How to choose a career that brings you happiness and fulfillment


Have you seen the Pursuit of Happyness?

Spoiler alert: It’s one of my favorite movies of all time. At the end, Chris Gardner (played by Will Smith) finally gets the dream job he had been working so hard for.

At the end, he’s overwhelmed with happiness and you can see it in this gif above.

This is how I want every single one of my clients to feel after they land their dream job. That’s what motivates me to keep doing the work that I do.

Over the last 13 years, I’ve coached over 100 students in intensive 1:1 sessions on how to choose a career and land their dream job.

On a really busy week, sometimes I’ll have as many as 35 one on one meetings!

Here’s an example of the 1:1 sessions I had just a few weeks ago (I blanked out the meetings to respect everyone’s privacy).

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Here’s an example of one of my calls with Dwij on Skype. (Thanks for letting me use this screenshot for my site Dwij!)


Out of all of these calls, I was really curious to hear what people’s #1 challenge was in finding their dream job.

Their answer surprised me.

The most common question I got was…

“How do I choose a career?”

And the reasons they gave me made a TON of sense:

  • I’m in college (or currently working) and I’m not sure what I’m really passionate and excited about

  • I want to try out 3+ different types of careers, but they’re incredibly different (for example: product management vs digital marketing)

  • I have no idea how to test out whether or not I’ll like a certain job

  • I don’t know where to start

So that’s why I decided to write this guide. The reality is that there isn’t always one linear path to figuring out how to find out what your true calling in life is. When I asked entrepreneurs, corporate leaders, doctors, nurses, finance analysts (the list goes on and on) how they found their dream job, I often got very different answers.

So…that gave me this idea. What if I compiled all of their advice into a single post? That way you could try out different methods and see which one works out best for you!

Here are some of the top ways to discover which career could the best fit for you:

  1. Venn Diagram Brainstorm: Use this Venn diagram below and try to write at least 5 answers down for each of the circles. Do any of those answers meet the criteria of each of the circles? This could be a great way to brainstorm and give you a starting point to work from.

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2. Use the “values” based approach:

  • Start by writing down your top 10 values (for example: health, relationships, financial freedom, learning and growth, etc.)……I’ll wait here patiently while you do that.


Done? Good.

  • Next, rank your top 4 out of those 10

Completed? Move on.

  • Based on the top 4 values, write down specific examples of what your ideal dream job would look like (ex: I want to be able to work from anywhere in the world or I am passionate about the vegan lifestyle)

Finished? Well done! It should look something like this now:

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Then write down possible job roles and companies that fit those values (ex: if I am passionate about the vegan lifestyle and making an impact on the world, then working at Impossible Foods as a marketer could be a great fit for me.)

3. Use the “5 Questions” approach: This one is relative straightforward and can sometimes be extremely effective because of the simplicity of it. Just fill in the blanks below:

  • If only I had the right skill sets for this role, I’d be doing this: ________

  • My colleagues, friends and family always mention who amazing I am at ________

  • If I went back to school, I would study ______ because _______

  • If I had free time tonight or this weekend to work on a project, I would do this: __________

  • When I’m 100 years old someday and looking back on my life, I want to say I was proud to have worked on this: __________


4. Coffee and Conversation: Once you have a list of companies you want to potentially work for, build a list of contacts that work in that role or an adjacent role that interacts with that role a lot. Then reach out to them to see if they’d be willing to take 15-30 minutes to chat with you about the role virtually by phone or video or in person over coffee.

Here’s an example of an email or LinkedIn message you could send below:

Hey (Insert name),

I hope all is well at (insert company name). (Write a personalized note about them using information from news articles or their LinkedIn profile). (Mention a shared social connection).

I wanted to reach out because I’m really passionate about working for (insert company) in the role of (insert role). I even spent (insert time) creating this customized deck (or video) to show you how I can contribute to the company.

With that said, I’d love to learn from you to hear your experience in the role and to see if you could share any guidance over a quick 15 minute call.

Would you be open to it? If yes - want to book a time here to chat? (Insert Calendly Link).


(Your name)

5. The Feel Good Test - This one is simple: when you spend time with your colleagues and you do the work, how do you feel? Are you energized and passionate? Are you excited to learn on the job? Are you feeling fulfilled? Do you feel good? If not, think about times in your life were you felt really good and break down why you felt that way. This may help guide you to your career calling.

I hope this guide helps you find your calling in life. Best of luck.

Nelson WangComment