Career transitions are becoming more common and are increasingly part of an overall career life. They can be a personal choice or a change imposed on us. In either case (and we may experience both during our careers), we are confronted with change and must decide how to respond to and navigate it.
I like to start these conversations with my clients experientially and holistically, as this provides a foundation for developing personally relevant and attainable next steps.
Guiding clients through a reflective process at the beginning helps uncover important information, including what the client has been experiencing that is fueling a desire for change or the experience of having change imposed on them, the client’s attitudes towards work and career, the relationship the client has with work and career, the meaning work and career hold for the client at their current stage of life, and what they imagine change will release, open up, make room for, or replace.
These reflective conversations reveal a client’s motivation and their acceptance of, tolerance for, or aversion to change. They also reveal personal dreams, goals, disappointments, and fears. They further reveal practical considerations unique to that client’s life, considerations that must be woven into any decision, plan, or strategy moving forward.
The following is a sample of 7 areas to help you begin reflecting and collecting personal information.
1. Why Change, why now?
It is common to want change—or to be confronted by it—at different points in your career. It is also common to feel stuck, even when you know something needs to shift. You may be unsure about what needs to change, what feels realistic in a rapidly changing world, or how to begin taking the first steps.
Break it down. Try these sample questions to help clarify what is driving the desire—or need—for change:
- What have I been experiencing lately?
- When did I first notice a change in my relationship, engagement, or connection with my current work, role, or position?
- If change is being imposed on me, how do I feel about it, and what are my immediate concerns?
- What do I imagine this change might release, make room for, or replace?
- Why does change feel important—or challenging—at this stage of my career?
- What do work and career mean to me at this stage of my life? Has that meaning changed? Can I describe that change?
- What would I like to learn more about, gain experience in, or contribute to next?
2. Motivation and stamina
A key question to consider is whether you have the motivation and emotional stamina for a career transition. You may not know the answer right away, but it is important to keep it in mind. Transitions can feel exciting and liberating, yet they can also be demanding and unsettling. Moving into a new role—or even a new profession—may happen quickly, or it may take much longer than expected.
For this reason, it can be helpful to check in with yourself regularly throughout the transition. Here are some sample questions to guide that reflection:
- How are my energy, motivation, focus, and mood today or this week?
- Where am I noticing progress or momentum?
- What feels challenging right now, and how is it affecting my motivation?
- What can I realistically accomplish today or this week?
- How do I feel about what I have accomplished so far?
- What needs to be adjusted, and what should I prioritize next?
- Can I identify when, and under what circumstances, my motivation tends to drop?
- Is there anything I am avoiding? If so, why?
- How organized do I feel right now?
- Where could I use more support or encouragement?
3. Capacity or tolerance for change
At different stages of life, many of us begin to imagine a different job or career. For a variety of reasons, though, we may feel resistant, hesitant, or fearful about the changes that most career transitions require. At the same time, we may also feel excited and eager to take a leap into something new. Most of us hold both responses in different degrees, and our comfort or discomfort with change is often shaped by our past experiences.
When we better understand those experiences and our attitudes toward change, we can move forward with more clarity and confidence. Reflective questions like the ones below can help you recognize both the desire for change and the realities that may come with it.
Some sample questions:
- How do I feel about change at this stage of my career and life?
- What kinds of change feel exciting to me, and how might I help create them?
- What kinds of change concern me, and how might those concerns affect other areas of my life?
- When have I embraced change in the past, and what made that possible?
- When have I resisted change in the past, and what were the circumstances?
- Can I accept the realities of a career transition, including possible changes in salary, professional status, responsibilities, retraining or upskilling, and new leadership styles or team dynamics?
An honest and compassionate “check-in” gives you insight into your capacity or tolerance for change and keeps you grounded in the realities and contexts of your life. This information provides clarity and perspective and opens possibilities, including the possibility of adjusting any career transition strategy.
4. (Re)defining your expectations of work/career
We all carry expectations and internal narratives about what work and careers should look and feel like—and about what we want them to provide, from financial security to personal fulfilment.
Taking time to understand these expectations can offer valuable insight. These sample questions can help you reflect more deeply:
- What are my expectations for work and career, and how do I feel about them?
- How have these expectations changed at different stages of my career?
- Have my expectations shifted because I am facing a career transition in a very different job market and an uncertain future?
- How do these expectations shape the choices I make about work and career, including the opportunities I am open to and the ones I resist?
- Are there any expectations I may need to redefine, expand, or change?
5. Reassessing skills and capacities.
We often link our skills and capacities closely to our current work or career. Because of that, many people experience a career transition as though they are losing skills, experience, or value.
In reality, each of us brings portable value and a range of learned and transferable skills. We also carry innate strengths and talents, as well as a growing body of “experiential expertise” shaped by our work and life experience. Added to this is the unique way we approach our work—how we think, solve problems, relate to others, and contribute—along with the knowledge and perspective our experiences have given us.
During a career transition, this evolving portable value can be reviewed, reassessed, and leveraged in new and creative ways. Doing so can generate new questions, possibilities, and directions for research, networking, and decision-making.
These sample questions can help you reflect on your skills, strengths, and transferable value:
- Can I identify and describe some of my innate or natural strengths? What makes them portable or transferable?
- Which skills or capacities would I most like to highlight or use in my next role?
- Are there areas where I could upskill or consider retraining?
- Can I describe how I work? What personal perspectives, experiences, skills, and contributions have shaped the roles I have held?
- How would I describe my unique value at this stage of my work and career? What am I capable of? What kinds of responsibilities could I take on? Where could I contribute? Given that value, what roles am I best suited for, and why?
6. Finances
Career transitions may involve a period of unemployment or, at the very least, a change in income. These are important realities to consider, as they affect both whether a transition is possible and how it can be planned.
- Is a career transition financially feasible for me right now?
- Do I need to stay in my current role or profession while I explore a new direction?
- Could I manage being without work for several months—or even up to a year? How might that affect other areas of my life, and how would I feel about not having a regular salary?
- Is it financially possible for me to enter a training program or return to school? Are there funding options I should explore?
7. Support and self-care
Support and self-care are essential parts of navigating a career transition. Take time to reflect on the kind of support you want and need, check in regularly on how you are doing emotionally, psychologically, and physically, and make any adjustments that will help sustain you through the process.
- What support do I already have around me? Do I have support from family, friends, colleagues, mentors, or career counsellors/coaches?
- How comfortable am I asking for help and support? Where can I turn for conversation, encouragement, or perspective during this transition?
- Am I practising self-care in ways that truly support me? Am I making time to rest and recharge, to stay connected to other parts of my life, and to care for my sleep, nutrition, and physical health?
- How compassionate am I being with myself during this transition? How flexible am I when I do not complete my job-search to-do list or when my motivation dips?
As you work through the reflective questions in this sample checklist, notice what personal insights begin to emerge. What new perspectives are taking shape? What would you add to your own checklist? And how might you use what you are learning to plan realistic, attainable next steps in your career transition?
For help, guidance, and support with navigating change and career transitions, contact me at [email protected].
