What’s it Like Being 56 and Looking for Work? Part One of Three.

My intention in this three-part work of art (grin) is not to grumble, bitch, whine or otherwise piss and moan about the fact that I’m a 56 year old high school graduate having a hard time finding a job, its to share my experience. Maybe it helps someone, resonates with someone else, who knows… maybe it will just exist in the ether and consume some unseen bits and bytes. But I’ll feel better. So, here goes.

Many years ago (2003–2004?), I bought a book a friend recommended called “Second Acts”, written by Stephen Pollan and Mark Levine. Did I read the book then? A little. I mean, who buys (or used to buy) books to read them, when they look so great on shelves? The premise of the book is that people in their “First Act” (career/phase of life) who may not be loving it can make a conscious and calculated decision to pivot and start a “Second Act” — the life of their dreams. Makes sense, right? Well, now, I’m actually going to READ the book to get a better handle on what I’m going through.

So, the long version of the story…

Today, I find myself in what I consider to be my “Fourth Act”, embarking on a fifth, it seems. And it scares the living daylights out of me.

Act One— I was a highly skilled, very successful Public Safety professional for about 12 years. In 1983, at age 23, I built a lucrative IT consulting business on the side while working EMS shift-work. Working EMS was great in most ways, managing EMS was pretty darned cool, but there were certainly there was a steep downside. With 48 contiguous hours off for every 24 worked, an ambitious guy or gal like me can have their cake (job security, guaranteed income, and good benefits) and eat it too (do something really interesting and financially lucrative besides the “day job”).

As my “side-business” became more and more successful it caused logarithmic interference with the “day job”. I wish I could say that my business success was all skill, even mostly skilled. But in truth I wound up with a skillset that large organizations desperately needed and had a hard time finding, but mainly wound up in the right place at the right time. I became an “expert” with my skillset, but mostly I spent my time calm, cool and collected in front of Fortune 100 clients while silently crapping my pants. Act Two began at The World Bank, in a meeting with the then-CIO and realizing that on the specific topic we were discussing, I was the expert and he was not. Interesting realization.

My Second Act began after careful consideration and conversation with my wife. We weighed the options and rather than playing it safe and keeping the “side job” on the side, we lurched into the newly emerging Informatio Technology world. Goodbye guaranteed income, goodbye cushy benefits, hello lots of excitement, lots of recognition, and plenty of financial reward. Eventually I merged with a Canadian software company, helped it grow from fifteen to over fifty personnel, and built a customer base that read like a “Who’s Who” of American business. Eventually we were acquired by a public company. Success, right? Sure, but not life altering financially.

The sale of our company (thank you Dave, Tim, Don, John, Fred and Darren) led to a much needed year off for me. Which led to being headhunted and hired by Apple. I had a very cool five years working for Apple — 90% of what I did and had done to me was positive, and I miss that. But, as I’ve written before, one day my manager woke up and said “I’m being promoted and moving to Austin, and your job is moving with me”. Maybe I’ll write about that sometime… it won’t be a pretty picture of that person or Apple.

So, when faced with a decision to a) take a crappy package to uproot my family (shame on you Mr. Manager) and sit outside my boss’ office for 60+ hours a week in Austin (don’t get me wrong… love Austin, the package not so much) or b) separate voluntarily and become unemployed, I jumped back into Public Safety. That’s Act Four. And while not as financially rewarding as Apple, it was fun to go back as a Chief Officer, part of the management team largely populated by folks who used to work for me (yup, that happened). At 49, ride that job into a fat retirement, right? Wrong. Life Happens.

Act Four chugged along swimmingly, then abruptly lost its polish about three years into its five year life-cycle. A colleague was retiring and I was to be promoted to Deputy Director of Emergency Management, my previous responsibilities having been focused on leading/managing (two distinctly different things) our 350-person Fire Rescue Department’s 15-person 911 communications center. The colleague’s retirement was scheduled for about six months out, and for those six months I spent about ten hours a day with my predecessor, learning the ins and outs of the position. Loads of work, loads of responsibility, but I was sure I would love the challenge, a few more bucks, and leaving Comms to slide back to where it was before I came.

Imagine my surprise when two weeks before my change of command was scheduled, the guy who “used to” have Comms and where I had expected it would return reacted to a casual comment I passed about him taking it back. “I’m not taking back Comms. Its moving with you” with a big grin. Needless to say, I was flabbergasted. How in the world would I pick up all the Deputy Director of Emergency Management position AND keep Comms? That all added up in my mind to three full-time jobs, each divergent from the other.

I do not think anyone lied to me, but certainly there were acts of omission on the part of folks who knew there was a reorganization involved in my promotion. Of course, we all know what we do when we “assume”, but there was literally no indication my current responsibilities would be included in my new duties, collapsing my “old” job. I was devastated, to say the least. Running Comms was more than a full-time job, and the “new” job already served two divergent masters. How could I succeed.

My well formed proposals and passionate requests to back-fill my Comms management position were… well, lets just say I didn’t get the job done. For over two years I felt every day that I was shorting at least one of my three areas of responsibility (each of which would easily have been a full-time job if done properly) I blame the lack of back-fill not on the Chief (he was a great guy, BTW, one of my old trainees!) but on myself… If I had put the brakes on when I found out what the “new” job would look like and refused the promotion, I’m confident I’d have been back-filled. My bad. We’ll talk more about that in Part Two…

This was me, Act Four

So what does all this history have to do with anything? Well, to understand how I got where I am its necessary to understand the story. Mostly my choices, a couple of key decisions “made for me”. I am not a victim. I am not a complainer. I am not a slacker. I again own an IT business, and literally EVERYONE reading this would recognize our primary customer’s name, but this business will fail unless something changes drastically. So, I’m teeing up for an Act Five, and am hoping this will be the last act for me. Not being fatalistic, but I’m not enjoying working for myself, scraping in small revenues for smaller profits, paying for my own benefits (lets not talk about Healthcare Insurance!) and not having the likelihood of the explosive growth my original businesses enjoyed in the early days of Tech. Time for some serious changes — already have a good start, and what I’m doing might prove insightful for some, even one, of you.

Give me a week to get some work done and gather thoughts, and in Part Two I will expose my experience in trying to rejoin the workforce. More insights and lessons learned there.

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Written by

Seasoned Business Development manager with deep Public Safety, Education, and High Technology experience. And a regular guy who likes to write crazy crap down.

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