Dave Culligan Gives 4 Ways to Work the Millennial #SideHustle

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A recent CBC article broke the old news that although a university degree improves the chance of landing a job, ‘The millennial side hustle,’ not stable job, is the new reality for university grads’.

“Hustle” is a dance, a strategy, a tactic, and a command. “Let’s hustle” means “let’s hurry”. In billiards, hustling is tricking a less skilled player into playing with a highly skilled player. The Millennial side hustle however, is a competitive career strategy that upstarts use to cover their butts in the long and short term. It might mean working several jobs at once, but the side hustle is a large part of building a sustainable career.


I spoke with Hali-famous videographer, Dave Culligan, about four concepts he used to move his hustle from social media consulting to a career in videography. Before leaving his job as president of BeHuman Clothing Co. Dave already had videography contracts waiting for him. “I was running a clothing company, making my 365 videos every day, running an organization called StartUp Grind as the chapter director, consulting for startups and digital strategy, and I was also taking large scale video contracts where I was traveling to sites to film and edit.”

The method he used to scale back his workload to full-time videography involved four simple concepts: side hustle, community, working for free, and reaching out.

1. Have a Side Hustle

The millennial hustle is the thing you do for money — working multiple jobs, taking small contracts, temporary work terms, or paid internships— the millennial side hustle is doing the thing you love until you prove you’re one of the best people doing it. Eventually, your side hustle becomes your main hustle, and you’ve created a job or started a career. By the time Dave Culligan was ready to leave the clothing company he was working with, he had video contracts waiting. “I’d spent long enough generating interest and business that I was able to leave and feel safe in the video world”.

When Clair Parker was interviewed by CBC about her side hustle, she told them that between her political science degree and public relations certificate, she hoped to grow along with the restaurant where she bartends. The main hustle is her bartending job, while the side hustle is the prospect of customers and her current employer becoming her first contracts as a media professional. Like Culligan, Parker tries to build connections in her job that will be waiting when she starts her career in a different field.

For Culligan, working several side hustles got him to a point where he was getting so many offers to do video production “I couldn’t say yes because I didn’t have the time, and then I decided I would rather say yes to those offers than running a clothing company.”

2. Bring Something New to your Community

Nova Scotia is a small province with a small, aging population. If someone in San Francisco is filming their day for 365 days and posting it on Instagram, you can guess no one is doing it in Nova Scotia. That’s what Dave Culligan thought when he used his iPhone (and later a camera drone) to start a year-long film project featuring Nova Scotian locations, while he also worked as a freelance social media consultant and president of a clothing company.Around here I had to convince people that social media was important and that building their brand was a real thing. But everywhere else, people know the value of social media, they know the value of bloggers and influencers. Nova Scotia and Halifax are behind the times in a lot of senses, but you can complain about that or you can look at what people are doing in bigger cities, learn how to do it and bring it here” said Culligan. 

Halifax blogs, for example, feature local hustles and side hustles. “Built Halifax” has less than a thousand followers on Twitter, but in Nova Scotia that is a successful blog. Written by an amateur architectural historian, the site recently drew attention to a court case that was revived by an Africville descendant for compensation. The blogger used a mapping tool to document Africville land titles he found in the Public Archives. Mapping tools can be found for free online.

3. Work for Free

I think people get caught up in saying “I’m not going to do free work” but who is anyone to say that when no one is offering them money?”

Working for free means learning how valuable your experiences are to others. If you’re really brave, you can build a portfolio by offering your time to a business or organization lacking expertise. According to Culligan, “you can go to a company, literally show up at their door with a resume and a business plan and say ‘hey, I’d love to take over your social media and do some consulting for you. If you see value in it after a month, then you could either pay me or refer me to a friend’.

At the same time, don’t work yourself beyond a comparable standard of self-care and mental health. Donating time doesn’t have to be a sacrifice, it’s meant to prove your skill is worth paying for.

4. Reach Out

Social networks are super social! If you reach out to someone who does what you love, they might actually respond, and often do. If you’re thinking about starting a website, use LinkedIn to connect to website designers. On reaching out, Culligan says it’s important to remember one thing:

“you’re reaching out to someone who’s busy and ambitious and has a lot going on. You can’t just say ‘can we talk’ or ‘can we get coffee’. You’ve got to have some kind of value proposition, like ‘I’d like to help you with this project that I see you’re working on’. I’m at the point now where I get a lot of invitations to coffee, and I hardly have enough time to grab a coffee with my best friends! Unless there’s something that’s gonna move a needle forward, it doesn’t make sense. I sound like a know-it-all, but I didn’t know any of this 8 months ago, or a year ago. But that’s why I’m so passionate about saying it. I’d rather save people from doing all the dumb stuff that I did.”

Read the entire interview about Dave Culligan’s journey and why he quit his job running a successful clothing company.

Follow @dave.culligan on Instagram


Author: Sandra C. Hannebohm

Political science major, some french and a lot of concern about the state of things.

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