Hmmm

It has been nearly 25 years now, but I went into sales for the noble reason that my pregnant now-Ex Wife (”Ex-Wife”) fell down the stairs.

Previously, I was a high school English teacher. For three years, I woke up every morning at 5am, made coffee, read the paper, got dressed (stylish slacks and a nice shirt), then zipped off to a large public high school where I spent my day trying to convince packs of 16 year olds that Shakespeare was still interesting and viable 500 years after his death. On evenings and weekends I coached debate, and during the summers I worked temp jobs as a receptionist, and all told I cleared less than 35K (in 1999) to support my young family of three.

Then one evening in March I was playing with my son in the living room when I heard Ex-Wife scream followed by a thump-thump-thump-thump. What in the heck was that??? I jumped up and sprinted in the direction of the sound and found Ex-Wife sprawled at the bottom of the stairs in tears. “I fell down the stairs,” she exclaimed. Then added, “I think the baby is okay.”

Oh my god!

We rushed to the hospital and eventually talked to her OB, and we learned that the baby (thank godness!) was okay and although Ex-Wife was okay she needed to be on bedrest for the next few weeks to protect the pregnancy and baby.

Oh my god!

Ex-Wife was a self-employed part-time tailor. She never made much money, even before we had kids, but she made enough that with my salary we could (just) barely stay financially afloat. And her being on bed rest meant she wasn’t going to make any income which meant that we were no longer going to stay (just) barely afloat.

Oh my god!

I had to spring into action. My first thought was to take a night job to make up for the lost income, but that wasn’t practical because someone needed to keep an eye on our spirited toddler child and also look after now-bed-resting Ex-Wife. So I did something I truly truly (truly!) hated to do: I asked my parents for a loan, just to get us through the rest of the school year when I could look for a higher paying job.

Then, when the school year ended a couple of months later, I updated my resume and hit the job market. At the time, tech was booming so I thought I’d be able to get into some entry level tech job. Turns out, I was wrong. Companies didn’t want to hire someone off the street with zero tech experience — they wanted to hire someone who knew something about tech. Who knew??? Hahaha. Anyway.

Just before I was about to give up and ponder other options, one of the tech recruiters I talked to said, “You aren’t a match for our tech openings, but you seem like a natural salesperson. Have you considered looking into sales?”

To make a long story short, I ended up in sales, partially because almost out of the gate I doubled my earnings going into sales.

This was circa 2000. It was a different world for me then. Different from my previous world as a high school English teacher. And different from the current world of technology sales, although despite any claims otherwise the basic rules of sales haven’t changed: get someone to listen to me, listen to what they do, explain how we might be able to help, then try to align everything so that they make a win-win-win investment.

I’ll never forget my first week in training. The job seemed to good to be true. “Wait,” I said to my trainer. “I reach out to prospective clients, get them to listen to my story, get them to tell me their challenges, then align what we offer to their challenges?”

“Well,” my trainer said, “It’s a little more complicated than that. But that’s the gist of it, yeah.”

On top of that, I was making nearly twice my previously salary, got a commission every time someone signed something, plus I had an expense account and free coffee (we had to furnish our own coffee when I was a teacher). I honestly thought I’d died and gone to heaven.

I can honestly say that nearly a quarter of a century later I’m just so grateful for that unexpected change in my life. Where I’d gone from working 50-70 hours per week for more 45 weeks per year for pennies on the dollar to working 40-50 hours per week 47 weeks of the year (including holidays and PTO) for dollars (multiple) on the dollar. Where I’d gone from barely affording my mortgage to actually having (a lot of) discretionary income and retirement savings. And I didn’t have to spend my youth studying computer science or engineering, or spending my free time studying computer science or going to graduate school. I just had to find out what a prospect’s problems were and try to align that to what I was offering. Which, honestly, was a HECK of a lot easier than teaching Shakespeare to packs of 30 16-year-olds.

NOTE: None of this article was generated or edited using AI. It is 100% organically human written by me. 🙂