Three Questions to Ask Before Changing Careers

I spent over a year planning my career change before taking the necessary steps to leave my job and start Wish Career Coaching. I often felt consumed by the idea that my previous job wasn’t the right fit for me long-term. Despite giving my all and trying to support my team, I wasn’t showing up for myself. Seeing a coach for the first time was a big help, but it was just the beginning of a journey that required extensive preparation.

Changing careers is a major decision that requires time and energy. If you are considering a completely new path, there are many factors to consider. You need a solid plan and must examine all possibilities.

If you find yourself daydreaming about other options while at work, it’s time to start asking yourself what a change looks like. Here are the first questions to ask yourself before exploring other career options:

  1. What are my values?

    This is the most important conversation to have with yourself. What do you value, not just at work, but in life more broadly? Does your work align with those values? If it doesn’t, which values are being compromised? Dedicating a massive portion of your life to something that doesn’t further your values will lead to resentment. It’s much better to resign from a job than to resign yourself to a future of unfulfillment.

    For me, it was about having a positive, tangible impact on individuals. While working in tech, I knew that my time as a product manager was helping people through the products we made. For example, when I was working on Interac e-Transfer for ATB, I knew that thousands of people benefited from the product I was supporting. However, real fulfillment came from having direct conversations with people, offering immediate support and relief. Career coaching allows me to impact individuals daily, something I wasn’t getting as a Product Manager.

  2. Do I dislike my work or my management?

    “People don’t quit their job, they quit their boss” is a common saying in corporate spaces. While this isn’t always true, there are times when career dissatisfaction stems from management or leadership rather than the work itself. It’s crucial to understand the root of your dissatisfaction before making changes.

    If you enjoy the actual tasks required by your job but not the environment, it might be worth considering staying on your career path but looking for opportunities at another organization. Changing careers because of toxic management might work out, but you could find yourself missing the tasks you used to do.

    I worked as a Product Manager in various organizations and teams before realizing that I didn’t enjoy most of the tasks involved in product management. While my teams and leadership were excellent, I didn’t enjoy the work itself.

  3. Where am I not willing to compromise?

    If you earn a six-figure salary and want to switch to a career in food services, it might fulfill your interests better, but it will come with a pay cut. A new direction might mean giving up remote work for an office job. Pursuing a PhD might delay buying a new house.

    Switching careers requires time and energy, and while it is worth it, you need to ensure you aren’t losing something more important along the way. One benefit of seeing a coach is that they can help identify compromises that fill the gap. If you want to work fewer hours with minimal impact on salary, a coach can help you identify options that fit those criteria.

    I had to decide if I was willing to give up stability temporarily for greater career fulfillment and freedom. We determined it was the right move for our family, but it took many conversations and weighing pros and cons before I felt prepared to take the step.

These questions form the foundation of any introductory career coaching conversations I have with my clients. Even if you feel like you have a strong direction set, take a moment to ask yourself these three questions to check your gut. Is it time to take the next big step? If so, I recommend starting with a coach to help work through what that plan looks like.

Previous
Previous

What Happens After Gold? How Athletes Change Careers Later in Life.