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How to use freelancing to land your first job

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The experience-work conundrum can be a bit troublesome: you need experience to get a job, and you need a job to get experience. For those of you without family and friends to get your foot in the door in your industry, you may feel a bit lost. It was incredibly frustrating for me to watch friends easily get jobs within their family or through their school’s programs – while I was struggling to land even just one job after dozens of applications.

Don’t despair. When in doubt, think about how many meetings Damon Dash and Jay Z had to sit through to try and get a record deal, only to be rejected from every one of them. What did they do? All those rejections forced them to build Roc-a-Fella Records, which would grow to become an empire.

That may be a long way away for you; maybe what you want is a first job, or an apprenticeship of some sort. How are you supposed to even get your foot in the door of the industry you want to work in?

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Your First Step: The Trojan Horse

If your challenge is getting the initial job experience that you need, then you’ll need to build a Trojan Horse to really differentiate you from the rest of the pack. It’s not enough to email someone and say, “What do you want? I’ll do anything!” They don’t have the time to tell you what they want.

Instead, you will have to build them something and show it to them (usually via email). For example, if you want to become a marketing strategist for a B2B company, and they don’t have a strong presence on SlideShare yet, build them a presentation. Yes, this means giving free work. Musicians do this all the time with mixtapes and free shows. Besides, do you have another alternative?

Consider this: how many hours do you spend searching around for BS internships or entry-level jobs (in roles or fields that you don’t even like)? The number of internships that bring actual merit and create high-growth learning experiences are dwindling; contrary to what many adults or professors may tell you, don’t just take what you can get. Time is a non-renewable resource, and four months as a young person are extremely valuable.

Instead of applying for jobs the “normal” way, and shotgunning dozens of cover letters and résumés, focus on finding companies or roles that really resonate with you or ones that afford you the opportunity to work with people that fascinate you.

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Here’s what I suggest: Find the CEOs (or VPs, or director’s) email addresses, attach your presentation or website or mockup or whatever it is you built specifically for her company and that specific team, and tell her you’re interested in helping out and you built this project to indicate your interest. Remember, this does not obligate her to hire you – this earns you the chance to hear the answer to your question: “What are some of your greatest challenges right now? What else do you need built?” Then, you build something more tailored and send it it to her again. This is how you figure out where you fit in.

Do this type of free work for three or four companies simultaneously during the summer, and one or two during the year so you’re not resting on your laurels. Worst-case scenario: If you can’t land a paid role with any of these companies (I’ll bet at least one pays you a stipend, though), then you ask for a recommendation on LinkedIn or an intro to one of their contacts (who may have larger budgets). Keep collaborating with the folks that start paying you, and switch up the ones that don’t. You are now a freelancer.

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In comparison, if you don’t get paid either way – four intros or recommendations are much better than the one you may have been able to obtain as an intern.

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It’s unreasonable to expect someone to pay you decently until you’ve actually earned a skill and proven yourself. To think you deserve your boss’s most important life lessons, before you’ve proven yourself, is similarly as entitled. Both of these rewards are earned. (And if you’re seeing neither at the place where you’re working right now, make sure you have the skills to go find it somewhere else.)

(Note: The strategy I just shared with you is also used in the B2B marketing world – it’s known as “account-based marketing”, where sales and marketing teams focus on only the few opportunities that offer the highest revenue opportunities. In your case, you’re going to focus on the few that offer the best life experience or the best education.)

Landing Your Dream Job

Now that you’ve gotten projects from three or four companies under your belt, you’re ready to start looking for a paid job. Remember your advantages: you have faced a larger variety of problems than anyone your age (or even a year or two older than you), in a greater range of verticals.

You are also, very likely, going to be more creative: because creativity is about connecting unusual dots together, simply immersing yourself in multiple jobs simultaneously also exposes you to a wider range of experiences.

Instead of working with one team, you’ve worked with three in the trenches. The best type of networking is done organically – and few connections from conferences or networking events are as strong as relationships between team mates.

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My first real job (after McDonald’s) was with a company called Xtreme Labs, which was recently acquired by Pivotal Labs. We build mobile and web solutions for brands. The benefits were great – they provided team members with free breakfast, pop, snacks, socials, and an arcade on the fourth floor. The role also involved writing, which was one of the skills I wasn’t terrible at and that I enjoyed. I was given an opportunity for this because I had previously freelanced for a Canadian technology publication called Techvibes. (Thanks Rob, Knowlton, Dan, and John – couldn’t have done it without you.)

Before I was hired, my friends at Xtreme Labs were able to show my future boss what I had done on Techvibes. He didn’t hate what he saw, so I started working with his team during school. When I graduated, we simply started spending more days of the week together. (Thanks Imtiaz for the opportunity, and Megan for your patience.)

Building Your Dream Job

You will change. And the company your dream job is in will change, and not always in the direction you want to go. You can choose to find another dream job. The ultimate dream job is one that you have control over.

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A lot of people think entrepreneurship is about building the next billion dollar startup. You’re not obligated to do that; in fact, the harsh reality is you may not be cut out for it. When Kanye West was working at The Gap, he dreamed about building his spaceship and freelance produced (and even ghostwrote some beats) until his beats got used to make almost a third of Jay Z’s The Blueprint album. He fit in as a producer, and pivoted his way into rap, and is now pivoting into design and fashion with his agency, DONDA. (By the way, when you think about it – an agency is often started by a bunch of freelancers.)

Think about comedians like Aziz Ansari, who basically earn money through freelance gigs, and have the freedom to write books or do television shows on the side because they have control over their time. If I choose to freelance, I could very likely fail, and so could you. That’s not the end of the world – before he was hosting MTV’s Jobs That Don’t Suck and before he was a bestselling author of Fresh Off the Boat, restaurateur Eddie Huang failed at his second restaurant and got sued by an established luxury fashion retailer.

Closing Thoughts

That’s a high-level view into how you can land – or build – your dream job. In case you’re curious, I’ve written extensively on other tactics and strategies I used to build my credibility. And here’s my first attempt at building my spaceship.

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Settling for what you can get sets a poor precedent. Rejection is good to practise, entrepreneur and venture capitalist Chris Dixon specifically highlighted it as the reason for his success (he still tries to get rejected daily).

In a worst-case scenario, you’ll end up “wasting” four months of your summer trying to do free work for companies and people you admire. I don’t think there’s any shame in that; consider it high-investment networking. Regret will weigh more heavily (hence the traumatic midlife crisis). And guess what? You will able to use this free work in a portfolio in the future either way. Accelerate your education by freelancing.

Tweet me @herbertlui if you have any specific questions. Best of luck.

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