Leaving Work Behind

4 Weird Side Gigs to Supplement Your Freelancing Career

Written by Anne Dorko on June 21, 2016. 12 Comments

A one man band.Freelancing can leave you a bit lonely, without even offering benefits like seminars or skills training. How can you gain hands-on experience without going back to a full-time office?

By taking on unusual side gigs, you gain invaluable insights to concepts you had no idea about. It’s fun, and it keeps you well rounded – all while earning extra cash to boot!

Freelancing enables me to treat the world like my playground. Today, I’ll tell you a bit about my own experiences dabbling in side gigs, and how they’ve helped my freelance game.

1. Car Salesperson

It was a hot Texas summer. I was fresh out of California, desperate for a new experience. Tired of laptops and screens, I wanted to work face to face with people.

The Craigslist ad read “Customer Relations,” promising $2,000 per month, with the potential for bonuses. There wasn’t much else. When I pulled into the address and found myself on the lot of a car dealership, it took a moment to reconcile what I might be walking into.

Anne Dorko car sales

Embrace the darkness inside of you.

I wound up hitting the melting asphalt that summer as a car salesperson.

It was a gnarly look into the universe of sales. Thanks to that job, my eyes were opened to the reality of hard, cold business.

What I Learned

  1. Everything is marketing and sales. All around you. Some people are scarily good at it. Because of this, everyone should learn the basics. For example, a salesperson knows to sell you on price per month, because $299.99 sounds pretty reasonable for a car. If you don’t understand the implications of this deal, you wind up with a severely overpriced vehicle.
  2. You will be taken advantage of if you’re green. It’s not a matter of if, but when. For instance, customers are more willing to buy from new salespeople. I was being sold on my job as a new recruit, with as much effort as they were selling the cars.
  3. Sales is about having the right bait. Companies don’t always make money in the places you expect. I learned that dealerships prefer to sell in-house loans, not the cars themselves.
  4. Building the right connections makes or breaks you. A customer won’t buy if they don’t trust you. Negotiators won’t work with you without incentive.

2. Bicycle Assembly

After dipping my toes into the car sales industry, my soul felt a bit dirty. It was time for something more honest.

I interviewed for several odd listings on Craigslist. None were so endearing as this one ex-convict who was hiring bicycle assemblers. My phone interview largely consisted of learning his backstory. He was passionate about work ethic and letting people prove their worth.

My first day involved getting picked up by a group of strangers at 6am in a retail parking lot. We drove two hours to the worksite. Thankfully, I lived to tell the tale.

The company was a third party hired regionally by Walmart. We assembled bicycles when the in-house team couldn’t handle the influx of new product.

There’s always a niche to fill, even in the least expected places.

What I Learned

  1. It’s useful to know that almost every big company contracts out third parties. Starting a business is a matter of finding one small gap and filling it.
  2. Showing moderate respect, competence, and reliability can land you a gig on merit alone.
  3. Best of all, repetitive hands-on work can be cathartic.

3. Brand Ambassador

An acquaintance was in town and invited me to dinner. Turns out he was managing a marketing gig, and needed extra hands.

He told me I could earn between $15–$20/hour to show up and hand out samples! There was even a bonus for coming early and staying late to take care of the equipment. For drives over 30 miles, they reimbursed gas costs.

Not only that, but because we sampled out food, we were allowed to take home whatever was left at the end of the day. Hello, fridge stocked full of expensive pre-made smoothies!

Free t-shirt included!

Free t-shirt included!

The job is called ‘brand ambassador’, and many companies hire for it. The position exists to make a good impression on guests. The idea is to bring positive brand awareness, contributing to a much bigger scheme designed to improve sales.

Basically, marketing budgets produce a lot of excess. You can be at the receiving end of it if you know where to look. I was earning over $1,000 in a weekend!

What I Learned

  1. Most people don’t bother to pay attention to details. The daily questions I fielded were simple. To be more knowledgeable on a topic than most, simply read the included instructions.
  2. Friendly banter and a genuine smile can get you a long way with coworkers and clients alike. This helped me more than hit my sample handout goals.
  3. Going the extra mile often means you’re the one the boss counts on when he needs to hire someone for an extra gig. I ran several side errands for extra cash, thanks to my reputation of always being ready to help.

4. Resort Food Server

I always liked the idea of seasonal work. Someone wants to pay me to live somewhere amazing without a long term commitment? Where do I sign?!

After much research, I settled on the Grand Teton National Park. Server positions paid best after tips and filled up early, so I pursued it aggressively the season ahead while I was still in New Zealand.

I touched down in San Diego and rode my bicycle to Salt Lake City, just in time to hitch a ride with a friend to the mountains for the summer. All the knowledge I gained while assembling bicycles came in handy for repairs during the tour.

On arrival.

I didn’t get photos on the job, but here’s what it looked like arriving.

On the job, I was constantly handling sensitive interactions in a high pressure environment. It made managing freelance clients feel like a cakewalk.

What I Learned

  1. Treat everyone nicely and with respect, no matter how tired, grumpy, or angry you feel. A good game face helps avoid a lot of drama. Most of our staff went out of their way to accommodate me in the kitchen, which translated to better service and better tips. By the end of the season, I was asked to return and manage the restaurant for the next year.
  2. The power of suggestion is strong. You get hands on practice by up-selling dishes or recommending the day’s special, getting to play off customers’ reactions.
  3. Tourism is an insanely profitable market – particularly where tips are involved. I made over $11,000 in four months.


Going freelance doesn’t mean isolation or restricted job experiences. You can create your own training by widening your understanding of the world and business through side gigs.

Just a few of the odd jobs I learned from were:

Do you ever feel pigeonholed by your freelance work? How have you found ways around it, to get these types of extracurricular life lessons? Share your own experiences, and what side gig you might like to try next, in the comments section below!

Image credit: Ramallo.

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12 Responses to “4 Weird Side Gigs to Supplement Your Freelancing Career”

  1. Mary
    June 22, 2016 at 10:20 am

    So interest to have all round knowledge. I hate staying idle. At least having brilliant mind can lead to perfection of chasing over finances.

  2. Vicky
    June 22, 2016 at 6:33 pm

    Writing can be so lonely. And boring. I’m doing housing inspections and in the fall I’ll be doing jeep tours. And refreshes me for writing.

    • Anne Dorko
      June 23, 2016 at 7:57 am

      Yes!! It’s definitely good to get some real life stories, I find it infinitely inspirational for my writing 🙂

      Best of luck on your jeep tour!

  3. Kim
    June 23, 2016 at 5:50 am

    Seasonal work can be a great choice. It has its downsides, as I have learned in the past couple months. But a lot of seasonal jobs offer housing at a reasonable rate. Plus, most companies that are looking for temporary workers are understanding if you’re also self employed.

    • Anne Dorko
      June 23, 2016 at 8:03 am

      Yeah, they told me that as long as it didn’t interfere with my job, they had no problem with me taking extra work on the side 🙂

      And it does have a few downsides but it really depends on personal preferences 😉 I loved it because where I worked, housing was included and the food was affordable

  4. Freelance Wave
    July 2, 2016 at 3:32 am

    Thanks for the great content, Anne. People often concentrate on their freelance jobs though they are not doing it 24/7.

    Experience is valuable. But the knowledge acquired throughout the experience is more valuable.

    Thanks for the post again, Anne.

  5. Rachel
    August 18, 2016 at 10:42 am

    This is great!

    I’ve worked in various positions in the past myself. Every single one of them taught me something but the one that helped me learn the most was retail.

    I worked as a stocker, cashier, and in various management roles, through store manager. Seeing every side of the process in-store was immensely helpful.

    The best thing, though, was how it granted me the ability to deal with people. I was incredibly shy before working in retail. Once there, it’s sink or swim. So I learned how to put on my ‘retail face’ and just deal with my people panic.

    It has been years since I last worked in retail but to this day, I still use that ‘retail face’ in a multitude of situations!

    • Tom Ewer
      August 19, 2016 at 8:54 am

      Great insight, Rachel!

      It goes to show that there’s a learning experience in everything you do – it’s what you take from it that counts. 🙂

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