Insurance Millennials…Would you rather be ARod or Jeter?

Insurance Millennials…Would you rather be ARod or Jeter?

Career management is an experiment in self awareness, personal goals, values, ambitions, development, etc.  It includes evaluating statements like “Live to work vs. work to live?” and other self awareness exercises.  As there has been many articles about the Millennial Generation written about job hopping, lack of patience, different career expectations and characterizing Millennials in both favorable and unfavorable ways, I bring up a question: Insurance Millennials…Would you rather be ARod or Jeter?



The comparison is based upon the following characterization:

  • Derek Jeter, joining the ranks of the Yankees, staying his whole career, not job hopping for more money, consummate professional on and off the field, good image, left the game and great send off from Yankees organization, great legacy on game (now team owner in MLB)
  • Alex Rodriguez, bouncing around to a few different organization, big money player, professional and winner, off the field issues/PR, didn’t leave the game with great send off, Legacy on game is strong (likable announcer sports commentator)


This question is driven around a couple different factors and issues:

  • Duration with employer
  • Compensation and rewards
  • On the field vs. Off the field
  • Image
  • Exit strategy
  • Legacy
  • Others


See also…Patience in my Insurance Career


How does this analogy or comparison relates to insurance professionals and Millennials?


This Millennial age group is of low supply and high demand for the insurance industry.   Filling the ranks of retiring insurance professionals is not an easy challenge for organizations. Young insurance professionals are constantly tested and while insurance companies have great organizational goals, somewhat different than winning World Series, and less transparent and easily quantified.  Morale is tested at times and individuals have to decide what is best for themselves, their families, and their careers?


The ability to hop for 20-30% more in salary or compensation is easily and regularly done by many, but is it better long term to remain loyal and have long duration with company?  If so, what are the long term benefits and rewards…do they outweigh quick increases in pay?


Examples of other rewards that come with more time with organization…trust, autonomy, job security, quality of life, leadership, promotions, etc.


As knowledge workers, insurance professionals performance should improve with age and experience vs. the opposite with baseball players, so time is on your side vs. these players….are you viewing these decisions in the true career marathon or short sprint?


Your image in the organization and industry is of utmost importance.  This is an integrity industry, the promise to pay is based upon the counterparty.  Clean on the field and off the field image is essential.  Therefore Stay in your Lane, keep head down, focus, work hard, continue to learn, and good things will come (mixed with a little luck).


If you are a team hopper….What duration is really appropriate for a 30-40 year career, will you run out of organizations to join or “teams”?  Will consolidation in the industry have you run out of companies to hop to?


See also...A few tips for greatness in Insurance career


Do you want to leave a legacy on the industry?


And what is your exit strategy?  Typical retirement and 401k savings are only parts of the three legged stool, but might not be enough.   Long term duration with organization may allow for long term employment benefits – like stock, restricted bonuses or stock, etc.


I know I am constantly tested on who I want to be ARod or Jeter.  I assume many other insurance professionals are also struggling with short term gratification and benefits for long term rewards and gratification.  I think you could assume I leans toward Jeter however, time may change things.


See also...4 books for the Insurance Millennial


Other recommendations include: Read, ask questions, ask for more responsibilities internally, focus on off the field passions, exercise, meditate, and finally get a mentor, mentors help you understand and see the long game.   They also give you perspective on your career, image, and what decisions will look like to outsiders (if that matters to you).


The corporate loyalty to employees has also changed things (people feel the need to earn as much as possible as quick as possible) vs. MLB players who are independently wealthy and protected by a players union (and public outrage).  But if we all take time to thing about our decisions and say is this career decision more likely to leave me like ARod or Jeter, it may guide us to better decisions (at least more informed decisions).



Comment below or leave your thoughts about this topic.  



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The Millennial Shark

The Millennial Shark

The Millennial Shark is a contributor to InsuranceShark, focused on topics that include Millennials in Insurance, personal finance, insurance topics, risk, the future of underwriting. He currently works in the industry and will be a regular contributor on various topics.

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