If you’ve ever found yourself with multiple job offers, or worse, a counteroffer, you know the feeling of stepping into the den of career choices. As we kick off the new year, January isn’t just a month for resolutions; it’s also a time when career ambitions take center stage. In our version of “Dragon’s Den,” job offers and COUNTER OFFERS become the entrepreneurial pitches of your professional journey. We wanted to dissect the drama, bring a touch of flair, and guide you through the world of counter offers in the Insurance Industry.

Picture yourself as the fearless insurance entrepreneur, presenting a groundbreaking venture. Just as the job offers start pouring in, here come the dragons—your current employer, ready to invest and keep you on their team. You enter the Den and here are some thoughts that may occur as you navigate this intense scenario of facing scrutiny from the dragons (your current employer) and exploring the entrepreneurial spirit behind career decisions.


Key Questions to Ask Yourself:

What’s Your Valuation – Money or Fulfillment?

In the den of career choices, assess the VALUATION of your options: a financial windfall (a raise now) or the fulfillment of your professional goals (a possible career that continues to fulfill your interests). Which investment ALIGNS with your entrepreneurial spirit?

Is the Counteroffer a Strategic Investment or a Risky Gamble?

Consider the counter offer as a potential INVESTMENT from the dragons. Is it a strategic move that aligns with your career vision, or could it be a risky gamble that might not pay off in the long run?

Stick with the Current Partnership or Pursue a New Venture?

The pressure of the den can feel intense as you weigh the value of your current role against the potential of a new venture. Is it time to STRENGTHEN the existing alliance, or are you ready to embark on a NEW JOURNEY?


Every decision has an upside and potential risks. If you are currently facing the Den of a counter offer situation, remember the PROS and CONS of accepting the offer on the table from your current employer:


  • FINANCIAL INJECTION: Like securing a deal from the dragons, a counter offer injects more funds into your professional portfolio.
  • STABILITY IN THE DEN: Staying put maintains the stability and comfort of your current role, providing a solid foundation for your career endeavours.


  • FULFILLMENT VS. FINANCIAL GAIN: Money may not necessarily fulfill your professional aspirations. Consider whether the counter offer aligns with your long-term goals or if it’s merely a short-term gain.
  • RISK OF STAGNATION: Staying in the same den might limit your exposure to new opportunities and hinder your entrepreneurial growth.


The Danger Zone: Accepting the Counter Offer

By now you may have gotten a hint of our thoughts on accepting counter offers, however; every candidate, company, and scenario is unique. Be sure to make the decision that makes sense for you, but keep these elements in mind.


Due Diligence on the Deal:

Conduct a thorough due diligence process. Does accepting a counter offer resolve the UNDERLYING ISSUES, or is it merely a temporary solution?

Navigating the Dragons’ Expectations:

Consider the dragons—your current employer. Will accepting the counter offer meet their expectations, or could it lead to FUTURE COMPLICATIONS?

Entrepreneurial Vision Alignment:

Evaluate whether the counter offer aligns with your CAREER VISION. Is it a strategic move that enhances your career trajectory, or does it fall short of your long-term ambitions?

Remind Yourself Why:

Remind yourself of the reasons that moved you to seek out this new opportunity in the first place.  If you were quite happy prior to being actively pursued, then perhaps staying with your current employer is the right decision.  If however you had applied for the role or were actively seeking a change in employment, there was likely a good reason why. Chances of the Counter Offer making you happy long term are statistically quite low.


If you haven’t had to face the Dragon’s Den of a counter offer before, you may think it would be a GREAT scenario. Most of our candidates who face this dilemma don’t relish the decision. If you find yourself facing the dragons in your career’s den, remember that the decisions you make are your own. January is a time that commonly sets the stage for STRATEGIC CAREER MOVES and calculated risks. Make choices that align with your vision, and may your career journey be a venture capital success story that leaves the dragons impressed!