Career progression in the Insurance industry:

Looking back on my career progression in the insurance industry, the biggest challenge was I didn’t know what to expect for my future.  I was regularly thinking ahead and looking to the future, but sometimes failing to appreciate the journey and the moments that made up that career.  Now as a retiree, I have time to think back, laugh, enjoy those memories and relationships built at all stages of my career.

As a youth, I was constantly looking for advice and guidance, I’m sure I was annoying at times to my superiors.  I asked questions but also made mistakes along the way…this was my path of learning.  This was before the internet and all the access to free information, I had to read these must read books to get perspective.


This is a simple career journey, however mixed in between the inside jokes are some truth and good takeaways.   In my next life, I plan on producing a reality TV show related to this topic, as I feel it was the greatest career journey and looking back it wasn’t a challenge to go to work each day.  The audience might only be the 2.5m insurance industry employees, but I think it has potential.  The Pilot coming soon…

As Warren Buffett put it, I felt like I skipped to work each day. I’m sure many others felt the same.

The biggest takeaway is BE PATIENT…all of these steps will come to everyone, in different forms, different opportunities and be prepared for opportunity.   This advice of Patience applies to companies looking to go from Good to Great as well as leaders.

As we discussed, this industry has great opportunity for young people if they follow the right approach.  


Starting your senior year, everyone is looking for jobs, setting up interviews, and reaching out or networking.  Hopefully your internships and relationships pay off.   You are looking at jobs in the insurance industry as other classmates are looking at investment banking, finance, etc.

You start to see the weird looks when people hear your considering insurance as a career (as they almost always assume you are looking to sell Life Insurance). Looking back you will laugh at this decision & awkwardness of how often people make this assumption.  You will value the security, stability, and rewarding benefits of this different approach.

Interview process

The interview process in the insurance industry is like other financial services industries, however, you will be confused at how excited someone can be about insurance.  Also, how many people tell you they “never grew up wanting to be in insurance”.

You will be asked your golf handicap in the interview and your so excited to get the job and proud to be regularly breaking 100  that you don’t realize the foreshadowing of the question.

In my opinion, it’s a good sign if your handicap is a question in your interview, not the classic brainteaser “how many ping pong balls can fit in a 747″.   If I heard that as an interview question, I would run the other direction.

It’s important to make sure you are honest in your interviews, and most importantly don’t stretch the truth on your handicap – the truth will be brought to light in your first spring/summer/fall in the industry.

First day

Excitement, energy, ready to conquer the world attitude…but you have no clue about the insurance principles.  Most of the day will be spent in your on-boarding process, HR, and meeting new people.  By the end of the day you will have met >50 coworkers and can’t remember a single name.   Write down names, take notes, and take deep breathes.  Remembering names is very important, do your best to remember everyone’s name – as it is the most important thing to them.  No one likes being forgotten and forgetting their name, although a simple mistake is a small form of forgetting someone.

Focus on earning your salary, most junior or entry level employees don’t start producing enough in their first year to equal their salary, but be patient, learn, volunteer for projects, take on responsibilities, and embrace the fact that your employer is paying you to learn.  Take golf lessons.

First Year

You’ve learned a tremendous amount in your first year and really enjoy your industry, with good managers and hard work you will be Happy.  However you get together for small “college reunions” on Thursday night at Happy Hours and hear massive salaries/bonuses of former classmates, you come to the conclusion you are underpaid and want a raise.   You have a recruiter a week contacting you about a new opportunity and tempting you with 20% increase in salary.

If you are smart you hold out from jumping ship…but sometimes the $$$ can make the grass seem greener…

You are turning those lessons into corporate golf, playing in scrambles and charity events…not shooting great but adding value to your team where you can.

Second Year

If your first year was fun, after your second year you realize quality of life has some inherent value…. you spent more time at sporting events, golfing, concerts and then your friends combined.  The client facing aspect of your insurance job and the hours you work, clearly outweigh the negatives.  While your former classmates are stuck in the office to 10pm each night in front of a computer, you are at the local NHL/NBA/MLB team one night a week with a client complements of  your company’s season tickets.

You have established some life long friends in the business and start evaluating where you want to be in your career.  Having a corporate card and being given so much opportunity to entertain, ends up in a lot of forgetful nights, rough mornings, and stories that are more appropriate for a fraternity house than insurance article.

You are starting to win the longest drive competition and some good prizes playing in scrambles and charity events…still not shooting great but adding value to your team where you can.

5 Years in

You have started to or looking to specialize in the industry.  Peers and competitors are starting to recognize you for your ability.  You may have bounced around already, if you have you would have learned some of the differences between companies, philosophies, managers, personalities, etc.  AND compensation.

You will spend more of your time on “Focused marketing” not buying drinks for anyone in the business.

You are getting out for golf regularly and developing your personal brand.

Now you are truly breaking 95.  No give me’s and one breakfast ball.

Over 10

This is when you starting to see major improvements in your ability.  You will experience clarity, understand the system, and your role in the industry or global economy.   Your network of friends and colleagues have all moved to new roles, new companies, and you are well connected.

As Malcolm Gladwell refers to in Outliers,  at 10,000 hours – you may have reached the appropriate time to develop expertise.  Depending on how many companies and roles you have been in, you may have reached the 10k hours multiple times by now.

Your marketing events include high end golf courses, vineyards, etc.

Your personal life may be developing with marriage, kids, house, and your focus is now leaning more to long term career stability.

You’re  looking to get the handicap down between -18 to -15.

Over 20

You most likely have 5-10 years experience with your current company.  You are an industry leader in your field.  If you have bounced around too often, you might be regretting it.  Loyalty has its perks right about now, compensation is very competitive and your stock options/bonuses are maturing or vesting regularly.  You are thanking your immature 20 year old for the career path, as your finance friends have either quit, been laid off, or left the industry all together.

Family life is getting complicated as kids are looking to college and your looking at the tuition bills.

You make sure you hire the right person to help fill the gaps in your marketing plan and lack of desire to entertain like your early 20’s.

You’re  looking to get the handicap down between -15 to -10.

The Back 9

You’re  looking to be a mentor or leave a legacy on the industry.

Focusing on retirement, your golf handicap, and financial freedom.  Kids are most likely in college or already out…your planning vacations and long term passive income.

You’re looking to get the handicap down under -10.  Find a state to move with no state income tax and a house in a golf community.

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Arnold Smith

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