Cultivating Connection: My Quest For Deep Relationships

I used to think relationships were something you maintained. Check in, remember birthdays, show up to social events, call every now and again...There is meaning in doing those things, but they feel more like maintenance, not depth. And as an adult, it felt like close relationships were way harder to keep than they used to be. I felt like something was missing. It felt like I had a lot of friends, but ones that I only connected on a surface level. I knew the big things about my friends: married or not, where they're working, how they feel about work, whether they have kids…I was good at maintenance. But for years, I think I was mediocre at the real thing - real, deep relationships.

Origins of Searching For Deeper Relationships

In my journey to find meaning in sustainability, I've come to the belief that the meaning comes from working on three pillars: health, happiness, and connection.

One of those 3 I've found to be more challenging than the others…connection. I think of connection as a sense of having close relationships with people, place, and yourself. Once I made the realization that my people relationships were not as satisfying or meaningful as I wanted them to be, I decided I needed to develop a new craft: cultivating deep relationships with others.

After all, humans are a social animal: we thrive off of helping others, gaining approval from others, feeling like you're facing and overcoming challenge with others, and plenty of studies have shown how much happiness levels are affected by the number of close relationships you have. You live longer, happier, and healthier with great relationships.

If I could be an expert at cultivating meaningful relationships, I could be a better friend, a better son, a better dad, a better husband, a better employee, and so much more. Is there any other craft that is more worth your time developing?

So I started reading and experimenting - what makes relationships deep? Is there chemistry that predetermines how deep relationships with certain people can be? Is there a secret set of questions that, if asked just right, will make people open up to you and reveal their innermost secrets? (Hint: no, no there is not.) What can I do to ensure I'm providing my relationships with the healthiest soil from which they can grow?

A few things I've learned

“Listen, don't wait to talk.”

The first thing I’ve learned to do is embarrassing in hindsight: I was waiting to talk, not listening. I assumed conversations go “you talk about you, then I talk about me…repeat.” Instead, I've now learned to listen, ignore the voice in my head that says “Oh! Oh! I have a similar experience! I have to share!” and instead push myself to get curious about what they're telling me, and then figure out how to engage by asking questions, or trying to rephrase what they just told me in my own words.

The second critical thing I learned was to recognize what kind of conversation my conversation partner wanted to have. When someone told me “My stupid friend didn't show up to dinner we had planned for weeks! They didn't even call!”, I used to always jump into solution mode: “Oh, well you should have called them before to confirm that they remember.” when they weren't actually looking for a solution, and were seeking understanding and recognition of how they feel. Now I go into every conversation trying to figure out if we're having a social conversation (just catching up, sharing news), an emotional conversation (talking about feelings and wanting to be understood), or a solutions conversation (actually wanting advice on what to do). It makes every interaction far better. Pro tip: if you aren't sure, it's OK to just ask! “Do you want me to give you some advice, or do you just need to vent a bit?” Most people prefer the assertiveness over an automatic assumption that you know what they want.

Third (and this is one I'm still bad at), I had to learn to sit with silence. I have a strong instinct to want to erase any chance of awkwardness and fill every gap in conversation. But most of the good stuff people say comes right after a pause and a lull in the conversation as they process what they are saying. If you jump in to try to kill the awkward silence, you've just told them the pause wasn't safe, and now the conversation can start to feel awkward or uncomfortable. So now I try to let it sit a beat longer than feels natural. It's uncomfortable. But when I can sit with it, it works.

None of this is a formula. I want to be clear about that, because I spent a while looking for one. Maybe the perfect combination of questions and body language and verbal cues would unlock people like a cheat code…But unfortunately, there isn't one. Relationships and communication are messy, full of misunderstandings and missed nuance, and every single person you interact with will have a different set of rules that make it feel “right” for you and them. To this day, I still leave a lot of conversations feeling like I could've been better: maybe I talked about myself too much, maybe I didn't ask enough questions, maybe I jumped into trying to solve their problems when it was clear they didn't want me to provide any. 

I still get into arguments, I still have misunderstandings, and I still hurt people's feelings sometimes. Sometimes I still default to fixing instead of listening. But now I try to notice and be aware of how I'm approaching conversations and be deliberate. Honestly, noticing is most of the job!

Connection for Meaning

This is what I meant, way back at the start, about connection being one of the hardest of the three pillars to work on. Health has a gym and a scale (oversimplifying here for the sake of argument). Happiness, messy as it is, at least mostly depends on you and your mindset. Connection doesn't work that way — you can do everything “right” on paper or according to the books and still get it “wrong,” because the other person is in the room too, with their own version of what "right" looks like. That's probably why it's the one I keep coming back to and working on. It's the pillar that refuses to be solved. 

But the questions I use on myself — what kind of conversation is this, am I actually listening or just waiting, can I sit in this silence without rescuing it — turned out to be the same questions I now ask when I'm coaching someone too. Half of coaching, in my limited experience, isn't giving people answers. It's getting curious enough about someone, and patient enough with their situation, that you help them find the answer themselves, with maybe a little bit of insight from me.

I’m starting to feel like a broken record here…But same question as always: the way you connect with people — your friends, your spouse, your own kids — did you choose that on purpose, or is it just the default you just fell into and never thought much about? I didn't choose mine for years, but I'm choosing it now. And so far, I love where it's taking me.