Quora Saturdays: Men leading, books, how to get to know people, and what jobs helps you become an entrepreneur

July 23, 2016 by Joshua
in Quora

Continuing my Saturday series on posting my answers to questions from Quora, here are my next questions answered:

  1. What are the best, most insightful questions to ask to find things out about and know what a person is like?
  2. How often should men be leaders in relationships?
  3. I have been reading a lot but it’s online like Quora and other sources. Is that of less value then actual books?
  4. Have you ever envisioned your life in 10years?
  5. What are the top 10 books of all time?
  6. What’s the best graduate job if your ultimate goal is to be an entrepreneur?

Q: What are the best, most insightful questions to ask to find things out about and know what a person is like?

A: More important than the first question you ask is the follow-up question. The first question, no matter how useful and valuable, will still often get standard responses, what I call cocktail party answers. People feel vulnerable revealing too much about themselves without you sharing something about yourself.

I like to start with “What’s your passion?”, but many of the questions in other responses here will work. They’ll usually indicate what they like but not share too much.

I recommend following up by connecting their passion with a person or two in your life with one or two sentences showing you care, know people like them, and support them. Then ask them to elaborate. The response to the second question will share much more about them.

Bottom line: more important than the question you ask is to make them feel comfortable sharing a potential vulnerability by showing you won’t judge and will support them.


Q: How often should men be leaders in relationships?

A:I assume you mean in an intimate relationship with a woman and not, say, a business relationship, a casual friendship, or any of many other types of relationships

The answer depends on

  • The interests of the man
  • The interests of the woman
  • The needs of the situation calling for leadership

among other things.

For example, if the man loves leading and the woman loves a man to lead, he should probably lead a lot. In a situation calling for skills and experience she has and he lacks, they’ll probably do better with her leading.

The question sounds like it’s looking for a hard and fast rule. Leadership usually benefits from adjusting to the people and needs of the situation more than fixed rules. The problem that needs solving usually determines the solution more than abstract perspectives.


Q: I have been reading a lot but it’s online like Quora and other sources. Is that of less value then actual books?

A: Depends on your goals, what you’re reading online, and what books you’d read. If your goal is to pass the time, anything you enjoy will do. If your goal is to improve your life, books will generally go into more depth. You asked about value, but only you know your values, and only your values determine something’s value to you.

So I would consider what reading is for. To read stories? To learn? To keep up with current events? Online rarely goes into the depth books can, but is more accessible.

A bigger issue is alternatives to either. If you want to develop skills and do things to look back on with satisfaction or pride, you’ll have to do things actively. For example, to play piano or basketball, books will barely get you anywhere. You have to practice. Even to write, as valuable as reading is for writing, you have to write too. It’s easy to read a lot and feel like you’ve accomplished something, but you may look back at it as wasted time, especially click-baity articles.

So you may find that as valuable as reading is, going out and doing things may trump it.


Q: Have you ever envisioned your life in 10years?

A: In college when I chose my classes for a semester I would plan my whole career out to follow.

In graduate school, I would plan until the end of graduate school, maybe four or five years out.

When I started my first business, investors would ask where I saw the business in five years, but I found that it changed more than I could imagine each year so I stopped trying to plan beyond then.

Now, with more experience, I don’t try to envision beyond a few weeks out. I know my values and I have direction, but I think and act more in the moment than ever. I also get more done than ever because of the flexibility it gives me.

Trying to plan farther out for me when I was younger was just youthful inexperience leading to inflexibility and missing opportunities. Living in the moment now is more liberating and productive.


Q: What are the top 10 books of all time?

A: I recommend rethinking your question to be more specific. Books in the abstract don’t have value. They have value for a person for doing something for them.

What do you want that books can help you achieve? When you know and can communicate your interests we can help answer your question. Some possibilities:

  • To entertain you
  • To help you learn about a subject
  • To help you learn how to do something
  • To see beautiful images
  • To connect with others
  • To have something to talk about

It doesn’t make sense for most people to compare War and Peace with How to Win Friends and Influence People even though some people would consider each great. Only your values determine your evaluation.


Q: What’s the best graduate job if your ultimate goal is to be an entrepreneur?

A: I agree with Megan Cox’s answer and will add that I heard that research at Columbia Business School found that of all the factors searched in a study on successful entrepreneurs, the greatest correlation with success was how early they started their first venture.

Sorry I can’t cite the original research, so you may want to verify independently, but I remember that the age of starting the first venture correlated with success more than choice of industry, educational level, amount of funding, and may other possible factors. They didn’t all succeed at that first venture, but starting it led to their ultimate success.

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