I talk to a lot of e-learning designers who currently work in organizations but dream about going out on their own. If you’re reading this article, chances are the thought has crossed your mind as well. But the world of freelancing isn’t always rosy. Just like anything, there are advantages and disadvantages to being self-employed. To get a behind-the-scenes look at what those are, I talked to community members Philippe Siwinski, Ray Cole, David Tait, Russ Sawchuk, Bruce Graham, Ashley Chiasson, and Matthew Bibby—all of whom have worked as e-learning freelancers at one time or another. I pulled together their insights below to help you decide if being a freelance e-learning designer is right for you.


  • Freedom to work whenever and wherever.
  • No commute (unless you decide to work in a co-working office).
  • Ability to accept or decline work (once you’ve got a steady client base).
  • No boss, so you can do things your way. Or at least in theory. As David Tait says, “This isn't always the case, as every client is your boss—he who pays the piper calls his tune.”
  • High demand, so there are many opportunities.
  • Opportunity to develop your own reputation and brand.
  • Less “busy-work,” such as department meetings, performance evaluations, etc.
  • Opportunity to work with a variety of people on a variety of topics.
  • Flexibility to charge rush fees for crash projects.
  • Ability to multitask (laundry keeps moving, dinner gets started, etc.) if working from home.


  • Risk of isolation if working from home.
  • Payments often arrive 30 to 75 days after work is completed.
  • Workloads can be volatile. Ray Cole says, “Income (and work hours) can be extremely bursty—feast or famine, with plenty of famine. Feast times often come during holidays. I was always busy over the Christmas/New Year/Winter ‘break’ as a freelancer.”
  • More administrative tasks (cash management, invoices, taxes, etc.). Take it from Matthew Bibby, “Running a business takes time. You'll have invoicing, contracts, tax stuff, sales calls, scheduling, website development, and discovery meetings that all need to happen ... but you likely won't be paid to do them!”
  • No paid vacation, sick leave, or other employee benefits (401k, health care, etc.).
  • Scheduling vacation can be hard. Ashley Chiasson’s recipe for success in this department is giving her clients plenty of notice for the time when she won’t be available.
  • No access to an IT person or department when computer issues arise.
  • More difficult to switch off from work at the end of the day.
  • Less space in your home if working from home because you need an office.
  • More difficult to get house or car loans when starting out.

Do You Have What It Takes?

If you’re still on the fence after reading the pros and cons list above, here are some questions to ask yourself to decide what path is best for you.

  • Are your e-learning design and development skills up to par? It’s generally a good idea to get some experience as an e-learning designer and developer in an organization before freelancing. That way you have a chance to learn from others and really hone your skills.
  • Do you have project management chops? As a freelancer, you’ll have to manage your own projects. If that’s something you’ve never done before, you might want to consider trying to get some experience doing that before setting off on your own.
  • Are you a good salesperson? As a freelancer, you need to be good at selling yourself. You need to be able to explain to people what makes you special and why they should work with you instead of someone else. In sales terms, what is your Unique Selling Point (USP)?
  • How do you handle uncertainty? There are a fair amount of ups and downs in freelancing. Sometimes you’ll have tons of work and other times you won’t have any. If you’re uncomfortable with uncertainty, then it might not be the best option for you.
  • Do you have any other sources of income? As Russ Sawchuk points out, it’s a lot easier to make the decision to be self-employed when your spouse or partner has a steady income that you can depend on. However, this doesn’t mean single people can’t be freelancers! It just means you might want to have more saved up before you start.
  • Are you an introvert or an extrovert? If you’re highly extroverted and love to be around people, you might feel isolated working at home by yourself. However, that doesn’t mean all freelancers have to be introverts! There are plenty of options to make sure extroverted freelancers get their daily fill of social interactions. Philippe Siwinski suggests setting up shop at a coworking space or, for a few hours a day, a local coffee shop. Another option would be to make a point of getting together with friends after work.

Tips for Starting Out

One of the scariest things about starting out as a freelancer is that you can no longer count on a monthly paycheck. Here are some tips for making a smooth transition:

  • Bruce Graham recommends doing some freelance work on the side for a year or so to see how you like it and how much revenue you’re able to generate. That way if you decide it’s not your cup of tea, you won’t have to look for a new job. And if you really like it, you’ll already have a couple clients of when you decide to give it a go on a full-time basis. Before you do this, make sure your current work contract doesn’t prohibit it. If it does, consider negotiating that aspect with your boss.
  • Save up enough money to last six to nine months, to give yourself a little wiggle room if your business takes a while to get off the ground.

The Bottom Line

Freelancing isn’t for everyone. It’s important to take your personality, skill level, and financial situation into account when you’re deciding whether to become your own boss. Hopefully this insider information will help you make the right call.

Looking for more information about freelancing? Check out these resources:

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