July 16th Newsletter- Are You Living Your Worst Case Scenario?

A friend of mine has a dilemma. 


He is employed, full time, in the world of insurance. The problem is, he makes good money. You might be thinking- why would making good money be a problem? The money, it turns out, keeps him stuck. He doesn’t like his job. It’s been a long time since he’s enjoyed doing the work. 


A quick backstory for you. He got into the insurance world twelve years ago after graduating from college. It was never intended to be a career. He had just graduated from college and with the 2008-2009 recession in full swing, it was a safe bet to get working in a safe industry and get started in the real world. 


He turned out to be good at it. So good, in fact, that a decade later, he was one of the best in his area. A few new additions were added to his life as well. A wife, their son and their daughter. Within the past few years  he noticed this uncomfortable feeling in his stomach regarding his career. When he started, there was the need to make a living. That was followed by the chase for success, and then the pressure to support a family and build ‘the good life’. 


He apparently achieved those things, but there was an emptiness he couldn’t describe. The awakening didn’t come in a lightning bolt moment. It happened over time, during the commute and while listening to different podcasts and videos that had nothing to do with insurance and more to do with business. 


He had a desire to build a business in a creative area that was always a hobby of his. It was actually more than a hobby. It was a passion that he put time into in the early mornings, evenings and weekends. 


“If I could,” he told me, “I’d do it for free.”


That is a great sign for starting a business or building a career off of. When you are willing to do something for free, you have made your mission about more than just money from the start. To handle the storms, challenges and the rocky waters that come with the world of entrepreneurship, it’s essential that there is a deeper passion than just money. 


It was impressive to watch him build this from an idea, to a basic business, to something that had momentum and the real potential to be something that could give him energy, passion and excitement. What it also potentially gave him was a solid income and potentially multiple income streams to be able to do this full time on his own terms. No boss. No commutes. No limits.


Unfortunately, he didn’t think it was possible. I asked him a few questions. 


“If you left your job on good terms, is there a good chance that you would get this job back, or one that is similar.”


“Oh, in a heartbeat,” he said confidently. “Not even just here. I’ve been offered better paying positions but I stayed here out of loyalty.”


His side business at this point was earning more than half of what his full time job paid, all while working part time hours on it. I asked him to imagine how much he could make if he was able to put in full time hours.


After a little more back and forth, I asked him the question that I was hoping would really open his eyes.


“If you went full time with your business,” I asked, “what is your worst case scenario?”


He gave it a good few seconds to think about it. 


“Worst case?, he delayed while thinking. “It doesn’t work out and I go back and and get my job back in insurance. I might even consider taking one of those other higher paying positions as well.”


I let the silence sit there for a few seconds. 


“So, at this moment” I stated, “you are currently living your worst case scenario.” 


His silence was deafening. Apparently, he got it. It had never crossed his mind that he is already living his worst case scenario. My friend is now on the fast track to leaving his job  and going out on his own, in a career that he is incredibly excited about and one where his income potential can dwarf his current salary. Sometimes, it’s a change in mindset that can be the catalyst in advancing a change in career. 


If you find yourself in a similar spot in your career. I would challenge you to ask yourself a few questions. 


Are you already living your worst case scenario? And if so, why aren’t you going after what you really want? 



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