Do You Think You Could Succeed As A Freelancer Or Web-Worker?

Can You Survive As A Freelancer?Two questions that I’m often asked (and quite frankly, dread) are:

  • Do you think that I could succeed as a freelancer?
  • Should I become a freelancer?

I dread answering these particular questions because most people don’t realize that moving to freelancing generally involves a major lifestyle change. It’s nearly impossible to give a correct answer to the questions, and it’s certainly not possible to give a single answer that fits every individual and every circumstance.

It is possible, however, to provide some guidelines to those who are considering freelancing as a career option – so that’s what I’ll do in this post. I’ll provide the guidelines in the form of questions that you should ask yourself. (The information that I’m going to offer here should not be construed as specific advice for any one individual.)

Here are some questions to ask yourself before you decide to become a freelancer:

Do You Have A Marketable Skill?

The programmer for XYZ Company likely has highly marketable skills. On the other hand, the mailroom clerk for the same company may not have marketable skills.

Some tips on taking a skill inventory:

  • Examine your responsibilities and not your job title
  • Look at skills that you may have developed outside of your employment (hobbies, volunteer positions, and so on)
  • If you do not have a skill, or cannot provide a service that others need, then you can’t freelance until you have something to offer, something people would actually pay for.

Are You Able to Communicate Your Skill and Abilities to Others?

Many sources say that public speaking is the number one fear for most people. From what I’ve heard people say about speaking in public, I believe it.

Making a sales call is probably the number two fear.

Yet, as a freelancer you will need both of these “frightening” skills:

  • You must be able to explain what you offer in a clear and concise fashion (sometimes this explanation is in written form, but it may also be in person or on the phone).
  • You must also “sell” potential clients on your ability to get the work done.

How Flexible Can You Be?

The freelancing lifestyle is known for its flexibility – but that flexibility is a two-way street.

Unlike a business environment where you are allowed to clock out at a particular time, in freelancing your working hours are determined by your workload and project deadlines. There’s no one there to pick up the slack if you fall behind or get sick.

As an example, I typically don’t schedule myself to work weekends – but after missing a day last week for a trip to the dentist I worked through the weekend in order to meet a deadline.

If you absolutely have to have certain times off, then freelancing might not be your best alternative.

Do You Have Self-Discipline?

While a few clients may nag you about getting their project done, most clients will simply give you an assignment and expect you to complete it on time.

As a freelancer, you must have the self-discipline to make sure that the project gets done.

You will need to schedule your time (making allowances for unexpected setbacks) and work without prompting from others or reminders. Not everybody can work without supervision. Can you?

What Are Your Financial Obligations?

This is a difficult question, but for anyone considering freelancing a full-time career it is a vital one. It is possible to make a good living as a freelancer, but any seasoned freelancer will tell you that there are also dry spells when you must go without work.

Here are some red flags to think about carefully before starting a full-time freelancing career:

  • Lots of people (children, spouse, parents, and so on) depend upon your income
  • You have a huge mortgage (car, boat, etc.) payment
  • You are behind on your bills
  • You are the only one earning an income in your family
  • You have no savings

The presence of one, or more, red flags doesn’t necessarily mean that you can’t freelance. However, it is certainly an indication that you should be cautious.

How Will You Provide For You Non-Cash Needs?

Typically, a traditional job comes with perks and benefits that most workers rarely think about. Some of the more common perks include:

  • Health insurance
  • Paid sick days
  • Paid vacation time
  • Office space
  • Work equipment

As a freelancer, you will be responsible for providing these all of these benefits for yourself and your family. How will you do it?

This list of guidelines is by no means exhaustive, but by going through it carefully and thoughtfully you should begin to get some idea of whether or not freelancing is for you.

So, what do you think? :)



About the author: Laura Spencer is a freelance writer from North Central Texas with over 18 years of professional business writing experience. If you liked this post, then you may also enjoy Laura’s blog about her freelance writing experiences, WritingThoughts.

image in this post: oberazzi (Tim O’Brien)


  1. says

    A simple rule of freelancing, have your work space in a seperate room… so you can close the door and escape from your work. When you work from home, you’re always at work & that leads to crazy thoughts of jumping from buildings while doing the dishes.

  2. says

    @AdamTheGr8: hehe I’ve never thought of jumping off a building while doing the dishes, but I see what you mean, freelancing certainly ain’t easy (I probably would not freelance if it was ‘too’ easy anyway) and you have to step away from your work from time to time just to recharge the batteries and be in a different environment since it’s easy to leave the door open and work all the time.


  3. says

    I don’t consider freelancing to be a replacement for a traditional job. It is a good way to find part time work for additional income and as a temporary solution when you cannot find a traditional job.

  4. says

    I do not think this statute is suitable for everyone. You must love to innovate and have a good sense of adaptations, and knowing impose its quality. The rest follows easily.

  5. says

    Hi All!

    Great feedback!

    Robert – it is possible to earn a full-time living, but acms is write when they say that it is not for everyone.

    I guess the thing that makes me most nervous about the question of “whether or not I should freelance” is that the people who ask it are usually in desperate financial straights. Freelancing is not a quick financial fix.

    Keep the comments coming!

  6. says

    I recently made the jump to freelance and I have never been happier. For some people, having a boss is just too irritating and I definitely fall into that group. I want to be able to choose what work I do, when I do it, how much of it I do, etc. and freelancing allows me to do that. You have to consider freelancing as a baby step towards owning a small business though or I think it can start to get old. A freelancer is only a freelancer until he has so many leads he or she needs to hire additional hep. Then they’re a small business owner.

    @Robert S. Robbins: I couldn’t disagree with you more. If you think having a “traditional job” is the only way to make a living I feel sorry for you. If you love what you do and you’re good at it you can most definitely earn a great living from freelancing.

  7. says

    Excellent advice, as always, Laura.

    I especially think that this question:

    Are You Able to Communicate Your Skill and Abilities to Others?

    Is key to successful freelancing. I’m of a mind that most folks can be taught to write (or learn another freelance skill), but it takes confidence to market yourself and actually make any money from your skills.

  8. says

    Laura — Great article. I definitely agree with your points and also agree that it is difficult to answer these questions. I think in the end each has to decide for himself whether he has what it takes. Your points are good ones to consider though.

    Robert — I earn more freelancing than I did as a corporate paralegal at one of the highest paying firms in Chicago. So it IS possible.

  9. says

    After having a job as a junior web designer for about 7 months I realised that I much preferred freelance life to office life. But I’d never really done it properly, before I would just freelance as and when I needed to. But as the rest of my friends were off at uni and I didn’t have many financial obligations I decided I had little to lose, so in many ways I was quite lucky as I was able to spend some time putting together resources etc to launch my blog and my business, and this seems to have paid off.

    I’ve been contacted by some amazing people and I’m very happy that I was able to secure some on-going projects, so for now (although early days) I’ve not had any major problems or bad experiences, but I am expecting them and trying to prepare for it.

    I do miss my weekends though, I tend to slow down a bit at the weekend, but still don’t get a chance to fully switch off like when I was working in an office.

    Great read, and another great article, thanks for sharing and bringing this up!

  10. says

    Great post Laura.

    I have been freelance now for little over a month, however have freelanced part time for many years. Going freelance on a permanent basis wasn’t really a choice for me (thanks to my day job disappearing – literally!). So far I have been incredibly fortunate and have loads of work lined up and more coming in.

    For one thing, I too am making more money now, I’m enjoying the flexibility however your question you ask about family – well, that is becoming more of an issue for myself, and while I’m looking for new fulltime work, I can’t bear the idea of answering to a boss again – just another reason why I’m working hard to ensure the freelance situation becomes very viable.

  11. says

    Wonderful article for those who need to assess their situation, Laura.

    Robert, I have to join the chanting crowd when I say I earn far more as a freelancer than I ever did, or probably could earn in any similar corporate job.

  12. says

    Wow! It’s great to see all the new comments.

    One of the exciting things about freelancing can be that you determine your own compensation by how much you charge, how many hours you are willing to work, the quality of your work, and so on. In a traditional job you could wait years to get a raise – as a freelancer you just make your own raise.

    I certainly offer up my best wishes to those who are just getting started.

    Mainly, I wrote this to help those who may be looking at freelancing as a “quick fix” for a desperate situation. It isn’t. (For some reason, those are the folks who seem to e-mail me most often for advice.)

    Of course, freelancing is also a YMMV (your mileage may vary) based on the differing degrees of talent, effort, and determination.

    Great discussion! Thanks to everyone who took part.

  13. says

    Great straightforward tips. I’d love to try freelancing and your article inspires me to try it as an add-on to my current full-time employment to see if it will work for me.


  1. […] Success as a freelancer or Web Worker – via Freelance Folder Pretty nice article on Freelance Folder by Laura Spencer on some questions to ask yourself to determine if you’d be able to be a stable and successful freelance designer. Check it out if you’re trying to determine your best course of action if you’re in a similar situation. […]

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>