Unsettled Asks: What Was Your First Job?

Before we grew up and began living unsettled, we all got our start somewhere…whether that was babysitting as a 12-year-old, umpiring a baseball team, or being a caddy for rich middle-aged golfers, the hustle often started early and often.

We asked 32 Unsettlers and members of our team from all around the world to share their vocational wisdom.

Here are humble, inspiring, hilarious (and questionably-legal) tales of managers, CEOs, founders, entrepreneurs and businesswomen and men…well before they had any of those fancy job titles.

Kalan, 15, in his (awkward) half punk teenage phase…

Jonathan Kalan, Co-founder, Unsettled

“My first real job was (and this is probably the only thing Barack Obama and I have in common…) scooping ice cream for Baskin Robbins. I started when I was 14, and it’s still one of my favorite jobs I’ve had. When you think about it, you’re literally getting paid to make people happy. Who doesn’t love ice cream? It was also the best place in town to pick up dates, and spike smoothies (when I was a little older, of course…). I worked there on and off throughout high school, before expanding my horizons to become a pizza delivery boy.




Michael Youngblood, Co-founder, Unsettled

“I worked at a Sonic Drive Thru – picture a classic American drive up restaurant with wait staff walking or skating out to your car. I wore the roller skates. I quit by making an announcement, “I quit!” on the loudspeaker and roller skated my ass home. Haven’t been back to one since.”

Jenny Maya, Serial entrepreneur of three different ventures

“I started my working journey by cleaning windows and ceilings for people – mainly senior citizens – in the neighborhood for 0.75ct/ hour. I was aged 10.”

Kyle Kesterson, De-Spaghettier, Swiss Army Knife, and Storyteller for hire

“I started working for my mom’s cleaning service when I was 10, vacuuming houses and buildings. I became a janitor and cleaner for her company for 8 years.”

Erin Brown, Client Services Director of an Insurance brokerage

“I was an entrepreneur of a pet-sitting business. I primarily watched dogs and cats with some rabbits and fish thrown in. I don’t think I had a business name. I typed up a flyer and then put them in mailboxes all over the neighborhood (clearly this was during the pre-internet era). From there, I got more and more clients via referrals…”

Fatinah Hayat, Founder at The Hayat

“At the age of 12, I started doing bookkeeping for my dad in the UK.

Patrick Elliott, Global Experience Leader, Unsettled

“My first job was as a baseball umpire for the local little league in West Chester, PA. I loved the sport and figured that I might as well be around the game when I wasn’t playing it myself. I was paid $20 for a game which wasn’t too shabby for a 15 year old. The best part: watching kids try to learn the sport. The worst part: the parents. I’m sure your seat in the stands has a much better viewpoint than mine behind the plate but sorry, I call it like I see it. And no, I’m not going to modify the strike zone because your little Bobby doesn’t want to get the bat off his shoulders. He’s gotta learn to swing!”

Liza Schmidt, Manager of Operations, Unsettled

“My first job was babysitting. I started at about the age of 12 in St Louis, Missouri where I would go over to neighbor’s houses to watch their kids while they ran errands. I continued to do so for years, all the way through college! We’d make rocket ships out of cardboard boxes, forts out of bedding and furniture, play tag and hide-and-go-seek, jumping through the sprinkler in swimsuits, and bake cookies or decorate cupcakes. We’d write and illustrate story books, come up with epic make-believe games in the pool, build elaborate fairy houses out of twigs and leaves and other natural materials in the backyard…”


Judith Barker, Founder/Creative Director Brandtivity.co

“I was doing farm chores at the age of 6. I don’t think I got paid for it, but it sure was work. It was a cow and pig farm, and we had to carry buckets of water to the animals and throw corn into the pens. It made my first paid job at a toy store (aged 16) at Christmas seem very easy!”

When not packing groceries, Shitika, 18, dressed models at fashion shows for extra $$

Shitika Anand, Social Media Manager, Unsettled

“Check-out chick at Woolworths in Australia. I grew up in India where working part-time for pocket money as a teenager is not a conversation you have with the rents. You wake up, study, eat, study some more, go back to bed and repeat until you’re about 17. And this is why I didn’t take this financial freedom at the age of 18 for granted. I packed people’s weekly groceries like my life dependant on it… and after just six months on the job, I was promoted to supervisor’s role (which meant I got the keys to the liquor and tobacco drawer – major win when you’re 18, hey!). I’m still very particular on how my groceries are packed… fresh eggs and fresh herbs stay on top. Always.”

Elyse Pachota, Global Digital Marketeer (currently getting her MBA)

“I worked at Panera Bread from 2003 until 2010. Yes seven whole years at a bakery.”



Gwendolyn DeSilva, EFL Teacher with VIPKID and Freelance Writer

“At the age of 12, I was a babysitter to three unruly boys and a newborn!”

Julia (right) in her finest German threads

Julia Otto, Finance and Account Manager

“I represented Germany in a Dirndl at Walt Disney World Resort in Epcot. I sold bier, sauerkraut and bratwurst to little kids and family visiting the theme park.”

Robert Crocker, Tech and data visualization consultant in the Silicon Valley

“I started cutting and mowing lawns – door to door at the age of 10.”



Jessie Rice, Marketing Manager, Unsettled

“My first job was as a referee for children’s basketball. I was 13 and my starting pay was roughly $10 – $15 per game, paid by the youth league in the town I grew up in. At first I was a referee for the youngest kids, aged 5 and 6. But as I got older, the age range I was certified to officiate increased. I worked this job for many years and my only regret was that it was seasonal – so only available in the U.S. winter. I could make as much as $100 in a weekend, which felt like a lot of money at the time.”

Mikey Voislav, Music composer and piano teacher

“My first “proper job” out of university was in an accountancy office for a food company. I lasted three weeks. After being reprimanded by my narcissistic boss for not following some arcane aspect of the record keeping (in lovely, buggy MS DOS – in 2005) I said “fuck this – there’s a universe out there” left my desk and never looked back.”

Chenaé Van Niekerk, Chef

“I worked at an Ice Cream shop, and I really miss the days where the biggest stress was hoping the soft serve won’t fall off…”

Wicks (left), live from a soybean farm near you

Jonathan Wicks, President and Owner of two contracting companies

“I worked at a seed farm bagging soybeans that had just been harvested. I was 13 when I started, and it was an assembly line style job; repeating the same process every 30 seconds. Not sure child labor laws were a big priority in Nebraska back in the day…”

Mattie Conaghan, Creative at Ogilvy & Mather in Chicago

“I was a caddy in the day – basically carrying golf clubs for rich folks. And Ice-cream scooper at night. Dual threat, you may call it.

Lynne Scullard, Global Experience Leader, Unsettled
“My first paying job was losing my baby teeth and waiting for the tooth fairy to bring me money…”

Betel Sanchez, Marketing researcher

“I helped my mom in her photo lab at the age of 6, and then I sold candies in my school and delivered flyers door-to-door. “

Lindsay Yeager, Yoga teacher

“When I was a kid I picked snails off plants from my dad’s nursery. I earned 5 cents a snail, 10 cents for mating snails.”

Jade, 16, kicking goals since 2004

Jade Doherty, Head of Admissions, Unsettled

“I was a football coach! I wanted to be a footballer when I was younger and had a nice little career playing for  Arsenal and Fulham Ladies in the UK. I started when I was 16, and the job was actually pretty well-paid for a first gig and set my standards pretty high. I used to make about £100 over the weekend, doing a few football parties (pro-tip: make sure the birthday boy’s team wins!)  and a couple of sessions. The hardest part of the job were the kids who had never heard the word “no” at home, and they had to hear it from me. Let’s say they weren’t too pleased with that. But there were so many best parts; the hilarious things kids say, the confidence I gained from it, the camaraderie with the other coaches, and getting paid to play football.”



Alia Hamza, Filmmaker and Writer

“l first got paid 50 cents to lotion my mother’s feet (really!). My first taxable job as a teenager was commercial cleaning.”

Jennifer Barnett, Network marketing mentor, MONAT

“I worked in sales for the cosmetics and skincare department at Stage store in Monroe, Louisiana. I was 20 years old. I went on to get a human biology degree intending on going to med school, but red lipstick won!”

Jen Myer in her prime teens!

Jen Myer, 15, embracing the unknown since her teens

Jen Myer, Copywriter

“I was a hostess at a restaurant called Fat Punks. It has since gone out of business.”

Judy Cogan, Deputy Editor at Oryx, Qatar Airways’ inflight magazine

“I worked at a men’s barbers sweeping up hair and making tea! Great training for when I started interning at magazines years later…”

Clari Mastronardi, Buenos Aires Location Manager, Unsettled

“I was an English and Math teacher for 7-year-olds in Buenos Aires. I was 16!”



Aoife Mooney, Legal Manager

“I was a lumberjack in France at the age of 18 and then a year later in Germany, I was a welder.”

Ashley Wilson, Operations Manager

“I worked at a dish pit in a below-average restaurant, at far too young age. The chefs used to throw butcher knives into the sink past us… until the eatery went under, not long after.”

Tom Spann, Founder and Vice Chairman at Accolade

“I was a paperboy. I started as a 12 year old and continued until I was about 14. Delivered (and collected payment) by bicycle. Yes, such jobs used to exist IRL before the video game.”

So, what was your first job?

1 Comment

  1. j

    I was bullied at school. My first job was as an Undertaker..

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