I wanted to go full-time freelance 10 years before I actually took the leap.
My biggest regret? Not doing it earlier.
After all, I had everything in place—the savings, the clients, the support, the willpower. The only thing that held me back was fear. If you’re yearning to start a freelance business too, now may be the right time. You may be in transition, underemployed, unsatisfied at work, or just have a nagging desire to freelance.
No matter your situation, if you’ve been tossing around the idea, here are 10 sure-fire signs you should consider when thinking about venturing out on your own.
You sit at your desk, dreaming of being your own boss. You tackle personal projects just for the challenge, and you’re a natural leader. Sometimes, you brainstorm how you would run your company if you were at the helm.
Sound familiar? Then freelancing may be for you. It takes an entrepreneurial spirit to succeed, and you have to enjoy being in charge. On the flip side, if you’re passive, hesitant, and unsure about taking control, you may want to reconsider if this is the path for you.
When you work for yourself, there’s one thing that’s certain. Uncertainty. As a freelance writer, there are some months when my income is higher, and other months when it’s low. Occasionally, a regular client disappears, and I have to trust that new work will arrive.
And, for me, it does.
But it can be hard to manage the emotional highs and lows of freelancing. If you have a mortgage, children, and other responsibilities, it can be especially stressful. Ask yourself if you’re truly prepared for financial uncertainty.
There are ways to make it easier, for example, having a partner with a steady job or finding retainer clients. But in the end, there’s always an element of risk. Decide now if you need more job security or not.
When you start freelancing, you immediately earn the title of Chief Financial Officer. That’s right—self-employed workers wear many hats, and one of them involves managing finances.
If you’re already good at following a budget, you’re in good shape. That’s because freelance work can be unsteady. To succeed, you need to stay frugal and avoid veering off your original budget. You’ll need some extra padding for those months when income dips.
Did you know freelancers need business insurance? When I first started my business, I had no idea. Self-employed individuals are at risk for lawsuits, accidents, and injuries too. For example, if you’re a graphic designer, writer, or marketing consultant, a client could potentially sue you for negligence in your work, libel, or slander, and you’d have to defend yourself.
The cost of hiring a lawyer can be expensive , so it helps to be financially prepared. Before you start your freelance business, investigate getting professional liability insurance and commercial general liability insurance, especially if you meet with clients onsite. In my opinion, purchasing insurance ahead of time is well worth the cost.
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Freelancing is a major lifestyle change. There’s more financial risk to working for yourself. You may have irregular work hours, and often, you work harder than you would at a corporate job. Make sure your partner, family members, and close friends are in support of your decision. This is especially important if you have a partner with whom you share finances.
If the going gets rough, you’ll need them there to support you. When you have major accomplishments, you’ll also want your loved ones to celebrate your successes. If the people closest to you aren’t supportive, start talking to them now. Address any concerns ahead of time and map out a plan for financially protecting your family.
How outgoing are you? Are you ready to promote your skills on LinkedIn, a website, blog, and through networking events? Or do you feel shy? If you have any hesitation, ask yourself if you’re really cut out for freelancing.
I joke that freelancing has fine-tuned my job interviewing skills. I’m constantly applying for new gigs, talking to potential clients, and promoting myself online. Make sure you can muster the courage to unashamedly self-promote. It’s one of the best ways you can keep your business going.
If you’re a dawdler, take heed. Freelancing requires self-discipline and focus. You’re the sole manager of your work as no one else will hold you accountable to deadlines or conduct yearly performance reviews.
It’s up to you to adhere to a schedule, get your work done on time, and keep your clients happy. If you’ll be tempted to clean your house, play video games, or scroll through social media during work hours, consider if this is the right job for you. You may just need to minimize distractions, create a private workspace, and stick to a daily routine.
Junior writers often ask me how they can freelance with no portfolio. Unfortunately, it’s pretty difficult. That’s why I recommend creating your own portfolio through volunteer work or considering taking on lower paying jobs at first.
Most clients will ask to see samples of your work, especially if you’re a designer, writer, or photographer. You’ll need something stellar to show. If you’re a bookkeeper or virtual assistant, your portfolio may consist of brand names and notable projects. In other words, do what you can to demonstrate your experience and skill.
I know, coworking spaces exist, but most freelancers work from home. After all, it can keep initial overhead costs down.
Do you have a quiet space in your home where you can do work? Will you stay focused or wander off to do personal tasks, like laundry, dishes, and mowing the lawn? Working from home isn’t for everyone, so ask yourself if it’s an environment in which you can truly thrive.
There’s also a social aspect to working in a corporate environment. Most freelancers work solo, so they have limited interactions with other people. I make up for it by connecting with neighbors, friends, and by getting involved in my community. Make sure you have a plan to combat loneliness if you do go freelance.
As a freelancer, I am constantly learning new things, whether it’s technology, financial strategies, or marketing techniques. It’s actually my favorite part of owning a business. Any one area, whether it’s sales, marketing, product, or finance could potentially contribute to a business’s success or ultimate demise.
If you want to fine-tune your trade, adopt a business mindset, and become a lifelong learner, freelancing is definitely for you. Don’t make my mistake and wait too long before taking the leap. There’s no better time than now, especially if you have all of the pieces in place.
I love writing about the small business experience because I happen to be a small business owner - I've had a freelance copywriting business for over 10 years. In addition to that, I also head up the content strategy here at Simply Business. Reach out if you have a great idea for an article or just want to say hi!
This content is for general, informational purposes only and is not intended to provide legal, tax, accounting, or financial advice. Please obtain expert advice from industry specific professionals who may better understand your business’s needs. Read our full disclaimer
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