After committing to making a career transition, you will have questions and likely some self-doubt. You might question your worth and start to feel foolish for thinking you could make a career transition. 

This is very normal. 

Here’s what to remember when you decide to make a career transition: 


You do not even know what the career change will look like. How can you judge it?


Your only job, in the beginning, is reflection and inquiry. The need for a quick answer and clarity is not as valuable as deep exploration.

Drop the defences.

Work with your career stories, and if self-doubt appears, notice where you feel it, you can even label it “feel” and keep reflecting.  If you are interested, it is worth learning how to deal with emotions and body sensations as you go through this process. 



Once you accept that it is not foolish to make a career transition and it is too early to judge the decision, then you work on opening up. 

  • Take notes
  • Think about possibilities
  • Take more notes
  • Make small decisions
  • Think about it on paper
  • Say things aloud

This is the beautiful time of change when anything can happen, and your job is to just listen without immediate resolution. 

If you need a starting place, here are six prompts to sit with. 


Do not treat these questions like things that will have answers today, they may not. Not having the answer today is part of the process of transitioning. It is also fun. If you are willing to upheave your career by doing new work, it is worth appreciating that you’re even thinking about making a change. It is worth spending time in this “don’t know” zone.

Shinzen Young says that the mind has a certain drive to find meaning. When your mind finds meaning, you will find a smile on your face or a rosiness on your face. When the mind is confused or spinning to no avail you’ll find in the body fear, tear, and agitation. This is pleasure in having an answer and discomfort in being confused or not having answers. He says we can “train ourselves with equanimity of don’t know.”

“when a human being works through the need to have answers, they don’t stop having answers, they start having answers in a deeply fulfilling and radical new way.”

This new way of knowing is called wisdom function or insight and ideally, this is where you want to start your career transition. If you can nurture a comfort with “don’t know” early in a transition, you will suffer less and have greater wisdom in the later parts. This means that the self-questioning and imposter feelings that commonly show up for people once they make a career decision will affect you less. You will have an openness to yourself that is freeing. 

This opening is related to Krumboltz’s Planned Happenstance career theory.  A major part of this theory is an encouragement to remain open to unplanned events because they might help your career. 

Later on, in your career transition, you will want to make decisions, set a target, and work on your career story, but in the beginning, nurture the ” don’t know” state of mind. 




Each one of these prompts was designed to move you towards paying attention to the opening. It could be opening to a memory, the present moment, an idea you had not thought of, playfulness, or accepting the truth about yourself.  Ideally, you could ask yourself one question a day for seven days. Ask it in the morning, journal about it in the afternoon, and see what answers or ideas came your way by evening. Work with another one the next day. 


1. What made me feel alive at work?

2. What can I hear right now?

3. What work is slightly beyond my experience, but would benefit from my top skills?

4. Where do you feel joy at this moment? Celebrate it.

5. If I was invited to a dinner party, and we had to dress as a different profession for each part of the meal, what would I wear as the appetizer, entree, and dessert? 

6. When and where do I feel wise?



Opening is the hardest part of a career transition 

The hardest thing to nurture in a career transition is the openness to explore without needing an answer. In a few weeks or months, you’ll have done enough opening and exploring and will put a plan in place, but honour the special time in the beginning to open. You want, at the end of your transition to feel that you truly explored every possibility and dream and that you did not put limits where limits were not needed. You do not need them in the beginning. A career transition is a process of learning about and trusting yourself. Enjoy the process.