I’m regularly asked about my switch from working in an office to working freelance, and once I started writing this I realized I have SO MUCH to say on this subject! I already have drafts for other posts about it, so if you ever wanted to know more about my work life, you are in luck. I have only worked in retail (my first job when I was 16!) and in various offices, so if your day job is not like this at all- and there are many, many professions that are not- please take my description of working in an office with a huge pillar of salt.
I worked in an office for many years, convinced I was working hard. Now I realize that I was being paid to breathe the air and drink coffee between 9 a.m. and 5 p.m., and work sometimes while breathing the office air. A lot of this has to do with many of the tasks that are assigned in offices- projects that go on for ages and require many different people to handle different parts, and output looks very different in those situations.
Switching to freelance, no matter what sort of work you do as a freelancer, means you only get paid when the output is complete. Maybe for some larger scale projects a percentage is paid upfront, but most of the money only comes in after you’ve sent the invoice, which is after you’ve done the work you said you were going to do.
When I say you only get paid based on output, I mean work that you can actually see. So if it took me twice as long to ghost write a blog post for a company, or I was taking photos and it took me longer than I quoted for because I was really in the zone, that time is time I’m not getting paid. I also now work at least a little bit almost every single day, including the weekends. It’s a combination of ‘if you love what you do, it doesn’t feel like work’ and ‘must work faster, I only get paid if I finish this!’
What I Wish I Had Known Before The Switch
So. Much. Accounting. Freelance work is for people who are committed to diligently tracking their hours, expenses, invoices, and bottom lines, otherwise you are almost definitely going to be losing money.
You Need to Establish a Routine, or you will not get as much work done. While it’s fun to feel like your days are free-form for a little while, you eventually need to get down to to work. It is a million times easier if you have a set schedule- maybe certain days where you batch a particular set of tasks, a couple hours in the morning for particular projects, weekly admin time to handle the aforementioned accounting.
Figure Out If You Can Afford the Lean Months. It’s worth taking a very honest look at how much money you spend each month, and then make a conservative estimate on how much money you will be bringing in each month. If you aren’t quite there yet, think about if that is because you aren’t yet making enough money on your side hustle (give it time, you’ll get there!), or if you have potential business opportunities in the wings waiting for you, and just need more time to pursue them.
Living with a SO? Then They MUST be on Board. If you are married or living with significant other and don’t mind having your entire financial future knotted together, then you have more wiggle room and can factor in their income. But that also means if you make the leap to freelance, it’s a decision you have to make together. I generally think that being financially dependent on your partner is a massive disadvantage for so many reasons, so if you are making the leap and counting on your partner, make sure that they are all in on your decision too. And be prepared to occasionally have to justify how you spend not only your day, but your money, too.
So. Much. Alone. Time. I’m an introvert by nature, and even I sometimes find it a bit much. Especially on a day when I’m dragging my tail and it’s hard to focus, it’s very easy to just get distracted by the internet or dance around to some music or decide that this is time to try out navy blue eyeliner and unearth EVERYTHING in my yarn stash. Which is why I am happy to go work in a cafe, and chat with the barristas. Keeps me on task.
What I Do
I write (poetry, short stories, working on a novel, etc), but it pays next to nothing. So I also do social media and content creation for a variety of craft and yarn companies, both as an account manager for Stitchcraft Marketing and my own clients. This means that I do photos, ghostwrite website content and blog posts, newsletters, work on every single social media channel out there, etc. I also occasionally do sponsored posts here on this blog, but I’m really choosy, so they aren’t happening every month. This means that when I’m budgeting, I’m basing the calculations on the typical number of hours I work for Stitchcraft and my clients every month. Anything else is a bonus, as far as my finances are concerned. I also tell myself ALL THE TIME that I’m going to work on more pattern designing, but it takes me along time, and then anything that pays gets pushed to the front of the queue, and design projects languish. I need to work on that.
Where I Work
Most of the time, I work right here, on my couch:
I don’t have a home office. I don’t even have a desk. Which I’m fine with it’s not like I have a Pinterest board full of home office ideas or anything because I enjoy working at home. And when that gets a bit lonely, I go work in cafes.
Toronto is full of gorgeous cafes, and I love them all. The trick to working in a cafe is determining what your must-have criteria is, and I have a long list: robust wifi, attractive surroundings, comfy room temperature, tasty lattes, assorted sweet and savory food options, other laptop wielding people. Those other laptop people are crucial- they are the ones you will ask to look after your laptop when you go to the washroom.
In January I joined a co-working space, Make Lemonade. I was googling co-working spaces in Toronto, it popped up, and I loved everything I read so I booked a tour. Make Lemonade is an all-female co-working space, and while I have no problem working alongside men, the atmosphere is so completely different without men. Men are allowed in the space, of course- I recently saw what I think was a job interview happening. I couldn’t hear anything they were saying, but he was leaning forward and moving his hands around like he was trying to convince of her something, and she was leaning back in her chair, legs crossed, looking at him with a completely neutral expression on her face (Resting Boss Face, I believe it’s called), and occasionally writing things down.
If I were interviewing someone, I would love to interview them here.
Photo Credit: Amber Ellis, Creating Light Studio
It’s pretty, bright, fun – not trying to be too cool, just a positive space. They run all sorts of workshops and masterclasses and networking events and everything I’ve attended has made me happy that I’m there. And of course, it was especially awesome when this happened:
Forbes.com ran an article on Rachel Kelly, the founder of Make Lemonade, and they featured my photo on the second page which was pretty fun. It highlights something that is sort of magical about finding the right co-working space – when you find other people who are like minded and like-hearted, you feel like you are all in it together. Having other people around you chasing their goals is like jet fuel for chasing mine, too.
Photo Credit: Amber Ellis, Creating Light Studio
Don’t let all those gorgeous photos from Creating Light Studio (they had a photo shoot at Make Lemonade one day, can you tell?) fool you into thinking that is what every day of my work life looks like. I go in a few times a month. Otherwise, it’s either the top photo of this post (hi, couch!), or I’m working in a cafe. Below is a photo I took last week, at a coffee-and-work hang with some friends. At the table: a geneticist, a graphic designer, an account director, and me (the uncool one with the obvious black PC laptop in front of the empty chair). All of us working. No, we didn’t draw the stegosaurus on the table. 
The day-to-day is different all the time, and while that sounded exotic when I was still working a 9-5, now I know it means that I have to spend time thinking about the shape of my day, every day, and where I am going to be. Then thinking through the logistics of what I need and what to bring as I change locations. It’s an extra bit of bandwidth that you just don’t need to worry about when you go to the same place and have everything you need at your desk, like you would at a typical office job.
Is it Worth It?
I love working with my clients, I love writing, but I don’t magically have more time in my day like I thought I would. I also work harder and make less money for the privilege (and make no mistake, I am very privileged to be able to take a pay cut to pursue my creative life) of working on amazing projects every day. Some days feel like winning. Other days I wonder who the heck I think I am to try to pursue my goals when it feels like Facebook/Instagram are already filled with people totally crushing not only their goals, but my goals too.
Some days are magic. Some days I feel like a failure.
I recently attended a retirement dinner for my former boss, and I thought I would only know a handful of the people there. Turns out I knew 90% of the room, people I had previously worked with from all across the country. Most of them asked me if I would consider coming back- including the incoming boss, whom I had worked with before from a different branch of the organization. And honestly, it was a good night with a lot of the things that I loved about my old job, and I was full of wine and beef wellington and crème brûlée and nostalgia…. I don’t know. Not having to work so hard, making more money again, those are attractive prospects. But then I love the flexibility of my days, the ability to respond to things that come up last minute, spend more time writing when it’s going really well, or be there for my kids or clients when something comes up last minute… it’s hard to say if one option is better than the other. They each have benefits and drawbacks, and it depends on the day which is more attractive.
No one can answer this question for you, and know that your answer could change from one year to the next. Our goals change, our values can change, and what we want almost definitely will change. Stability, medical/dental benefits, a work-paid RRSP, possibly more money are on the day job side of things. Freedom, potential to make even more (or even less!) money than a day job, flexibility and the chose-your-own-adventure of every day are on the other side.
There are a lot of crossroads in everyone’s life, where you are standing in front of a forked path and you have to make a choice. It takes a really acrobatic mind to look far ahead on those paths and see not just the immediate results of choosing one or the other, but what the second, third, and fourth results are from those decisions. Each choice we make in our lives ripples out in a series of consequences, challenges, and opportunities that stem from an earlier choice, and the leap into freelance can be one of the biggest.
From where you stand right now, which would you choose?
