I wasn’t born with a silver spoon in my mouth. You probably weren’t either. So when people in dire financial situations with dreamy work dreams email me asking for a little career advice, I sometimes want to whack them on the head with something less luxurious than silver, like my kid’s plastic spoon.

silver spoons

There’s a Ricky Schroder joke in there somewhere.

I get it — we’re told, “Do what you love and the money will follow.” But on the road to making it as a heavenly musician, artist, writer, or whatever, sometimes you have to face hell by sucking it up and taking that $hit job to pay the bills. This holds true for careers requiring a lot of time and eduction too, such as: doctor, lawyer, engineer, computer scientist, or my psychiatrist. Going to school costs money, and many students — even mature career changers — may need to buck up and work hard in unrelated (perhaps menial) positions to pay for those degrees.

I know $hit jobs can take time away from mastering your craft. I get it that few people live for cleaning, factorying, waitressing, dish washing, flyer stuffing, call centering, pizza delivering — this list never ends, really. I understand we want our dream jobs served with a side of amazing and a paycheck to match, yesterday. But sometimes the road to awesome is paved with awful, today. You’re not too good to take a lesser job.

I’m not sorry to break this news to you. Your emails and pleas to ‘live the life’ without working for it are lost on me. If you inbox me your dream job and demand I trace your path to getting there without pain, I’m gonna tell you to go suck it up and take that $hit job. Sorry.

As a gal who sells words for a living — many of them financial-related, others IT-based — I’ve had my share of awful to get the dreamier job done. Sure, I like to think big. But over the years I’ve had to measure this fantasy against the reality of paying for my own clothing and toys as a kid, surviving as a starving journalism student, and now feeding my own kid while covering very real costs. Maybe you’ve been there too.

I agree $hit jobs can suck. On the surface they may put you in a place you’d rather forget forever (like cleaning public toilets), but deep down these gigs can teach you a lot about yourself and force you to get past the terrible by rising up to get that better gig.

I don’t get invited on TV shows, pitched to write columns in fancy newspapers, and have a popular blog because someone just handed it to me. I had to work for it. And many of the $hit jobs I’ve sucked on over the years have made me who I am today. Go me!

So if you’re ready to stop dreaming and start doing something real to get there, here’s the very honest path I walked and the ungorgeous gigs I gagged on to become whatever I am.

I think everyone’s LinkedIn profiles should be this honest.

Pennysaver Carrier
Stuff at least 10 flyers into 144 newspaper-like things (that’s 1,440 flyers, people), then dodge mean dogs to deliver to homes spanning an 8km radius. Since the Pennysaver was just a compilation of classified ads with countless flyers, my neighbours would often reject this delivery and yell at me for cluttering their mailboxes. Fully stuffed Pennysavers were heavy to haul, and the summer I broke my shoulder playing soccer, I needed my mom’s help to finish the task. Not cool. Having money to pay for movies, clothing, and music was very cool though.

Neighbourhood Babysitter
Get whacked on the head with toy hammers, flying balls, and baby vomit. Smile like everyone’s kids were perfect little angels. Parents around my block loved my willingness to work after school and on holidays. I loved saving up the money to invest in bonds. Yes, I bought Canada Savings Bonds. Cashed them out to pay for school years later.

Tim Hortons: Donut Finisher
Pump a coagulated jelly substance into fried circular dough, dip in white powder, repeat 1,000 times, and then stack in neat rows for people to eat. The donut baker in the back of the store, a guy who worked three meters from me, was a convicted criminal — of what I have no clue. The gal selling the donuts in the front worked tricks after shifts as a prostitute — her name was Sue. I know Sue “hooked” after donut hours because she told me so on my first day, and said if I had a problem with it I should “shove off”. I worked well with Sue, mostly ’cause I liked her and she protected me from the wandering eye of the ex-con in the back. No job has ever taught me more about office politics, getting an education, and respecting others than my donut dipping days.

Soccer Referee
Summer work was a must growing up in my household. So when my father insisted I take my “passion for soccer” and turn it into “paid labour” he happily covered the cost for my referee’s course and then took the class with me. Learning the rules of the game alongside my dad and scoring higher than his best on the final exam kinda, sorta sucked. But the real test came later during a heated game when I made the ruling to red card and expel a kid for spitting on me because he didn’t like “the girl ref”. Spitting is an automatic red card in soccer, whether you have girl parts or boy parts. Being the first female referee in that little boy’s league was a harsh introduction to the realities many gals can face in the workplace.

Christmas Kiosk: Glitter Glue Specialist
My very first attempt of using a crappy job as a stepping stone, I took a seasonal gig at a kiosk over Christmas to gain “mall experience”. My job was to write names on Santa stockings using glitter glue. The problem was no one wanted to wait for the glue to dry, so people would pick up their wet socks and yell at me for getting covered in glitter. Merry Christmas, jerks.

Le Château: Sales
Bustiers were big in the 90s, so my store manager expected all sales girls to support the trend by boosting the booby look to pump sales. Being an avid athlete and a shy soccer player to boot, I wasn’t really into the Madonna-inspired look. I just wanted to hide behind the comfort of my sports bra and sell suits. Suits were big ticket items that brought home the biggest commissions, so I convinced my manager that I should dress more business-appropriate to attract the more office-oriented customer. It worked! I wore fitted blazers that covered my boobies and sold a heck of a lot of suits to guys shopping with their girlfriends or wives. Learning how speak up and advocate for myself were lessons learned for sure, but learning how to be exceptional with customers was golden.

Jazz Band, Trumpet Player
Play your heart out in some dirty bar and earn five bucks. That was my take after a long night of playing jazz with some guys I met in school. I’d been playing a horn since the age of six, so my so-called talent wasn’t natural — I had done the hours. The problem was a “girl trumpet player” was a bit of a novelty act, and I didn’t appreciate the cat calls from the crowd. I also needed to earn more than $5 to cover rent. I’m over it.

Hotel Housekeeping
Push a heavy cart stuffed with cleaning supplies into rooms once occupied by sometimes filthy people. Scrub shower stalls, rotate linens, try not to vomit removing pubic hair from toilets. The thing about cleaning hotels is the bosses time you per room, so if you land a particularly nasty floor, you’re doomed to not make quota. I hated this job, but working nights was a great way to pay for school during the day. The things I saw also proved to be awesome fodder for my journalism class assignments. I wrote many of my best school stories during cleaning breaks. This is called creative multitasking.

Tabloid Paper: Proofreader
Getting relevant career experience before graduating is always a good idea. So when the Wednesday night proofreader position opened at the local tabloid, I leaped at the opportunity before my journalism classmates caught wind of the position. (I may have eaten the job posting. Gulp.) Anyways, the job started out as fun. I’d take a marker and correct the weird spacing and typos in the draft pages before the paper went to print. Finding photos in the library when a reporter was tight on time also happened frequently. The real issue I sometimes found hiding in my stack of pages to proof! The newsroom can be a strange place, and I guess some of the staff there liked to mess with transient proofreaders a bit, so finding a pornographic photo of some chick (not a bikini-clad girlie girl) in my pages to proof was a common occurrence. At first I freaked, not sure what to do. Over time I just accepted the increasingly vile photos as “jokes” and refused to react. The images contained no text so there was nothing for me edit, after all. Keep your head down and move on was likely my motto, but in hindsight I should have recognized this as harassment.

Phone Mail: A stupid name for telemarketer
Call university graduates and ask them to donate to the Alumni Association. This was a campus job, so it worked well with my academic schedule. I learned how to cold call people and ask them for something special — their money. I once called and asked to speak with a recently deceased man, which was terribly awkward. Don’t ever try to leave a message for a dead guy.

Technical Writer
I never wanted to be a writer-thing. After studying journalism and not feeling it, I went back to school to become a computer scientist. Science tickled my left-brain sensibilities, while writing words and sitting alone at a desk was lonely. But sometimes you have to listen to the market, and the market wanted someone who could program code and write enough words to build a sentence. With a 17K student debt hanging over my head and a sweet job offer in hand, I decided to take the seemingly sucky ‘Technical Writer’ job to pay my bills. But a funny thing happened when I discovered my amazing colleagues, enjoyed the technical challenges, and wrote manuals only programmers eyes would read — I actually liked the job! The benefits were amazing, we had free beer on Fridays, and I kinda rocked at being technical with my writing. Go figure! Give a gig a chance and it may be a career path you nearly passed over.

Blogger
Blogging is not a job, it’s an accident. Writing technical procedures for a living left the right side of my brain open for business. I needed a creative outlet and my friends wanted to know how I managed to save money. Having worked my whole life, I knew the value of a dollar. I also knew how to invest my savings and pay off debt. The idea to start a money-saving newsletter came to me while riding my bike to work one day. Riding bikes was cheaper than driving cars — my friends needed to know this! So a fluffy story about “How riding your bike is great for the butt and bank account” happened. The story was mostly silly and slung together with a little math for credibility, but my friends dug it. Almost all of my newsletter subscribers commuted to the office on two wheels that week, and many more wanted to join my money saver’s list.

Enticing my friends to follow my tips without turning them off was a tough balance to strike, so I did my best to make the stories fun. I’d email a new frugal financial tale every Friday while chugging my free beer, and then wait for the newsletter’s responses. After a few months of this routine, the list got too big to handle with replies and questions, so I started one of those blog things to serve up my stories.

Anonymous to start (I didn’t want my employer to know), I bought the domain Squawkfox.com because it was weird, sounded financial like a Squawk Box, and “squawking” some money sense made me smile. A year of writing in the evenings while working days as a technical writer paid off — I got a mention in The Globe and Mail and HarperCollins Canada offered me a book deal. That’s how my book 397 Ways to Save Money happened.

So where am I going with this?

I shared my 12 worst jobs to prove that paying the bills can trump pride. Taking that $hit job may stink at the outset, but you may be surprised by the lessons learned and the skills earned while making enough money to cover your expenses.

So before pressing “send” on that email asking me how to land that lofty dream job without the cash to cover your current costs, get in the know of where I stand from my own (sometimes unsavoury) jobs of past.

So please stop complaining with that silver spoon stuck in your mouth — sometimes you have to suck it up and take that $hit job. And I’m not sorry.

Love,
Kerry

Your Turn: What’s the worst job you had to take to pay the bills?