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Book 33/52 of My #52Books52Weeks Bucket List Challenge

I first came across Derek Sivers on The Tim Ferriss Show podcast, and I’ve been a fan ever since. He’s an amazing thinker, philosopher, minimalist, and anti-matrix communicator. So when I had the chance to have him as a guest on my Bucket List Life Podcast, it was a real privilege.

You know that classic question people ask?
“Alive or dead, who would you love to invite to a dinner party if you could?”

Derek would get a seat at mine. In fact, it’ll probably happen at some point!

This book, How to Live, is small, easy to read, and brilliantly thought-provoking. It doesn’t give you just one answer to the question of how to live—it gives you 27 different, conflicting answers!

And then, in true Derek Sivers style, he wraps it all up with one weird conclusion.

The 27 Conflicting Answers on How to Live

1. Be independent – Rely on yourself. Avoid attachments and commitments that restrict your freedom.

2. Commit – Devote yourself fully to a mission, person, or cause. Deep commitments lead to deeper fulfillment.

3. Fill your senses – Chase experiences, indulge in beauty, and live in the present moment.

4. Do nothing – Slow down, embrace stillness, and stop chasing after external validation.

5. Think super long-term – Play the long game. Make decisions based on how they will impact your future self.

6. Interact – Life is about relationships. Prioritize social connections and surround yourself with great people.

7. Don’t die – Prioritize your health, safety, and longevity. Your life’s potential depends on how long you live.

8. Learn – Never stop expanding your knowledge. Read, explore, and develop new skills.

9. Make memories – Life is a collection of moments. Prioritize adventure, travel, and experiences that create lasting memories.

10. Master something – Dedicate yourself to becoming world-class in a skill, art, or profession.

11. Let randomness rule – Say yes to unexpected opportunities and let serendipity shape your life.

12. Pursue pain – Growth comes from discomfort. Lean into challenges, failures, and struggles.

13. Do whatever you want now – Stop waiting for "someday." Do what excites you in the present moment.

14. Be a famous pioneer – Aim to be a leader, innovator, or disruptor. Leave a legacy.

15. Make a million mistakes – The faster you fail, the faster you learn. Success is built on trial and error.

16. Follow the great book – Seek wisdom from religion, philosophy, or historical teachings.

17. Just chill – Don’t overcomplicate life. Relax, enjoy, and go with the flow.

18. Work hard – Hustle, grind, and push yourself beyond your limits to achieve greatness.

19. Live for others – Shift the focus from yourself to service. Make the world a better place.

20. Open your mind – Challenge your beliefs, question assumptions, and embrace new perspectives.

21. Think for yourself – Be a contrarian. Don’t blindly follow trends or societal expectations.

22. Enlighten yourself – Seek spiritual growth, meditation, and self-awareness.

23. Follow the leader – Find a mentor or a proven path and follow it instead of reinventing the wheel.

24. Be a creator – Build things, express yourself, and leave something behind that didn’t exist before.

25. Get rich – Money gives you freedom, security, and options. Make wealth a priority.

26. Love – Prioritize deep relationships, family, and human connection.

27. Matter – Live a life of impact. Make sure what you do actually makes a difference.

And the One Weird Conclusion?

👉 There is no one right way to live.

Each of these 27 principles can be the answer, depending on what season of life you’re in. You might spend years living by one, only to pivot and embrace another.

How How to Live Relates to Living a Bucket List Life

1. There’s no one-size-fits-all formula for a great life. Find what works for YOU.

2. Your priorities will shift over time—and that’s okay.

3. A fulfilled life is about exploring, trying different ways of being, and adapting.

4. At different points, you might focus on independence, mastery, randomness, love, or creation.

5. What matters is that you live intentionally—not just by default.

How to Live isn’t a book with one clear takeaway—and that’s what makes it brilliant. It’s a book to reflect on, revisit, and apply in different ways at different times.

It challenges you to question your beliefs, redefine success, and ultimately, craft your own path.

Highly recommend this one. And who knows? Maybe I’ll get to have that dinner party with Derek one day.

Stay tuned for Book 34 of 52 as I continue this adventure of learning and growth!

#BucketListLife #UltimateChallenge #52Books52Weeks

Are What if there's no single right way to live - only the path that's right for you?

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