Why I Left My 9-5 For a Freelancing Career


When engaging in normal, “single-serve” conversations that occur in grocery stores, medical offices, coffee shops, and other public places; I have found myself increasing explaining the fact that I “work from home” as a freelancer and what such a choice has allowed me to do. As a result of this, I estimate that I end up explaining my choices in doing so around one hundred times per year.

As freelancing slowly infiltrates and replaces traditional workplaces for many different roles in the workplace – ranging from administrative assistants to software development – writing an article explaining these choices seemed only to be the next logical step forward for me, especially since most of my freelancing involves writing in some form, be it legal writing for one of numerous paralegal gigs or a story for a blog post. Even though I have been a freelancer for several years now, I only started using the Upwork platform a little over 6 months ago, and I have found it to be one of the best opportunities for new freelancers to build their careers. In fact, I have written extensively about this, as seen in this article I published a few weeks ago.

1. Freelancing is the future. My first year as a freelancer, I made a little over $19,000 from independent gigs alone. During this year, I was still working a W-2 job, as I was unsure how going full freelance was going to pan out. I found that by April, I had left the W-2 job and was pursuing freelancing and independent contractor (IC) jobs more often than not.

Now, in the spirit of full disclosure, I kept one of the IC jobs for 3 years, basically as a back-up source of income if going full freelance did not work out. I was a bit scared of the fact that going full freelance meant that I took full responsibility not just for doing work assigned to me, but finding and executing contracts for said work to even begin.

Of course, now I realize that the trade-off for taking this extra responsibility means that I am able to work wherever I choose, wearing what I want, and saying “no” to jobs I am not interested in. All freedom comes with massive responsibility, and freelancing is no exception.

The simple fact remains, though, that as of 2017, approximately 35% of the U.S. workforce is comprised of freelancers. This powerful statistic meant that if I did not jump on the freelancing train, I was sure to be left behind. For decades, the fear that automated factories would make human labor obsolete, but the other side to that coin is that the human workforce that cannot be replaced by automation will have their full-time employment replaced with freelancers. This is not a bad thing; simply the evolution (or revolution) of the workforce, which was bound to occur as it always does.

2. The opportunities are mind-blowing!

Already, I have surpassed any income I ever made at a traditional workplace, and instead of scheduling and competing with others for vacation time, I can pick up and go wherever I want, so long as I have my laptop and internet access. I currently work as a paralegal, journalist, professional writer, and customer service representative. Where else can one find such flexibility and such diversity?

The answer to beating back the possibility of boredom and burn-out is by learning discipline and by spreading your skill set out across all possible categories of work, while at the same time stepping out of your comfort zone by learning new job skills and applying for gigs that allow you to utilize them. Then, if you can get an hourly, long-term gig that you can count on; you can make this your security cushion. Knowing that you have your financial security worked out, you can reach for the skies for fixed-price jobs that can supplement your income by thousands per month.

3. You can find the perfect mesh for where you best fit in and what you love to do!

We’ve all heard the ultra-optimistic quote that everyone attributes to their father: “Never work a job that you don’t love doing.” Of course, while such a statement is not always within the grasp of those who actually have to work for a living, freelancing is the closest you can get.

Not only will you get to experience professional freedom that you have never experienced before, but if you branch and market your skills out to a wide variety of professionals looking to hire freelancers, you have a much better shot at finding that perfect symbiotic relationship between where you fit in professionally and what you love to do.

I have always loved writing, but I never really thought about it as a career until I started freelancing years ago. I started out writing these 250-word pieces for a massively-produced, low-quality content, Chinese-to-American English site for $2.00 an article. I did this religiously, and because I always make it a point to write in my best possible hand, I showed the proprietor of the said website that my quality deserved an increase in pay and a bump-up to his higher-quality content categories.

While this increase in pay was nominal at best, I slowly carved out positive feedback after positive feedback on fixed-price, single-serve articles for clients as far apart, genre-wise, as a highly technical, peer-reviewed cardiology journal to a survival-based guide reviewing rugged gear to have in case of a remote emergency.

That was years ago, but that beginning portion of my freelancing career introduced me to the vast opportunities available, and those small, low-income articles gave me the feedback I needed for more complex, long-term clients to take a chance on me. Combined with an impressive portfolio of legal pleadings with client information redacted, I slowly started to get invitations from law firms and was able to make a name for myself among some of the best.

I currently bill out at $29.95 per hour, which I just increased a month ago after receiving my “Top Rated” status, and clients have no problem paying this upon review of feedback from other clients. So, with a mix of hourly gigs that includes my old rate of $22.50 and the new rate of $29.95, I have been able to guarantee a sizable “backbone” income no matter what happens with “fixed-rate” projects. Combined, it is not difficult to visualize how I am able to make more freelancing than I used to make at a single job; but also that I did not get to this point without hard work, just like with anything worth anything in life.

4. Being at the forefront of any major evolution in society historically leads to large rewards.

Now, I know I touched on this briefly above, but as its own area of appeal, just the very thought of being at the forefront of the freelancing revolution probably means that I will be rewarded down the road in ways I never dreamed possible. Think of those who got onboard with the forefront of the new technologies that were unveiled in the 1800s through the Industrial Revolution. Fortunes were made because people took calculated risks that the evolution of the workplace would pay off. Most of my readers and clients alike do not know this, but I am part of the founding team of a prominent cryptocurrency, and my position as a founding member was due solely because of my decision to freelance full-time. The project made me a ton of money at the end of 2017 during the Bitcoin Bubble, and did it all without jumping on the “ICO bandwagon.” Now, as a project with 2 years of history, we are about to have a full public launch, which is bound to reap even greater rewards to those of us who have been smart enough to hold on to a good portion of our assets. This would have never come about had I not decided to take the chance to work on the initial project as a freelance developer and an agreement to be paid for my services with the new currency instead of in dollars. While these types of payoffs are not common at all, the fact remains that I would have never even known that such a project was forthcoming had I not built a freelancing network, which brings me to my final point…

5. Freelancing builds amazing professional networks.

When I first got into freelancing, I didn’t have a contact in the world. As I mentioned, I started by writing those tiny articles for pocket change. However, over the course of the first year and a half, even those who did not hire me retained my proposals and my CV (resume) for future projects. Some of them passed my information on to their professional contact, and on and on the cycle went; until I started receiving full-blown offers from clients without even having an initial conversation. I do not use social media for personal use whatsoever and I barely use it for professional reasons, except for platforms like LinkedIn and freelancing sites like Upwork, Fiver, and Guru; to name a few. However, I have built an amazing professional network that includes everything from politicians to prominent attorneys and even a couple of actors. This could have never been accomplished had it not been for my choice to go full-time as a freelancer.

Now, it’s important to note that there are also characteristics inherent to freelancing and telecommuting in general that can be difficult to overcome, and are the main reasons why people do not stick to it. This would not be a fair and balanced article if I did not at least skim through these topics, so without further ado…

  • It takes discipline. The main reason that people fail as freelancers or telecommuters (work-from-home) is because of the discipline required. It can be tempting to watch the TV, get a sandwich or drink from the fridge, or browse the internet while you are supposed to be getting work done; and many times, people look at this hurdle as simply too difficult to overcome and give up on the industry. There are 1500-plus-word articles dedicated solely to overcoming such obstacles with great tips for doing just that. I will not sugarcoat this – distraction can be a huge, huge problem. However, besides reading up on articles like the one linked above, my advice on the topic is simply to stick with it. Eventually, you will find your groove and learn to understand when you can afford to take a quick look at your personal sites and when you simply cannot. If you simply cannot make it without seeing your social media – buy a used laptop and set it up next to your main workstation. Use it to log in to all of your personal pages and set it off to the side at a right angle. Some people may think that this is bad advice, but the fact of the matter is that some people simply do not have the discipline to cut the likes and retweets out of their daily life, so pragmatic solutions like this can be just the thing to keep you going during those first aggravating months. Eventually, you will find that you focus less and less on the laptop and more and more on your professional workstation.
  • Freelancing simply is not for everyone. The plain and simple fact remains that freelancing is not for everyone. There are those of us who simply cannot work a productive job without having constant supervision. This is not a character flaw, it just means that these people work differently. Some people may be able to train themselves to work without supervision, but there will always remain those who cannot. There are also people who simply cannot work from behind a screen and prefer manual labor or jobs that require travel and face-to-face interaction. These people have some choices within the freelance market, such as freelance journalism that requires investigative techniques to write their work. There is definitely room within the freelance economy for these people, but they may find that working for a traditional employer better meets their desire for a career choice. Before you decide to freelance because your neighbor is making beaucoup bucks writing for Men’s Health as a freelance contributor, consider your desires when it comes to your career goals and determine whether or not your goals line up with freelancing. If you think that you may be a fit but you have some reservations, fear not, there is a solution for you (and for all freelancers just starting out, actually). Before you commit to freelancing full-time, get an account with a freelancing platform and find a couple of small gigs that are open to everyone. Work these single-serve gigs over the course of a single week during your time off from your current job. If you find that you like it, slowly build your income foundation with small hourly or fixed-price gigs that want a little bit of work from you per week on a long-term basis. As you continue to pick up gigs, you will eventually get to the point where you have to decide whether to freelance to supplement your regular job or if it is time to replace the 9-5 with the freelance society. This process may reveal to you that you may be a good fit but not full-time, and in the process, you may have found yourself some nice supplemental income. Either way, you will soon get a feel for whether or not freelancing is for you.
  • Your taxes, insurance, and record-keeping is your responsibility. This is one of the biggest concerns for newcomers to freelancing, but in all honesty, I have found it to be liberating instead of a burden. Being that I have prepared taxes back-and-forth over the course of my career as a paralegal, I find that dealing with your own taxes is not as daunting as many make it out to be. As an independent contractor, you are supposed to pay your taxes quarterly. However, in my case, I usually see a pretty large refund every year, so I simply wait until the end of the year and have my self-employment taxes deducted from my yearly refund. For instance, I did this last year – had a refund due to me of close to $6500 but owed around $1600 in self-employment taxes, so I simply allowed this to reduce my refund to $4900. This should not be construed as tax advice, because I do not know your personal tax situation, but if you usually have a tax liability (meaning you owe every year), filing quarterly is probably better for you, so that you will not be hit with the extra $1500-3000 in self-employment taxes on top of what you normally would owe.

Health insurance can be purchased through the Health Insurance Marketplace (Click Here) or through a freelance-friendly health plan. The Freelancers’ Union can help direct you to health insurance companies with special rates for freelancers as well as dental insurers who do the same. As freelancing overtakes traditional employment in the labor force, more and more options will become available.

Finally, record keeping can at first seem like a good reason not to jump on the freelancing train, but in all actuality, if you are working through a platform such as Upwork, your records are kept for you. You are actually given access to run very powerful reports based on your earnings, clients, and more; and you can easily download an earnings statement that you can present to any entity as proof of your income, broken down quarterly, over the past 12 months. Furthermore, there are tons of apps available that help you with record-keeping, time tracking, and client invoicing, as outlined in this great article on the Freelancers’ Union blog.

Conclusion/Final Thoughts

The decision to jump into freelancing is not something that should be made overnight. Six years ago, as I started to write my first $2.00 article, I thought that there was no way I would be able to completely replace my W-2 income with a freelance career. Now, as a Top Rated freelancer with a vast sea of networked professionals, there is nothing I would rather do. I can work while I travel, when I cannot sleep at night, while on a vacation to Hawaii, or while doing anything that life throws my way. I can write an article while waiting for a doctor’s appointment or bill a client from the grocery store. The flexibility and the ability to work across multiple fields to make full use of the wide variety of tools in my skill set make freelancing my preferred method of getting work done, and I cannot see that changing at any time in the foreseeable future. However, those considering a career in freelancing should be aware that success is not an overnight accomplishment and that there is hard work that must be put in to become a highly sought-after freelance agent. Discipline is a must and the dedication to succeed without supervision and a direct set of instructions will either make you or break you. However, the rewards that can be reaped are just now starting to come into focus for those who get in at the forefront. Taking all of this into consideration, I suggest that anyone looking to change their career path into something where you can set your own hours and basically write your own paychecks consider taking a look at what freelancing has to offer.

Source Material:

1. The Conversation. (August 15, 2017). Is Freelancing the Future of Employment? Retrieved from https://theconversation.com/is-freelancing-the-future-of-employment-80253

2. Smooth Business Growth. (July 31, 2017). Overcoming Distractions for the Work-at-Home Professional. Retrieved from https://www.smoothbusinessgrowth.com/overcoming-distractions/

3. The Health Insurance Marketplace. Government Agency. Provider link: https://www.healthcare.gov.

4. Upwork.com. Professional Platform. Product link: https://www.upwork.com.

5. Christian, A. (April 8, 2014). Don’t Get Mad, Get Paid. The Freelancers’ Union Blog. Retrieved from https://blog.freelancersunion.org/2014/04/08/dont-get-mad-get-paid-6-invoice-apps-freelancers/


Published by BetterCallPaul

I am a freelance paralegal investigator, journalist, writer, and blogger determined to bring the amazing world that comes with having a freelance career to all of my readers!

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