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Freelancing Your Way into a Dream Job

freelancing to a dream job

“He started in the mailroom and now he’s worth millions!”

There are few journeys more inspiring than those taken by millionaire or billionaire CEOs who started their career with a couple of qualifications and a brain full of grit and tenacity – but honestly, does it really happen?

Perhaps it used to – back when David Geffen and Simon Cowell were opening letters for record labels and talent agencies – but what about now? Could the mailroom still be a good starting point for your dream career? Or could freelancing be the new foothold you need to propel yourself into the perfect position?

Hidden talent stays hidden

Part of the problem with considering the mailroom (or any other entry-level employed role) as a good starting point comes from the lack of visibility it offers.

Sure, you might have mastered the entire Adobe suite and be shooting world class video in your spare time – but who’s looking for that in the mailroom? If a company’s creative director bundles into the mailroom of a big company looking for help with a next week’s marketing campaign, they’re more likely to be fired, rather than lauded for finding an incredible hidden mastermind.

So, with that in mind, where do these people look when they need talent?

Well, it’s likely to be LinkedIn, PeoplePerHour, Fiverr – or their friend that’s worked on a similar project that they can call for a recommendation.

Self-promotion wins the day

Photo by Rawpixel

A big part of why mailroom talent will now remain hidden comes down to the entrepreneurial landscape we find ourselves in. Most studies now suggest that 50% of the US workforce will be freelance within 5 years – so, in a talent pool that’s likely to total over 100 million people, you’re unlikely to be noticed unless you’re shouting about what you can offer.

Sure, it’s a romantic notion to think that someone’s coming to look specifically for you to take the next step on your career ladder – but honestly, they’re not. No one has time for that. If you want to fly, you’re going to have to impress the right people – and the right people are only impressed by solid experience and an outstanding attitude.

Why freelancing?

Why am I so sure freelancers stand the best chance of landing the best opportunities?

Well, it’s part of the job – at least, for the hungriest freelancers. When you work for yourself, solid experience and an outstanding attitude are musts if you want to consistently pay the bills.

Of course, it’s not just grit that wins the day. As a freelancer, there’s also the fact that there’s no predefined progression tree – you decide where you want to go and focus your sights on that. When you’ve got a plan in place, you can think about what you need to do each day to make the goal at the end of that plan happen.

It’s this kind of flexibility that a standard ‘bottom rung of the ladder’ role just doesn’t give you.

Where to start?

Photo by Mimi Thian

So, what should you do if you want to freelance your way into the perfect job?

A great place to begin is by understanding what the perfect job really entails.

You might daydream about the position of Chief Creative Officer for a big company and imagine sitting on a yacht waiting for ideas to spring into your mind – but, even if this were true, there’s literally a lifetime of hard work before you get there.

Instead of daydreaming about what’s involved – look for the job descriptions, interviews and talks about what life looks like for these people. This is when LinkedIn comes in handy – because you get to look at the person’s career path. If you need to connect with someone to have a look at their employment history, then do it; and send a message explaining why you’re looking – you might be surprised at how many people message you back and offer their advice.

Shaping your experiences

When you know where you’d like to go, look at building experience that makes you the right candidate for the job.

Now, this is a time where it might be easy to get disheartened – after all, you could be staring down the barrel of 20+ years’ worth of experience before you get a shot at the job you want – and when you’re starting out, that’s going to feel like a long time. Hell, even 5 years can feel like a lifetime if standing at the bottom of the mountain looking up.

The thing is, you’re not working in the mailroom for 20 years.

Instead, you’re setting up on your own, finding exciting opportunities and testing the water. Effectively, you’re starting your dream job now; the digging is very much a part of finding the gold. Learn to love the fact that you’re on an exciting journey – and, if you just can’t find that love, then perhaps the journey and the destination need some tweaking. If your dream job doesn’t look so appealing in a couple of years, then adjust your sights and move in the direction you want.

Make a plan

Photo by Alvaro Reyes

I’m an enormous advocate of having a plan – whether that’s for life or just for a trip to the grocery store. Without one, there’s a world of interesting things that’ll take your eye from the ball.

Somewhat obviously, the difference between the grocery store and your work life is significant though; coming back from the store without the fruit juice you went for isn’t a big deal – but finding yourself a decade down a career path without taking a step forward is much more difficult to swallow.

Bite-size chunks are the way forward here. Don’t wake up each day thinking about what you need to do by the end of 5, 10 or 20 years, instead, break your plan down into months, weeks, or even days. Ask yourself, frequently:

  • What kind of opportunities should you be looking for?

  • How should you document/journal/portfolio what you’re doing?

  • What kind of training should you be doing?

  • What should you be reading, listening to or watching?

  • Who should you be networking with and talking to?

Make yourself an incredible work in progress

Organizations rarely recruit the ‘finished article’ when they’re filling a role. Instead, companies often recruit on attitude – but this is an enormously misunderstood trait.

People tend to think that attitude is a series of personality traits that establish you as someone who’ll get things done, or who’ll maximize every hour they’re working for a company – but that’s not attitude, that’s veneer – a glossy surface that tells people nothing about what you actually get done. The only real way to measure attitude is based on what people have done before they stand in front of you as a potential candidate for the dream job on offer.

You can shape that right now – today.

Document your freelance journey. Don’t worry about making it coherent at this stage, just make sure you note everything you do, the training you take, the books you read, the breakthrough moments you have and the jobs that you work on. When the time is right, this is going to be the resumé that you put in front of someone to demonstrate exactly why you’re the right person for the job.

Understand what you need to do to land your perfect job – then start doing it – and prove that you’ve done it and will keep doing it. That might sound like hard work – but the alternative could be 50 years sitting in a mailroom dreaming about what could have been…

SEE ALSO – 101 Freelance Business Ideas for Creative People


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