I woke up on Monday, July 19th, 1999 at 9:00 am. After 20 minutes of lying there half awake, I decided to get up and start my day. On my agenda for the day was to mow three lawns in the neighborhood: Mrs. Rubis’, Mrs. Palmer’s and Mrs. Schultz’s.

NEVER Sell Your Summers For Cash... You'll Never Get Them Back

I took a trip to the gas station to fill up my lawn mower with gas and I was all ready to go. After eating a quick lunch, I went through two gallons of gas and made my client’s lawns look superb. “Looks great, Kraig! Thanks so much,” my clients would say as they wrote me a check for $10 here and $20 there.

A Typical Day in the Life of a Teenage Entrepreneur is Pretty Great

After finishing up my lawns for the day, I jumped on my bike and headed over to my friend Tony’s house down the street. After filling up our tires with air and grabbing a cold drink for the road, we headed off for a 10-20 mile bike ride. Tony rode at a pretty fast pace and was tough to keep up with, but it made me stronger to be pushed that extra bit. When the day came to a close, I hit the sheets physically exhausted but full of happiness and life.

That Monday was an accurate glimpse of my typical day during the summer of 1999. I worked really hard, but only for myself and on things I really enjoyed, like taking care of my clients’ lawns. I was a business owner and I took pride in doing a really great job for my clients (who were also my neighbors) and adding value to their lives in return for getting paid.

Life was grand. I got paid to do what I enjoyed. I spent most of that summer outdoors and I was as free as the wind blows.

Life Changed Drastically When I Became Old Enough to “Get a Job”

Less than a year later, I turned 16, and I was told to “go and get a job”.

I’ll never forget Thursday, June 1st, 2000. It was orientation day at my local Walmart Superstore, where I was just hired for the summer. “At least I’ll be making good money…” I thought to myself, as I filled out a form that asked for the days I could and couldn’t work over the summer.

Outside, it was a beautiful 85 degrees and sunny. Inside, it was 70 degrees and the room I was in was lit up by florescent tube lights. During that orientation was when I learned about this thing some people did called “clocking in”. “Clocking in” was where people scanned their name badges into a computer to notify the system to start or stop paying them. I didn’t know what to think of it at the time. I felt as though I was being domesticated, like a pet.

I was now an hourly employee working at a real job and an “associate”, according to Walmart.

It took less than a month to realize what was really happening. Like my gut feeling from the beginning suggested, this job was proving to ruin my summer, as I now was scheduled to be there at least 4-5 days every week, during the best part of the day. My weekends were mostly all gone as well.

I had voluntarily signed up to exchange my summer for money. Since I had such a crazy schedule that took up most of my days and most of my energy, I had to shut down my lawn mowing business. I also stopped riding bike and instead drove everywhere during the summer of 2000. Instead of eating at home, I was now eating out at fast food joints during my 30 minute lunch breaks.

Fourteen years. That’s the number of subsequent summers I followed the same, miserable script. I exchanged those 14 summers for a paycheck that was never worth what I gave up.

After 14 Years, I Broke the Chain of Miserable Summers

Fast forward to today. I’m enjoying my first summer since 1999 without a job. I can honestly say, it’s everything it used to be and more. Once again, I’m on my bike several times per week, challenging myself physically while enjoying the serenity of it. Like the summer of 1999, I once again am only working on things I enjoy and taking great pride in my work.

If I can make it the rest of my life only having sacrificed 14 of my summers, I’ll be reasonably happy. I’ll never get those summers back, but I definitely will be happy if I can not let that damage happen again.

Life isn’t worth any amount of money. We should all be doing what we enjoy and accepting nothing less.

All along, I could have chosen to be self employed and worked only on what I cared about, but I settled instead. I listened to what others told me I should be doing.

My dad, and others, told me to go get that job at Walmart at 16 and I listened. I gave up a business that could have flourished and paid for all my expenses during my high school years to spend that time working the worst hours possible at jobs I disliked.

There’s no need to get into my next job either. Let’s just say I started at $5.15 per hour and prepared food for people. Once again, my summer days and weekends year-round were gone, in exchange for a measly paycheck.

Not worth it. None of it was worth it.

I Now Know How Important It Is to Free Yourself from Needing a Job

I learned some incredibly valuable lessons by going through all of that. I learned how important it is to get yourself in a position to not need a job.

The number one reason I got out of debt and saved up 5 years worth of living expenses is to get myself in a position where I never needed another job again.

From here out, I plan to live like I did during the summer of 1999. I plan to be free to do work I care about. I plan to work only with people I enjoy working with. I plan to take pride in my work. Finally, I plan to ENJOY MY SUMMERS and all the other seasons too for that matter.

No more:

  • Working weekends while my family and friends are making life-long memories without me
  • Sitting under florescent lights while my summer passes me by
  • Exchanging my time for a measly wage per hour.

Last of all, no more “clocking out”… Ever again.

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