Finding A Job

5 Questions To Ask Yourself To Make More Money Where You’re Already Working

By | Friday, July 15, 2016

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One of the many things that I value about the TFD community is the resourceful drive and scrappiness of our contributors and readers. TFD-ers are unashamed of their double work lives, and they regularly bring their introspective powers to bear on the professional benefits of side hustling. I have the privilege of reading these stories, learning from them, and giving them the ol’ grammatical spit-shine so that we can collectively revel in each other’s school-of-hard-knocks wisdom. *Cue the shrill chorus of orphans from Annie.* (And bring it home with extravagantly creepy ballad. Brewing your own bathtub gin = A Super-Duper Sad Budgetary Wet-Bar Hack, or 1 Quick Way To Turn Yourself Into A Delerium-Tremens-Rattled Childcare Professional Up For Trial In Small-Claims Court. Annie is a dark musical, you guys.)

All the side hustle stories I’ve read, written, and edited for TFD have included helpful resources and How-Tos. But — after editing one piece about breaking into the music industry and getting a Grammy nod, and another article about one teacher’s experience with working at a rich-kid school — I realized that we were focusing almost exclusively on the back-end of side hustles. That is: we’ve shared the philosophies of self-discipline and the time-management hacks that hustlers use to accomplish their side gigs. But what about the process of self-evaluation that will help you assess which of your skills might lead to lucrative side gigs? What about the concrete steps you can walk yourself through to gain a macro perspective on the supply-and-demand market within your full-time or “main” workplace?

Well, here’s what. I want to point out the Important Questions that all our profitably-hustling contributors are asking themselves in order to find side gigs, get hired, earn extra cash, and climb the ladder within the industry they are already qualified for and are invested in pursuing.

1. What task does my supervisor NOT want to do, NOT know how to do, or NOT have time to do?

In his article about becoming a highly successful freelance audio engineer, Beau Vallis explains his realization that “however musically-gifted artists are, if they don’t know how to mix their own tracks and records, they still need people with my skills (audio engineering) to make the music they’re passionate about and put it out into the world.” Essentially, Beau saw that the “way in” to working with internationally-famous recording artists was to deliver to their unmet need for behind-the-scenes, skilled engineers to run the recording booth and mix tracks.

When I began working in my comedy theater, I realized that most performers didn’t know how to run the light and sound boards (essential equipment that sets the tone of every performance). Many of the theater’s producers and directors could run lights and sound, but they didn’t have the time to do it. I put two and two together: the theater had an unmet need for “techies;” I investigated that demand, and found freelance gigs in short order.

Whether you’re in a government office job or retail, I guarantee you that your managers are stretched thin; if you identify where they need help and meet them 90-10, you just might get paid to do it.

2. When does my manager choose to pay extra and hire outside the company to get help?

One summer, I got a volunteer position at a public radio program. While I was delighted to be working (for free, alas) alongside the core staff members — and I gained invaluable insight into how producers structure and release a popular show on a weekly basis — I also wanted to explore work options that might be profitable in the future. I quickly realized that (because of the sheer volume of tape we needed to cut each week) the radio program was hiring a free contractor to come in a few times a week and edit on an hourly-paid basis. I grabbed lunch with the engineer (a really chill, genuine, helpful dude) and asked him questions about how he’d gotten the training and contacts for his job.

Almost every company relies on outside contractors to accomplish some of its work. If you have a friend in the HR department (or better yet, a buddy who swings through the workplace to knock out freelance work throughout the week), ask them about the workload that isn’t being done by the core staff. Then, pounce on any opportunity to help with that workload.

3. Do I already possess the skill set or technical knowledge that my boss is paying freelancers for?

One day, while I was working my job an assistant editor in publishing, one of the senior editors walked up to my desk. “You speak French, right?” she asked. (One of my coworkers regularly teased me — over the cubicle wall, for all to hear — about my fancy-pants language skills after he overheard me speaking French with one of the graphic designers, a kindly Frenchwoman.) Turns out, the teasing was worth it. The senior editor had overheard everything, and now, one of her staff writers needed someone to translate a document from French into English. She approached me because walking ten feet to my cubicle was infinitely easier than sending dozens of emails through the corporate network in search of a freelancer who would have to negotiate a contract.

The lesson here: be upfront and open its coworkers about the unusual, outside-the-box, or off-the-job skills that you possess (especially if they relate to a well-compensated freelance industry). It could be anything: a foreign language, an academic specialty, research skills, transcription experience. Ask around and see if your superiors have ongoing relationships with freelancers, and ask if you can take on any of that workload. Adrienne, the rich-kid teacher, realized that she could make a buck in private tutoring, because her “bosses” (aka, the parents of her students) were hiring specialized tutors outside of school hours.

4. If I have to develop new skills to get hourly-paid extra gigs, is there someone in the company who will teach me for free?

Back to my example of working the tech booth at the comedy theater. After hearing from a few friends that they scored $50 for each hour-long show that they ran the sound and light board for, I emailed one of the night managers and asked if I could participate in the (free) training program that my friends had signed up for. The manager was all too happy to organize “shadowing” sessions (where I observed experienced, staff “techs” work the board during live shows) and formal training sessions (where I stepped up to the plate and ran lights and sound by myself). Not only did I develop payable skills; I acquired them at the cost of zero dollars!


Though companies don’t always have a formalized process or program for teaching new skills to their workers, there’s always a way to further your training: ask your trusted coworkers (who are friendly and willing to help) if you can “ride along” during their workday. Begin by observing how they do their job (and minimize the questions you bother them with). Next, ask if you can stay a little late after work and fool around with the equipment (or server, or database) and get a hang of accomplishing those tasks independently. (I logged a bunch of post-5pm hours at the radio station, hacking my way through audio tracks to teach myself how to use ProTools, the radio-standard editing software).

5. Before I negotiate my hourly rate with the hirer; how much are other freelancers (who possess these skills) charging for their work?

This is crucial, folks. If you’re on the scent for paid work, and you’re already putting tons of time and energy into mastering a new skills set or tracking down work opportunities, it is worth your timdo to a little market research. While online forums will give you a sense of pay scale (Craigslist for-hire posts, or Glassdoor wage averages), it’s always better to go local. Ask friends (and friends of friends) how much they charge for their work. If you’re learning about a gig from a freelance coworker (and asking about finances wouldn’t be a violation of your professional relationship) ask how much they company offers her for her work.

Image via Unsplash

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