’t right for you, or at least not right now. But if you passed the above reality checks with flying colours, and you feel like you’re ready, then you’ve got this! We’re rooting for you.

Whether you plan to hire an accountant, need a simple tool to send invoices, or are looking to automate your accounting workflow entirely, we’ve got a solution for each. Try TrulySmall Accounting today using a free 14-day trial to find out exactly what solution you need.

TrulySmall Accounting helps small business owners save time

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