Contract work

My first contract role with the Turnstyle Solutions crew (now  Yelp WiFi )

My first contract role with the Turnstyle Solutions crew (now Yelp WiFi)

College can be a stressful time for a number of reasons. For starters, the endless flow of information is a plus, but the similar flow of assignments is a drawback. Beyond the classroom, there’s the responsibility of extra-curricular activities, sustaining a social life, and finding a job.

Jobs can be tricky, and in college, usually fall into the realm of ‘I don’t like it, but hey, it makes money’. Read: cashiers, waiters, etc. Don’t get me wrong, I have a lot of respect for those jobs and for the people who take them. However, I think there’s another category for jobs, which goes more like ‘I like the work and it makes me money’.

Contract work is a great way for students to dive into what they’re interested in, learn new skills, and most importantly, make some extra cash. In this post, I’ll walk through my experience with contract work, and tips I’d have for getting into it.

Marketing… Yeah that sounds cool!

Wrapping up my first internship, I realized that as cool as sales was, I was more excited by marketing. The only issue was that I knew nothing about it. This introduces the paradox of job hunting — they’re looking for people with experience, I don’t have any experience, but I need experience to get a job.

The first step I took to become prepared for a marketing role was to start reading up on it. Like with other skills (programming, design, etc), a lot of the content is available online (usually for free) that can help you break into that career path. Although I’d recommend anyone interested in marketing start here, I personally read a ton of posts on HubSpot and listened to Neil Patel (SEO) podcasts.

The plot twist? A lot of that information (and to be frank, some of my earlier posts on this blog) wasn’t very effective. It wouldn’t help me kill it in a marketing role, or even have a thorough understanding of that skill, whether it be email marketing, SEO, etc. What it did give me was a foundation — a basic understanding of that field, and a list of questions I could ask that would show that I was (a) genuinely interested in it and (b) eager to learn.

As I mentioned, this parallels a lot of different paths. If I was really interested in learning how to code, FreeCodeCamp and Codeacademy are both incredible resources. Odds are I won’t become a good developer through either, but it’ll give me a head start on knowing what to learn. The same goes for other jobs that build off a skill set, like Design.

Hit me with your best shot!

With a basic skill marketing skill set, I set out to find my first job. As many new grads will notice, there aren’t many roles out there that require “0 years experience and a smile”, even if you have a genuine interest in the job. The difference-maker is proving to the hiring manager that, despite your lack of experience, you’ll pick things up quickly. This is perfect for most ‘junior’ roles where the work doesn’t really require you have done it before.

My first contract gig in marketing came through Turnstyle Solutions (now Yelp WiFi). It was a fluke really — I was at a hackathon in Toronto (didn’t know how to code), and I reached out on their website for a demo account so I could help my team use their product in our hack. The ‘demo request’ went to someone on their Customer Success team, who was actually a Western University grad.

Where to go from there? Well, I had to be a little ambitious and flaunt my (limited) marketing knowledge. I mentioned in the reply to him that I had some background in email marketing and user acquisition, and I’d love to chat with someone on their team to show what value I could bring.

Note: The “I have background in X and want to chat with someone to see how if I can add value” is a fool-proof approach. Even if you definitely can’t, they’ll be willing to take a call with you in most cases.

I ended up getting an intro to their VP Marketing (now a great mentor of mine), and took a call to learn about their marketing efforts. Looking back, he could probably guess I had no clue what I was doing, but he could see that I wanted to learn. So he took me on as a contractor, where I’d get paid $20/hr for a few hours a week to help with their marketing.

Note: Experience is rarely a requirement if you’re looking for roles as a student. They know you have no full-time experience, and are typically open to helping you out if you’re driven.

Not your typical retail job

At this point, it’s worth noting that I wasn’t making an incredible amount of cash. I was, however, getting tangible experience in something I was interested in, AND I could do it from the comfort of my room (on my own schedule), since the work was remote and based on what I delivered (outcomes). That’s another beauty of contract work; in many cases, you’re not tied to a schedule, so if you want to wake up at 2pm and work until 10pm, as long as the work is done for the next morning, you’re golden.

Throughout this time, I also want to stress that I was still learning. There were a lot of tasks I got that I didn’t know how to do, so I spent a lot of time digging on the web and reaching out to people I thought might be able to help. The latter is amazing for finding mentors in your space, or even new jobs. Look at the two questions below:

“Hey I’m interested in marketing and want to learn more about it, can we chat?”

“Hey I’m doing email marketing for XYZ Company, can I see how your company tackles it?”

This works especially well for marketers, but imagine the same question for a designer or developer? I.e. “I’m putting together a branding guideline for XYZ Company, would love to see how you did yours” or “I’m developing a mobile app for XYZ Company, curious how you guys tackled it”.

With a bit of experience and a growing skill set, I stumbled upon my next contract job a few months later, and have kept up with part-time gigs since. Contract work initially helped me splurge on a meal out once a week, but after gaining experience and a portfolio, now helps me pay for trips and school fees.

Where do I start?

If you’re interested in doing contract work for a specific skill, try the same approach of (1) learning about the role (2) reaching out to people to see how they do it (3) offering your services. Even if you don’t have a specific skill, you can try sites like Upwork to get some solid paid work — whether it’s testing an app or conducting Google searches. For obvious reasons I’d recommend the former approach of targeting a skill, but whatever floats your boat.

A couple of things I’ve learned over my time doing contract work:

Communicate frequently. In most roles, you’ll be taken on as a remote employee, which means you won’t be in the office and your work is project-based. The former means you’ll miss a lot of context on projects that happen in casual conversation, and the latter means that you can’t ask questions or give updates on-the-fly. It helps to set check-ins with your manager at a certain time every week, and don’t be afraid to ask questions if you’re unclear on a task.

Give specific value. In the initial outreach, and throughout the contract, it may be tempting to ask for ‘general’ work related to your skill set. I.e. “Can I help with marketing”. For a lot of companies, being a generalist is fine if you’re a full-time employee, but they hire contract workers for specific purposes. So even in the initial outreach, saying “Can I help with your email marketing strategy” or “Can I help with the design of your homepage” is a lot better than “Can I help with marketing or design”.

Learn constantly. As a student, contract work is (should) not be seen solely as a source of income. It’s an opportunity to sharpen your skills in a specific field, work your way up to bigger (and higher paying) roles, and eventually launch your full-time career in that area. If you’re doing work that is repetitive, that might be a red flag where you should ask for new tasks, or better yet, think of new skills you want to learn and tasks at the company that involve that. For some of my earlier roles, that meant doing solid work in their CRM (more repetitive) and asking to help improve their SEO strategy (new waters). That helped me broaden my skill set to include SEO, and have tangible projects to practice on.


Clearly there are professions that don’t allow for contract work; if you want to go to med school, any ‘contract doctor’ role is probably sketchy and might get you arrested. But for work in tech (and a number of other fields), contract work is a great way to make money, gain new skills, and prepare yourself for full-time work, all while being in school and in the comfort of your home!