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Transitioning to full-time freelance with Lisa Omore

Lisa talks about the trade-offs of being self-employed and how Canadian freelancers can make the leap to working full-time on their business.

Lisa Omore is a multidisciplinary designer with a background in advertising. A year ago she left her agency job to dive into the world of freelancing as a branding and logo designer. To date, Lisa has worked with some of the biggest brands including Shopify, Timberland and Moosehead Breweries.

In this episode, Lisa and Mohammed talk about how Canadian freelancers can make the leap to working full-time on their business and how they can better prepare to increase their chances of success.

Short on time? Skip to the parts you're most interested in.

[01:01] Getting started with freelancing

[04:27] Reasons to start freelancing

[05:52] Personal growth as a result of freelancing

[08:02] Developing a pricing structure

[11:12] Planning to make the leap to full-time freelancing

[14:20] Leveraging a recruiter to find freelance gigs

[19:12] Tips for those planning to make the leap full-time

[21:58] Registering your freelance business

[24:37] Things to keep in mind as a few freelancer

[29:32] When it doesn't make sense to transition to freelancing full-time

If you enjoyed the conversation, check out more episodes of our podcast. You can subscribe to Freelance Canada on Apple Podcasts or listen to it wherever you get your podcast. What follows is a lightly edited transcript of the episode.

Lisa: I'm ready to just dive into it really.

Mohammed: Perfect. Perhaps we can get started by getting a better understanding of when you started freelancing?

Lisa: So, that's really interesting. My first experience with freelancing was way back at the end of 2016, the beginning of 2017. I was still in college. If you were in Ontario at the time, the colleges were on strike. I used to be a note-taker and I worked on campus, but because of the strike, I couldn't do any of my work.

I needed a job. I needed money. So, I went on the campus job board and found a freelance job for a designer for reports.

Mohammed: Okay.

Lisa: It was an interesting job. Because I had all that time, I could do it. But, at the beginning of the year, I got an internship at an ad agency and I felt that as much as it was an internship, I felt so insecure [job-wise] that I had to keep freelancing. Except I did it completely the wrong way.

I would wake up at 6:00 AM, get on the TTC; work on the TTC for two hours to get to my internship; work my nine to five; then get back on the TTC. At the end of the day, I’d do my freelance job till I got home. I was sending files with TTC wifi. It was crazy. Luckily I got hired on to that internship into a full-time position and I stuck there for two years before making the transition back into freelancing.

Mohammed: And, I'll go back a little bit, which school did you go to? What were you going there for?

Lisa: I went to Humber and I was in the creative advertising program which was super good. They're really good at getting you into the industry, which is exactly what I wanted and it worked.

Mohammed: And so now what is it that you do as a freelancer?

Lisa: Right now, I'm a designer, first; art director, second. I’m mostly building brands and identities at the moment, and I'm really enjoying that work but in the past, I've done digital work, websites, social media —  I've even dabbled in and out of home and TV. So, my skill set is pretty diverse and [I] have worked in different industries: beer, cannabis, CPG.

Mohammed: E-commerce.

Lisa: E-commerce, yes.

Mohammed: Yeah. You've definitely worked with some big brands. I mean, you've got Shopify, Moosehead. I think there was like King Ursa or something.

Lisa: Yeah, [that was the] agency I worked at so, by default, you do some work for the agency.

It's been a journey, but I can say now I'm just really starting to reap some of those benefits of freelancing.

Mohammed: And how long have you now been freelancing full-time for?

Lisa: About eight months. I transitioned back in November of 2019. It's been a journey, but I can say now I'm just really starting to reap some of those benefits of freelancing. But it did take a while to do it better than I did in 2017. When I was sending files on the TTC.

Mohammed: And when you say reaping some of the benefits, I'd love to know what you mean by that. Could you dive into that a little bit, please?

Lisa: One of the major reasons I started freelancing was the opportunity to pick [the] projects. I was passionate about what I really wanted to work on. For me, that has been the biggest benefit — to work with people who value design for their brand or for that specific project, but then also for me to be super interested, super into the project and want to deliver the best product possible.

I can say I've not been bored, which is such a good feeling to have. And some people never really get to attain that in their work. So, that's been the biggest benefit for me.

Other than that, it's also having to be in charge of my own growth. When you're in a full-time job, sometimes you can delegate that to somebody else, which isn’t really a bad thing, but I have taken ownership in the growth and the changes I want to see in my freelance work and there's nobody else to do that, but me and that's really empowering for me.

I usually find it really hard to say ‘no’, and freelancing has taught me, sometimes in a very difficult way, when to say ‘no’ and when to say ‘yes’ and where to draw the line.

Mohammed: I tell people, entrepreneurship is the best form of self-growth because it's essentially a journey that you're on and you're constantly learning so much about yourself. I'd love to get a better sense of what has been some of the changes you've started noticing in yourself, or perhaps, in your own development as an artist and as a creative director.

Lisa: I think as I started to pick projects I was more passionate about, I started to refine my skills in a very specific area. As you know, freelancing is like a business. You have to have an audience and you're essentially going to sell. Being able to just focus on brands and identities has really helped me fine-tune some skills that I was touching in my full-time job only once in a while. That's kind of where I've seen the biggest growth and started realizing things about my skill set that I never realized. I've had a couple of people tell me that I was really good with colour, and I somewhat knew that, but now I actively use it as a marketing tool and tell people I'm really good with colour.

Also, one of the things that I noticed right away is that I usually find it really hard to say “no,” and freelancing has taught me, sometimes in a very difficult way, when to say “no” and when to say “yes” and where to draw the line.

There can be a tendency to always say “yes” to work. Sometimes that work doesn't pay what it should [and], depending on your finances at the time, that can get a little tricky, because you're like, “Well, I gotta make money sometime.” But I really had to look at putting a value on my time and then saying “no” to projects where the cost/time equation didn't make sense.

Mohammed: And are you pricing yourself and your services on an hourly basis on a daily basis or project basis? How have you structured that so far?

Lisa: Mostly on a project basis. I think I get the most value with that structure. When I'm consulting here and there, I'll probably do [it on] an hourly basis because the ask is usually a lot less. Very rarely do I do an hourly basis. I feel like when I have a project, I can look at the client and their budget and the scope of work and then price accordingly.

It was almost like a purge, but once I was done with that, I really felt like I had a clean slate and I could start this freelance journey properly.

Mohammed: How much of those have you learned along the way? How much of it has been just a sheer necessity? Because you've been freelancing now for eight months. So, what has that transition been like for you? How did you go about saying, “I'm going to leave my full-time work and then be able to transition doing freelance full time”?

Lisa: I think a couple of things had to align for me before I left my full-time job. The first reason was family. I grew up in Kenya so most of my family is there. I found that the vacation time you get in a full-time job was not enough for me to reconnect with my family every year. It was very limited. And I love to travel, so to have additional days just to go wherever I wanted to go. I felt very restricted in that sense. I had also reached the end of a really big project at work and I thought it was the right time to do something different. And there was actually a passion project I'd been sitting on for a year.

I wanted to start a textile business and I was like, “What if I quit my job? This is the time for me to dive into that and put all my energy into that.” So, I gave my notice and the first thing I did was take a break. I find it really helpful to reset once you've finished one chapter and you're about to start another and my way was to travel and see my family and do every single thing that I essentially didn't feel I could do that year. I went to five countries, visited my mom, and visited my family for three weeks. I started a business that stopped in a week; a ton of passion projects. It was almost like a purge, but once I was done with that, I really felt like I had a clean slate and I could start this freelance journey properly. So, that's essentially how it started.

Mohammed: A big purge.

Lisa: It was a big purge. Yes.

Mohammed: You mentioned you went travelling, went to go see your family. To travel and to even take such a large amount of time off, most freelancers think that that's not always possible, if possible at all. So, how did you plan to make sure that you were able to take time off, to go travel, to go see your family in Kenya? What has been your time and your project structure?

Lisa: I think what makes this kind of a unique situation is that I took the break before I started to freelance “officially.” So, right from the moment I quit my job, I took the next month off and I had planned to do this like six months back and planned to also save for it because no one was going to pay me to do any of this (I wish).

That was the one way I structured it and planned ahead of time to take that month and a half off. It really helped. It was right before Christmas so the projects I did get in that time were really small or like an end-of-year wrap up type project. There weren't any that were really significant. That's the one way I did it. I saved and I made a buffer between my full-time job and my freelance job.

Mohammed: I'm sure you're probably glad that you went on this vacation cause I don't know when the next time most of us will feel comfortable flying anywhere.

Lisa: Yeah.

One thing I did during my full-time job, because I anticipated not having a ton of work in the beginning, was I started to work with a recruiter.

Mohammed: Your timing could not have been better to go do that and then get started on your freelance. So, you did a big purge, you went away, travelled to five countries, saw your family Kenya, came back to Canada, and then what?

You said you started freelancing around November and a lot of times, it seems to be not the best time because a lot of employers or companies or clients are thinking about their December holidays. I'd love to get a better sense of what happened when you got back and how did you dive right in and go full-time.

Lisa: Yeah, it was hard. I can't say I had a ton of work at that time. You're right —  it's the end of the year, everyone's trying to wrap projects up. Not necessarily trying to spend money. So, the projects I did get in November were very small. I wouldn't even count them as significant at all, but it was still the beginning of my freelance journey.

One thing I did during my full-time job, because I anticipated not having a ton of work in the beginning, was I started to work with a recruiter. Recruiters can be helpful, especially if you're in the design/advertising space. My recruiter at the time was really helpful in sending me projects that agencies couldn't handle [due to] overflow work or really tight deadlines. That's how I got some work in December. 

Mohammed: You mentioned that you used a recruiter. How did you find a recruiter, reach out to them, build that relationship, determine how much their fee is versus what you will get? What was the process there?

Lisa: There are a few agencies in Toronto. There are a couple of agencies in Toronto that focus on finding candidates as freelancers, but also for full-time jobs. I reached out to one agency and they called me in for an interview, essentially just assessing my skills so that they could place me in appropriate jobs.

I was able to determine my fee for myself, which is really helpful. Because that's one of the things I was scared of, not getting paid properly. But using a recruiter in the beginning was really helpful in terms of building a little bit of a client-base. I'm getting my work and my face out there in different companies and industries; it really helped me. It's someone helping you find jobs for free. It's almost like having an assistant. It's great and if you're starting out and you have zero connections, it's helpful.

I always say, “Say the highest number that you're almost uncomfortable with.”

Mohammed: And you mentioned this gave you an opportunity to determine your pricing structure. What did you mean by that? What was that process like for you?

Lisa: Oh, it was really simple. They just asked me how much I wanted to get paid. I know freelancers do this all the time; they just scream a number. I always say, “Say the highest number that you're almost uncomfortable with.”

Mohammed: Hmm.

Lisa: I did not get that number. It was a little bit less, I'll be very honest, but it also taught me to get comfortable with asking for what I was worth at the very least. The practice now, and I do this continuously with potential clients, is that I'm just going to say my price. And when we can, we can have a conversation from there. I'm not closing the door.

We can negotiate. You know, it's really important to get some negotiation skills, but I'm not uncomfortable talking about my price anymore, just because of that one trick.

Mohammed: So, now you've got a recruiter. You figure out your pricing. You didn't get the highest that you were uncomfortable with, but I'm sure you at least got close to it. And from there, when did you start getting clients like Shopify, Aphria, Moosehead? How far along into your freelance journey did all those brands start coming up?

Lisa: Well, Shopify, Moosehead, Aphria were all in my full-time job. That's work that I kind of left in my past life. When I started working with a recruiter, I was placed in different media agencies, ad agencies, sometimes a standalone company that I got to work for.

I no longer get or prioritize work from the recruitment agency because I've got into a place where I can find clients on my own. She's helpful, but once you get your foot in the door in one place and you do good work, they keep asking for you. That was really helpful for me to start getting into the swing of freelancing. There's one agency in particular that I did a ton of work for and they just kept asking for me. That was helpful for me to see how it worked and then I also did get some work from my past connections from the agency, which is what I think the full-time job is really helpful for, at least starting out with one, is that you start to build your network there and it comes in handy when you're freelancing later. Out of some of those connections came some more work and then you start to do some good work for them and they keep asking for you. So, it's almost like a domino effect for me. That's how freelancing has built up to the situation that I am in now; a lot of good work turning into more good work.

Six months’ worth of saved income is a good place to start. If you're thinking of going into freelancing, it's a nice security net.

Mohammed: Amazing. And it seems you feel comfortable pursuing your idea or your desire to want to work full time as a freelancer. It affords you the flexibility that you're looking for while also enabling you to really hone your craft and grow even faster than perhaps you may be in a full-time job.

With that in mind, what are some insights or learnings that you could share with others considering working full time as a freelancer?

Lisa: Save. If you're gonna transition, you never know. I anticipated not having a ton of work in the beginning, but you still have bills to pay. Your bills don't necessarily go anywhere. Unless you moved back in with your parents, which I'm very jealous of if anyone can do that.

I did not have that luxury so I definitely had to have enough money to cover my bills. I would say about six months’ worth of saved income is a good place to start. If you're thinking of going into freelancing, it's a nice security net. And while you're starting to reach out to new clients and find business it's one less thing to worry about (if your bills are covered) and maybe you won’t have to take jobs that are not worth your time or don't pay enough. So, you can really focus on doing work that you're proud of.

Another thing is taxes. Oh my God. I hate them.

Mohammed: Go on...

Lisa: I do not know any freelancer who likes taxes. I absolutely hate them. Especially for me, because I'm not a permanent resident. I'm not a citizen. I am an individual with permission to live and work in this country. A lot of the tax rules, if you've ever been on the CRA website, it's always permanent resident or citizen.

I've always had to find something that can tick the box I fit in and the rules have always been not so clear for me. And that's part of the reason why I hate taxes so much now as a freelancer. But it's helpful to know some basics, like when to get an HST number, where you can get write offs. I mean, I don't have to file these taxes till next year, but I'm learning every day.

Mohammed: And what has that process been like for you? Did you register as a sole proprietor or have you decided not to register at all at the moment? Or are you a corporation? What's your setup so far?

Lisa: I’m an individual sole proprietor but, because I am not a permanent resident or a citizen, applying for an HST number is tricky. You can voluntarily apply for an HST number, but you have to either call in or do it by mail. You can not, as far as I understand, do it online like every other advice page tells you to.

Mohammed: Wait, really?

Lisa: Not if you're just on a work permit.

Mohammed: Oh, okay.

Lisa: Yeah. If you're a permanent resident [or] citizen, you can do it online. And it's really easy.

Mohammed: Okay.

Lisa: In my case, I have to call in or do it by mail, which is going to take forever so I’ve been procrastinating about that. I will do it. I promise it will happen.

Mohammed: Well, there's no rush. I mean, yes, as you get to the $30k mark, then definitely you have to. I'm sure you can do it voluntarily as well, too, but I always tell people, “If you're just getting started with freelancing, wait to register for HST.” There is no rush for it. 

A lot of people will try and get it at the same time because they think registering for HST is the same thing as registering a business, and it's not.

Lisa: That's right.

Mohammed: I guess [it comes down to] personal preferences. It keeps things simple while the person is exploring, because there are people that will start freelancing and, three months into it, think, “I don't think this is for me. I'd rather go full-time.”

Now you have an HST number that you still have to collect sales tax on for any gigs in the future you decide to get and you have to calculate how much you owe. So, I just tell people to keep things simple when they're getting started and then, as the business progresses, they can start moving things around a little bit.

Lisa: Yeah, that's pretty good advice. I would say the same. Like, wait till you need to.

Mohammed: Yeah.

Lisa: Essentially.

I try to make it as easy as possible for my clients to pay me. I still have to chase invoices. [As a freelancer], I don't know how to escape this. If you have ideas on this, please tell me.

Mohammed: I like your summary a lot better than mine. Now that you’re well into working as a freelancer full-time, what are some tips or insights that you believe other freelancers should keep in mind as they decide to get started? You mentioned putting aside six months of your income, definitely touched a bit on [your] thoughts around taxes, and when to go about collecting GST/HST.

What other considerations are there that you've experienced or perhaps you yourself have questions about? Insurance or work-life balance, or even invoicing tools? I'd love to know what sort of problems you're running into.

Lisa: I think it's a good idea to get as organized as you can in the beginning. I liked that you mentioned invoicing; I try to make it as easy as possible for my clients to pay me. I still have to chase invoices. [As a freelancer], I don't know how to escape this. If you have ideas on this, please tell me. It’s in my calendar [so when an invoice is] due in two weeks, I send them a reminder because clients forget. Two weeks ago, I sent an email and the invoice hadn't even been processed on their end and it was due in 12 days or something.

One of the tools I do use is Wave. It's free and they give you reports and you can keep track of your income, too. They also give you a way to process payments online so you don't have to wait for checks or anything. They do have a small fee, but I think it's worth it for the ease of processing payments, so that's been really helpful.

In terms of bookkeeping and keeping track of my income and expenses, I use a mix of Mint and QuickBooks. Mint, QuickBooks, and Intuit, are part of the same system and owned by the same company.

[I use one login for all three]. Mint is really good for budgeting and keeping track of where you're using your money, even on a personal basis, not just for business. QuickBooks is really good for saving your receipts so that, when it comes to tax season, you're not scrambling to know where all the paperwork is and if you bought a whole new computer or a laptop that you'd like to write off, then it's already saved there for you. These are some of the tools I used to get organized in the beginning.

If you're really serious about staying in freelancing, I would highly recommend getting a mentor or a circle of friends in your industry or a business coach to really keep you focused on your goals and where you want to go.

I've been lucky that my friends are in this industry and we're constantly reaching out to each other for advice and that has been really helpful and also a big motivator, because they're like your cheerleaders at the end of the day. It's helpful to have a circle like that to keep you going because sometimes freelancing can get tricky or sticky. 

Mohammed: I'm definitely going to have to get you to try Benji for my own selfish reasons.

Lisa: I think what I love about Benji — because I did learn about Benji way before you reached out to me. I've been lurking around it, just looking at it from the sidelines every now and then. When I need to know what a tax write off is, that's the first place I go.

Mohammed: Oh, that's amazing!

If you don't have enough money to cover your bills, you're just going to be so stressed out when you're trying to freelance or try to get clients because you're just worrying about your bank account (most of the time).

Lisa: It's good for the people to know.

Mohammed: I don't want it to feel forced or feel like a product placement because the goal with these podcasts is to ensure that we're making this as much about the guests that we have on and [as well as] their information and experiences, not trying to place Benji in here. Because if we can ensure that we help and support and educate people, it's up to them to be like, “I learned a lot and this is a solution that makes sense for me and I'm happy to try it.” 

For me, that’s the goal here. But I'll transition back to talking about freelancing. We've talked quite a bit about what your experience has been from getting started, to transitioning to becoming a full-time freelancer. At the same time, we touched a little bit about people that will start freelancing for three months and decide it's not for them. So, maybe for those who are thinking about freelancing full-time or are transitioning to freelance full time, when does it not make sense for somebody to transition full time and stay part-time?

Lisa: I talked about saving, so I'm not going to go into that again, but if you don't have enough money to cover your bills, you're just going to be so stressed out when you're trying to freelance or try to get clients because you're just worrying about your bank account (most of the time). But my second point is that if you are new in your industry, right out of school, I strongly believe it is in your best interest — and this is an individual thing — to go into a full-time job first.

Only because I find that clients like to see a record of success or a demonstration of skill depending on what industry you are in, that might be easier to show without any experience, or it might actually be harder if you have no experience. If you're a designer, of course, you can build your portfolio without getting into a full-time job but sometimes clients want to see proven real-world work and getting a full-time job can really help you start to build some of that. That's what a full-time job did for me. Now I can speak to projects like Shopify and Moosehead. But, just off the top of my head, if you're in HR and you have never managed clients you have never helped people and you're just starting into freelance. I mean, I know nothing about HR, but I can imagine that it's difficult to prove to a new client that you can do that job. So, if you're in a full-time job, even for a year, even for a short while to get some of that experience could be really valuable in proving a record of success when you're trying to get clients as a freelancer.

Mohammed: And, outside of this, what would you say your overall experience has been so far? If you had a scale of one to 10, one being not so great and 10 being superb, where would you currently put your experience so far?

Lisa: At the beginning of the year, I'd have probably said a five. I was neither here nor there.I was still hoping that it would really work. Now, I would say it is more like an eight or nine. I am confident that I'll probably be doing this for the rest of the year. and I'm loving the experience right now.

I mean, sometimes it gets tricky with scheduling and balancing, you know, when to work and how much to work. There's no HR; you’re HR.

But I'm really enjoying it right now.

Mohammed: Well, Lisa, I really appreciate this opportunity to learn from you, to get all of your insights and I'm just really grateful for this. Thank you so much! I'd love to know where people can find out more about you and your work online.

Lisa: You can find most of my work on my website, lisaomore.com, and on all major design platforms, Behance, Dribbble [and] Instagram, by my name: Lisa Omore.

Mohammed: Perfect. Thank you so much!

Lisa: This is great. I love that we can just have a conversation about getting into a new field or diving into a new opportunity. I love the whole format of this and just making it very conversational. It's fun. I'll do other podcasts again!

Mohammed: Awesome. I will take that!

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