Most Common Career Change Dilemmas & How to Overcome Them

31 Dec 2018 Posted in ⟨For Learners⟩

At some point in our lives, each of us will feel that we have outgrown our current career. Although the desire to change things up may burn brightly, our minds naturally stop ourselves from taking the leap.

Rather than succumbing to our doubts, we must dive into them to discern whether there is truth to them or not. By piecing them apart consciously, we can move through them and find a way to shift ourselves onto a new and fulfilling career path.

Here are the most common career change dilemmas that career transitioners face and how to overcome them.

“How can I just give all of this up?”

The more time that you have invested into your current career, the harder it will feel to move away from it. This is so much so that many people wonder, “how can I just give all of this up?”

While continuing what you’ve always done makes logical sense in the short run, you must ask yourself whether it will bring you closer to realising your career vision. If you are considering a career change but are finding it difficult to let go of all the years of work that you have invested, dive deeper and ask yourself the following questions:

  • Is my current career providing what I need to feel motivated and fulfilled?
  • Is my current career allowing me to utilise and develop my skills and strengths?
  • Is my current career enabling me to have the kind of impact that I want to have?

If the answer is a consistent “no” and there is absolutely nothing that you can do to change it, then you must ask yourself, “what am I actually giving up by changing my career?” Don’t let pride nor your past stop you from making a career switch which is more aligned with who you are. Work takes up such a large part of our lives, so it is important that we not only do what pays, but what also fulfils us. As Confucius once said, “choose a job you love, and you will never have to work a day in your life.”

“I don’t have the experience”

Switching to a new career can make you feel like you’re starting from scratch all over again. One second you’re managing a team – the next you’re being managed! Every career change involves an experience gap that you must strive to overcome. There’s no easy way around it. You can’t just snap your fingers and suddenly have experience in a new area of expertise. Experience takes time and the only way to gain it is to continuously invest your time and energy into mastering a craft.


Seek out training programmes and volunteering opportunities to cultivate a new skillset. Experienced mentors who are already doing what you want to be doing can also be a godsend to accelerate your progress.

“It’s too late for me to change my career”

There’s no doubt that there are some industries and vocations that favour the young – especially those that rely on physical ability. However, in terms of creative and white collar work, you can only become wiser with age.

If you are someone who constantly tells themselves, “it’s too late for me to change my career,” conduct some research to find out whether this a reality of your desired industry of work or whether it is a personal belief. In the personal development classic, Think and Grow Rich, Napoleon Hill states, “seldom does an individual enter upon highly creative effort in any field of endeavor before the age of forty. The average man reaches the period of his greatest capacity to create between forty and sixty.”

“Should I just quit my job and take the leap?”

It is important to note that changing your career will not happen overnight. In fact, changing your career will often take a minimum of six to twelve months to pull off given the time it takes to overcome the experience gap and discover the right opportunities.

One way to go about this is to use the financial stability of your current job to research the market, network, attend interviews and invest into training programmes to upgrade your skills. This route will take a long time given that you will need to balance working in your current job and preparing yourself for your new career, however it will shield you from the financial stress involved with quitting your job.

The other option is to take stock of your current savings, monthly living expenses and the costs associated with upgrading your skills. By working out these figures, you will be able to work out how many months you can afford so as to give your new career change 100% effort, or at the very least, to define a target amount of savings to work towards. Jia Jiang, the author of Rejection Proof, concocted a plan with his wife to set aside six months to work out a new career change, and this resulted in 100 Days of Rejection – a social experiment which has grown into a TEDx talk and training business.

Want to change your career but don’t know where you begin? Take our SkillsFuture-accredited Career Transitions Package which will enable you to explore new frontiers such as leadership, service innovation, change and effective communications.


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