I was starting to get good at sales.
It just felt empty.
That is how I ended up answering a Craigslist ad from an insurance agent.
I had believed in life insurance for years before I ever thought about selling it.
When my wife and I were raising our kids, I had put coverage on myself because I knew if something were to happen to me, my family would lose my income. We had kids to raise and bills to pay. I wanted to know my family was protected.
I had spent my entire career on the technology and operations side of the house before being thrust into sales. I was finally finding my stride, but I still could not help but feel that something was missing.
The agent told me I could take the sales skills I had been learning over the last couple of years and use them to help families put protection in place.
This really made sense to me.
I was looking for more purpose in my work. Maybe insurance was it. I believed in it. I had made that choice for my own family years before.
I didn’t decide right away.
He was pretty blunt about the time commitment. I would have to buckle down and study for the state licensing exam. Then I would have to learn a whole industry that I knew only from the outside as a consumer.
I was already working full time. Insurance would mean two or three nights after work, sometimes more, plus Saturdays and Sundays.
So no, I did not make that decision overnight. I talked it over with my wife because it was going to take a lot of my time.
Fortunately for him, he was persistent.
I would not call him the pushy sales guy I was never fond of, but let’s just say he followed up.
I did eventually decide to move forward.
If you’re looking for more purpose in your work, sometimes a different perspective is all it takes.
The Kitchen Table
The first few insurance appointments were awkward.
You could almost see people coming to grips with their own mortality right there at the kitchen table. A little squirming in the chair. You could see them realize they weren’t going to live forever.
And then the harder part.
What happens to your family if you do not come home tomorrow night?
I’m not sure if those conversations were more uncomfortable for them or for me.
As part of my training, we had done role-playing. Nothing prepares you for looking across the table into their eyes as these realizations come to light.
Over time, I got more comfortable with it.
The awkwardness was still there, but it felt less awkward, if that makes sense. With each conversation, I started seeing similarities. Pattern recognition kicked in.
But I would never say those conversations became easy.
A lot of the fear was the same thing I had worried about years earlier with my own family. What happens when that income is gone?
The answer was different for every family. For some, it might mean they can’t fund their kids going to college. For others, it could mean losing the house.
That was where I learned to ask good questions and really listen to the answers.
Not sit on the edge of my seat waiting for them to stop talking so I could ask the next question.
Let them say their piece.
Ask good questions. Be a good listener.
That ended up helping me in technology sales too.
10:30 on a Saturday
One Saturday morning, I drove about an hour for an appointment with a business owner and his wife.
She was supposed to be there in about ten minutes.
While we were waiting, around 10:30 in the morning, he reached into the refrigerator, grabbed a beer, and offered me one.
I passed.
He tilted his head back and drank the whole thing pretty much in one shot, then went back for another.
At that point, I was feeling pretty uncomfortable.
Ten minutes later, his wife still had not shown up.
If I’m being totally honest, it sucked.
I had driven an hour to get there, and because of the circumstances, I couldn’t ethically proceed. The salesman side of me was super bummed.
On the flip side, I had no business proceeding with a meeting with somebody who had been drinking and whose spouse had not shown up.
I knew talking to him about the alcohol was not going to get me anywhere, so I basically told him we couldn’t proceed without his wife there because they both needed to make the decision together.
I would need to reschedule.
Have you ever found purpose where you least expected it?
Nobody Ever Collects
I had one couple where the husband was very skeptical and downright combative.
Pretty much every negative thing you could say about insurance, he said it. Nobody ever collects. The house always wins. They know exactly what they’re doing. We’re going to pay into this and get screwed.
His wife was on the other side of it.
She was very concerned about what would happen if something happened to him. She worked, but she did not make enough money to pay the mortgage and all the other bills they had.
I got a crash course in marital disagreements played out right in front of me.
I mostly let him vent. I definitely did not want to poke the bear.
I kept trying to bring the conversation back to what would happen to his wife financially, which she visibly appreciated.
I was definitely walking a tightrope.
The meeting ended with his wife saying she definitely wanted to move forward.
He was a firm, “We need to think about it and talk this over.”
I was not able to overcome that.
A lot of times, “I’m going to think about it” is the end of the road.
But I was able to schedule a second meeting about a month later.
That time, we put the coverage in place.
The Call
A few years later, she called me.
Her husband had died.
It was surreal.
I get goosebumps just thinking about it.
It was the first time I had ever gotten a call like that, and I remember not really knowing what to say. I probably fumbled through my words.
She was crying and very thankful that I had followed up and helped them get the coverage in place.
There definitely was a real emotional weight to that call.
It was the first realization that the work I was doing mattered.
And that gave me the sense of purpose I had been looking for.
Time Back
Insurance also helped me realize that I had been overlooking the value of what I was doing for restaurant owners. It wasn’t just about selling technology or helping them make more money. I was also helping them get some of their time back.
Around that time, we came out with a new app that let restaurant owners see their sales in real time, how many guests were in the restaurant, labor, and other things like that.
Now mind you, this was about 13 years ago.
It doesn’t sound like much today. I get it.
But back then, it was a big deal.
They could literally sit at home and see what was happening in the restaurant. If business was slow, they could make a decision about cutting labor without having to drive in and look for themselves.
I had several restaurant owners who were jacked up excited about it.
That gave me a real sense that I was providing value.
I was helping give them some of their time back. They did not necessarily have to be in the restaurant all the time just to know what was going on.
That could mean more time with their family, friends, or even taking a vacation, which can be a luxury in the restaurant business.
One owner in particular became one of my best unpaid salespeople.
He loved that app so much that he started promoting his system to other restaurant owners based almost entirely on that feature.
Two or Three Nights a Week
Insurance made me feel like I was doing some good in the world.
For a lot of my career, working in technology, operations, and then sales had felt kind of empty. Like, what real good am I doing other than making a living?
Helping people put financial protection in place so a family would not go without if the breadwinner died gave me a real sense of pride.
Looking back now, I think that sense of purpose was one of the things that kept me going.
I was working full time and then spending two or three nights most weeks, plus weekends, doing insurance. I was exhausted much of the time.
I’m not sure I was thinking about purpose while I was in the grind.
But in retrospect, I know it mattered.
When you feel like your work is making a difference in somebody else’s life, you don’t mind getting up early, staying up late, or giving up part of your weekend.
For over a decade, insurance gave me a sense of purpose I had been missing.
The part I never expected was that it also helped me to see the purpose in the work I was already doing.
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Thanks for reading.
~ JP
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Related reading: On the skills we collect and the judgment we build.
Swiss Army Knife Generation
My grandfather carried a Swiss Army knife for years and used every freaking part of it. The little scissors. The tiny screwdriver for his glasses. The knife. The file. Whatever the problem was, he usually had something in his pocket that could handle it.