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  • Writer's pictureMark Olivito

The Value of Your First Few Jobs….

Updated: Jul 1, 2022

Sometimes it helps to think back to your first paying gigs, waaaayy back in the day.

It’s amazing what years of separation can do for lending new insights, lessons and perspective for years to come. Anytime you travel back to the Old-school and gain new insight, write it down and share with people you mentor, lead and work with. It will spark conversation that helps people grow.

Gaining insights into what matters with people is a fundamental that will never go out of style.

I applied this with MY first paying gigs, before I graduated high school. There were 3:

1. Cutting lawns around the neighborhood (first entrepreneurial gig)

2. Answering phones at the local church rectory (receptionist!)

3. A retail assistant store manager at a liquor store. Most glamorous of the bunch!

Ask yourself some basic ?’s:

  • What did you like?

  • Not Like?

  • What major learning principle helped shape you?

Lawn Cutting Biz

  • Was my own boss, so nobody forced rules upon me as I long as I made the homeowners happy. Be nice, provide a little extra service, more value (sometimes cheaper) and people will give you a shot, even when your under-age (13!) & uninsured. But you need to hustle. It took over 150 flyers in mailboxes to generate 5 gigs. Probably not bad direct response rates in 2013, but you don’t know that at 13.


  • Below minimum wage, but “under the table.” Answering phones, greeting congregation that wanted to donate or buy mass cards. Typically no more than 5 interactions with humans in a 4 hour stint, so had to find a way to occupy my time (homework, reading, etc). Most exciting part was riding my moped to the job, about a 4 mile trip. Felt like there was purpose and responsibility in showing up. Showing up, became a bedrock principle I live by.

  • I also learned that a position of sitting back on heels and waiting for action to come to me was not a recipe for career satisfaction.

Liquor Store

  • LIFE SHAPING. Did it all, stocked the shelves, ran the cash register, lottery machine, trained people, cleaned the floors, sold wine, delivered beer, filled ice bags, went to a wine show and sampled at the age of 17. Recorded back room inventory and memorized what the back room looked like, so when that $30 bottle of Absolute sold, I knew there was one in back room to replace it.

  • Knew many loyal customers by name (and their preferences) and learned that this knowledge and delivering genuine service can equate to a premium price, sometimes as much as 20% for the same item.

  • Most important? I earned a key to the store and the trust of the owners to open and close. I cherished that trust more than key itself. For a teenager, keys to a car are a big deal. Keys to the store they work out should be a bigger deal.

If you want a fun and insightful exercise, jot down a few of your first gigs. Reflect on your key learning’s. Ask people you work with to do the same. SHARE. Question. Learn. And if your business is doing well, call it quits and head to your local watering hole to celebrate life after the conversation.

What was your first job and how has it shaped YOUR life? Would love to hear your comments….

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