Connection and Conversation: The Questions Worth Asking

A few months ago, I stopped going out. I don’t mean out of the house, I mean out socially. Of course I still see my friends regularly, usually in a more intimate setting, but I don’t go to bars or clubs anymore. Why? Because I got bored. Not of meeting new people, or being sociable, or drinking, but of the inane conversations that tend to dominate in social settings, and the lack of real connection between people.

What happened to intellectuals hanging out in bars, discussing the state of the world, lofty philosophical ideas, technological advancements and current trends in literature whilst knocking back the odd shot of absinthe? Is it that the intellectuals of today are all specialists and can only discuss their particular field? That no one reads newspapers anymore (although they’re full of crap nowadays anyway)? Is it simply that the MTV generation doesn’t possess the intellectual capacity to lead meaningful, diverse conversations?

The quality of communication is also an issue. Speaking with someone who is very conscious is a totally different experience to speaking with someone who operates at a lower level of consciousness – I don’t mean in an esoteric way but simply how awake, curious, alive they are. A conversation with someone who is very conscious is characterised by depth, authenticity, focus and deep listening, which makes it highly productive and equally satisfying for both parties.

James Redfield says “We all have a truth inside of us that we must tell. The synchronicity of life is all about becoming clear, knowing what that truth is, watching and taking advantage of the opportunity to express that truth, and knowing how to present it”. In his massively popular book “The Celestine Prophecy”, he maintains that when we meet someone (randomly, not when you go and chat up the hot guy at the bar), there is part of this person’s “truth” which we need to hear at precisely that moment in time. Superficial chitchat will not reveal this.

What happens when you have a highly conscious conversation with someone is that you get to that person’s “truth” very quickly, which means that connection, interaction, integration and synthesis can all happen at much faster pace than during a regular exchange. Imagine if all our conversations were like that? Our individual and collective evolution would be massively accelerated and our connections to others would have a much deeper quality.

Recently I’ve started to feel the pull to get out and mingle again (days getting longer, spring in the air and all that), so I’ve been wondering what I can do to try to have more meaningful encounters with people. I’ve never been good at small talk, mainly because I just don’t see the point – life’s too short and I don’t care what you do, I want to know who you are. So I started making a list of questions with the aim of getting to someone’s core as quickly as possible. Here’s what I’ve got so far:

  1. What are you passionate about?
  2. What are your three most important values?
  3. What drives you in life?
  4. What are the three things that interest you the most?
  5. What is the most important thing to you right now?
  6. If you could do anything, what would you do?

I figured I should probably be the guinea pig for this experiment so here are my answers:

  1. Every single facet of the current paradigm shift (social and individual)
  2. Honesty, humility, gratitude
  3. The knowledge that we can do better
  4. Consciousness, Social Potential, Cocreative Evolution
  5. Defining my purpose and working at becoming financially independent doing work I enjoy
  6. Not sleep. Ever.

I would love to hear your ideas and input!



8 thoughts on “Connection and Conversation: The Questions Worth Asking

  1. In today’s world (and perhaps yesterday’s as well), those types of questions must be asked, directly, and almost as if wrestled from individuals. One would think our age of information access ease would spurn more intellectual debates, but I think it has also brought the age of advertisement ease and too many flashing lights. We’re ADD, not chemically, but culturally. And culturally as well, I think we have recently become more preoccupied and worried with how others view our opinions (but again, yesteryear could have been the same).

    All the same, I effing hate it and empathize highly with what you say you’ve walked through socially. In earnest, I crawl the cyberwordpress space to feed that hunger as is.

    But then again, I guess we should thankful that we are now in age allowing the consideration of personal opinion, depth, and purpose. After all, a little more than a hundred years ago we were just trying to survive (and elsewhere this is still true). Perhaps that is a large part of our frustration.


    1. We’re ADD, not chemically, but culturally – great point there and I do think that overwhelm plays a role. And you’re certainly right about the frustration, I think it’s a really interesting point and one that I keep coming accross – the idea that now that we finally have the luxury of asking ourselves what makes us happy and what our individual purpose is, we have a duty, a responsibility to pursue it.


  2. Inane conversations can also be used by people with depth (people who do possess the intellectual capacity to lead meaningful, diverse conversations) as a gentle ice breaker in order to sense if their counterpart gives them the perception of being worth a highly conscious conversation.

    Regarding the odd shot of absinthe, well, it is odd. Especially in its plural form.


    1. Hi Marcelo, absolutely, but sometimes we miss the opportunity to have an awesome conversation because we are making that judgement based on small talk, appearance, behaviour etc, all of which is only an expression of a tiny part of that person. I feel like maybe we would lose fewer chances if we just went for it and dug right into the deep questions. I have met people who did that before and although it might catch you off guard, if you feel that the person asking is being sincere you open up. And then BAM! Connection and sharing and aliveness :)


  3. I agree with this post on multiple levels. I have driven a lot of my friends bananas over this in the past. Particularly, my declaration that small talks in bars and clubs suck, not gonna do it and being totally okay with it.
    I will have to think about those questions you ask though. Most of the answers have changed over time, in the past, as I have learned more, met more people and understood more.
    Oh yes, sleep is a total waste of time, in my opinion. I joke that I am not sleeping, but just waiting to be awesome again ;)

    Thanks for inspiring these thoughts, Steph.


    1. Haha love that :) And so glad to hear you feel the same (sometime’s I think it’s just me and I’m just missing something fascinating that everyone else somehow gets) It’s wonderful and fascinating that they change over time, imagine if you wrote down your answers every 6 months starting age 10!? What an awesome timeline of your interests and personal development! We are only ever who we are today. I really believe we should ask ourselves these questions daily or at least weekly..after all, they’re the most important things right? If we can’t answer them we’re not really awake. Thank you for your thoughts Amit :)


  4. Hi Steph, I absolutely love this post and it’s so timely for me because deep and meaningful connection with others is what I’m craving right now and I am even in the process of writing a post on this very subject. I thought to advance my connection with you, another like-minded soul, I’d have a go at answering your questions: 1. I’m passionate about my personal growth and being the best that I can be and working with others to do the same. 2. The three most important values to me are honesty, integrity and kindness. 3. What drives me in life is the desire to define and fulfil my purpose and live a life free of regret 4. The three things that interest me the most are people and what makes them tick, theories of personal development and spiritual growth. 5. The most important thing to me right now is connection and how I enhance my connections with others. 6. If I could do anything it would be to overcome the fears that stop me from fulfilling my true purpose and potential. Thank you for such a great post!


    1. Hi Caroline, thank you so much for your lovely comment and your answers, they have made my day! You know what just totally stood out to me is that all of what you wrote in response to the questions really comes accross on your site….which is amazing! Your ‘kindness’ value reminded me of this project I love, – always makes me smile if I’m having a bit of a grey day :) I can’t wait to read your post on it!


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