Small Business

Things You Should Expect If You Start Freelancing And How To Prepare Yourself

There’s no better way to scrape up a few bucks in this economy or free yourself from a boss you dislike, or makes you sick with stress than doing some freelancing or starting your own business on the side. If you’re thinking about taking the plunge, here are some things you should look out for, and some tips to help prepare before you take the first step.

Image: dmitrieva (Shutterstock).

What You Should Be Ready For

If you have a job that pays the bills now, that’s great, and you definitely shouldn’t quit to start your side business or start freelancing, but walking the line between full-time employee at one place and working for yourself on the other hand presents some challenges you’ll need to be ready for before you do it. It may sound like the easy way out since you can work on your business without risking a steady pay cheque, but here are a few things you should be ready for.

  • Be ready to make your passion “work”. They call it “work” for a reason, and speaking from experience, I know how it is to start freelancing on the side, working on the thing you love, and suddenly realising sometimes that your passion, that thing you could never get enough of, is starting to wear on you a bit. Brazen Careerist has a great article on this topic, and points out that even if you’re doing what you love, there will be times when you don’t want to do it anymore, wish you could take a break, or otherwise just get a little tired of it. That’s completely normal, and don’t let it convince you you’re on the wrong track. Image: imageegami (Shutterstock).

  • Be ready to firmly manage and maintain your boundaries. Many of us work in jobs that require us to be on call sometimes, travel, or work late. If you’re planning on doing side work, even if it’s manageable and you set your own deadlines, you’ll need to make sure your full-time job doesn’t encroach on your side gig, and vice versa. You’ll have to be ready to tell you boss “sorry, I’ve got plans tonight”, if they ask you if you’re available after hours, especially if you really do have something related to your freelancing planned.
  • Be ready for people to question your motives. If you’re getting your hustle on and trying to carve out time to do the things you love while simultaneously doing the things that pay the bills, there will be people who’ll question why you spend so much time on the side gig at all when you could devote that energy to your full-time job. Others will try to convince you that you should quit your full-time job and work on the side job. What you ultimately do is up to you, but you should think about and be ready for those questions when they come — especially if they come from people related to either gig. Be ready to hold your ground, and justify why you’re following your passion — even to yourself.
  • Be ready to keep your side projects secret. For every person that’s supportive of your side gig, there’ll be someone else — possibly a manager at your full-time job, most likely — who’ll take every opportunity to assume that any mistake you make or displeasure you express at your full-time gig is because of your side-gig. Call in sick? It’s because you’re working on your freelancing, of course, not because you’re actually ill. Having trouble meeting a deadline? It must be because you’re working on your personal business at the office, not because it’s a lot of work. Be very careful who you tell and who you keep in the dark and be prepared to keep it a secret if necessary — both for perception and possibly policy reasons depending on how your full-time job looks at side work. Some companies don’t care as long as it’s unrelated to your job or their business, other companies wouldn’t hesitate to fire someone for owning an Etsy shop. Image: Artsem Martysiuk (Shutterstock).

  • Be ready to have your personal life turned upside down. One of the best and worst things about freelancing or working for yourself is that you can easily find yourself getting lost in your work. If it’s your passion, that can be a great thing and you can make a lot of headway. The downside is that you’re whittling away personal hours you would otherwise spend relaxing, picking up another hobby, or worse, spending time with your family and friends. This is in line with making sure you manage your boundaries — make sure your freelancing is in check, as much as everything else is in check to allow you to work for yourself. It’s going to take hard work and lots of time, but that doesn’t mean you have to sacrifice your life for your passion.

This is just the tip of the iceberg, but they’re some of the things you should be ready to face aside from the logistics of how you’ll find the time to follow your passion, what you’ll do, and how you’ll find work. Those questions are ones we’ve hit on before a few times. Even if you have that stuff all worked out, these are a few things that can come out of the blue and hit you if you don’t expect them. Now, let’s discuss how to prepare.

How To Prepare Yourself

  • Hire a great tax professional. It may seem like an odd first suggestion, but when you start freelancing or building a business of your own, one of the first things that can get unwieldy and complicated is your tax return. You’re suddenly dropped into a new world of deductions and estimated tax payments and other income and expenses that, if handled properly, can work in your favour, but when handled improperly can lead to an audit. Do yourself a favour and make it an accountant’s problem so you can focus on both of your jobs.
  • Remember you don’t need the money. If you’ve been living on your full-time salary up to this point, follow your side passion because it’s your passion, not because it offers a second pay cheque. Use that second pay cheque to help you get to your financial goals, whether it’s an emergency fund, a deposit for a home, buying your next car with cash, or saving for retirement. Sure, you could just use the extra money on gadgets and booze, but you’ll miss it when it’s gone. Invest it in yourself. Photo by Images of Money.

  • Put together a strong invoicing and payment system. When you get started, you’ll probably want to spend more time doing the things you love and less time making sure your customers actually pay you for your work. Before you even take the plunge, give some thought to how you’ll invoice clients for the work you do for them, and how you’ll keep track of whether the invoices have been paid. Determine how frequently you’ll follow up with people who haven’t paid, and stick to it. Putting a system in place from the start will make it easy to avoid relying on your customers to actually pay the bills. Some of them will be happy to, others won’t bat an eye if you never ask to be paid.
  • Have a great productivity system. Whatever it is, you want to make sure you’re very good at juggling priorities, schedules and deadlines, and that you’re really good at communicating what you can and can’t do. You’ll still owe a lot to your full-time job, so you’ll need to be able to force yourself to go to bed so you can get up for a full work day, even if you’re in the garage working on your side-business all night, and you’ll need to be able to decide which one is more important when there aren’t many hours left in the day.
  • Plan for time off and sick days. When you’re hustling on the side, you have to plan your time away from work even more carefully than you would otherwise. Sure, you can just take a sick day or use holiday leave from your full-time employer, but when you take off from a freelance or personal business, you’re not making any money. You’ll need to account for that before you do it, and if you still have a steady pay cheque to fall back on, it won’t hurt. Even so, remember the fact and plan accordingly — and don’t fall into the trap of taking a holiday from your full-time job only to spend it working on your side project. You’ll still need real vacations to recharge, even if your personal business is your passion.
  • Find other people like you. Like we mentioned above, your choice to strike it out on your own while working full-time may confuse a lot of people. Find people like you who understand the decision you’ve made or who have also taken steps to follow their passion. Whatever you do, remember you’re not alone, and find people who can help affirm that fact.

Striking it out on your own without quitting your day job is a tough way to go. It’ll demand a lot of time, energy, priority juggling, and dedication to your passion to make successful. I managed to do it for something like five years before making the leap to full-time freelance and then shortly thereafter being scooped up by my dream job. I still wouldn’t trade the experience though and if you’re thinking about doing the same, weigh your options carefully before getting started and make sure to prepare yourself accordingly.

Have you started a side business or taken up freelance work while holding down a full-time job? How would you suggest others prepare? Share your tips and suggestions in the comments below.


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