The Many Paths to Freelancing

With more and more workers turning to freelancing, you may wonder whether you should freelance. Are you ready? What is the best path to take to become a freelancer?

In this post, I’ll identify five different routes people take to freelancing. I’ll discuss the advantages and disadvantages of each.

Path 1. Right After College

Faced with a weak job market, many new graduates turn to freelancing to find employment. There are some positives and negatives to freelancing right out of school.

Here are three advantages to freelancing right out of college:

  • Find a job quicker–In today’s economy, new grads may wait months before finding a job in their field. With freelancing they can start right away.
  • Earn more money–New graduates are often relegated to entry-level jobs with entry-level pay. With freelancing they decide how much to charge.
  • Fresh training–College graduates are often equipped with the latest information about their field. Often this means more enthusiasm.

Here are three disadvantages to freelancing right out of college:

  • No proven experience–A recent graduate often has no paid work experience relative to their field. They may have trouble providing samples of their work.
  • Lack of confidence–Because they’ve not yet worked for pay in their field, recent grads may be unsure of themselves. Prospects can pick up on a lack of confidence.
  • Culture shock–Going from an academic environment to the freelance marketplace is a big change. Working on an assignment for a teacher and working on an assignment for a client is different.

Of course starting freelancing right after college is not the only path. Let’s look at another.

Path 2. After Working for Someone Else

Many seasoned professionals eventually strike out on their own as freelancers. Freelancing after spending a few years in the traditional workforce also has some pros and cons.

Here are three advantages to becoming a freelancer after working for someone else:

  • Plenty of proven experience–Seasoned professionals can point to years of relevant work experience. They will probably have many samples of past work.
  • Good references–Because of their years of work experience, most transitioning professionals can provide references. In fact, for some their first client will be their former employer.
  • More confidence–Since they’ve already worked as a professional, an experienced worker is likely to be more confident about themselves and their work.

Here are three disadvantages of becoming a freelancer after working for someone else:

  • Less hungry–A traditional employee may have had time to establish savings and may have worked up to a higher pay level. They may not be driven to freelance.
  • More obligations–A seasoned worker is also more likely to have made major purchases such as a home and may even have dependents. All of these obligations may make them more comfortable in a traditional job.
  • Accustomed to traditional workplace–There are many differences between freelancing and traditional employment. Seasoned employees are not used to wearing the many hats freelancers wear.

Of course, not all freelancers are full-time. In fact, one of the paths to freelancing is as a part-timer.

Path 3. As a Part-timer

Is having a traditional job and being a freelancer mutually exclusive?

Of course not! The thousands of workers who successfully combine freelancing and employment will tell you that this is a very real path to freelancing.

One of the greatest benefits to freelancing part-time is that you still get to enjoy all of the benefits of a full-time employee (such as insurance, paid vacation, sick days, and other employee perks).

Part-time freelancing is not without its hazards, though. Time management is probably the biggest challenge that part-time freelancers face.

Many part-time freelancers do eventually move on to become full-time freelancers, but many others are happy to continue freelancing on a part-time basis indefinitely.

Not everyone is a freelancer by choice, though. Some people turn to freelancing because they feel that it is their only option for earning an income.

Path 4. Job Loss

The path to freelancing that no one wants to talk about is job loss. Some freelancers turn to freelancing because they have lost a long-term job and feel that they cannot replace it. Freelancing is their last resort.

These freelancers often the most stressed out and desperate. Often, they never planned on being a freelancer at all. They may not even enjoy freelancing.

Some of the challenges these freelancers face include:

  • Low budget–Being thrust into freelancing as a last resort sometimes means these freelancers may be so desperate that they take jobs below market rate. They also can’t afford to make an investment in their freelancing business.
  • Financial Distress–A freelancer who turns to freelancing because of sudden job loss may be caught without savings or they may have already exhausted their savings.
  • Culture shock–The differences between traditional employment and freelancing are even more stark for those who feel freelancing is their only option. Remember, these freelancers never wanted to freelance.

Path 5. A Need for Flexibility

The final path to freelancing is taken by those who need a more flexible working arrangement. They may have others to care for during the day or they may just prefer a non-traditional work schedule.

For these folks, freelancing fits the bill like no other type of job. As a freelancer, you can choose when you want to work, how much you want to work, and even which projects that you accept. You can’t get more flexible than that.

Your Turn

Did I miss a path to freelancing? What was your path? Why did you become a freelancer?

Share your answers in the comments.

Image by Laenulfean


  1. says

    lol, yeah, feels like have gone through at one time or another all of them except the first, right after school, was probably too conditioned to even consider it at the time. Then #2 was the first time and since then have been hooked on one type or another, such as if back to a regular job, would always have something in progress on the side.

    If one thing didn’t work out, the other could get a little more focus to fill the void, a new bridge so to speak. Helpful especially for projects or activities that can take longer to get to be an expert of, such as turning a hobby into something more.

  2. says

    After having children, my priorities have radically changed. The thing that has become the most important on earth was to be with them. And I discovered how much I like the freedom and creativity of freelancing and, has you said, the flexibility.


  3. says

    I was a freelancer after working for someone, but now I freelance part-time while I work a full-time job. This fits my personality better and I definitely love having the benefits of a full-time gig.

  4. says

    I wonder if it takes a certain personality type (those who are energized by work) to work full time and freelance on the side. It’s pretty exhausting to do both!

  5. says

    We started out on a ‘project by project’ basis two years before we actually decided to run it as an official full time business. Not sure if it can be called freelancing then as it was a group of us. A lot of the ‘delay’ was caused by planning. It was a period where we discovered ourselves, ways of working together, dynamics, skill set application etc.

    In a way, it was like an engagement before that actual marriage thing took place.

  6. Adam Hunter says

    I wish I’d discovered the need for an accountant much sooner in my freelancing career. At the start I was really cynical about accountants, believing that they cost the earth and just looked at your books to make sure your sums were correct. I could get my wife to do that!

    After getting a short trial with my now contractor accountant it really opened my eyes on how much money they can make you. My initial take home pay wasn’t great, but once they showed me how you can claim almost everything on expenses and make the most of your earnings through dividends I really saw the value. So I’d definitely recommend taking a little leap of faith with an accountant once you get started.

  7. says

    I started freelance writing while employed to have additional income. When I had enough experience and saved a little money, I went full time. I guess it’s better to start freelancing as a part time job so you can slowly learn the ins and outs.

  8. Karin Flanders says

    Back in the days I used to get some side jobs or getafreelancer. After a few years I noticed being a freelancer isn’t really my thing, so I’m actually really happy with being a manager for a larger company. It can still be stressful, but it’s definitely not the same stress as being a freelancer.


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