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Sell Yourself—Get Creative

The Old Man Snags a Gig.

Creative Humans
Published in
9 min readDec 7, 2018

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My life-choices have led me through Hell, celestial peace, away from, then back to spirituality, and into numerous money-making opportunities. I’ve been an electrician, a business owner, investor, success, and failure.

Through it all I have been, first and foremost, a salesman.

Five years ago my wife and I were granted custody of one of our grandchildren. Sam will soon be a teenager. He’s a major asset in our home and I am thrilled to have him with us.

However . . . having already raised four children, my wife and I were hoping for some down time. We’re respectively sixty-five and sixty-six years old and we’ve prepared for this time, believing that we’d travel, yoga, service work, you know—whatever the day offers.

What we did not plan for is another college education, braces, and the raft of peripheral expenses of child-rearing.

So it is that, after four years of semi-retirement, I made the decision to poke around and see if there was a suitable opportunity for me to make some extra dough. This decision was driven by several factors. About the same time Sam came to live with us we started an extensive remodel of our home. This process took two years and we blew the budget out of the water. My ‘semi-retirement’ was organic — not meticulously planned — and while we have assets, we aren’t flush with cash and certainly don’t have the funds on hand for another college education.

So, I took the plunge. I scoured the usual suspects: Monster, LinkedIn, etc.

I’m sixty-five. My history includes business ownership, extensive sales experience, a thirty-two-year writing career, and years of foreign service assignments. I’m tri-lingual.

On paper, I’m a desirable asset, right?

Maybe. Here’s where it gets sticky.

☛ I’m not willing to give up writing. So, I can’t be tied down for forty-plus hours a week beholden to someone else’s business. I am adept at sales, but I’m done managing and building teams.

Too much to ask of me; been there, done that, the answer’s no.

☛ I won’t prospect, cold call, or write in-depth reports.

Yawn. Pass the sunscreen.

☛ I have high-income expectations. My time is valuable, and I won’t get out of bed for less than an outrageous income potential.

What could go wrong?

☛ Did I mention? I’m sixty-five years old.

It took me six months to identify the company and sales position that would accommodate my wish list. One of my daughters works for this company as a salesperson. She raves about the company, the culture, and the income. She does this, by the way, from her cabana in Bermuda.

Sounds good to me. I want in

In consideration of the fact that I last worked for somebody else in 1993, I created a new resumé. The damn thing scared me. I pared it down, boiled it, condensed and distilled it. I wrote a professional cover letter. I walked into the company reception area and handed the resumé to the receptionist. I told him I’d like an interview.

I was informed that the sales manager, Harold (fake name alert!), was out of town, to return in a few days. He asked if I was responding to their ad? Unaware of a job-posting, I replied no, but I had determined that they were the company I wanted to work for. I had not seen an ad. I was assured that the manager (not-Harold) would contact me.

The next day, a sales position was posted by this company, on all the major job websites.

Something went wrong (1.0)

I didn’t get the call. After about two weeks I contacted HR. I was asked to forward the resumé directly to Rose. She assured me that she would put it in front of the sales manager.

Something went wrong (1.1)

I didn’t get the call. I waited another two weeks, during which time I continued to see this company’s job-post. Three times the posting expired, then re-posted.

“Let’s review,”I told myself.

I suspected that two things were working against me.

(1) If looking for a salesperson, most HR managers would be impressed with the broad and extensive experience outlined in my resumé. But, is it reasonable to believe I was over-qualified for the job?

Of course.

(2) The dude is 65 years old!

Again, I reviewed my resumé and cover letter. I asked a couple of my big-shot friends to review them as well.

“Looks great, nice bait, what can I say? Blah, blah, blah.”

Around this time I took a business trip to Indianapolis. Remember my daughter, the one who works for the company I hoped to join? Her boss’s office is in Indianapolis. I decided to do something unconventional, off-the-wall. My daughter had been working with this company for four months and she was the sales leader. She used to work for me, in my real estate business. I trained her in the art of the sale.

My daughter had encouraged me to consider moving to Indianapolis, saying that her boss would hire me on the spot because she had gushed about how I’d trained her. While I had no intention of moving to Indianapolis, I called and set an appointment for an interview with her boss.

Why? Two reasons. First, if required, I would consider moving—but it would take an act of god. Second, I had a plan. I had a plan to sneak in through the back door and get the job I wanted, without moving. Sound odd? Of course; I’m odd. So, I interviewed. Her manager, Bob, made me an offer on the spot. I told him I was flattered, but my first choice was to stay put and work on the west coast.

“Would you consider speaking with Not-Harold, the sales manager in my area?” I asked Bob. He assured me he would be glad to recommend me to Not-Harold.

Grinnnnnnnn. Chuckle . . .

Shortly thereafter I discovered another sticky wicket. I realized my cover letter was B.O.R.I.N.G. (see people’s exhibit A, below 👇🏿).

Boring cover letter 👆🏿

Hell, I’m a writer! So, I asked myself: ‘Ya’ think ya’ll oughta write somethin’?”

My answer: “Get yo’ ass in overdrive, boy!”

I replaced the boring cover letter with this one (see people’s exhibit B, below 👇🏿).

Folksy cover letter 👆🏿

I got the interview.

“Can you come down in an hour?”

Yessireeee!

I sat for the interview. It was a forty-five-minute rectal exam given by the sales manager, a forty-ish bald guy — Not-Harold. I was amazed how much I learned during my time chatting with Not-Harold. One of the tidbits he shared was that, during this time (over two months), he had interviewed dozens of prospects. In fact, he’d already hired four, and he had room for only one more on his sales force.

Be still, my heart. Boom-boom, pity-pat, thummmp!

Suffice it to say that I passed through several interviews and a Briggs-Meyers-like test, and got the job. In the offing I was paired with a guy twenty-five years my junior. The guy has schooled me like an errant high-school football jock in detention.

This old dog learns new tricks. Saints be praised!

Let’s review. What have we learned today?

Prologue: I contend we’re all sales pros. Some of us get paid for it. If you believe it, it’s true.

1. Don’t be afraid to use your god-given talents. Only after I crafted an eye-catching cover letter was I called back. Was it the new cover letter that made the difference? Believe in yourself first; success will follow.

2. Content matters. I had a difficult sale to close. For a cumulative total of forty years I have owned businesses, managed offices and workforces, and made middle-six-figure income. Why would HR consider hiring me for a sales position? Because content matters?

3. Be yourself. I’m a jokester. But I’m also a heavy-hitter, at home on the top of the leader board. Don’t soft-soap any inconvenient truth, and don’t shy away from a mid-twentieth-century birthdate. Believe it. Own it.

4. Interviews: If you don’t get the interview don’t assume a damn thing. I almost allowed myself to write off one of the best jobs I could have possibly found — due to assumptions. Get that interview by squeaking, but not by text or phone-ambush. Be professional. I waited ten to fourteen days between my telephone inquiries and in the end, it was my persistence that put me in the interview chair, according to Not-Harold.

5. Ask intelligent questions. By asking questions in the interview you show the potential employer that you aren’t there like a steer at the auction. You know what you want, you’ve done your homework, and the company is being interviewed. Job offers, should they come, should never come from a company you know nothing about. Duh.

(6) Ask for it! Be a squeaky wheel. Stay in tune, stay in touch, but don’t be that guy. The prospect who shows persistence has the better chance—but don’t be a pain in the tush.

This final point is huge. Are you tuned in?

(7) Sell your weakness. That’s right, I said, ‘your weakness.’ Resumés boast of talents, experience, and skills. They outline your employment history. What they avoid is your weaknesses— but I’m not suggesting you outline your frailties in your resumé.

Broadcast your truth, your skills, your experience. Brag about the bigshots who will recommend you. If you’re a funny guy, crack an appropriate joke. If you don’t know a damn thing about the job you’re seeking, do some research — but admit your frailties. In fact, advertise your weaknesses, but only to the extent you can put them into proper context.

  • No experience selling? You’re a blank slate.
  • Can’t speak Spanish? You’re learning! Can’t wait!

“Why bring that up?” you ask. Thanks for asking. Here’s why: having caught the attention of the owner, or HR, you have been asked to interview. You earned that opportunity the old-fashioned way. You wrote a puffy resumé and followed up. Your strengths got you the interview; do you realize that? How are you now going to leverage your weaknesses?

Let me answer that question. I’ll give you an example from my career. In 1993 I dropped my twenty-three-year career as an electrician and became a real estate salesperson. Add one cup of complications: I had recently relocated to a mid-size metro area, twenty-two hundred miles away from friends and family. My first task in this new career was to build a client base consisting of buyers and sellers. When I turned in the paperwork for my first property listing my boss, Not-Ben, looked at it and shook his head.

“How did you get this listing?” he asked.

“I dialed for dollars, got the appointment, and asked for it,” I replied.

“What? How did you get them to agree to pay a ten-percent commission??”

“I told them I was new to the area, new to real estate, and had no other listings.”

Not-Ben narrowed his eyes and shook his head. “You did what??”

“I told them I was new and had no other listings to sell. My only job would be to promote and sell their property. Then I shut up. They signed.”

“And the commission?” he asked. (Commission in that area was normally six or seven percent).

“Is there something wrong with ten percent?”

“Of course not! But how did you get it?” he asked.

“I told them that’s what I charge, that’s all.”

I believed and acted like there were no limits to my success — and guess what happened? In three months, I owned the leader board and didn’t relinquish it until I left six years later to build my own brokerage business. The year I started, 1994, I earned the honor of state-wide “Rookie of the Year.”

Boom, baby! Nothing but net!

How did I get ten percent commission in a seven percent market? I believed I was worth it and I asked for it.

And, what made the difference in my job search? Was it the truth of my extensive business experience, streamlined but true, that earned me an interview? Or was it the clever cover letter? What about my ‘seasoned’ age?

What did it? What got me that interview? Cover letter? Phone calls? Content?

Who knows? I just know I’m hired.

I can see you on Wednesday. Is 3:00 or 4:30 better for you? I’ll bring a pen.

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Dr. Feem
Creative Humans

Visiting conservative fellow at Medium. Contrarian. Equal opportunity critic.