7 Jobs I Hope You Have – A Letter to My Teenage Son

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Restaurant cashier


Dear son,

You’ve been trying hard to find a part-time job, and I’m sorry it hasn’t happened yet. You’re still at the beginning stage when you have to leave the ‘Experience’ section blank on applications, but it won’t be long before someone smart takes a chance on you and you’re launched.

I was 15 when I landed my first job at McDonald’s restaurant in Boulder. The uniforms at that time were blue polyester with matching pointed hats. Unfortunately, the only pants they had on hand were a size XXL. I had to secure the elastic with a large safety pin, which gave the pants a nice bunchy, balloony effect.

In all my working years I never had a more high stress, pressure-filled work situation than McDonald’s. I still wake up sometimes in a cold sweat hearing an angry customer shout, “I said NO PICKLES!” 

Beginning jobs are a rite of passage. They often feel menial, but early jobs shape and prepare us in ways we can’t always fathom at the time. If you’re lucky, you’ll get to work at a wide variety of early occupations like I did. Here are some of the work experiences I hope you have.

7 Great Jobs to Have Early in Your Career


Janitor cleaning floor


1. I hope you have the opportunity to work in a restaurant serving others. (Unfortunately, this may require wearing a themed uniform… and possibly, matching headwear.) For the rest of your days you’ll have compassion for restaurant employees, and you’ll be empathetic when your order is wrong or the service seems slow. 

2. I hope you get to have a sales job—maybe peddling something intangible like memberships at a tanning salon. You’ll learn how to handle rejection, which is a very handy life skill. You’ll discover that it’s listening, not talking, that makes the sale. You’ll also have compassion for the eager man at the front of the grocery store who asks if you’d like to buy a newspaper subscription.

3. I hope you have the opportunity to work on an assembly line, as I did when I worked 10-hour shifts stapling fiberglass to foam cores at the Kryptonics skateboard factory. That experience will remind you of the hands that make the things you own. You’ll always appreciate the true, human cost of a manufactured item.

4. I hope you have a cleaning job, like emptying grease fryers at a chain seafood restaurant or scrubbing down bathrooms at a football stadium. Then you’ll know the satisfaction of making something look clean and shiny, along with the disappointing reality that everything clean gets dirty again. You’ll never take the garbage collector for granted, or overlook the quiet worker mopping the floor in the airport bathroom.

5. I hope you have a job where your work is critiqued—perhaps something like writing, graphic design or photographing toddlers for the mall portrait studio. Being able to accept constructive feedback will help you do better work. You’ll quickly learn to recognize unconstructive criticism, too. 

6. I hope you have a job in customer service, like working in a cable company’s bill collections call center. Handling customer complaints all day will make you tough. Going forward you’ll know first-hand that customer support reps are people, too, and you’ll always treat them with respect.

7. I hope you have a job managing a group of people—maybe a position like assistant manager of an all-night Waffle House. Then you’ll understand the myriad challenges of being responsible for your team’s success while simultaneously meeting a company’s objectives. You’ll learn to reward the person with a great attitude, which is a highly valuable trait in any employee. You’ll develop a deeper appreciation for the truly great bosses and leaders.

Yesterday you put in another application, and I’m proud of your perseverance. When the door opens, I know you’ll approach your first job with dedication and hard work. And who knows? Facing the inevitable challenges and overcoming the obstacles might be the very experiences that lead you to do great things and make the world a better place. 

I can’t wait to see where you land. 

Love always,


How About You?

What was your first job? What was the toughest work you ever did? Did you learn any lessons early in your career path that continue to influence you today? 

I’d love to hear your stories and thoughts, either as a comment on this post or at mail @ elizacross . com.

Best always,

Eliza Cross's signature

P.S. You might enjoy this fascinating true story from 1965, “When the U.S. Government Tried to Replace Migrant Farm Workers with High School Students.” 

10 thoughts on “7 Jobs I Hope You Have – A Letter to My Teenage Son”

  1. A flood of memories, some bad, some funny, but the struggle was certainly real. I watered lawns, mowed grass and shovelled snow starting at age 10. Learned about exploitation as a paperboy, and a concessionaire at CU football games. I saw my first Grateful Dead concert vending Coca-Cola at the tender age of 13. That was an eye opener. Vacuumed apartments age 11. babysat, collected pop bottles, and aluminum… sold my first art work at fifteen, it was a still life I’d made in school. Pencil on newsprint. Recently the owner told me it hangs proudly in their living room even after all these years… sold a painting at 16. I delivered auto parts, worked at Burger King, made fruit pies for Kwik Lunch, ha ha, even brushed the ants off before I put them in the fryer. I pumped gas for Bud Cox on the corner of Folsom and Pine in Boulder. We put beer in the pop machine, and ate all the Lions cashews out of the nut machines. used a gas cap key, ask you Ma about locking gas caps… Worked as a school janitor, at 16. Later I worked at Kmart and I’ve forgotten some. I got fired from Thompson Respiration products, I was an assembler of artificial respirators… went home in tears, took a shower, changed cloths, made a call, and was a prep cook at Goldini’s 45 minutes later… I worked in the process plant at Watts-Hardy Dairy, when it was a dairy. I was a security guard, and framed houses on Shanahan Ridge… that year too. Don’t be discouraged Michael, you really don’t want a job, you just need some money… working is a means to that goal… work is fun with the proper attitude. Keep your eye on your goals… Ask around church for a job, and be a willing worker, it will get you a good reputation if nothing else. You will find work as soon as you look in the right spot. Don’t be timid.

    • Your job history is so much fun to read, Scott. Along with being a hard worker willing to do whatever needed to be done, you had resilience to bounce back when you were fired and have a new job within the hour. It’s so cool that you started selling your art as a teen, too! Thank you for your encouragement, and I love this: “You will find work as soon as you look in the right spot.” Great perspective from one who has been there! Thank you so much for sharing your very entertaining stories.

  2. My first summer job was at the movie theater in concessions, but it wasn’t many hours, so I also got a job busing tables. But then I got offered my dream job–working at Waldenbooks! So for two weeks I worked all three jobs after I gave notice at the movie theater. At the end of the summer I dropped down to working only at the bookstore. When the manager at Waldens saw I had no work experience, she then asked me, “Well then, what else do you do with your time?” I was in music groups, service organizations, clubs, taught Sunday School, did sports, etc. She was then able to ask questions that showed her my skills. Most places didn’t ask.

    • Trina, most teens couldn’t handle two jobs (speaking for myself), let alone THREE! That’s great that you were able to draw from your school experiences to show the Waldenbooks manager that you had skills. Working in a bookstore no doubt influenced your future career path, and I bet you were such a great employee. Thank you for sharing these early work experiences!

  3. I loved this post Eliza, and all the wisdom you gained from those challenging early jobs. It challenged me to think back on some of my early jobs, and the lessons I hopefully gained from them.

    1. Babysitting, getting so hungry that I snitched some chocolate ice cream from our nice neighbors after a particularly long session with their sweet children who went to bed pretty early, leaving me to face starvation alone. I learned to be sure to tell babysitters who took care of you and your siblings where there were snacks for them to help themselves to.

    2. Junior Counselor at camp, having to wait for all the kids in my cabin to fall asleep before junior counselors were permitted to go to the counselor’s cabin to hang out and eat Ritz crackers with peanut butter. I learned, at a cost, to be patient, and that Ritz crackers and peanut butter are lifesavers after a long day (food as a theme again!)

    3. Wrapping Christmas gifts in a back room of a department store, only to discover after finishing that a belt had been hiding under the paper and the package, double wrapped for mailing, had to be rewrapped correctly another time. I learned to put up with tedium and to value gift bags!

    57. Working as a fill-in employee after the job I was hired for was reconfigured, being sent to 11 different locations over the 18 months before being offered another permanent assignment. I learned to trust that God has a purpose always, even when it’s hard to see, and sometimes it’s to bring healing through difficult circumstances.

    Love, Mom

    • Hi, Mom! It’s fun to hear about your past jobs, and I especially loved the lessons you’ve learned. Your babysitters no doubt appreciated knowing that they wouldn’t starve at your house, thanks to your compassionate spirit. Your gift wrapping story made me chuckle, and also really empathize for how frustrating that must have been. It’s never fun to do a job twice, and yet sometimes that is exactly what we have to do. Your last job had so many curveballs, and through it all you maintained grace and a great attitude. You inspire me, and I love you so much. xoxo

  4. My first job was working at the candy counter at Sears and Roebuck in Cherry Creek. I was told never to give anybody more candy than they had paid for, and I was so tempted to taste a piece of candy in every bin. I often rode my bike to Cherry Creek after school because my parents were working.

    • Thank you for sharing that wonderful memory, Ann! Working at a candy counter (especially a nice one in Cherry Creek) sounds like a splendid first job, but the temptation to taste the candies must have been so strong and you had a lot of willpower. Riding your bike back and forth, wow – you really earned your paychecks. Great story!

  5. Loved your advice to your son and I give your “Momisms” a Ten (10). My son always called my sage advice Momisms!
    Today my son is a VP of huge car dealership (I’ll keep it on the downlow) but he started as a busboy, then waiter, then bartender then sales, and the rest is history. When people come to his place for a job, he highly values any restaurant work on a resume

    • ‘Momisms’ – love it! I’m definitely going to borrow your phrase. Your son sounds like a special guy and a compassionate boss. That’s really wonderful that in his position now as a hiring employer he values the hard work and challenges of working at a restaurant. Thank you so much for sharing your perspective, Heather!


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