The Lateral Freelancer: How To Make a Living doing a Little Bit of Everything
Photo courtesy of Laimes Kudikis.

The Lateral Freelancer: How To Make a Living doing a Little Bit of Everything

Written by Emilie

Topics: Self-Employment, Work

Note from Emilie: This is a guest post by Saul of Hearts. Saul is a member of the Puttytribe and we got to meet and hang out while I was in LA. Awesome guy, and a bonafide multipotentialite who is making it work in a very creative way.


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:

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:

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 (, 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 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 He now offers “Lateral Freelance” consulting and sends out a bi-weekly newsletter with freelancing tips and off-beat work ideas…


  1. ldf says:

    I loved this post. I’ve been trying to determine what I want to do as a freelancer and the thought of doing something specific (i.e. writing) fulltime for other people as well as my own projects wasn’t working for me – I’d get bored, burn out and my writing would suffer.

    This was so informative and acts as a foundation I can play with, as a nomad, to find the right mix for myself.


  2. Laura says:

    I love this! I especially love the line “You don’t have to be the best at your skill — just better at it than your client.” As a creative freelancer I frequently undervalue my variety of skills b/c I don’t always think of myself as an expert. Most of the time through my client’s eyes I am an expert. In the end as long as I can get the job done well that’s all that matters.

    • Saul says:

      Thanks! “Most of the time through my client’s eyes I am an expert” is a great way of putting it.

    • Em says:

      That’s one of the lines I have to remind myself of very often ’cause otherwise I’d never be able to go out with my skills, being too afraid that I’m not good enough or not an expert. In this, what most helped me, was the site Expert Enough by Corbett Barr :) Definitely recommended for checking out ;)

      It’s definitely true, ‘though, very often I get surprised just how little my clients know about a thing I used to consider totally common and known by everybody. Or a skill that I would never believe people would pay for, like just simple hoovering or thorough bathroom cleaning – but they do! For many people, some things are just not their priorities and they are happy to pay for somebody else to do that and take that task away from their schedule. I’m an au-pair and my host-mum/boss actually knows nothing about computers so she’s happy to pay me even for things like deleting her pictures which she doesn’t want, which is like “wtf, how can somebody not know how to delete a picture!” :D But that’s it, she’s the kind of customer who is happy to pay for it instead of listening to me for five minutes of explaining. She just couldn’t bother, she doesn’t realize it would save her a shitload of money and that creates opportunity for people like us :)

      Whatever you know and can do, there are clients out there, you just need to know where to look for them.

      In a long term, though, I kinda find this way of living a bit stressful as you have to constantly search for gigs and I’m worried it might feel like, you know, constantly searching for work :) With not having anything for sure. I had the trade certificate but there was too much of uncertainty connected to it. But I guess hiring someone to look after my schedule and find me gigs would be my solution – that’s where I sucked.

      I believe in future I will reconsider this way of earning money and living simply because I can’t stand any “regular” job for too long anyway. For most of jobs I ever did, year was enough. But probably I wouldn’t do it in my homecountry, it’s way easier for instance in UK.

  3. Dima says:

    I am in a similar situation – with lots of things I know about but not really specializing in anything and I am facing with the same dilemma. And to be honest, I do not really see how this write up helps. Earning $15-$20 an hour, especially in California, especially as self-employed with additional costs for insurance, etc. is not much at all. What am I missing here?

    • Saul says:

      Thanks for the feedback, Dima! I definitely don’t mean to imply that this lifestyle will make anyone rich, but for me the end goal is variety. I love that I can put in about the same amount of hours as my “employed” friends, while doing something different every week. For me that variety is worth the lack of insurance and other benefits. Also in my experience, short-term employers have been more generous with tipping, and a lot of my gigs come with other “bonuses” — boxes of veggies, surplus wine bottles, T-shirts — that make up some of the difference.

  4. Brian says:

    As a fellow film school graduate and multipotentialite, I really appreciate this take on freelancing. It resonates with what I’ve been experimenting with and it’s great to see another person living it out.

  5. I love this post and only wish that I had learned the insights the author did years ago. As a high school student, I was only programmed for two things: either get a factory job or go to college. I chose college, but when that panned out (financial aid) I had to rediscover from the ground up. My current life follows the pattern mentioned in this book. Weirdly, I have had more stability along with flexibility and control on a path that I thought wouldn’t last 2 weeks!

  6. Leah says:

    Saul, great post! Very informative and thought-provoking. It was also quite timely for me, since I’ve been looking into ways I could freelance lately, and coming up against a brick wall due to my Puttypeep tendencies and all the advice out there that seemed to scream, “Specialize! Find your niche!”

    Which, as we multipotentialites know, is pretty much the worst advice ever for us. If we had a soundtrack for our lives, I think the particular track for such advice would be something akin to, “DUNDUNDUUUNNN.”

    Anyway, I’ll definitely be keeping your post in mind. In fact, it’s bookmarked. Thanks for sharing, and congrats on making this work for you!

  7. Joshua Lundquist says:


    Great article, and thanks so much for introducing me to vayable! That looks like a great way to give tours without much hassle. I set up a day tour of some lesser known spots / parks in Tokyo, so hoping the next few saturdays I will get bookings!

    I might experiment with the tour contents also, maybe make them seasonal, especially since the next few weeks will be getting into cherry blossom season, which is a big deal here.


  8. Iain says:

    One of my teachers in teacher’s college said the exact thing you said here.

    You only have to be more of an expert than the other person. Sometimes it doesn’t take much to be considered an expert. It is surprising.

    Sometimes what happens is that you amass knowledge without knowing it until you start talking to people who know less. It is crazy

    Sorry if that came out weird. :P

  9. Cassie says:

    Really enjoyed this post, Saul. I’m currently doing the freelancer-or-employee dance, and my lack of steady income fear–the reason I’m “dancing” in the first place–was lessened some with this post. Just takes some creativity…or lateral thinking, as you say. :)

    • Saul says:

      Great to hear that, Cassie! One thing that helps me is to have a few “recurring” gigs to fall back on each month. I’ve been working with a few monthly subscription boxes that need help with packing a few days each month … Frequent enough to depend on, not frequent enough to get bored :)

  10. Kelli says:

    Thank you for sharing these golden nuggets! There is not much activity in my metro area (Minneapolis/St. Paul) so that could be a neat opportunity to be one of the first active on these sites. If they take off, then we’d be among those to have the most ratings or history. I love me some Puttylike. :)

  11. Josh says:

    Great post, Puttybrother.

    This whole internet venture is out of my comfort zone! lol

    The multipotentialite way: If there’s something that compliments your skillset that you don’t know already and can benefit your lifestyle…Learn it!

  12. Holli says:

    I really enjoyed this post, and that you opened up your real life experience including resources!

    Item number 2 is the biggest one that resonates, and is so powerful for freelancers. I think it is also the key to triggering fear in myself: I know I can be so much better than I am at x, but I am better than clients, and that is all you need to get paid for it:)

  13. Hannah says:

    I enjoyed reading this post Saul, thanks for sharing your experience!

    What really struck me while reading it is that I had the potential to do what you were doing a few years ago. I was working several ‘jobs’ that were all things I liked to one degree or another. The flexibility was amazing, but I felt so much pressure to get a ‘proper job’ that I gave it all up…. and realised my mistake soon after, of course. Now, I’m learning to embrace my multi-potentialism and I’m trying to find more ways to incorporate my skills and doing what I love into my work and personal life.

    Thanks for your insight and tips :)

  14. Lakshmi says:

    Very informative post. I did not know about many of these sites before.

    It’s great if someone can make a living doing jobs that don’t force one to dedicate oneself to a single career while gaining freedom to pursue other interests.

  15. Janet says:

    Saul, I remember reading your piece on ‘lateral freelancer’ on your blog and loving it!! I’m glad to see you featured on Puttylike. It’s absolutely awesome information and I had never heard of these resources. I think I mentioned before, either on puttytribe or your site, that there’s another one called Amazon Mechanical Turk. It’s another task-based freelance site I love that these opportunities are out there now. I love how you’ve coined the term ‘lateral freelancer’.. never heard of that before!

  16. Jon says:

    Late to post, Saul, and really enjoyed reading it. But am I right in thinking it only works if you have a track record or references? Because you mentioned how a few start-ups screen their applicants.

    I used to be an events contractor, but unfortunately all my references are dead now, thanks to companies closing down, or restructuring so they’re completely different, or people I worked with having left. So basically: no proof of my working life.

    So while lateral freelancing looks cool (in theory) – it’s not clear as to what you need for it or who it can apply to.

    Also: the sites you listed – these are all American sites, right, only for American nationals?

    • Saul says:

      Hi Jon,
      I started down this past with no specific track record or references. The sign-up process varies from site to site (RelayRides and Lyft require a clean driving record, for example, and TaskRabbit does a background check), but most are as simple as logging in with a Facebook or G+ account. The key is building references as you go — you’ll get more opportunities once you’ve had other folks vouch for you or leave references, but it isn’t too hard to get started without. Not having a traditional resume or work life wasn’t a problem for me.

      As for the sites listed, they’re mostly active in large US cities, but there similar sites in other places. Airbnb and Vayable is global, Taskrabbit has clones in the UK (TaskPanda) and Australia (AirTasker), and Europe has a lot of new sites popping up as well. I’m planning to compile a new list soon with some updates!

  17. Peachy says:

    Hi here, I think you just gave me that glimmer of hope during this time in my life where I’m u sure of my value anymore. Good at what I do but only for about a year. Can’t figure out why. This may be part of the reason. there may be a way I can add value to the world and be happy yet!

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