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Green Grass, Greener Grass, and Three Tips for Changing Jobs in Your Career



Whenever I hear the phrase "The grass isn't always greener on the other side," it reminds me of a famous Saturday Night Live sketch involving John Belushi and Chevy Chase. On Weekend Update, Belushi delivers his thoughts as a weatherman on tired old expressions like "March comes in like a lion and goes out like a lamb," plus about 20 other crazy variations on the same theme. When working with my job search clients, I attempt to avoid over-simplification. Detail and context matter in both your job search and career decisions.


In a recent article from Inc. magazine, the author argues that "The Great Resignation" is turning into "The Great Regret" for employees and employers in an identical fashion. The author states, "Evidence for this shift comes from a host of recent polls and surveys all showing that many employees who went off in search of fresher pastures soon discovered the grass isn't actually greener on the other side of the fence." Should we be surprised? I don't find this revelation particularly illuminating. There is a reason the "green grass" maxim has been in our lexicon for so long. It's true (even when it is our parents dispensing this specific nugget of wisdom). In this post, I want to dig deeper into this simple phrase for more context and detail with three tips to consider when considering a job change in your career.


#1: Throughout a 30-year professional career, you will, on average, hold between 12-15 different positions. That means you will, by design, resign at least ten times in your career. There is nothing "great" about resigning from a position where you contributed positively to the success of a team or an organization, and others will be left to fill in the gap after your departure. As you prepare to walk out the door, I recommend you keep several best practices in mind.

  • Across all the aspects of your resignation process, always remain professional. You have likely heard the saying, "your reputation proceeds you," but I believe your reputation also follows you in a professional career. How you leave an employer will have lasting consequences down the road in your career.


  • Leave your current job better than you found it when you started. Take the time to organize a transition plan for whoever your replacement will be when the position is backfilled (or other individuals absorb your work). Document your work processes, organize your files and materials, and leave your contact information to support any onboarding questions.


  • Be professional. Nothing is more critical in this process. Be like one of the greatest and most gracious football players ever, Walter Payton. Do not speak negatively about your current employer or management. Be gracious and thank the organization and the administration for the work that you accomplished together. You do not need to celebrate the new position (the touchdown) while still in the current position. Just professionally hand the ball (a complete transition plan) back to your manager (the referee) as you prepare to depart for your new job and organization.

#2: Regret is nothing more than wasted energy. And to create a headline like "The Great Regret" is just sensationalist journalism. One of my favorite quotes about regret goes, "Never regret. If it's good, it's wonderful. If it's bad, it's experience." That is precisely how I recommend you look at the jobs along your career path. With the obvious exclusions for safety issues and any form of abuse, each position you take in your career is an opportunity to learn and enhance your skills. Think of your knowledge and skills like an investment portfolio. Successful investment portfolios grow yearly with various asset types invested across equities, fixed income, and commodities. The same goes for your career. Growth in your career demands learning and accumulating a diversified and expanding set of hard and soft skills. Every position you take is an opportunity to acquire new skills. Lose the regret and focus on the learning.


#3: The phrase "Look before you leap" comes from a proverb dating back to the 1500s. It is as accurate today as it was 500+ years ago. If you want to minimize regret in your career, invest the time to research before making a job change or career transition. Focus your research on two critical areas: Target Organizations and Target Position.

  • When researching the target organization, you should address areas such as 1) current trends in the organization's specific industry; 2) Growth prospects for that industry over the next five years; 3) Leaders in the organization's industry and what they are saying; 4) What analysts are writing about the industry and organization you have targeted; 5) The competition for your target organization; 6) Challenges your target organization is facing and whether they are hiring or contracting human resources; 7) The top 3 to 5 elements of the organization's vision and mission; and 8) The organization's top 3 to 5 values, focus areas, and current business priorities.


  • When researching the target position, leverage your job search network for insight into the role. Also, consider the target position description (or posting) as a Request for Proposal. The pain point in this proposal is the open position, and the requirements for the desired solution are spelled out in the job description. Dig deep, and determine if your solution (i.e., your value proposition) is the best solution for the proposal.

Great resignations don't always have to lead to great regrets, but they can lead to great careers. In the mid-1970s, a country rock band called the Outlaws sang to us about "Green Grass and High Tides" in the song of the same name. No, the song is not about the cannabis industry. Instead, it is a tribute to rock and roll legends that had passed before their time. To me, the lyrics encourage us to both celebrate and learn from the past while also looking toward the future. Also not a bad strategy to use in your professional career.


Dan Troup is the author of Selling You: The AdvantEdge Job Search process available through multiple channels in Paperback and eBook formats. He is also the Managing Director of the AdvantEdge Careers coaching service. If you are interested in learning more about how a job search expert and certified career coach can assist you, please contact AdvantEdge Careers for a free initial consultation.

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