How to Not Die Alone By Eliminating Self-Sabotage – A Book Summary [Podcast]

This podcast episode dives into the details of what I learned from a book called How to Not Die Alone. The book provides very useful tips and insights about three self-sabotaging tendencies that stop us from succeeding in our love life in the modern world. I believe these tendencies can also be applied to the professional world, with our pursuit of a dream job and following our passion. I explain how you can map these tips to the career world. Hope you find it valuable! I certainly did. I think this book is a little less known than it should be, so I think it’s worth putting this podcast episode out there.

You’ll learn:

  • How modern dating didn’t happen until the 18th century. Arranged marriages for resources was the norm for thousands of years before that.
  • How we’re in another revolution with online dating, and that’s why we’re all so confused.
  • The three tendencies that self-sabotage our success and keep us from getting out there and/or committing.
  • What attachment theory is and how it self-sabotages.
  • Various tips on how to enhance your dating success.


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Will's Personal Development Podcast

Will's Personal Development Podcast

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Book Review

Throughout the podcast episode, I point to the merits of the book and how it’s worth reading. But since this is the book review section, I will focus more on the things I thought could’ve been better. That doesn’t detract from the fact that overall, I found this book to be useful and an enjoyable, actionable read.

Dating advice from women has notoriously been made up of a lot of bad advice based in too much theory and not enough experience. On rare occasion, you can find some gems. The classic example is the most common, terrible advice to be yourself; men throw their hands up in the air in frustration in reaction, complaining that they have been being themselves for years with little success. While good intentioned, the advice focuses on the spirit of how being fake repels women, but fails to account for the fact that you should probably present your best self, not just your normal self, if you want to see a change from your typical, drab results. I, for example, am a slow talker who doesn’t like to mention that much about me in the fear of bragging, but people may conclude that I am boring from that snapshot. Being myself can put me into a disadvantage.

Returning to my main point, this book has generally good advice. It has advice that’s tested with various real life examples. You can tell the author has coached a lot of people successfully. That said, I did notice pockets of advice that missed the mark a bit. She suggests using two factors to decide which events you should go to meet people in real life; these factors are how much you’d enjoy the event and how good the conversations will be there. Just from experience, I knew immediately that she was missing at least one other important factor: how likely it is that the mates you want to meet will go there. For example, I love the gym, board game meetups, card meetups, and nerd/anime/game meetups; but the girl guy ratio there is consistently at least 1.5:1, sometimes 5:1, 10:1, or 1:0. That’s right. Sometimes, there isn’t a woman in sight except for people paid to coordinate the event. You may love Magic the Gathering or Dungeons and Dragons, and that’s totally fine, but not the best strategy for meeting people.

A large portion of the end of the book has various tips themed around giving people more of a chance. Go on that 2nd date before you write them off, keep at it even if they’re a few inches short – identify what’s a real deal breaker and what you think is a dealbreaker that isn’t, don’t look for a “spark” – realize that people grow on you for time, notice the positive traits rather than just the absolute worst about them, be open to a larger age range. This is generally good advice. So many people are quick to judge and write someone off for small things. In reality, if you give them more of a chance, you can be pleasantly surprised. The tip about the age range did give me a flashback to a time when a woman emphatically told me to reduce the age range of people I would be open to dating on my OKcupid profile because she thought it looked strange or too desperate; I suppose there’s conflicting advice everywhere, and it’s a different story if others can see that range.

All that said, I think the book has good intents and generally, a good framework of tips and principles that will help you more than most advice out there. I liked how the book was thoughtful and told you to be careful about trying to date friends. It gave the right tips by saying that you should consider it because of the power of network and people you have known for years, but also how you should bring it up in a playful way and test the waters because you want to be careful of boundaries and risks.

I mention in the podcast that there is no perfect advice out there in this area. There’s just a bunch of people trying to get as close to the truth as possible to help you make better, not perfect, decisions. And this book is more on the mark than most. The book does a great job referencing the psychological, self-sabotaging tendencies we have; not enough people acknowledge or reference the internal, psychological blocks that may be the biggest obstacles to our success. The three tendencies mentioned (maximizers, romanticizers, and hesitaters) have likely never been crystallized and defined in this way, and will surely, help many people who fall into these traps.

The only other piece of feedback I have is that it does seem like a lot of the client examples in the book seem to be people who are generally doing fairly well and just need a few tweaks. The advice may need some changes when you’re dealing with someone who goes to tons of book club events for years and still doesn’t get any dates (I’m referencing a story in the book about a client who had trouble meeting people online, and went to a book club based on advice, to come out of it with several dates).


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By Will Chou

I am the the founder of this site and I am grateful you are here to be part of this awesome community. I help hard-working Asian American Millennials get rich doing work they love.

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