Pen{g}sieve Vol 9: A guide for the reluctant to decide when to leave a job

In a culture of constant job-hopping, I am the type who tends to stay in a job for a very long time. In my twenty-year career, I only changed jobs twice — my first job lasted thirteen years, my second seven years.

This post shares my most recent job-changing experience and sheds light on what holds people like me back and how to break the indecision.

The external trigger

When shall we decide to move on? Some recommend changing jobs or areas every 5 or 6 years to stay out of their comfort zone. This is excellent advice but hard to follow for the reluctant.

I was lucky to have an external event to trigger my recent move to a new job. In the summer of 2019, my old company suffered a major setback. I stayed, at the time, to keep the team together, while secretly hoping that the external event would reverse its course soon.

The situation did not get better and team members started to exit one by one. When the team was down to three (including myself), I still thought we could sustain. Then, in February of 2020, HC decided to leave. I could not delay the decision any further.

Get out of the reluctant zone

But yet I still could not make up the mind. It seems that behind any indecision lies some deeper emotions that one tries to avoid. In my case, I was trying to avoid the unease of job search and the fear of rejection.

To break the inaction, I separated the decision-making from the action that follows the decision. The decision to be made is very specific: should I stay on the old job or not. As for how to find the next job, I would only worry about it after the decision was made. To decide, I wrote down the following observations:

• I am still able to learn, but it is despite this job not because of this job; 

• I am staying for the wrong reason (i.e., the fear of facing job search); 

• It is plainly irrational to maintain the status quo after receiving so many signals on the job’s uncertainty.

Looking at the list above, I could not help but decide to leave.

The strategy worked because I sort of knew which one I ought to choose but the right decision required hard work, whereas the wrong one required none. By separating the decision from the action, I removed the bias towards the easy option and made it possible to choose the hard one.

The decision to leave moved me into action. But it was a slow start. I spent the first three months talking to former colleagues and updating my profiles. Then came the recruiters. Soon one opportunity gained momentum and became my first interview. From that point on, I was definitively out of the reluctant zone.

Reframe job search as a learning experience

Interviewing is a vulnerable experience but also an excellent opportunity for learning and self-discovery. Not only was I super motivated to brush up on the technical skills, but it also allowed me to fully integrate my past experiences.

In preparation for the project retrospective interview, I chose a project that I was really proud of but had not looked back at because it involved one of my most painful episodes on the old job. The interview forced me to re-examine that past. To my surprise, what was deemed as an irreconcilable conflict back then seemed totally acceptable to me now. I saw how my old mindset led to a zero-sum situation and knew I would have handled it very differently today. It took two years and a job interview to fully integrate that experience, turning a past resentment into true learning.

I ended up really enjoying interview preparation and the interviews. By reframing the whole process into a learning opportunity, I turned my aversion to interviewing into the excitement of sharing and self-discovery.

Stay in the tension

“Life is about making strategic transitions when it makes sense. There is no need to cut from one scene to another immediately.”

— You don’t need to quit your job to make

While most people like to get over the job search as soon as possible, I recommend taking it slowly because a job search is a perfect learning-zone activity.

Nine months passed between my decision to leave and my first day on the new job.  My job search became a nine-month self-improvement project. Thanks to the pressure, I developed my own decision-making system, dived deep into my negative emotions, and learned to be vulnerable while landing a great new job.

With a prolonged in-between period, it is essential to mentally keep both options open so that one can stay in the learning zone without being overly anxious. I made sure that my last nine-month on the old job were as enjoyable as they could be so that if I had to stay longer, I could.

The in-between time offered me a rare chance to experience the old job differently. For instance, after deciding to leave, I no longer cared about promotion, recognition, or saying yes to everyone. In the next nine months, I experienced a new kind of freedom that I have never experienced during any time of my career — listening only to my inner truth, not anyone else’s. That state of mind was so liberating that I carried it to my new job today.