In Part One of this series, Break Free From Career “Shoulds” and Choose Your Own Path, we unpacked what “shoulds” are—those external expectations that often sneak into our decision-making and lead us down paths that don’t quite fit. If you haven’t read it yet, click here to catch up.
If you have—and you’re realizing just how often you “should” yourself when it comes to your career—then read on. This post outlines a four-step process to help you shift from obligation to authenticity.
Step 1: Notice Your Shoulds
Before you can make a change, you have to see what’s there. Start by listing out all the times you catch yourself saying things like:
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“I should go into law.”
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“I shouldn’t waste my degree.”
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“I should choose a safe, practical career.”
Pro Tip: Use your phone notes or a journal and jot these down whenever they come up for a few days.
At Canada Career Counselling, one of the most common “shoulds” we hear is:
“I should pursue law, math, science, or business.”
Let’s use that example to walk through the rest of this process.
Step 2: Ask Where These Shoulds Come From
Most of our “shoulds” didn’t start with us. They come from:
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Parents and family
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Friends or partners
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Media and TV shows
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Cultural or community expectations
For each “should” on your list, ask:
“Where did this come from?” and “How is it affecting me?”
Example:
“My parents encouraged law school because it’s practical and well-paying.”
That belief might push you to work hard—but it could also lead to burnout or dissatisfaction if law isn’t a fit for your interests or personality.
Step 3: Figure Out What You Actually Want
This is the turning point. Ask yourself:
“Do I really want this—or do I just feel like I should want it?”
When you learn to recognize your true interests and values, your career decisions start to feel more authentic, aligned, and motivating.
If you’re stuck, a Career Counsellor can help you sort through your thoughts and clarify your direction.
Example:
Do you truly want to pursue law? Or do other fields—like marketing, education, or social science—spark more curiosity and excitement?
Step 4: Start Making Choices Based on Your Wants, Not Your Shoulds
Now that you’re clearer on what you want, it’s time to start aligning your choices with your real goals and values.
This may mean letting go of the urge to please others—or releasing a long-held belief about success. It’s not always easy, but it’s freeing.
Try this:
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Stop saying: “I should go to law school.”
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Start saying: “I want to explore a career in marketing.”
Shifting your language helps shift your mindset. It replaces guilt with motivation and brings clarity to your next steps.
It’s easy to fall into the trap of doing what you think you should do. But when you take time to explore what you actually want, everything changes—from your energy to your engagement to your overall sense of purpose.
You don’t have to follow a path that doesn’t feel right. You get to build one that does.
Need help figuring it all out?
At Canada Career Counselling, we specialize in helping people just like you untangle career confusion, let go of pressure, and move forward with confidence. Book a session with us today.
