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Insurance Careers: Pursuing Your Passion, Reality or Myth?

February 9, 2022

At some point in our lives we have all heard the saying, “Do what you love, and you’ll never work a day in your life.” The person uttering those words has likely already achieved some form of financial or personal freedom and is at a different stage of their life than the brave souls kicking off their career in sales.

I have spent the last 25+ years in sales as a risk advisor, mostly for Oswald Companies. While I truly enjoy my career, it wasn’t always the case. I spent my first 15+ years trying to get appointments with people who wanted nothing to do with another insurance sales guy. There were hours on the phone listening to office administrators ask my name, company, and the proverbial:

  • “What is this call about?”
  • “Are they expecting your call?”
  • “Send your material and we will call if interested.”

Struggle Today for Strength Tomorrow

If there is someone that can genuinely say they enjoyed their first few years selling insurance or any other financial service, they are far and away the outlier. They call it work for a reason. While we are not digging holes, erecting steel, or moving bricks, the mental strain of the day-to-day activity is a grind. It is very difficult to see a career as a respected risk advisor while you are making calls four-to-five hours a day just to get two-to-three appointments with new prospects all while knowing 10-15 percent of the appointments will probably cancel before the meeting. The roller coaster of prospecting can be demoralizing, humbling, depressing. All those words describe the process and certainly support why the failure rate of insurance sales professionals is well over 50 percent.

In my years of experience, I have learned there are several undeniable facts which impact the worlds perception of our industry:

  1. Insurance carriers billing procedures are clearly much faster than their claims payment processes.
  2. Policy holders understanding of indemnity is much different than the insurance companies.
  3. The information required to prove a claim is a bigger undertaking than expected.
  4. Pricing of insurance is a mystery.
  5. Misunderstanding between my property’s replacement cost and the market value are often miles apart.
  6. Insurance language is very difficult for most to grasp.

The Light at the End of the Tunnel

Today I consider my profession invaluable and an integral part of the worlds economy. Gregory Case, former CEO of AON, made a speech to the British Brokers Association in 2011 that helped change my appreciation for the insurance industry. To paraphrase, without the assurance of an insurance policy:

  • Boats could not cross the ocean
  • Planes could not leave the ground
  • Trucks could not cross the country
  • Cranes could not build buildings
  • Doctors could not perform surgery
  • And the list goes on!

As a young insurance sales professional, it took me longer than I would have liked to see the role of insurance in our world. However, once I did, my cold calls became much warmer. Now when I pick up the phone to call a potential new client, I know I am providing an invaluable service that is critical to the success and growth of their business. Matching an organizations exposure to risk with the right insurance policies can be a complex process that takes time, resources, and technical expertise. In the words of my former colleague Pat Butler, a 40-plus-year Oswald partner,

“Insurance is really boring, until you get it wrong!”

As your confidence grows so will your book of business. Then one day you will wake up and realize you built an amazing career as a risk advisor to your clients. You can take great pride in having built from long days of making calls and doing things you didn’t necessarily start off loving.

Nothing is ever perfect. I suspect even Bill Belichick debates how much he loves coaching the perennial Super Bowl Champion Patriots. My best advice is to continually remind yourself of the importance of what we do. Try to see the long-term perspective on your career.

Good Luck to the 2022 class of insurance sales professionals!

Stay Hungry and Curious!

Contact me direct or learn more about our careers, culture, and the benefits of employee ownership at Oswald on our Careers page.

Dale A. Kaprosy
SVP, Property & Casualty


This post was originally published in Feb. 2020; updated Feb. 2022.