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How I Got Started Working Remotely

How I Got Started Working Remotely

Exactly three years ago I was sitting on the floor of the living room at my parent’s house, laptop in hand, trying to find a temporary, yet fulfilling job that would provide a valuable learning experience before my next adventure. 

I typed into google “Jobs at Instagram,” a search that would completely change my life.

As a fresh college graduate, I was obviously vastly under qualified for anything available at Instagram itself. But it was the second search result that changed everything for me. 

Before I tell you more about that search, let me take you back a bit. You see, two months earlier, I had graduated from McGill University with a degree in Economics, and I was looking to fill the next five months before I had to leave for Switzerland where I was going to be a ski instructor for the season. 

For a while, the only thing I was able to find were unpaid internships, which felt like a slap in the face and a step backward after working four years for a degree from a great school. Briefly, I considered going to Vancouver to intern at a fintech startup, but after crunching the numbers I realized the entire thing would cost way too much money to make any sense.

While I had studied economics at McGill, my true passion has always been marketing and tech startups. Ultimately, this led to me working internships during school in social media marketing at startup accelerators, where I was mostly focused on Twitter and Facebook.

During my last year at McGill, I was sitting in my drafty Montreal apartment scrolling endlessly through my feed when I came to the realization that I was obsessed with Instagram – in an unhealthy and unproductive way. This was back before the algorithm existed (#tbt), and every time you opened the app it would refresh with latest posts. My epiphany about my obsession came when I caught myself mindlessly opening and refreshing the Instagram app, with nothing new at the top because I’d just refreshed it 30 seconds before.  ??‍♀️

I had to turn this obsession into something productive. 

So I decided I was going to take everything I had learned on Twitter and Facebook and figure out how to win on Instagram. My mission was to answer these questions:  

  1. What type of content worked best? 
  2. How did you grow an audience? 
  3. How did you monetize your account?

Later that week, I created the page @altitudeiseverything and spent the next 8 months until graduation learning the answers to these questions. 

After graduation came around, I planned a few epic cross country road trips with my best friends, and with a new camera in hand, captured some beautiful content that I used to start my own Instagram @Splorin.Lauren.

As the last of these adventures came to an end, I found myself in Sandpoint, Idaho, sitting on the floor, trying to find a job to put my mad social media skillz to use. 

Oh right, the infamous Google search I mentioned earlier. I’m guessing you want to know what came up second. 🙂

It was a little website named Upwork, and it told me I could make money managing people’s Instagram’s online. 

Want to get started on Upwork? Click here to read my crazy long guide with alllll my tips for how to get started and be successful on Upwork!

Naturally, I thought this was a complete scam. I signed up with my fourth grade junk email address just to see what it was, and thought nothing would come of it. 

A few hours later, I had my first job managing a high fashion shoe company’s Instagram. 

Two days later, I had my second one managing social for a label printing company.

I was able to use my personal accounts as proof that I knew what I was doing on social, enough so that companies were willing to give me full reign on their accounts!

The same week that all of this happened, I was interviewing with a local tech startup that had recently received Sharktank funding. I had a great interview and they offered me the job, but said they couldn’t pay me, and that I would have to commute 45 mins each way to work. 

Taking the internship might have looked better on my resume, because I had no idea what would come of this weird job website I had found online. It definitely felt safer, but the lack of pay given my education and relevant experience made me feel completely undervalued. 

On Upwork, I had set up my profile at $25 an hour, which felt like a million dollars compared to the unpaid offer on the table with the startup.

After mulling it over, I decided to turn down the internship, continue on upwork, and pursue my freelance work. 

At the time, this space felt very foreign to me. I didn’t know anybody else doing social or digital marketing work online, and had no friends working online or remotely. But I also think that’s what made it exciting. I’ve often gravitated towards the new and unknown, and that’s exactly what this was. 

I had no idea where it would take me, how long it would last, or if I could even make a living off of it. Fervently, I googled everything I could about the freelance world, managing client relationships, budgeting, invoicing, you name it. What scared me most was this concept of feast and famine, that freelance work seemed to be heavily project based, with lots of work and money coming in all at once, and then all the work drying up after that, forcing you to spend all your time hunting for new work.

Luckily, I continued to work with my first client for eight months, and the second one for a year and a half. 

At the time, my goals were short term – find a job to fill the time before the ski season. But it didn’t take me long before I realized what a cool opportunity I had stumbled across and I started wondering how far I could take this. 

Since then, a lot has changed, and a lot has stayed the same.

Here’s a few fun milestones from the past 3 years:

  • I stopped calling myself a freelancer and became an entrepreneur
  • Corey joined me full time
  • We hired a team and have grown to 7 people
  • One of our clients was acquired
  • One of our clients got a deal on Sharktank from Mark Cuban
  • We’ve lived in Halifax, Idaho, Banff, Bali, Switzerland, and Toronto
  • We launched a new company that’s going to change the photography space

Over the years, many people have come to me asking for information, advice to get started, or other random questions about working remotely and traveling so I’m going to do a little series here about everything I know, have learned, and am working on to try and pull back the curtain as much as I can on this world! I truly believe there will only be more and more opportunities to work remotely in the next few years and think there is room for everyone if you’re curious and willing to put in the work.

Drop your email below if you want to know when the next post in the series comes out. I’m currently thinking of doing a deep dive on Upwork (how to get started, how I got my profile highly ranked quickly, why it’s worth it, and how I expanded my niche, etc) but would love other questions or suggestions for topics to cover, so be sure to leave them below 🙂



Thursday 17th of December 2020

Can I just come work for you ?

Ivy Caparas

Thursday 3rd of December 2020

Cooool! Can I work for you? Haha

Nur Husna Nazifa

Sunday 20th of September 2020

This is the future ive been dreaming of! I want to be like you in future ??


Monday 13th of July 2020

This is amazing!!!! Is it a secret, or can you tell us beginners what the answers to the 3 questions are? (Or even how to find them for ourselves)


Monday 13th of July 2020

Great article, and very inspirational!

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