Questions to Ask Yourself Before Becoming a Freelancer

Questions to Ask Yourself Before Becoming a Freelancer

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Freelancing at home

This is a guest article contributed by Lior Levin.

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Everyone has the dream of working from home and being their own boss. Who wouldn’t want to enjoy that luxury? Freelancing is one of the many jobs that one can do from the comfort of their own home because you get to use your skills to work on your own time. Contrary to what many believe though, freelancing is not as easy a job as it seems. This is why it’s important to choose a niche that you truly enjoy and can see yourself doing for years to come.

The ever growing changes of the web and how we use it guarantees that there will almost always be some type of freelance work available for those who are up for the challenge. Remember though, whether your niche is designing, writing, programming, or anything else, there’s a lot of work that goes into it. Additionally, before you even start, there are a lot of questions that you’ll need to think about before venturing into the wonderful world of freelancing.

Can You Handle the Business Side of Freelancing?

Business Organisation

As a freelancer, you’ll have to learn how to run your own business, which is not a light task or subject. Many professionals go to school and earn Bachelor degrees in Business Administration/Management and Entrepreneurship so that they can learn how to properly run a business. So, if you don’t have a 4-year degree in on of these subjects, will you able to handle the business side of freelancing?

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You’ll also have to be constantly learning new things, keeping up with trends, and applying what you’ve learned. If you’re a designer, you’ll have to keep up with coding standards and learn new design techniques. If you’re a writer, you’ll have to do a lot of reading and keep up with the latest news and developments in your speciality – like new gadgets in technology or new social media services. Learning is a never-ending job and you’ll need to be able to retain all of that knowledge as well.


As your own boss, you’ll have to make sure that you start working on time and stick to your daily, weekly, and monthly schedule. It’s up to you to be organized; there won’t be anyone there to make sure that you’re staying on task. It’s very easy to lose focus and start doing something unrelated to your work like visiting social networking sites, chatting with a friend on IM, or watching TV.

It’s fine (and definitely recommended) to take breaks, but you’ll need to be disciplined enough to know when enough is enough. It’s important that you’re self driven enough to do what you need to do for the day without letting distractions get the best of you. You’ll have deadlines to meet and you’ll need to meet them by all means necessary.

Another thing to remember here is that yes, you do create your own work hours, but often you’ll have to work well over 8 hours a day. So ask yourself, are you willing to work over 40 hours a week? Many freelancers have to do this on a regular basis. You can’t be afraid to burn the midnight oil from time to time, especially if you have a really involved project or somehow underestimated the time needed for a project time.


Let’s not forgot about the legalities, paperwork, marketing, and financial duties that come with starting and managing your own business. As a freelancer you will have to register your business, pay taxes, create invoices, find clients, handle your email messages in a professional manner, schedule meetings, and communicate on the phone among other things.

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Also don’t forget that you’ll be your own receptionist, accountant, and manager (of all kinds) until you can afford to hire help. It will be very exhausting and stressful, but you have to make sure that you can handle it all when first starting out.

Do You Get Stressed Easily?

Stressed Woman

Do you have thick skin? You’re sure going to need it. You’ll be handling a lot of requests. Some clients will never be satisfied and will request an insane amount of additions and subtraction. Are you able to handle this or will you get stressed out at even the slightest amount of pressure?

Everyone handles stress differently. How do you handle it? If you’re one that does get stressed easily, make sure you have a remedy that works. Some preferred methods of handling stress are: drinking tea, meditation, getting a massage, playing games, or listening to music.


As a freelancer, you have to be able to take constructive criticism because you’ll be getting a lot of feedback, both good and bad, from your clients. Criticism and professionalism go hand-in-hand because you’ll need to be able to handle yourself and the feedback you receive, in a professional manner. At times you may want to give one of your clients a piece of your mind, but you can’t do that. These clients help build your reputation and you’ll need them as references; so you can’t go burning any bridges. Make sure you think before speaking or taking action.


It’s one thing for a client to give you feedback, but when they’re making demands, calling you out of your name, and treating you like a piece of meat it’s a totally different story. You will have some clients that really feel like they own you, so you’ll have to be able to stand up for yourself if needed. Will you have the courage to do this?

Can You Handle the Technology?


Let’s face it, nothing is done the old-fashioned way anymore – technology is taking over everything. We talked about invoices above, but paper invoices are just about obsolete. You’ll have to find the right type of software to use for creating and managing invoices, plus you’ll want to make sure that it’s a program within your budget.

Will you be able to keep up with the constant changes in technology? You’ll have to constantly adapt to knew devices and features on the devices and services that you use. With the rapid changes now, this can be a job all in itself, but it’s also a huge part of being a freelancer.


What about communicating with clients? Will you use an actual phone or a service like Skype or maybe even Google Voice? If you’d rather text chat with clients, which IM service will you use? There’s Google Talk, Yahoo Messenger, MSN, and even Skype can work for this as well. How will you hold meetings? This can be done on the phone, on IM clients, and even via web apps with the use of your webcam.

Are You Organized Enough?


Thanks to technology, it’s much easier to be organized now than ever before. There are countless online task management tools available for managing tasks, to-dos, events, and calendars. Plus, most of them let you sync between your computer and mobile devices so that you can keep track of your work and duties wherever you go. These tools don’t work by themselves though.

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You’ll need to create monthly, weekly, and plans. Larger projects can be broken up into smaller projects and then individual tasks. Each week you should know at a glance what needs to be done. Each day you should then have a task list of things that need to be done before you go to bed. Will you be able to stick to this? Will you be able to keep this up on a regular basis?

You’ll also need to keep good notes and know how to manage your email. Since email will more than likely be your main way of communicating with clients, you’ll need to be sure that you don’t delete important messages. You’ll also need to check your email frequently (at least 3-4 times a day) so that you don’t miss any important messages. Keeping good notes is also important because you want to be sure you do everything that your clients ask for.

The most important part of being a freelancer is being organized. If you cannot be organized then 9 times out of 10, you won’t make it as a freelancer. It’s just something that you can’t play by ear because nothing will ever get done on time and you’ll end losing all of your clients.lea

Do You Know Your Worth?


This will take some research, but you’ll need to know your worth so that you know how much to charge. You should see if you can find out what other freelancers with similar experience charge and go from there. Also remember that you won’t get things that come with full-time jobs like insurance, 401K, sicks days, vacation, etc. Of course you can do these things on your own, but in the end it will cost you more as a freelancer, so you might want to compensate for that when quoting prices.

Do you have a Backup Plan?

If freelancing doesn’t work out for you, you’ll need to have a backup plan. Freelancing is not for everyone. There will be some that will try, but it just won’t take off or fit them the way they thought it would. Obviously you shouldn’t go in with the intent of quitting as soon as the slightest thing goes wrong; you just need to make sure that you have yourself covered financially and emotionally if things get rough.


This is where financial stability comes into play. When just starting out, freelancing will not be a reliable source of income; therefore you should not be dependent on it in any way. You’ll need to make that you have a decent amount of money saved up or a spouse or roommate that has a reliable source of income. You don’t want to things to go wrong and then you end up without work or money.

You could even start freelancing on a part-time basis and have a part-time job on the side, just so that you do have reliable income coming in. Just make sure that you have some sort of stability to hold you up in case thing make a turn for the worse. It often takes 1-2 years to build up your reputation, have steady income, and be able to totally rely on freelancing. Are you willing to wait this long?

What is Your Final Decision?

Question Mark

So you’ve answered and evaluated all of these questions and you feel that you have what it takes. Well think again! Not to scare you off, but it’s even more hard work once you get started, so be sure that you’re ready to be in it for the long haul. We’re talking long work hours, late nights, stress and frustration, demanding clients, not nearly enough days off, and that’s just for starters.

With a lot of hard work, dedication, careful planning, and organization you can start out on the right track and take your career to the higher levels that you need to go. Before you know it you’ll be at the top of your game, in high demand, and making the big bucks from the comfort of your own home!

Are you a freelancer? Was it tough getting started? What are your biggest challenges? If you’re not a freelancer, do you plan on becoming one in the near future? Are you ready for the long haul? How do you plan to overcome any initial obstacles or challenges?

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This was a post by Lior Levin who works for a psd to html service company from New Jersey and also advises to a neon signs store that sells neon and LED signs.

Photo credits: Shutterstock; Pamela Uyttendaele, Zadorozhnyi Vikto, Diego Cerv XYZ, Aperture51, MareKuliasz

14 thoughts on “Questions to Ask Yourself Before Becoming a Freelancer”

  1. Great (and challenging) post, Lior!

    I recently started freelancing because I was laid off from my job and was only able to land part-time work, and I had a lot of associates want to pay me to do graphic design and branding work for them. It definitely has been a lot of work getting organized and learning how to price, budget my time, handle the finances and all that, but I do love the work. You gave me a lot more to consider that I hadn’t thought of yet. Thanks!

  2. There are a lot of valid points that Loir has made, some of them I have experienced for myself as a part-timer such as discipline, organization, and stability.

    Working around a full-time college schedule and meeting all deadlines for classes and clients are my biggest challenges today until I graduate.

    Do I think I can make it as a full-time freelancer in the near future? Yes. Am I planning to do that just after college? No. Like Lior said, it will take time to build a strong clientele. So will I still freelance? Of course, but because having a plan B is strongly recommended, I will want to also apply for a design firm/business.

  3. I love your advice and your style of writing. It’s listening to a real story and pulling it altogether to make sense. Decision is the only reason for taking, at the time of season, but we are giving the reason for the decision.

  4. I totally agree with you on a part with over 8 hours a day work. On my first freelance project i was working 12-14 hours just to be sure i can catch the deadline. It was the and of the year an i have to work on New Year’s Eve too. It’s not so easy as it seems to be a freelancer, and working alone at home can be very depressing.

  5. Very well constructed post, kinda like a check sheet for the ‘ones ability to freelance’. It is hard work being a freelancer but the rewards and time flexibility are worth it.

  6. My partner is a freelance journalist who has definitely employed the techniques you speak of in this article. Nice to know that we’re on the right track :)Good article, thanks!

  7. Some great tips – thanks for passing these along. You make some great points, especially about organization.

    Funny that I ran across your blog just after I googled this very same topic this morning….

  8. It was the and of the year an i have to work on New Year’s Eve too. It’s not so easy as it seems to be a freelancer, and working alone at home can be very depressing.

  9. I appreciate such a thorough article on things to consider before freelancing. Might I add another thing for those considering freelancing to take into account – RELATIONSHIPS. I have seen freelance designers go through the fire (and some not come back) because their work conflicted with their partner who is not involved in design. So is your partner understanding – would you rather invest 100% in your work or 50/50 in a relationship?

  10. This is a massively important topic to think about when deciding whether to go freelance or not. The pressure that will solely rest on your own shoulders after choosing to go it alone will increase dramatically. Invoices, customer relations and expectations, time scheduling, general organisation… on every level, you will be solely responsible and will need to have a firm hand on all aspects of business.
    Personally speaking, one thing that I would find really difficult would be the lack of other colleagues. Forging strong relationships with them and creating a good working environment leads to a positive atmosphere and is conducive to productivity levels. To leave that and go it alone, I would imagine, is a rather lonely and difficult to adapt to. For some, sure, the prospect of starting their own business is a massive lure, but take into account all that has been mentioned in this blog post as it’s only brushing the difficulties that one can face alone.

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