Restoring Connection, vol. VI: Connection to Others
Volume VI of a nine-volume series on restoring connection in our world (and the 3rd of 3 posts on connecting with others)
This is the sixth in a nine-part mini-series about restoring connection in our world and why and how disconnection is at the heart of so many of the grand issues of our time. If you haven’t already, check out the series introduction and table of contents.
NOTE: this topic (connecting with others) is such an important one that I’ve split it into 3 parts. This is part 3, covering connection skills and practices; click here for part 1 (understanding your connection style) and click here for part 2 (the 3 ingredients of deep connection).
In these dog days of winter in Canada, when the light gets low and forlorn, it can become an innate reflex to shutter in and turn inward; spending time with others isn’t as easy as it might be in the warmer months, when sitting on a blanket in the park feels like a perfect way to spend an afternoon.
In some ways, this is a natural response to the season, mimicking nature’s turn towards dormancy and stillness. Yet connection with others is such an integral part of our well-being, hardwired into us after hundreds of thousands of years of reliance upon each other for survival.
In these months - already challenging for our mental well-being for a variety of factors, including sunlight/vitamin-D deficiency and the fact that it’s so damn cold most of the time - it becomes all the more critical that we bring intentionality to our relational lives.
Which is why I felt so fortunate to have someone else bring that intentionality to a dinner I attended a couple of weeks ago.
The dinner was hosted by the lovely Amanda Kwok and consisted of a roughly equal mix of people I know and people I’d not met yet.
What made the dinner so particularly gratifying and nourishing was the intention, depth, and care that our host put into it. For 3+ hours, among multiple dinner courses, we shared intimate, inspiring, thought-provoking conversation and vulnerable details about our lives. I left the evening feeling nourished and grateful.
A few days after the dinner, Amanda sent me this screenshot on Whatsapp (we both share a love and passion for human connection):
This is an HRV reading that one of the participants sent to Amanda the next day. Heart Rate Variability, or HRV, is a loose measure of overall health; as the Cleveland Clinic states, “in general, low heart rate variability is considered a sign of current or future health problems because it shows your body is less resilient and struggles to handle changing situations.” High HRV ratings thus translate to better health.
Along with the screenshot came this text:
Adrian posted this the day after the dinner and Dan just told me "I have been feeding all week from last Sunday. So so enjoyed the experience on many levels. My HRV reading that sleep was the highest since Bhutan*.”
(*For context, Amanda, Adrian and Dan all joined me at my Wayfinders event in Bhutan in October 2022).
With Amanda’s permission, I’ll break down some of the elements that made this such a special dinner:
Intention: This wasn’t just any old excuse to get a few friends together over drinks. Amanda put thought and care into making this a curated and facilitated experience, with the express purpose of creating an opportunity for people to meaningfully connect. In her words, this was to be ‘an intimate dinner gathering with some of my favourite people in Toronto focused on the topic of community and belonging - what brings us together, what holds us back, how to foster more.’
A theme: As referenced above, the theme of the evening was ‘community and belonging’. This formed an anchor point for our discussions, as well as the reflections she invited of us prior to the dinner (“Come to dinner with a question related to community + belonging - something you are curious about or struggling with. Nothing is off-limits.”
Curated connection & conversation (1): The day before dinner, Amanda asked me to share something unique about myself that others might now know about me.
Upon arrival at dinner, we were asked to take a piece of paper from a bowl (the bowl contained our collective answers to the above question) and then try and find the person described on the paper.
This made for some interesting conversation right off the bat, and also cultivated curiosity, something I described in last week’s post as one of the 3 primary ingredients that make up deep connection. (For context, my unique fact was that I used to be in a band that toured around North America and Europe).Curated conversation (2): With the exception of about 15 or 20 minutes prior to our first course, the rest of the evening consisted of a rich conversation that engaged the entire table. Instead of having 5 or 6 different one-to-one conversations that may have stayed at a small-talk level the entire night, we had a deep and engaging 11-person conversation around the above-mentioned topic of community and belonging.
Each person had reflected on Amanda’s invitation (“Come to dinner with a question related to community + belonging”) and had brought a question. We then took turns discussing each person’s question. It was the first time I’d been involved with such a large table conversation; it opened up a space for vulnerability, curiosity, and even personal exploration.Followup: The day after the dinner, Amanda sent an email to the whole group (she had asked our permission), inviting us to connect with each other if we felt called to do so. It was an opening and an invitation - to people who might otherwise be shy about reaching out to others - to deepen a connection that might have been forged at the dinner.
As someone who also feels called to foster more human connection in the world (which is why I’m publishing these emails and why I do the work that I do with Wayfinders), I appreciated the skill and care that she put into this dinner - so much so that I’ve invited Amanda to contribute her skills and passion to the new membership program and community I’m launching for Wayfinders (if you’re an entrepreneur, I encourage you to join our wonderful community)
I share this experience with you as an illustration of what can happen when intention meets action meets a desire for connection.
Nourishing, meaningful human connection takes intention, and it takes effort and commitment.
With all my heart and soul, I wish that more of us lived in contexts, neighbourhoods, and societies where this type of human connection didn’t require so much effort. I believe we are slowly starting to recognize the extent of how disconnected we’ve become and I believe there will come a day when we return to our natural state of living communally, deeply and nourishingly intertwined with each other’s lives.
For now, and for most of us, however, intentional effort is required. We don’t always have to go to the lengths Amanda went to in order to create an opportunity for meaningful connection, but neither can we leave our relational lives to chance.
Too often we end up seeking connection wherever we can find it, often disappointed that the time we spend - often with people that are easy to meet out of convenience or proximity - feels hollow or forced. We long for the sorts of connection that nourish and replenish us, with people that make us feel seen and heard.
Don’t just take my word for it - how about the world’s longest study on human happiness?
Since 1938, the Harvard Study of Adult Development has been investigating what makes people flourish. After starting with 724 participants—boys from disadvantaged and troubled families in Boston, and Harvard undergraduates—the study incorporated the spouses of the original men and, more recently, more than 1,300 descendants of the initial group. It’s the longest in-depth longitudinal study on human life ever done, and it’s brought us to a simple and profound conclusion: Good relationships lead to health and happiness. The trick is that those relationships must be nurtured.
Have I convinced you yet of the value of spending time on our relationships?
If we’re in agreement, then below are a few practical tips for living a more connected life.
Make Connection A Priority
There is a saying that to know someone’s priorities, look at their calendar. How you plan your days is how you live your life, and your calendar is a reflection of your priorities.
I know many people who lament the lack of connection in their lives, yet when I ask if they make connection a priority they often sheepishly admit that they don’t.
I’ve come to understand, many years later than I should have, that my relationships are like plants that need continual nourishment and attention, and cannot be taken for granted.
I have several decades-old friendships of the sort where we can easily pick up where we left off after years apart, but those too are in need of attention; in the busyness of life, it’s easy to forget about certain people I care about and find that years have passed, when both of us feel that more frequent contact - if even a quick phone call - would nourish us both.
With this in mind, and with the understanding (both theoretical and visceral) that my relationships are critical to my well-being, I have made human connection a priority by putting it on my calendar.
Every day, at 9:00 am, whenever possible, I have half an hour set aside as ‘Connection Time’. This doesn’t necessarily mean I use that time for connecting with the people in my life (although it sometimes does); often it means that I use that time to plan out time spent investing in relationships and connecting with other people.
This takes many forms:
Sending a text message (often an audio message) to a friend, letting them know I’m thinking of them and asking how they are doing
Sending an invitation to someone to connect in the future, either over a phone call, a coffee, a lunch, etc.
Scheduling a get-together (such as a dinner - see below) and sending out invitations
Random phone calls to friends (these days I have to be more selective about this approach, with a ‘don’t call me unsolicited’ culture that has taken root)
I also have time set aside in my calendar for coffee ‘dates’ as well as lunches. All of this ensures that I keep connections and relationships a priority in my life.
Bringing Efficiency to Human Connection
As I’ve said, it takes effort and work to live a connected life. That doesn’t mean that the work has to be hard. A little effort up front can make the work easier. Here’s how I’ve brought technology and efficiency into the mix:
A database: I use Airtable to keep track of a database of people that I want to stay in touch with, generally people with whom I enjoy spending time and in whose presence I feel good. I then assign a rating to the level of our connection, with then informs how often I want to see that person.
As crude as that may sound, we all - whether consciously or subconsciously - assign these levels to the people in our levels, using labels such as acquaintance, friend, inner circle, bestie, etc. I simply take an implicit internal process and make it explicit. I also recognize where I might want to deepen a connection that is shallow and again bring intention to that desire.A scheduling tool: I’ve automated the scheduling process by using scheduling software (in my case, Mixmax) to set aside certain times and days of the week in my calendar for coffees, lunches and calls.
For example, Wednesday and Friday morning are set aside for coffees. Friday afternoons are when I am available for lunches. I also have a few windows for calls available.An invite: I then send emails out to people I want to connect with, and send them a link to book whichever one of these is most feasible for them (call, coffee or lunch), along with an invitation to suggest other times/dates if needed. Most of the time this helps us avoid having to go back and forth to find a time to meet.
A tracking system: After we meet, I update my database so that I know when the last time we met was. This helps me ensure I’m not letting too much time elapse in between get-togethers.
An assistant: To make the process even more efficient, I’ll be handing off this work to my assistant, along with a few specs and guidelines. This allows me to focus more of my time on what I want to do (meet and spend time with people I love and care for) and less of my time on the admin work to make that happen.
If that all sounds a little mechanical and calculated, well… it is. I wished I lived in a rainbow world where I rode unicorns on the beach with my friends all day and we ate around a big communal table every evening, but the reality of it is that I live in a city of 6 million people with very little chance of consistently running into the people I want to spend time with. I have to put intention and effort into maintaining my relationships - and if I’m going to do that I’d rather put the effort into the actual time we spend together and the presence I can give them, rather than the admin work of making it happen.
So if we know each other and you get an email from my assistant next month asking if you want to get together with me for a coffee, rather than bristling please remind yourself that I’m not leaving our relationship to chance and I’m prioritizing my time with you rather than the multiple emails or phone calls we might have to invest in to hang out.
(NOTE: I don’t use this system to manage my entire social life. There are close friends, and neighborhood friends, whom I am in frequent contact with and our plans are of a more ad-hoc nature.)
The Connected Meal
Back to the dinner theme.
In my experience, meals - especially dinners, that generally allow more time and space than lunches or breakfasts - are one of the most effective and natural ways to foster and deepen connections among people.
At my Wayfinders events, and other dinners I have hosted, I put a lot of thought and attention into my dinners, first via the seating arrangements and secondly via the guidance of the dinner conversation.
I often provide that guidance via questions or exercises that are surreptitiously hidden behind their name cards.
Armed with the understanding and knowledge that vulnerability is a critical ingredient for human connection, these questions and exercises invite guests to a deeper level of vulnerability and sharing than they might otherwise bring to a meal.
At my events I also look at the weeklong series of dinners through the lens of a narrative arc, building up to a peak over the course of a weeklong event by gradually increasing the vulnerability quotient of the questions and exercises that I invite my guests into.
Toward the end, having established a deeper level of personal safety and trust, many of my guests share, with people who a week earlier were complete strangers, aspects of their lives they may have shared with no one else. This level of vulnerability and authenticity establishes incredibly deep bonds among people.
You can use these same principles intentionally and with care, to nurture deeper connections among the people in your life (in the process deepening your own connections with them).
You can use intentional meals - or even shorter gatherings such as a coffee get-together - to deepen some of your existing relationships or to foster relationships with people whom you’d like to get to know (or a mix of both). I’ve hosted intentional dinners with people who were already good friends and with people who were complete strangers. The end result is always a deeper connection with those people.
When you provide guidance, via skillful invitation such as Amanda did, for the flow of conversation you invite your guests to a deeper level of vulnerability than they might otherwise bring to a dinner conversation. When done well and with care, they will accept your invitation and meet you at that deeper level.
Left on their own, people will generally default to surface-level conversations about work or weather - especially if they don’t know the other people at the table - and you will miss an opportunity to create those deeper connections that arise from authenticity and vulnerability.
A few tips for hosting memorable connection-focused meals:
Table size: Four (or five if you have a round dining table) is an ideal number of guests, including yourself. With four guests you can easily keep a group conversation going all night. With 6 people or more, there is more potential - unless you are very intentional about your facilitation - for the conversation to drift toward paired conversations, which may steer back toward surface-level discussions that don’t serve your intention of deep connection.
I like to host multiple-course dinners (e.g. 3 courses or more). This gives me an opportunity to pair each course with a question or exercise, providing an organic ‘container’ and start/end point around each question/exercise. This allows you to explore different aspects of each other over the course of a night.
If you’re doing it at home… you don’t have to do all the cooking! If you’re not used to cooking meals for others (or yourself), then host a potluck. This is a great opportunity to use the dishes themselves as a means of connection. Ask people to bring a dish that has personal meaning for them: this could be a dish their parents made frequently when they were growing up, a dish that carries cultural significance, or even a dish that is attached to a specific story. When it comes time to eat, ask everyone to tell a short story about their dish and why it’s meaningful to them. Stories are the window to the soul!
Build your questions and exercises gradually. Start slow and easy, inviting your guests into the shallow end of the pool first before you invite them into the deep end. It’s incredible what you can get people to share if you take a gradual approach, one step at a time toward the deep end - for instance, starting with a question such as ‘What was your most memorable travel experience?’ and building toward a deeper question such as ‘What was one of the most difficult periods of your life and how does it impact you today?’
How you time the flow of questions is important: you don’t want to interrupt a meaningful conversation that has everyone engaged just so you can transition to the next question or exercise; likewise, you don’t want to let an awkward or strained conversation go on too long. Look for opportunities to transition to the next question and then gently interject (‘So, should we try another question? ___, what’s on your card?’). Of course, if you follow my advice above about doing multi-course meals such as tapas, then the courses can dictate the flow of the evening and the dialogue.
If you’re not quite ready to take on hosting a full dinner, or you don’t have the right setup at home for this, consider hosting a coffee or tea gathering. The same principles apply, only you are serving coffee/tea - and maybe a few snacks - and the event duration will probably be shorter.
Creating an opening and an opportunity for people to connect deeply and meaningfully can feel awkward and scary at first, as if you are doing something a little bit dangerous (you are, and that’s the point).
In my experience, most people are starved for genuine human connection, and will accept the invitation to vulnerability because they understand intuitively that it creates an opening for connection - and they’re tired AF of small talk.
Although I’ve used my dinners and other events to connect with people I may not know well and would like to get to know better, you can of course also use short gatherings such as these as an opportunity to foster deeper connections with people you already know. An intimate story or two, that you have shared with friends over a warm meal together, can often form a repeating point of connection and set a new bar for how you will relate in the future.
That is, in essence, the power of a well-executed, intentional dinner: it permanently establishes a new level of connection between the participants. Now you and your guests may feel more comfortable asking each other for help; you may feel more inclined to support each other during difficult times; you may simply establish that you value a connection more than you did previously, and want to keep nurturing it.
I don’t want to overstate what can be achieved over the course of one meal, and it’s possible for attempts at connection and vulnerability to fall flat; I have, however, seen what conversations over just one dinner can achieve. And, of course, you can make get-togethers such as these a regular, ongoing occurrence, deepening bonds over time. Just make sure you bring the same intentionality to each of your get-togethers.
Ask For Help
In North America and much of the western world, we’ve turned help into a pejorative four-letter word; a cult and culture of individualism have taken root that glorifies the rugged individualist.
If we are to restore a culture of connection in our world, a big piece of the puzzle is to remember that we humans have relied on each other for hundreds of thousands of years.
Most of us no longer need to live in 150-person tribes to ensure our basic survival, yet we still need each other. We need each other to live full and nourishing lives, and the research shows it.
The rugged loner, on his own against the elements, may make for a great cigarette ad, but he’s a terrible role model to follow. That cowboy is lonely and sad and will probably die of cancer and loneliness.
Asking for help, in contrast, can be a deeply flattering and connective act.
Last night, a friend reached out to me to ask if I could meet up for coffee and help him with a problem that he’d been wrestling with. I met up with him this morning and we had a wonderful talk. I asked a few probing questions to help him get some clarity on the problem - a problem that was causing him to lose significant sleep - and in the act of speaking and listening, I felt our connection deepen.
Our friendship has reached a point where he feels comfortable asking me for help, yet for most people, this is a struggle. It requires a certain level of vulnerability, a willingness to say “I’m not OK” or simply “I could use some help.”
Coupled with that reluctance to admit that we’re not OK is a somewhat-guilty feeling of imposing on another when we ask them for help. From my perspective, however, I felt honoured that my friend valued the depth of our connection enough to ask me for help and show his vulnerability. It told me that he valued our friendship enough to reach out to me in a time of need. Far from imposing on me, he offered me a gift: the opportunity to help a friend, an act of giving that studies show increased both the giver's and receiver’s well-being.
For much of human history, this ‘gift economy’ of helping each other out formed the basis of our relationships and our relational lives.
It’s time we recognized helping each other out for what it is: a gift and a basis for connection.
In short
A quick recap before I close off this lengthy post (I’m very passionate about this topic and once I start it’s hard to stop):
Nurturing and deepening connections with the people in your life takes intentional effort: you can’t take your relationships or your relational life for granted
Getting intentional means setting aside time for relationships
Developing some structure around your social life can reap huge dividends
Dinners and meals are a great way to build and nurture relationships
Be intentional about your meals
Get comfortable asking for help; by doing so you are offering a gift to others
This concludes this 3-part treatise on Connecting With Others. I have so much more to say about this topic, and so many more tips and strategies I’ll share, so if you appreciate my words, please subscribe if you’re not already a subscriber.
In next week’s post, I’ll write about another important part of the Restoring Connection recipe: Connection to the Natural World.
If you’re an entrepreneur and are looking to connect with other amazing entrepreneurs and humans, have a look at my new Wayfinders membership community. We launch in March with a slate of exciting events, get-togethers, workshops, and more.