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How Do You Know When To Hold ’em And When To Fold ’em

How do you know when to hold ’em and when to fold ’em


I am not a gambler..neither is gambling an activity that I encourage. However, when I was thinking about this post the song by Kenny Rogers came to mind. Careers in this age are not the careers that our parents grew up with. While it was an achievement then to give your employer your whole life and retire from a company that literally hired you from school, things are not the same now. We are much more fluid with our career choices and decisions. But, even in that fluidity, it’s always a tough choice (almost a gamble) when you do decide to look for greener pastures. You never really know if walking away is going to work out to your advantage. Question is, how do we navigate that process?

A couple of years back, I got an answer to that question that plagues many twenty something’s that have been working with the same company or in the same role for ‘ages’. I had been having this argument in my head for far too long (okay maybe a year or so) and finally the answer came dawning on me like some grand epiphany -which, if I was to be honest with myself I had known all along but I had decided to wallow in denial.

So anyway, how do you know it’s time to jump ship? I should give this caveat that I am no expert in this, I wrote this in the hope of clearing my thoughts and hopefully find someone that can relate.

One of the ‘annoying’ traits of millennials is that they never seem to plant their feet long enough in a job to get some actual ‘’job experience”. Side note: I remember attending a conference or other before I got my first job where the guest speaker more than emphasized the disadvantages of job hopping in an attempt to discourage us ‘young’ job seekers from calling it quits within three months of landing our first jobs. I hadn’t realized just how much that talk was engrained in my mind until the said epiphany happened.

This thinking kept me from walking away after temping for two years with the carrot of permanent and pensionable employment being dangled on my face every so often as some sort of twisted motivation. I was still thinking this way even after staying in the same role for four years and had the tingling sensation of dissatisfaction in my heart…I stayed put, all in an attempt to keep myself from being a career nomad. Was I being impatient? -typical millennial trait- is the question I constantly asked myself.

So I took some time out and asked myself some really tough questions trying to get to the bottom of this ‘behavior’, trying to trace the telltale signs to the beginning of it all.

  1. Simply put, I wasn’t happy with my job anymore
  2. I didn’t feel challenged, there was nothing I felt I needed to learn in my current role. I had become an ‘expert’. I had become comfortable.
  3. I could see in my mind’s eye something more attractive, that would bring me more satisfaction, something that would utilize my skill set (that I had become more acutely aware of over the past five years)
  4. The possibility of losing my job didn’t scare me as much as I think it should.
  5. I had spent too much time researching and looking into this attractive future and less time being relevant in my current role and before I knew it I had slipped into this lethargic unrewarding routine that was about to cause me to snap.
  6. I didn’t have a clear career trajectory within the organization if I stayed there longer.

Well, all these brought me to the said ‘epiphany’ and I realized it’s time to call it quits. I was not being productive and I was doing a disservice both to myself and my employer. It took me a couple more years after this epiphany to actually cut ties, even then, it was not absolutely my decision. I keep telling people that it was a mutual decision. Would I have walked away if I was not being pushed out? I don’t know.

When did you know it was time to quit a ‘perfectly good’ job? Tell me about it.

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