14 Strange Questions to Help You Find Meaningful Work
By: Dan Mowinski
Tags: Self Improvement, Work, Personal Development, Purpose, Passion

I searched for my “one thing” for years. I spent endless hours reflecting, experimenting, and pulling my hair out.

But I eventually realized I didn’t have one specific “purpose”. There wasn’t a vocation, calling, or craft I was destined to pursue. Instead, I had options. Multiple options that would be a good fit.

So instead of, “What’s my purpose?”, I asked, “Who am I?” And that’s when things got interesting.

Here are some questions to help you on the path to self-knowledge:

1. What would you do if you had one month left to live?

You’ve probably already been asked, “What would you do if you had one day left to live?” The problem with this question is that it prompts short-term thinking, which is useless for finding a lifelong purpose. Try it without the pressure of a 24-hour deadline.

2. What are your Sisyphus myths?

Sisyphus is a character from Greek mythology. A former king punished for his deceitfulness, he was forced by the gods to endlessly push a boulder up a hill. Which jobs would you find equally unbearable?

3. Who are your present-day role models?

Who are your living, breathing role models? It doesn’t matter who they are - celebrities, friends, or acquaintances. We’re often drawn to those people we want to be like.

4. What is your strangest positive trait?

Getting clear about your positive qualities is essential for finding your purpose. And your strangest traits are a big part of what will shape your unique contribution.

5. What’s your most-watched Youtube genre?

Try this: log into your Youtube account and open your history. Start scrolling. You might be surprised at what pops out.

6. If you could only read three books for the rest of your life, what would they be?

Imagine you can only read three books for the rest of your life. You’re allowed to read them repeatedly, but you can only pick three. Which ones would you choose?

7. If you had to live one day over and over again until you died, what would that day involve?

This question is a play on Friedrich Nietzsche’s idea of “eternal recurrence”. He proposed it as a kind of thought experiment: if you had to relive your life again and again, would you be distraught or joyful?

8. What one gift would you give to every human being on the planet?

You’re only allowed one. Would you give something practical, like a tasty meal? Or something more general, like freedom or peace?

9. What ethical principle would you die for?

Or at least lose an important body part like your leg or…nose. Uncovering your values is a big part of understanding who you are. Start by pinpointing your central tenet, the principle which you would never surrender.

10. What real-life talent would you like to have (but currently don’t)?

No superpowers allowed. Which skill, if you could pick any, would you like to develop overnight? You could choose to be a polyglot, a great singer, or the world’s most charming seducer.

11. What genre of fiction would you write?

If you were a fiction writer, what would your genre be? Personally, I’m more of a George R.R. Martin and Tolkien kind of guy. Not a fan of high fantasy? What about grizzly crime thrillers or technically-fastidious science fiction?

12. What carries you away to happy land?

Everybody has a favourite form of “dropping out”. For me, it’s ambient music. There’s likely an underlying reason why one type of escapism transports you farther than all others.

13. Are you introverted or extroverted?

I’ve always thought that “introversion” and “extroversion” are too narrow as categories. In my opinion, everybody exists on a spectrum. Nonetheless, the camp you lean towards has a big impact on the kind of work for which you’re best suited.

14. Does your “passion” need to be your work?

The advice “find your passion” is a double-edged sword. Some people have a deep longing to express their interests and values in their work. Others don’t. And for people that derive meaning from things like family, hobbies, or charitable work, an enjoyable career that’s a means to an end is often the best option.