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I’m friends with a lawyer named John, and I had an interesting conversation with him recently. He told me he hated his job and regretted his career choice.
He said not only is it a problem at his firm, but among other lawyers, regret is a common feeling for their career choice. Lawyers are often overworked, and the job itself is usually not the glamorous position that is portrayed on television.
I felt sympathy for him. I can only imagine going through all those years of schooling and passing the difficult bar exam just to hate your career choice when you’re finished with it.
Then, you feel trapped in the career because you have committed so much blood, sweat, and tears to achieve it.
If you ever tell yourself: I don't know what career I want! Take comfort that at least you’re not my friend John, and you have time to figure out what to do.
If you’re worried about why you will fail to have a great career, here are a few steps you can take to get started, find a great career, and start to make money.
1. Make a list of all the careers that you are interested in
Think about everything you’ve ever read about careers, or movies or tv shows you’ve watched, or interesting jobs you might have heard about. It can be anything you want at, from an accountant to a nurse, or even an astronaut or NHL player.
Write down anything you can think of. You can read lists like this for ideas.
You can even make a list of companies you are interested in working for. If you’re really interested in a certain company’s vision and mission, this could be a good starting point. Maybe you’d love to work for Apple, Nasa, Mercedes-Benz, or Walmart.
Or maybe a smaller company appeals to you. Make a company list, then research all the careers at that company.
2. Separate the careers into categories
After you have a long list of careers, you can separate them into categories. Then, get rid of the obvious ones that you won’t be interested in, and try to narrow down the field to about 20 jobs.
3. Give each career a score
Come up with a list of the career attributes that are most important to you. Here’s a list of common qualities you can base your score:
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Earning potential
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Autonomy
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Job security and demand
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Freedom
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Likelihood of success
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Stress-level
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Free time
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Passion for the subject
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Job satisfaction
Weight the scores to how important they are to you. For example, I value freedom and earning potential over anything else, so I weigh them higher, but what you value might be very different.
After you have your scoring system figured out, assign a score. You can then narrow the list further to the top five highest scores.
4. Research each career
After you list five jobs, research everything you can about the career. Here are some ways you can do that:
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Read everything you can about each career online.
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Watch Youtube videos about the career.
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Find job reports about each career.
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Attend job fairs
5. Reach out and shadow real people in those careers
This step is important. My friend John thought he would be a hotshot trial lawyer like he saw on television. If he had actually spent more time to find out what lawyers do daily, which is a lot of paperwork and contract writing, he might not have wanted to become one.
Here are a few ways you can reach out to people to shadow:
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Make a nice profile on LinkedIn, then reach out to people in the field you are interested in. Ask smart questions to each person to see what potential careers could come, and then try to shadow them.
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Do it the old-fashioned way, by phone or in person.
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Tap into your existing social networks, either through social media or personally reaching out. A simple post on Facebook asking if anyone knows a person in a career you are interested in could provide some leads.
6. Adjust your score with the new information
Now that you have a lot more information adjust your list of five job scores. There could be some drastic movement now that you know a lot more about the job.
7. Narrow your choices to one or two
Now you should hopefully have one or two clear-cut choices. If it’s a toss-up between the two, repeat steps 4-6 above until you come up with a choice.
8. If you’re really not sure, try taking a personality quiz like Myers-Briggs
If you’re still not sure, you can take a test like this Myers-Briggs personality test designed for careers to figure it out. It’s a personality-based quiz, and it could give you some ideas about which path to go.
9. Go with your gut
If at the end of all this, you’re still torn between two or three choices, just listen to your gut and go for it! As a wise man once said, more is lost by indecision than the wrong decision.
Don’t worry if your career choice is not perfect
You’ll experience a lot of change throughout your career. Careers will change, and you will personally change also. It’s impossible to predict the future 10, 20, or 30 years from now.
Pick one path, apply yourself 100% towards it, and a whole world will open up. No choice is set in stone and there are always options, even if you’re stuck in a job you don’t like.
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Christopher Liew, CFA, CFP®
Christopher is the founder of Blueprint Financial and a CTV News personal finance columnist. As a dual-designated CFA charterholder and Certified Financial Planner (CFP®), he helps Canadians reduce financial stress through clear, customized financial plans.
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This content has been reviewed by CFA® charterholders and Certified Financial Planners (CFP®) with over a decade of experience in Canadian financial markets. All information is fact-checked against official Canadian sources and regulations.
Why these credentials matter: CFA® charterholders complete 900+ hours of rigorous study in investment analysis and ethics. CFP® professionals are held to the highest standards of financial planning competency and fiduciary duty in Canada.
⚠️ Professional Disclaimer
This content is for educational purposes only and should not be considered personalized financial advice. While our team brings professional expertise, individual circumstances vary. For personalized guidance, consult with a qualified financial advisor, tax professional, or mortgage specialist.


