Is Freelancing Right For You?

Updated: October 9, 2023

Is freelancing right for you? How do you know if you’re ready to become a freelancer? More importantly, do you have what it takes to be successful at freelancing?

Those are the questions we’ll answer today with the help of a friend, whom I personally invited to write and share some thoughts about freelancing.

Let’s read what my friend, Greg, has to say.

Around 2002, I invited a friend to join in a project as a freelance programmer, just like me.

The pay is excellent and the hours, flexible. But there’s a catch – the work is only guaranteed for 9 months and it may or may not continue after that.

He didn’t accept the job and the project, fortunately, continued for another 2 years. However, after that gig, I switched back and forth between corporate jobs, freelancing, and a mix of both.

If you were my friend back then, would you have accepted my invitation or not?

Some are terrified of being a freelancer. While others would pick the flexibility of freelancing over the stability of a regular day job. Others simply follow the money.

Freelancing offers a lot of benefits like more money, more control of your time, and finally a chance to make decisions without worrying about your not-so-smart boss’ comments. Are these enough to motivate you?

Motivation will get you started but the journey towards self-employment and success is a long and arduous one. You really need to assess your values, beliefs, and skills to find out if your personality fits the life of a freelancer.

Here are some questions to ask yourself:

Are you excited on the idea of being responsible for your own destiny?

I bet you would say you are in charge of your destiny. As an employee, are you sure you’ll get promoted next year and get that raise so you could finally buy a Nissan Z? You really don’t.

Freelancing neither guarantees the Nissan Z as well. But it does guarantee control of your time and making your own decisions. If you’re not comfortable thinking where and when you’re going to get your next paycheck, then freelancing may not be for you.

Can you work under pressure?

I bet you can, but freelancing has pressure you don’t normally get at work – irregular income. Whatever stresses you out at work, at the end of the month you still receive a paycheck, which (ideally) should be more than enough to buy a couple of beers or a Thai massage.

With freelancing, you deal not only with the pressure of deadlines and commitments, but also with cash flow problems, delayed payments (God forbid), taxes, and other money-related mambo jumbos.

The ugly truth is freelancing is more demanding than a regular day job.

Do you like to be alone?

Freelancing requires you to be comfortable with working alone. Although there will still be instances where you need to work with another person but for most of the time, you are on your own.

From the important things, like preparing for a project bid onto the stuff you normally take for granted if you had a day job like the kind of paper and the design your business card. All these things will be done by you.

Freelancing could also take a toll on your social life that you may want to go back to a normal day job if only to be able to work with other “normal” people. (Yes, you’ll miss having officemates)

Are you persistent and disciplined?

Just because you’re the boss doesn’t mean you could take a vacation anytime you want to. If you are freelancing, chances are you can’t take any.

In the corporate world, the business still runs when you take a vacation because someone else takes over your tasks. In the freelance world, your tasks just pile up when you take a break.

But this doesn’t mean you shouldn’t take a break but between meeting a deadline and taking a vacation, you would choose the former.

The good news is since you have control over a lot of things, being organized can solve many of your problems, but that’s another story.

In summary, going freelance requires responsibilities beyond what you normally have as an employee.

Your day job provides the structure, resources, and support system so you could get things done. If you go into freelancing, all these corporate advantages will go away. So if you are reluctant to take additional responsibilities, freelancing may not be for you.

Remember that freelancing is not a job replacement. It’s an entirely different ball game – you need to think long and hard whether it’s the right move for you.

About the author: Greg Moreno has been working from home (sometimes at the mall) since 2007.

What to do next: Click here to start your financial journey with IMG Wealth Academy

Photo credit: dollymixtures, blmurch and bu7amd


  1. […] post is for people who are contemplating on moving from a regular employee to a freelancer. Whether you want to try freelancing as an escape from the corporate world or you aspire to become […]

  2. Nice tip Fitz! I think freelancing or work at home jobs are ideal for moms who are only staying at home since they can use their free time to work while also doing the household chores at home.

    Alternatively, even if you are employed, you can also entertain freelance jobs from time to time as long as it doesn’t affect your performance in your current job.

    The test is really independence (time and boss) vs. security (job tenure and other benefits that regular employees may have).

  3. Freelance is more challenging than full time. It has been true for me. You have to really be good at pricing and software estimation, otherwise your income could be potentially less than what a full time job could offer you (and often for full time jobs – especially if you work for really organized companies like the one I’m working for now, there is less stress and less liabilities than freelance jobs wherein you have to support your clients longer than expected).

    I think for those who are young (say early 20’s), being a full time freelancer is not ideal. Get a full time job, deal with all company headaches… Learn to work for less first.

  4. Nice tips. I totally agree that freelancing requires more of you than a regular employment. I haven’t tried full time freelancing but ever since I shifted to contracting work I can see the similarities of the two.

    Similarities of Freelancing & Contracting:
    1) demands your focus and time
    2) no work, no pay
    3) harder to take a vacation

    The big benefit is that when you go through it, you will learn to become more responsible for your own time and money.

  5. Interesting post. I’ll post something like this in the future as well as I freelance online to earn a living.

    Freedom from corporate slavery rocks!

  6. @Tyrone
    I think that security is relative. Me and a lot of other friends of mine who are freelancers would agree with me that they actually feel more financially secure now than when they were employees.

    Yeah, magaling ka kasing houseband. :P

    I would have to agree – learn to work for less first. The corporate world can teach you valuable lessons which you won’t learn anywhere else.

    The important thing to remember is not to get stuck in the rat race and plan for financial freedom.

    Not to mention freelancing / contracting is more self-fulfilling than working in an office.

    Yeah, freedom from the rat race rocks! :D

    Many health institutions offer insurance for freelancers. I actually have medical coverage from an HMO which I pay annually.

    @Credit Card Chaser
    Me too. I think I could never ever come back to having a boss. :P

    I think that’s how we all started, freelancing while working. And when the right time comes, we “jump off the cliff”. :D

    Yeah, I understand. But in any case, I know that making money online is your freelance job. :D

  7. I am working as a Full-Time Freelancer for a year now. Yes, It really needs more discipline and strategy. But somehow, you can get used to it and conquer the challenges. You can also get hired offshore full-time (Well, not legally because its not possible) like ME plus you can do other extra works when you have time. All you need is Discipline, Strategy, and Honesty. Well, I am much satisfied and I think I don’t need a boss…hehehe :)

  8. Also, freelancing / contracting is more self-fulfilling than working in an office indeed :)

  9. i just found this website few days ago. i am working in a call center (back office job) and i am making use of my free time browsing the internet. your articles are really interesting and very helpful! i am thinking of going into business on my own than to be in the office for 9 hours. i want to manage my own time at my own place. but like what you’ve written “be a saver first”, i am starting to discipline my self when it comes to my finances so that when i start investing, i can easily manage my own business.

    i’ll be reading all your articles in the next days, weeks, months and so forth.

    more power to you!

  10. How do freelancers pay taxes? I have been looking at different forums and blogs but what I’m seeing so far is inconclusive. I think the problem is because our government have not yet recognized what a freelance virtual assistant/writer/etc. is so when freelancers ask bir how they could pay taxes, the bir cannot even categorize them…I don’t know…i hope you could help with this matter…

    I’m a freelance virtual assistant with client from a US-based company and I want to do my duty as a Filipino citizen with regards to paying my taxes but I fdon’t know how to…thanks and more power! =D

  11. @Jostine: Wow! I must say KUDOS to you for wanting to do your duty to our country despite all the negative images of our government now and where our taxes actually go.

    I learned a lot here. More than ever, this affirmed my belief that as someone in the early 20’s freelancing really is not for me yet. Not if I am heiress to some large sum from my parents, which I’m not. Hehe. No wonder, my first foray into the freelancing world was a big fiasco. I needed the lessons I’m learning now in the corporate world to still survive. Yet somehow, despite having a generous and wonderful boss who constantly recognized my skills and plans for my future career path in the company, I cannot fully say that I am sold out to actually being in the top of a corporate company. There are too many other issues that keeps nagging in my mind – i.e. raising great kids and managing my own household – which I know would be very challenging once I am in a high corporate position. So now I know. When that time comes in my life, I must be in the position to quit my corporate job, become a full time mom and a full time freelancer.

    But who says that right now I cannot begin part time freelance jobs? :)

    Thanks for this!

  12. Hi Fitz, Do you have any recommendations on which Internet plan provider is suitable for people always on the go?

  13. @julz

    You can ask inside FB freelancer groups. They can help you better, depending on the skills you have.

    The most popular is Upwork. Locally, you can get short-term, fast-cycle projects at

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