The Lateral Freelancer: How to Make a Living Doing a Little Bit of Everything

For most of the last five years, I was chronically under-employed. About six months ago, I made a few changes in my approach to finding work that completely altered my job prospects. I went from earning almost nothing to making about $3,000 per month from half a dozen different freelance opportunities. 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.

When I moved out to LA five years ago, my goal was to make it as a “freelancer.” My friends were convinced that in order to make that happen I was going have to specialize. Sure, there were freelancers that we knew, but they were all editors, or camera assistants—there weren’t any jack-of-all-trades types like me. I began to think that unless I found a way to specialize, I was never going to make a living.

A few things happened at the end of 2012 that completely changed all that.

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 and undervalued 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 need 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 complimented my film school background? These were the areas where competition was reduced and the opportunity to meet someone who needed my skill sets was vastly increased.

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

• delivering organic vegetables (LoveDelivery.com)
• mapping local neighborhoods for a major website (Airbnb.com)
• packing and shipping for subscription-based start-ups (LootCrate.com and Tonx.org)
• editing videos for Mommy bloggers (MomAngeles.com and Zookieskids.com)
• judging a high school debate tournament
• building a Kickstarter campaign for a local cafe
• working behind-the-scenes at a wine tasting (SecondGlass.com)
• working as a personal assistant for an MBA student

Not only did I earn more per hour working one-time gigs than I would have earned at a day job—many of these paid $15-20 per hour, plus perks like free bottles of wine or boxes of organic vegetables—it meant I had a flexible schedule to work on my own projects.

I could 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 life experience in the process.

There has never been a better time to be a freelancer. The proliferation of service-based websites and applications makes it easier than ever to find the kind of work you want to do, when you want to do it.

Here are five simple ideas to help you freelance laterally:

1. Put yourself out there. Everywhere.

I create a profile on nearly every new start-up 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. It’s good to get in on the ground floor, since some start-ups screen their applicants and might close their doors or limit new sign-ups. Here are a few that I recommend:

• Can you run errands? Try Taskrabbit.com
• Have a room you barely use? Airbnb.com
• Or a car your hardly drive? Relayrides.com
• Do you babysit? Urbansitter.com
• Walk dogs? Rover.com
• How about airport pick-ups? Lyft.me
• Are you an awesome tour guide? Vayable.com
• Can you teach a skill? Lifecrowd.com (coming soon)

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. There’s no need to be the “#1 guitar instructor in Los Angeles”—if you know more about guitar than the average person, and charge less than a full-time instructor, then you’re the perfect fit for someone who just wants to pick up a few chords.

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 delivery gig to a neighborhood that I was going to anyway.

But that’s not all: When I road-trip up and down the coast this summer, I plan to look for Taskrabbit gigs in every city that I stop in. Technology makes it easy to find gigs while you travel, so you don’t have to feel guilty about missing work—just set up a few day-jobs while you’re in town to cover your expenses. You’ll get to see a different side of the city while you’re at it.

4. Set a price. Get the work done. Get paid.

Even well-meaning clients can get distracted and forget to pay an invoice. Follow-up e-mails and reminders can add an extra hour or two of work (and stress) to your gig. That’s why I like sites Airbnb and Taskrabbit, which charge the client’s credit card, so you don’t have to. If you are getting paid directly, I recommend using the Square credit card reader for your iPhone (squareup.com), so the customer can pay you in person as soon as the job is completed. You’ll have to 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. I recently hired an assistant to drop by for a few hours each week to organize and schedule my gigs. Now, I can focus on the work itself, and cut out the (unpaid) hours that I was spending searching for new gigs and communicating with clients.

I hope these tools can set you on the right path to living a vibrant and varied freelance lifestyle, in which each day brings new opportunities and new skill sets to learn.

All of this isn’t to say that I’m in the clear yet—I still have a sizeable amount of student loan debt and other bills to pay off. But now I can actually enjoy the process.

And when that happens, it doesn’t feel like work.

Your Turn

What out-of-the-ordinary jobs have you found lately? What kind of gigs would you look for outside of your training or comfort zone?

Saul of Hearts is a film school grad turned all-around freelancer who moved from Boston to LA in search of adventure. He lives in a co-operative neighborhood known as the BLVD, and blogs about work, travel, Burning Man, and community living at www.saulofhearts.com. He now offers “Lateral Freelance” consulting and sends out a bi-weekly newsletter with freelancing tips and off-beat work ideas.