happy little biz

So you wanna be a freelancer...

Been thinking about working for yourself? Love the idea of making your own hours and taking vacation whenever you want? Dream of working from home, in sweatpants, with your cats snuggled next to you?

Your life could be like this, if you really want... Thanks Hyperbole and a Half!

Most folks think the idea of freelancing is really awesome, and tell me (rather wistfully) that they'd love to do it, if only they could. I'm not here to tell you if you can or can't, but I'd like to share some of the things I've learned from my experiences with running my own businesses over the last 8 years.

You need to be ok with uncertainty.

I think most people tend to shy away from uncertainty. We like knowing things and being secure in our positions in life: financially, socially, and in our careers.

If you freelance, there will always be a level of uncertainty in your work. With a regular job, there is an agreement: you show up for the agreed hours, do your work, and get paid accordingly. It's pretty predictable, and you can plan your life knowing you have a certain income and certain hours you have to be at work.

But with freelancing, some months you might have lots of work, be really busy (sometimes too busy!), and be making good money. Other months might be very quiet, or you may even have no work at all. Even the most successful freelancers can have quiet months, where they are earning significantly less than average. It's all a normal part of the lifecycle of a year in business, and you need to be comfortable with that.

The upside of the uncertainty is as a freelancer, you are free to do whatever you choose with your time. Have a slow week? Take time out to go for a long walk with your dog and enjoy the fall leaves, meet a friend for coffee, or catch a matinee of your favourite movie. As long as you've done your job, things will get busy again, and you'll be thankful for the bonus day(s) off.

This does bring me to my next point, however.

You need to do a fair bit of work that isn't directly paid.

When you work for yourself, you need to take the time to do all the extra business planning tasks that don't directly earn you income: accounting and billing, marketing, advertising, replying to emails and phone calls, booking and preparing for meetings, and so on. All of this stuff is critical to the success of your business, so you need to be ready and willing to put aside time each week for these tasks. This stuff isn't directly paid, of course; your clients are not cutting you cheques for the time you take to do marketing. But they are indirectly paid, as keeping up on these tasks makes sure you are aware of how your business is doing financially, helps promote your business to bring in more clients, and maintains positive relationships with your current clients.

If you dedicate time regularly to these tasks, you should find they get easier over time. You'll also find that you're able to regularly take time off, because you made sure to keep up on these things so you don't need to take vacation time to catch up.

This is really an area that is non-negotiable for freelancers. If you aren't willing to do the marketing, accounting, and other business planning aspects of being self-employed, and don't have the budget to hire someone to do them for you, you really won't have a viable business in the long-term.

Which brings me to...

You need to be organized and a good planner.

As a freelancer, generally speaking, you're going to need to be working on more than one project at a time, but still put in hours doing your business planning tasks. This means being organized and having good time management skills.

This also means having good financial planning skills. You need to have a budget and be smart about spending, so you don't overspend during the more profitable months and end up with nothing left for the slow months.

But being organized is actually a really good thing! Not only will you feel positive after a day of getting through a chunk of your to-do list, but you'll often find being organized means you can more easily squeeze in time for personal projects and downtime.

You need to be self-motivated

You might have kids, a partner, or pets who like to wake you up at a certain hour, but ultimately no one is going to tell you when to get started on your work day. If you aren't a good self-starter, it can be hard to get things done. It's not good for business if projects that should take a few days take a couple of weeks because you were procrastinating!

It's also important to keep work time for actual work. If you work from home, you shouldn't usually be doing loads of laundry or baking cupcakes while you're supposed to be running your business. Set aside specific time for those other things.

As with the other points, there are positives here too. Want to work in the evening and into the night, because that's when you're at your best? As long as you don't have other obligations preventing you from doing this, go for it! Want to take a fitness class mid-morning a few days a week? Sure! Want to pack everything up and go work from a buddy's cottage for a week? Yep, you can do that!

Essentially, you need to be motivated to get the work done, but generally speaking, there are no rules about when and where you need to get that work done. Do what works for you and your clients.

And speaking of clients...

You need to be a good communicator

It's extremely important to be able to communicate effectively with your clients and anyone who you might subcontract work to. It's all fine and good if you've got amazing programming chops, but if you cannot explain technical concepts to non-techy people, you're going to run into issues when working with clients. Similarly, you need to be able to articulate details about a project in a way that gives your clients confidence in your skills, while still allowing room for discussion and client feedback. You also need to be firm in contract negotiations or when clients ask you to do things that are outside of the agreed-upon project, while still being professional and understanding.

The upside of all this is that these skills come in handy in all parts of life. Being a good communicator helps your relationships with friends and family, and also helps in situations where you're the client. So these soft skills are really worth working on.


I've got a few tools I use to help with keeping organized and sane in my work. Anyone else have any to recommend? Just leave a comment!

  • Freshbooks: Bookkeeping, billing, and time tracking software for freelancers.
  • Remember the Milk: Reminder software, that I use for pretty much everything! I put in reminders about work-related stuff, volunteer commitments, events I've bought tickets to, coffee dates with friends, and so on. I've got a lot going on most days, and I am very sure that without RtM I'd forget things.
  • CodeKit: Helps me keep projects organized code-wise. Also a time saver! Auto compiles code, built-in frameworks, helps with debugging, Bower components... it's just awesome.