Knowing When the Right Time to Move On Is Upon You

Jean du Plessis

Senior Engineering Manager at upbound



I once stayed at a job three years too long for the wrong reasons. I’m always thinking back on that time. Why did I do it? I’ve spent a lot of time thinking about when leaving a comfortable position is one’s best option.

What stops a person from moving on at the right time? Being scared, for one. At that point, I had been with the company for more than eight years. There is a sense of comfort in doing something that you know and fear in the prospect of stepping out into the unknown, into something that you don’t know. I think that another part of it is the relationships that we forge with those that would be left behind. Will you enjoy working with the people at your new company? As an introvert, building relationships is draining. It takes time and a lot of effort.

I was focused more on fear than I was on the need to grow and to move on. Things worked out fine in the end for me, but it was three years that could have been put to better use. Why did I stay so long? What impact did it have on my journey? What are some of the signals indicating when it is time to move on?

Actions taken

When your growth opportunities within the company are not in alignment with your desired career trajectory, that’s one factor to take into consideration. I’m not a big proponent of having a specific professional goal to chase after. Instead, identify the type of life that you would like to live. Work toward that rather than a career goal. Otherwise, you may achieve that goal and find yourself in a life that differs from where you would be in an ideal sense. You’ve alienated your friends and your family in order to get where you are. When what's in front of you at your current company is not in line with your desired trajectory, you may want to potentially consider something else. This is a proactive point of view to take.

If you’re no longer learning in the role that you’re in and you find that you do not have the opportunity to bring new ideas to the table, that also may be a sign that change is in your best interest. In some ways, you also need to be reactive. If there is bad management that needs to be addressed, nobody needs to put up with that. If these support systems are not in place, you’re in the wrong room regardless. Don’t suffer.

You should also consider what impact that moving will have elsewhere. You don’t necessarily need to be risk-averse, but you need to be sensible about it, as well. You want to make sure that you’re in a position to make your move. Assess the market opportunities. And if your relationship with your manager is good, you will want to start talking to them about these things. No manager wants to be blindsided, specifically from a succession-planning point of view. If you have the trust and the psychological safety needed to bring the topic up, it is always recommended to do so. I am a firm believer in not surprising your manager with a resignation if it can be avoided.

Lessons learned

  • Identify what it is that you want from your next opportunity and ensure that this move will be aligned with your career ambitions. When you interview with a new company, you’re interviewing them just as much as they’re interviewing you. You need to make sure that what they can offer is not just good from an outsider’s perspective, but also in a long-term sense, as well. Otherwise, you may find yourself in a position where you are still not growing as you would like to be. You will not be full or satisfied. You’ll just end up feeling like you need to move on again.
  • I do not encourage job hopping. Move toward something rather than running away from something. Even if you’re leaving to get away from something dysfunctional, you don’t want to go for the first thing that’s readily available. Make sure that the next company’s values are compatible with your own. Doing your homework is very important. If you can, reach out to people involved with the company and ask them questions about the place. Nobody goes and buys a car, just randomly. You want to make sure that what you’re buying is what you like. We should be doing the same thing for our careers, as well. You should be just as diligent and deliberate.
  • Making the right move at the right time for the right reasons has the potential to have a multiplier effect on your career, and on your personal life, as well. You will feel a sense of energy, passion, and momentum. When you know why you’re moving, it’s not just another job. Sometimes, you have to take a leap of faith. What is the opportunity cost on your career and personal growth that you risk by staying where you are, in a safe environment? I look back on some of the choices I’ve made and the exponential growth that has come as a result of these choices.

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Jean du Plessis

Senior Engineering Manager at upbound

Career GrowthCareer ProgressionSkill Development

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