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5 Lessons I Learned From Freelancing My Gap Year

When I graduated last summer, I had no idea what the next year would have in store for me.

I intentionally kept my vision relatively short – spent the summer traveling with friends and family, savouring the ending of my undergraduate life chapter.

When I landed in Toronto early September, I threw myself straight into the fray of resumes, cover letters and interviews.

I had made the decision pretty late in my undergraduate career that I might want to try this writing thing. Up to that point, my whole working life had consisted of building up a strong teaching trajectory. The decision to switch so late meant that I graduated from university with a resume for writing that resembled a first or second year student. But I was 22, fresh out of university and unemployed, looking to take whatever anyone would or could offer me.

I ended taking the part time route, just so that I could gain the equivalent of a few years of job experiences in a shorter time frame.

This past year I’ve worked at least 8 different writing gigs of varying lengths, ranging from 2 months to 8 months.

Now, emerging from the other end of my gap year and heading back into grad school this September, I’m still hunting for my final summer work contracts, but also reflecting on the experiences of the last 10 months.

Here are 5 lessons I’m taking with me into the future:

Being your own boss is less fun than you might think.

Yes. The freelance life has its perks: I work from home a lot of the time, I set my own schedules and organize my weeks. Free of the 9-5 structure, I can afford to have brunch with a friend and still meet a work deadline for that day.

But the lack of designated space and structure means that I own everything I do (or not do). It means that if I am not on my own case, nobody will be on it, and that is a dangerous place to be as it can compromise discipline, and quality of the work I complete.

Over the last 10 months I’ve had to learn to set standards for my work that were consistent, and reinforced regardless of how motivated I was, or how unideal the working conditions were. Admittedly, I also made plenty of errors, and delivered subpar work while still learning to adjust.

This experience has strengthened key skills for my own entrepreneurial sensibilities, however, and I’ve definitely come out much stronger.

Apply to every job you think possible, at least you get practice.

I’ve lost count of the number of resumes and cover letters I’ve sent out this year. Last September, I developed a habit of combing through 4-5 job boards daily to look for potential jobs I might qualify for, and it’s a habit I have yet to curb.

I quickly realized that weekends were slow, but that meant that whenever weekends rolled around I would be extra antsy about waiting for Monday to arrive. This became a bad habit – an uncontrolled emotional anxiety that would prevent me from both working and resting. I eventually came to actively control the amount of time I spent on job boards.

What this anxiety did do, was embolden my sense of shamelessness, and I would plough through job applications, writing and rewriting cover letters and sending them to jobs that fit, jobs that didn’t fit, jobs that were a little above my reach, and jobs I didn’t even really want – all just to satisfy the need to curb the anxiety from being unemployed.

That habit I have kept with me, and why not? The worst that could happen is that you don’t get an answer. The best? An interview opportunity.

Understanding what I have to offer is hard, and offering it well is harder.

I bombed the first three interviews I did. In fact, I had a history of not doing very well at them. It seems counter-intuitive, after all, I am a writer and a good public speaker, why wouldn’t I do well in an interview?

An interview space is a weird exchange of cues. Both parties know what is happening, but pretend that the ensuing conversation transcends it. I had to be upfront about what I could offer, and yet, always position that intentional selling point in a reactive, responsive way, contextualized by what the interviewer was asking, and the company they were asking on behalf of. Tricky? Yes.

I’ve since learned to do a lot of homework, and to walk into interviews with all the key points about myself I would like to stress, key aspects of the organization I am hoping to join, all tucked away in a corner of my brain. The interview experience is about waiting for opportunities to segue from the conversation at hand, to these key points, and then to link them to other parts of the conversation, so that the entire experience seems cohesive.

There is always someone else who is a better fit for the job. But that’s okay.

a shot from a post i drafted, and never uploaded.

I have done great interviews, and not gotten the job. I have done (in my opinion) mediocre interviews, and been offered the position. I have also done great interviews, known that I nailed it, and did get the offer. Basically – there is no guarantee.

Most of the time, emails coming back say something like, “We’ve decided to go with someone whose skills more closely match the position.” The key word is “skills”, and that word is used broadly, to mean personality, work experiences, overall vibe, qualifications and many other things.

Every little thing about you is a potential deal-breaker.

I had the opportunity to interview a range of candidates to take over for an intern position that I was vacating, and it was one of the best work experiences I had. We ended up hiring someone whose resume we’d dismissed, over a solid candidate with work experience that fit the position perfectly, because the former had a vivacity that fit our organization.

Getting rejected for a job is in no way a reliable measure of your value as a worker. It’s just the world is quite large, and everyone in their own remarkable way, has something to offer. It’s a matter of fit.

Every opportunity is a lesson, insight and direction, especially the bad and the missed.

The best lesson I’m taking with me this year, is a reinforced, well-exercised, growing muscle of synthesis.

Nothing is beyond this process. Every single moment, from the mistakes and oversights to the risks and successes, can be streamed into a better understanding of who I am, what this world is like (little and large), and how I should continue navigating it.

I’ve worked under bosses I would never want to emulate, and with coworkers I admire greatly. I’ve done the grunt work of copyediting, and also kickstarted dynamic project campaigns.

Either way, I’ve gained a whole lot more than I lost along the way.

This year of growing is documented pretty well through my outfit posts, many of which are interview outfits, or work-wear.

I’m excited for what the next season of learning and living will bring.


  1. The Sartorial Coquette says

    great post!! you learned so much ❤
    instagram: the_ch1ara

    Liked by 1 person

  2. Great post! I love this particular insight:

    “Getting rejected for a job is in no way a reliable measure of your value as a worker. It’s just the world is quite large, and everyone in their own remarkable way, has something to offer. It’s a matter of fit.”

    😀 😀


  3. I love this post so much! Being a writer seems like the dream life, I love to write as well.


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