Is Freelancing Right For Me?

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To freelance or not to freelance?

To go solo and become self-employed or work as an employee? Many millennials, like myself have thought about freelancing at least once. Maybe it’s the thought of having control over your daily schedule and flexibility with your time that makes it appealing. You no longer have a boss, just collaborators. You get to set your own rates, give yourself a raise and work from home. There are many advantages to freelancing but of course there are disadvantages too. If you’re on the fence about freelancing as a full-time career, hopefully this article will help you move closer to making a decision on what’s right for you.

If you prefer to watch a video on this topic, view here:

The first thing you must understand...

As you evaluate whether to freelance, stop calling it “freelancing.” I will call it that often because that’s what you call it and I want you to understand what I’m talking about. As long as you’re a “freelancer,” your clients will treat you as an employee, not as a partner and business owner. The difference between Jack, your cousin who does freelance photography for weddings, and food, and nature and everything on the weekends and Matt, the photographer who brings the best out of executives and captures their confidence so they can have a good headshot, is that the latter sees himself as a business owner and brands himself in a certain way.

One thing that holds freelancers back...

Do not think that your talent is enough to find success. As long as they know how to take a good picture or write code, they’ll get hired right? Wrong. If that’s where your value ends how are you supposed to compete with the $5/hour freelancer from another country? As a freelancer, you are running a business. I thought my video editing talent was enough to bring me freelance success. It didn’t. When I finally saw myself as a business owner, partnering with other businesses to provide my services became easy. My clients no longer saw me as their employee. If they didn’t like the schedule, I set for myself where I only work 9-5 Monday through Friday, then we wouldn’t work together. I never actually had a client argue with my schedule once I started seeing myself as a business owner. When I saw myself as a freelancer (employee), they expected me to put aside my life to get projects done with unrealistic deadlines.

As long as you see yourself as just a freelancer, your clients will see you no different than the rest of their employees.

And they will compare your rate with their wages, which is ridiculous because you are paying all your taxes, benefits, and overhead to run your business. Their business is partnering with your business, it’s a business to business relationship. 

So, “Should I freelance?” is the wrong question. You should be asking, “Should I start a business?”

The type of business I’m talking about is different than other businesses. You don’t have employees, you aren’t selling a product, you aren’t finding investors to fund startup costs. You are selling yourself as a service to another business. The only startup cost is your time and occasionally some equipment if you’re a videographer without a camera or a programmer without a computer.

Many people think of freelancing as something to do on the side to make extra income. I teach you how to freelance full-time as your career. That’s why I like the term “solopreneur” because it means that you really are starting your own business, you’re just not hiring any employees, you don’t have a co-founder, you’re on your own. Maybe one day if you decide you want multiple streams of income, you’ll scale or evolve into something else but for now, it’s just you, and that’s enough.

I’m going to share with you a few of the reasons why I chose to go solo and then I’ll share a quiz with you that will help you determine your path.

I've always wanted to be self-employed, but after college I didn't have the courage to attempt freelancing. I was married 2 years prior and right after I graduated, we got pregnant. Things got real and I needed to find a job fast so I could support my new family. So, I accepted a full-time salary job for one company as a videographer and editor. I'll be honest with you, at first, I really enjoyed the benefits of a corporate job, the consistent income, the paid vacations. But I still felt uneasy about it.

5 months into that job, the company I worked for had to make a big downsize and I lost my job. I was 3 months away from my son being born. I started thinking, maybe it's less risky if I diversify my employment and so the thought of freelancing resurfaced. I then decided to start my own videography business, although at the time I wasn’t calling it a business, I was calling myself a “Freelance Videographer.”

For the next 9 months I struggled. I didn't have the right mindset or skillset to make it work. I sank into massive debt, had wildly inconsistent income, and suffered with anxiety. The few clients I did find didn't value my work or my time. I was too desperate to say "no" to anyone willing to give me work. It was miserable.

So, I gave up on freelancing and went back to a salary job. A year into that, I realized that freelancing was the only way I could be fully happy in my career. I had consistent income again but still felt insecure. So, after much debate, I quit my job and attempted freelancing a second time. This time though, I made a list of all my weaknesses that contributed to failure the first time and consolidated them into 6 key areas that I needed to improve; my vision for where I was heading, my awareness of where I was at, my internal communication with myself, my external communication with other people, my time management, and my money and sales skills.

I then found mentors, read books, attended workshops, and listened to podcasts on all 6 of those areas until I had mastered those skills enough to start finding success. Within 3 months of restarting my freelance career, I was earning enough income to support my family, that was stable and predictable, while also having work-life balance, control over my time and very low stress. And what was at the center of my success? Seeing myself as a business owner and treating my business as a business. I had to get educated on how to run a business. I had to learn how to market myself and sell. It was uncomfortable to have to change myself but as a  solopreneur, your success only grows as high as your willingness to change. You are selling yourself, you’re not selling a product that is separate from you as a person. So, YOU have to change and learn new skills. You need skills that go beyond your technical or creative skill that you are offering as your service. You need accounting, marketing, sales, communication, business, and time management skills, to name a few.

Just reading my story may have helped you know whether freelancing is right for you or not but in case it didn’t, I’m going to share with you some simple questions you can ask yourself that will help you make the decision.

Each question will be a rating system, 1-10: 10 being the strongest, 1 being the weakest. Write down your score along the way. Then afterward, you’ll add up your points and I’ll tell you what your score means.

  1. If you’re currently working a salary or wage job for another company, what level of excitement do you have going to work every day? Write down a rating 1-10.

  2. How much do you see yourself enjoying working at home?

  3. How excited are you to set your own schedule each day? You may prefer someone else give you your tasks and schedule for the day. And that’s okay, but consider the possibility that you don’t like that.

  4. How exciting does it sound to be in total control of your own time? Anything below 5 crosses is overwhelm. Above 5 is excited.

  5. How willing are you to do your own marketing? This question isn’t asking your skill level with marketing. If you’ve never received sales training before, this can scare you but don’t worry because I teach you how to do your own marketing as a freelancer. So even if you know nothing about it, how willing are you to learn? Because in a typical job, the company does all the marketing for you and you just show up and do the work and get paid, unless you’re a sales guy or marketing director of course.

  6. How often do you keep commitments to yourself? 10 is all the time, 1 is almost never. This doesn’t include just large commitments. Even simple things like waking up to your alarm, exercising, new years goals etc…count.

  7. How willing are you to integrate personal development into your daily life? This includes reading books to get educated, gaining new skills, developing your mindset, your physical body, and emotional management. Anything related to developing yourself.

  8. How badly do you want control over your income where you can set your own rates and give yourself a raise whenever you want?

  9. How comfortable are you with not receiving benefits like health insurance, retirement and paid holidays? 10 is really comfortable and 1 not at all.

  10. How comfortable are you with the idea of not receiving a standard, guaranteed paycheck every 2 weeks?


Those are the 10 questions. Add up your score with all the ratings. If your score is 100, you should dive right in to freelancing ASAP. You are 100% ready but that doesn’t mean to quit your job right away. It just means, make your freelance business a top priority this year.

If you’re score is anywhere between 50-100, then there is a good chance freelancing is the right path for you, take some time to get educated and explore the option. Also, meet people that are doing it and ask them what it’s like and what it takes.

If you’re score is between 25-50, there is still a chance freelancing is right for you, but you’ll need to take things slowly because you may still have quite a bit of insecurity about it and you might need some career coaching to really figure out whether it’s right for you or not.

If you’re score is below 25, there is a good chance that the typical corporate job is your best option. I’m not against corporate jobs, some people are better off working for another company as a valuable employee and team member. And some people literally prefer that lifestyle. I don’t, but it’s okay if you do. If you’ve made it through this post, there is a good chance your score is above 50, so I encourage you to subscribe and get educated. A great place to start is my free video masterclass called The Solopreneur Journey: Access Here

1 Comment

  1. […] about it. Make a decision so you can start acting on it. If you’re unsure, read my blog post Is Freelancing Right For Me and take the quiz. It will help you evaluate whether you should start putting time into the rest of […]

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