Thinking About a Career Change? Questions to Ask First

Maybe you have felt restless at work for months. Maybe a recent change made your job feel like a poor fit. Maybe you have always wondered about a different path and now feel like it is time. Whatever brought you here, a career change can be one of the most meaningful decisions of your life.

It can also be one of the most disruptive. Before you make the leap, it helps to ask honest questions. This post offers a set of questions in five groups. Work through them over a week or two, and you will have a much clearer picture of whether, when and how to change.

Questions about why

Start by understanding what is driving the desire for change.

• What specifically is frustrating me about my current work?
• Is the problem the work itself, the workplace, my manager, my schedule or my pay?
• Have I felt this way for a long time, or is it tied to a recent event?
• If my current job changed in one or two ways, would I still want to leave?
• Am I running from something, running toward something or both?

These questions matter because some frustrations follow you to a new career. If the real issue is a difficult manager or an unsustainable schedule, a change of employer might solve it without a change of field.

Questions about what you want

Next, think about what you are moving toward.

• What kind of work gives me energy? When do I lose track of time?
• What problems do I care about solving?
• What do I want my days to look like: people, projects, outdoors, at a desk, flexible, structured?
• What values do I want my work to reflect? Name Your Core Values in Five Steps can help.
• Which careers or roles have I been curious about, and why?

If you struggle to answer these, that is useful information. You may need some exploration before making a move.

Questions about the cost

Every career change has costs. Jesus used a familiar example when He talked about counting the cost of commitment: "For which of you, intending to build a tower, sitteth not down first, and counteth the cost, whether he have sufficient to finish it?" (Luke 14:28, KJV). That wisdom applies to careers too.

• Will I need more education, training or certification? How long will it take?
• How might my income change, at least at first?
• How much financial cushion would I need to feel secure during the transition?
• How will this affect my family, schedule and commitments?
• What will I be giving up, such as seniority, benefits or a familiar community?

For decisions involving savings, retirement accounts or major financial changes, talk with a qualified financial professional before you commit.

Questions about readiness

Now consider your timing and capacity.

• Is this a good season in my life to make a big change?
• Who will support me through the transition?
• What skills do I already have that would transfer? How to Find and Describe Your Transferable Skills walks you through this.
• What fears are holding me back, and are they warning me of real risks or simply of discomfort?
• Have I prayed about this, and what sense of peace or unease do I have?

Questions about testing it

Before you leave your current job, consider how you could test the new path with less risk.

• Could I talk with three people who already do this work?
• Could I shadow someone for a day?
• Could I take a short course or workshop?
• Could I volunteer or freelance in the field on a small scale?
• Could I make a gradual shift within my current organization?

Testing helps you discover whether the reality matches your hopes. Sometimes it confirms the change. Sometimes it reveals that a smaller adjustment would serve you better.

Putting your answers together

After working through the questions, set aside an hour to review what you wrote. Look for patterns:

• Are your reasons for leaving clear and lasting?
• Do you have a clear sense of what you want instead?
• Are the costs manageable with planning?
• Are you ready, or do you need more preparation?
• Have you tested the new direction?

Then write a short summary: "Based on my answers, my next step is..." That step might be to research, to talk with people, to save money, to take a class or to begin applying. It might also be to stay and make changes where you are.

If the decision still feels tangled, How to Make a Hard Decision Using Your Values offers a structured way to compare your options.

Frequently asked questions

How do I know if I should change careers?

Look at whether your frustrations are about the work itself or about your current workplace, whether you have a clear sense of what you want instead and whether you have tested the new path. Clear, lasting answers suggest a change may be right.

Is it too late to change careers?

Many people change careers at different stages of life. Consider your financial needs, training requirements and family situation, and test the new field before making the full leap.

Should I quit my job before starting a new career?

Often it is wiser to explore and test a new career while still employed, if possible. That reduces financial pressure and lets you make a clearer decision.