November 25, 2023




How to Find Your Life’s Work

At a glance

Today’s Fast Summary:

  • The question of “How to find my life’s work?” is one of the most important questions we’ll ever face.

  • Questions that examine our inner desires are effective tools to discern life’s meaning and make decisions. 

  • Consider your abilities, potentially lucrative opportunities, and passions when choosing what to pursue.

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How to Find Your Life’s Work

“Your time is limited, so don't waste it living someone else's life” - Steve Jobs, 2005 Stanford Commencement Address

As my long-time readers will know, the topics I choose to write about are typically those I’m pondering myself. So, lately, the question that’s on top of my mind has been, “How do I find my life’s work?”

To that end, I’ve compiled a list of questions and resources that I’ve been reviewing to help me get closer to answering this.

Whilst questions help instruct what to think about, I fully appreciate that finding your life’s work often requires a lifetime of experience and reflection.

If you’re reading this and feel like you’ve found your life’s work, I’d love to hear your thoughts in response to this email. What was most helpful for you in getting there?

And, to the rest of us, I hope these questions and resources are helpful. 

Questions to Ask When Considering Your Life’s Work

1. What am I still envious of?

This question illustrates what you truly value in your subconscious. 

Envy is a sign of discontent. As you get closer to doing the work you’re called to do, you become less envious of people doing other things. 

2. What does success require? And, are you willing to go there? 

Consider the top 1% of people in your field. What did they endure in exchange for success?

Let’s say you’d like to become a content creator, or you are one already. Ask yourself “What are the actions, skills, and evidence you’d need to succeed?” 

Ask yourself if you’re willing to do those things. This question is the price of admission to your pursuits. 

3. Who should I become?

Any serious inquiry into what you should do must start with who you want to become. 

4. Where do you feel great resistance or fear? 

Resistance is a sign of dissonance: What you’re doing is important. 

The more resistance you experience in response to a change or idea, the more certain you can be that there's a big dream there and it’s yours to obtain. 

5. What do you do that looks hard to others but comes to you easily? 

Everyone has unique strengths and weaknesses. It’s likely there’s something you’re adept at that others are not. Each of us is programmed differently. 

It also works vice versa. 

6. Fast forward 60 years. If you were just about to die and an angel allowed you to go back in time to this very moment, how would you view life?

And, would you view it differently? 

This question requires perspective and self-reflection. 

Another great question is, “If I'd already made a change, would I want to revert back to what I have now?”

7. What would you keep doing no matter how much money you had? 

Or even better, what couldn’t you get paid $1 Billion to stop doing? This is your life’s work. Pursue it. 

8. What’s the weirdest thing you spend a lot of time on? 

Or, what’s a passion you’d be embarrassed to admit publicly?

Passions, even odd ones, have value. Engaging in your passion cultivates long-term meaning. 

Related to this question is, “What am I excessively curious about—curious to a degree that would bore most other people?”

9. What hidden, ugly back-end tasks look exciting to me?

Back-end tasks are things like sitting at a desk for hours, running a company’s operations, or endless phone calls. 

However, some find sending emails to be cathartic or relaxing. 

Which annoying tasks do you enjoy doing? 

10. What front-end success is so good that I’m willing to pay the ugly hidden back-end price?

Front-end success is success earned through back-end work. Consider what success you’d be willing to pursue, given the back-end cost. 

Let’s say you hate emails. What kind of success would make a full inbox worth it? 

11. What do I have a natural aptitude for or a deep interest in? Where can I do great work? 

Remember your hedgehog concept. The work you do must satisfy the following: 

  • Something for which you have a natural skill

  • Something you’re deeply interested in

  • Something lucrative, or opportunity-bringing. 

Another good question to ask in this context is, “What do I want to wake up and do every day for the next 3-4 years?”

12. If I were going to take a break from “serious” work to work on something just because it would be really interesting, what would I do?

The happiest people are those whose work doesn’t feel like it. Their passions are intertwined in what they do. 

Ask yourself, “What is your passion? How can you harness it into a career?”

13. What advice would I give to a friend in my situation?

Giving advice is easy. Taking it is more difficult.

Consider what you would tell a friend in a similar predicament. What do they need to hear? 

14. What would I want to do, have, and be if I already had $10 million in the bank? 

Consider where you’d like to be if you were a millionaire. Then ask, “How can I get there?” 

15. If I were a character in a movie, how would I respond to the question, “Why don’t they just do that already!?”

You’re watching your favourite TV show, and a character is contemplating leaving their job. You wait with popcorn in hand for them to finally do it—you’re cheering them on. 

If you were that character, would you, as a viewer, react that way? And, what might your viewers react to? That’s what you should be doing.

Resources I’ve Enjoyed

Julian Shapiro’s “Personal Values ” Exercise 

Shapiro, the investor, suggests that your true passion lies at the intersection of your values. 

Identify the values you care about when pursuing a certain problem or opportunity. In other words, what does that opportunity have to be to be worth it? 

Shapiro listed knowledge, adventure, fame, power, money, exercising talent, and human connection as his key reasons for pursuing opportunity.

Then, order these by importance. 

Finally, ask yourself which pursuit best satisfies these. 

Derek Sivers’s “Happy, Smart, and Useful” Framework 

Derek Sivers, the American entrepreneur, uses three questions to determine whether something is worth pursuing. 

Like the hedgehog concept, this framework asks you to consider three things while making large decisions: 

  • What makes you happy

  • What is good for you long-term (Smart)

  • What is useful to others

Sivers says that humans “[tend] to forget one of these.” Happiness alone doesn’t pay the bills, but work without meaning is fruitless. 

Something smart and useful evokes the ‘strict parent obsessed with their child’s future’ stereotype. This is the rational choice. 

A happy and smart pursuit would be the “self-help addict: always learning, always improving.” Instead of adding value, these individuals look for what allows them to sustain their lifestyle. 

Charity volunteers or nonprofit leaders evoke the ‘happy and useful’ stereotype: While these people could make significantly more otherwise, they choose what makes them happy, and what adds value. 

Of his framework, Sivers says, “When life or a plan feels ultimately unsatisfying, I find it’s because I’ve forgotten to find the intersection of all three.” 

Steve Job’s Stanford Commencement Address, 2005

“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” - Steve Jobs

Near the last portion of his address, Jobs discusses some advice he read at age 17: “If you live every day like it’s going to be your last, someday, you’ll most certainly be right.” 

So, for 33 years, Jobs “looked in the mirror every morning and asked [himself], ‘If today were the last day of my life, would I want to do what I’m about to do today?’”

Asking this question negates our personal expectations, our pride, and our fear of “embarrassment or failure.” In the face of death, all but is truly important falls away. 

Jobs says this of his framework, “Remembering that I’ll be dead soon is the most important tool I’ve ever encountered.”

Honorable Mentions: 

As Jobs says of finding your life’s work, “Keep looking. Don’t settle.” I don’t plan to, and armed with these questions, you shouldn’t either. 

This week, focus on a major decision (personal or professional) you’re apprehensive to make. Implement the tools discussed in this article, and make a choice. And, as always, be honest with yourself.

  1. Who am I? Ask yourself the following questions to analyze your personal strengths, weaknesses, intentions, and motivations. Write down your answers.

    a. Who should you become? 

    b. What are you still envious of? 

    c. What looks hard to others, but comes easily to you? Or, what are your natural skills? 

    d. What’s the weirdest thing you spend a lot of time on? Or, what’s a passion you’d be embarrassed to admit publicly?

  1. What are you willing to do? Write down your answers.

    a. What does success in your field require? List the steps and examine the habits of successful people. Then ask, “Am I willing to go there?” 

    b. What hidden, back-end chores look exciting to you? Ex. emails, phone calls, boring meetings, long hours, etc. 

    c. What front-end success would make you willing to pay the hidden back-end price? When is it worth it? 

  1. Employ the “Personal Values” Exercise. 

    a. What values do you analyze when considering pursuing a problem or opportunity? What does that opportunity have to be to be worth it? 

    b. Order your list by importance. 

    c. Ask yourself if your pursuit satisfies these.


I’d love to hear from you:

  • Which of these did you find helpful? 

  • Are you pursuing what makes you happy? 

  • How can you harness these tips? 

Tweet at me (@_alexbrogan) or respond to this email — I’ll try to respond to everyone.

Have a wonderful Saturday, all.

Until next time,


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