How to Succeed as a Freelancer

A recent study showed that 80% of freelancers would not go back to traditional jobs. But what is freelancing really like? We sat down with Jared Lindzon, a seasoned journalist and freelancer to share his journey and lessons he picked up along the way. A must-watch story for any aspiring and experienced freelancer and entrepreneur. Enjoy!


Jared Lindzon, Freelance Journalist:

There’s a woman at the what a bagel counter on Spadina who knows me very well because every single Sunday I would go in there buy half a dozen bagels tub of tuna and a pack of cheese and that would be my lunch for the week. It was $20 for six tuna melts on a bagel and that kept me alive for my first year freelancing.

Like many freelancers I started it because I was working a job that I didn’t enjoy. I graduated with a journalism degree in 2011 which statistically was the worst time to graduate with a journalism degree in like the history of the industry. I was unemployed for about six months just packing boxes in my dad’s warehouse to make a few bucks and then finally landed a job and was really excited about it, but the job was after a while not what I was looking for. I was getting a little frustrated that I was so excited to get into the world of journalism and I felt like I was trying to get more and more removed.

A former classmate of mine from journalism school mentioned that his editor of the Toronto Star was looking for a freelancer to do some work on the side and so I started to pick up a little bit of work for them. I had this idea that I should start interviewing people in different time zones. If I woke up early enough I can catch people in the East Coast at you know 9 a.m. their time before I had to leave for work and if I raced home after work and got home around 7:00 I could still reach people in Vancouver. For a few months I was doing this work for the Toronto Star on the side on top of a full-time job and neither were paying me very well but I really loved what I was doing and just loved being back in in the world of journalism and then one day my uncle who knew an editor at the Globe gave me an opportunity to meet with him over coffee and we started chatting and I told them that I was a millennial and that I was working remotely for the Toronto Star as a freelancer and he stopped me right there and he said, “Those are all the words that our careers department is trying to figure out what they mean and they don’t know what any of them are so why don’t you try writing for them?”.

Sometime around February of 2013 I quit my full-time job and pursuing freelancing on a full-time basis. I mean financially at that point I think I was earning like my rent plus $500 that was where I was it for a little while and so the extra $500 had to be stretched really far. I was petrified and rightfully so. It’s tough those first few weeks and months especially because it’s one of those things that really snowballs over time. Over time you get more contacts you have people coming to you. When you’re first starting out, you’re nobody, nobody’s ever heard of you, no one has any reason to answer your emails and you really got to hit the pavement and you got to be used to hearing the word “no” a lot. I understood that every “no” was gonna get me closer to a “yes” and I kept reminding myself of that but when you spend day after day just working so hard to get someone to notice you or to give you a little bit of work and you know at the end of the week you’ve got nothing to show for it…in a few moments of weakness I  started applying for jobs, and knowing that journalism jobs weren’t going to be a possibility I even applied for stuff in you know public relations and unrelated fields. I was at that early point of my career ready to leave journalism out of desperation. I’m so glad no one ever got back to me on those applications and I’m glad that it stuck because things didn’t really pick up until after my first year of really struggling but when they picked up, they picked up quickly.

The best thing you can do is finding a niche or finding a level of expertise in a more broad category is getting more competitive out there. I mean there’s more freelance opportunity than there used to be but there’s also a lot more competition and that’s across a lot of different industries not just mine. Freelancing is a lonely existence. In professional environments you often have the opportunity to mentor or be mentored you have people around you that you can you know bounce ideas off. You’d be surprised when you when you find someone who’s working independently and successfully they may seem unapproachable from afar but I found that a lot of the times if you express an interest in emulating their career and interest in learning how they operate, they’re usually very open for the same reasons that I’m now open to anyone who asks. Because I see it as as my duty sort of continuing on that chain. I’ve wasted a lot of hours doing things that I thought might help me that didn’t but then at least I knew what to look for moving forward.

I think the most important thing as a freelancer is concentrating on your pipeline. It’s so easy to get so into the work that you’re doing because again that’s why you’re doing it that’s the thing that you’re passionate about but then that assignment ends and you realize that you haven’t taken the steps to set up your next assignment and now you’ve got nothing to do except dig for more work. That’s where those you know slow periods and those those troughs and income start to happen. I would recommend especially if you’re in a creative field balancing out those creative projects with business development and I think it’s an important part of freelancing in general is focusing on not just this assignment but where’s the next assignment going to come from. As a freelancer, organizational skills are paramount. You need to run a business just as much as you need to do the thing that you’re being paid to do. I have had absolutely no formal training in running a business I didn’t know how to even keep an Excel spreadsheet organized.

I had to learn how to change my relationship with money in a lot of ways because you know there were times where a big check comes in, and you put that big check in your account and you got a big number in your account and you’re  starting to think like “wow I have money!”. You don’t have money! That money is mostly the government’s it’s a little bit going towards your hydro bill and your rent and everywhere else. It’s hard because you get a big cheque like that and you start to think that’s yours to enjoy without realizing how long it might be before the next one comes. Everything in the world is built for the person who has a regular income whether it’s paying a set monthly rent or mortgage whether it’s you know the tax coming out of your paycheck before you see it and have the chance to spend it. There are so many systems that were built specifically for people who have traditional salaries and income that just don’t really lend themselves well to a fluctuating income. I liken it to being left-handed, it’s like the world wasn’t built for you and you kind of have to adjust around it.

When I first got into freelancing, people were concerned, primarily my parents and also my peers, that there was no job security as a freelancer. It turns out that that my peers who had gone from journalism school into traditional institutions, major newspapers, news organizations, a lot of them had been let go in the year since and ironically taking the least secure path to become a freelancer I’m now in a position where it would take almost two dozen strangers from around the world to cut me loose all at once for my income to disappear entirely. There’s very few roles in the journalism industry right now that could potentially match my freelance salary and that’s actually something that a lot of freelancers experience because you’re taking on more risk and because the employer is only paying you for a single project or a specific period of time you make more per hour and if you’re able to fill those hours you can potentially make a lot more. So like many freelancers I don’t think there’s very many employers that could match my current freelance salary.

I wouldn’t be eager to jump into a full-time job anytime soon. I really enjoy waking up when I want to, working in my sweatpants, taking a day off without asking anyone’s permission – that sort of freedom I will never let go of lightly. I don’t see myself ever taking a long term full-time job again. I’ve seen the evolution in just the seven years that I’ve been working as a freelancer – it went from being totally on my own to now there’s accounting software specifically built for freelancers that could do all the things that I struggled with most when I started. There are now platforms where people can find work for whatever your thing is. There are websites like “99designs” where designers can compete for work. I personally use a website called “Contently” which is specifically for written content. There is a lot more infrastructure now than there ever was for freelancers.

When I finally did get to a point where there was a level of stability and starting to get a little bit more noticed, I think it was two years into freelancing, I read a study and I was actually ironically reporting on the state of freelancing in America. I read a study that said that 80% of freelancers at that time, at least 1/4 didn’t want to go back to the previous roles that they had or into the traditional workforce. Freelancing was a way out of the job I didn’t like in a way back into journalism but it wasn’t the long-term solution. I was constantly looking for job postings and wondering when will I have enough of a portfolio as a freelancer to get a full-time job with a place like the Star or the Globe or elsewhere. Then I read that report and I started speaking to other freelancers and I realized…why was I so keen on jumping back into the traditional work force? I hadn’t really had a great experience with that before, I was finally starting to have some sort of consistency and I had a ton of autonomy and I got to do what I wanted to do and how I wanted to do it. I remember vividly thinking after writing that story “I’m writing the story about myself”. This isn’t just a statistic about the other freelancers out there, this is my story I got into it as a means to an end but the more I thought about it the more I realized that that it was better than where I was coming from and better than anywhere I could go from there.

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