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The Lateral Freelancer: How to Make A Living in the Share Economy

For most of the last five years, I was chronically under-employed.

The Lateral Freelancer: How to Make A Living in the Share Economy


For most of the last five years, I was chronically under-employed. Aside from occasional short-term gigs, I spent every day looking at Craigslist posts, sending out my resume, and trying to find myself a job.

When I moved out to LA as a film school grad in 2008, my plan was to make it as a “freelancer”. My friends were convinced that in order to make that happen I was going have to pick a focus and build up my client base and resume. They thought that unless I found a way to specialize — as an editor, or camera assistant — I was never going to make a living. For a while, I believed them.

About a year ago, I made a few changes in my approach to finding work that completely altered my job prospects. For the first time in my life, I was turning down gigs because I didn't have time to accept them all.

I didn't do this by becoming more qualified or by building a bigger portfolio. I did this by thinking laterally.

I ended up getting a series of editing gigs, not by sending out my resume or scrolling through my contacts, but through an errand-matching website called Taskrabbit. After years of feeling overlooked while all the "good" jobs went to my friends, a start-up website earned me more money than those networking events and alumni meet-ups ever had.

I realized that I didn't have to be able to compete with the specialists. I just needed to stop working on the same playing field that everyone else was. Instead of thinking vertically — climbing the industry ladder — I had to think laterally: What contacts did I have outside of the film industry? What skills did I have that I could sell along with my film school training?

Over the past few years, I’ve made money working dozens of different gigs — some related to my college training, others from completely different fields. Here are just a few of them:

I’ve delivered organic vegetables;mapped LA neighborhoods for a travel website; packed boxes for a subscription-based start-up; edited Kickstarter videos for local businesses; judged a high school debate tournament; worked behind-the-scenes at a wine tasting; and helped an MBA student get organized.

I started to take gigs on a case-by-case basis and turn down those that I didn't have time for or didn't want to do. Some days, I managed to squeeze in two or three different gigs — or work on personal projects during down-time. Best of all, I got to do something different every day — going behind-the-scenes of various industries and start-up businesses, and gaining valuable work experience in the process.

As far as I’m concerned, there has never been a better time to be a freelancer. The new generation of peer-to-peer websites — the “Share Economy” — makes it easier than ever to find freelance work. Here are five simple ideas to help you freelance laterally:

1. Put yourself out there. Everywhere. I create a profile on nearly every job-matching website that I come across. You never know which will prove most useful to you. Some I haven't been back to since, while others have become a substantial part of my monthly income.

— Can you run errands? Try Taskrabbit
— Have a room you barely use? Try Airbnb
— A car you hardly drive? RelayRides
— Do you babysit? Urbansitter
— Walk dogs? Rover
— How about airport pick-ups? Lyft
— Are you an awesome tour guide? Vayable
— Can you mystery shop? Gigwalk
— Can you cook? Feastly

2. You don't have to be the best at your skill — just better at it than your client. Let's say you're a film school grad, like me. Videography is only a small part of my freelance work, so it doesn't make sense to invest in lights or other equipment that a full-time videographer would have. This means I can't take the really well-paying gigs that some of my friends can. But simply knowing more about video than my clients do means I'm valuable to them.

We often confuse proficiency with mastery. We forget that the “experts” are just a small portion of the people working in their field, all with varying degrees of proficiency. Sometimes, becoming an expert an a field isn’t the best way to earn a living.

3. Take advantage of smartphones and geography. I live in LA, where many of my friends face hour-long commutes to and from work each day. While I can't avoid traffic, I can make the layout of the city work for me. If I'm on a gig in one part of town, I'll hop on my iPhone and see if there are any other gigs in the area. I might luck out and score a gig in a neighborhood that I was going to anyway.

4. Set a price. Get the work done. Get paid. Even well-meaning clients can get distracted and forget to pay an invoice.That's why I like sites like Airbnb and Taskrabbit, which charge the client's credit card directly, so you don't have to. If you’re getting paid in person, then get a credit card reader for your smartphone, so the customer can pay you as soon as the job is completed. You'll pay a small fee for each transaction, but it's better than waiting months for a customer to pay your invoice.

5. Finally, don't be afraid to outsource work. Freelancing is a lot like running a business. It might seem counter-intuitive to hire outside help if you're still struggling to get by, but a little bit of weight off your shoulders can earn you more income in the long run. Sure, it’s good to be self-reliant, but not if it’s taking you hours to add page numbers to your manuscript or change the color of your website. Find a friend to give you a tutorial, or hire a virtual assistant.

Lateral Freelancing isn’t for everyone — some of us really do want to be specialists — but for those of us who enjoy novelty, or who aren’t ready to commit to a single career path, it’s a promising option.

For more information, check out my website, The Lateral Freelancer, or download my PDF e-book. You can also read some of my other articles:

5 Reasons to Become a Lateral Freelancer
5 Tips for Breaking into Freelancing
5 Tips for When Good Clients are Bad at Paying Up
5 Ways to SEO Your Social Life