Deep conversations — will I be doing this when I’m their age? Will I be white?! Lots of questions.

‘Small talk’ is a concept almost everyone is familiar with — it could be with a stranger sitting next to you on an airplane, with a new colleague at a team lunch, or even with people you know well in time-constrained situations.

In sales, it’s easy to game the system around small talk and establishing connection with a prospect. I can shoot the breeze with an older gentleman from the mid-west as well as I could with a young social justice warrior out of San Francisco. Except for the select socially awkward friends we all have, we’re conditioned to read social cues, avoid certain topics, and respond accordingly to co-exist.

My perspective around this has changed a fair amount over the past year, and I want to share my thought process & approach through this post. If you’re looking for a tech / marketing-focused read, this probably isn’t your cup of tea.

Ingrained in leadership

Positions of leadership are acquired through a combination of things — qualifications for the position, passion for the work, etc. Above all, I’ve found that many positions are secured via respect and admiration for the individual — you want to be associated with them, hence it makes sense to put them in a position of leadership where being a follower / subordinate brings a sense of pride.

In my high school days, I was heavily involved in student politics. Voting was obviously a key component of this —being recognized and liked by a wider audience. For students looking to get elected, this meant meeting as many students as possible, and establishing a minimum level of rapport with them that would elicit a vote.

This continued into my college days, where ‘leadership’ positions required a base level of competency but were still largely a popularity contest. Network, build rapport, climb the ladder. This spilled into my social life as well — I found it difficult to spend too much time with one friend / friend group, since I always wondered what the opportunity cost was of doing so.

This made it very difficult to build deeper relationships, since I never knew one person well enough to be vulnerable and share what was really on my mind. It started with ‘How are midterms going’ and transitioned to ‘XYZ sucked at work’. To clarify, I was far from a loner; I had plenty of friends, but the majority were functional — i.e. enjoyable in the context they were made (during work, men’s soccer, etc.).

A generational problem

I’m convinced this is an issue that plagues the younger generation, due to ‘instant communication’ and online connection. I have the illusion of lots of friends (i.e. on Facebook), and even for people I would consider true friends, I have the illusion that I’m up to date on their lives (i.e. their Instagram stories).

What’s the effect of this? For starters, it gives me the impression that I know how someone is doing VS how they’re actually doing. I think this plays strongly into the rise of poor mental health in young people: I.e. ‘yes I know you went to New York City last week, but what was keeping you up while you were there?’ or ‘Congrats on getting into law school, moving across the country will be fun! How’s your relationship with your parents?’.

These are deep questions, and to be fair, I wouldn’t feel comfortable asking them with 95% of the people I know… Is that not a good thing? There’s only so many hours in the day, why not spend them building deeper relationships with the 5% that matter the most to you?

From a different lens: A friend recently told me that he only keeps in touch with (5) friends from college. That shocked me at first, but it made a lot of sense. You’re obligated in certain environments (work, school, etc.) to interact with people and even be ‘functional friends’. It’s only once you leave this environment do you have to reflect on who you want to keep in touch with. Unfortunately, at that point, it’s too late to invest in the relationships you value if you haven’t already.

How I’m changing my behaviour

As the title says, there are two things that I started focusing on in the past year (even less) to develop a stronger support base and deep relationships. I’ll break them both down, in terms of my approach + how I built up to tackling them directly:

Genuine interest

I’m guilty of not letting people finish their sentences. Not in terms of cutting them off (mansplain), but more that I stop giving them my full attention about 60% through and start thinking of my response. This is typical in a ‘networking’ conversation — you want to show the person that you’re listening to them, while also trying to accomplish your own agenda (i.e. feel out for referral if job, or potential client).

My goal in the near future is to eliminate this tendency and focus explicitly on taking a genuine interest in the people I’m chatting with. If they’re boring, and I realized I’m not actually enjoying the conversation, I should either dig deeper or end it. If not, it could yield some very interesting conversations where I learn more about a person + their passions, along with better understand my interests and what I want to discover.

Vulnerability

With genuine conversations comes a deeper sense of connection; strangers become acquaintances and eventually good friends. The second step in this path is to focus on being more vulnerable with people I consider ‘good friends’. How often does someone ask you ‘So what’s new?’ and you immediate jump into a recap of your week? For me, catching up often entailed this, and it made me dread the conversation after 5-10 minutes, even if it was with someone who I would consider a ‘good friend’.

My goal is to increase my level of vulnerability with people who I want to develop deeper connections with. There are a few stages to this that I’m going to try, to help ease myself into this new behaviour:

#1 Starter questions

Switch from starting conversations with ‘What’s up?’ to ‘How are you feeling?’ — this should immediately change the nature of the conversation and skip the formalities / small talk that usually take up the first 5-10 minutes. Shorter interactions will be more fruitful, or spur on future longer conversations that wouldn’t have been had otherwise.

#2 Flow of consciousness

Recently, with people where I’m looking to be more vulnerable with, I’ve stopped worrying about how I articulate a thought or feeling. I.e. instead of saying ‘I’ve been having trouble with XYZ’, I switch to ‘XYZ is tough, here’s how I’m feeling, and what I’m thinking — does that make sense?’ This way, I get them to engage with what I’m going through VS just commenting on it from their perspective. It creates a bond, so you don’t feel like you’re tackling anything alone, with the other person ‘spectating’.

#3 Intentionality

I think in many cases, I’m afraid of vulnerability due to the fact that it might involve placing a burden on someone else, or taking someone else’s burden. A friend goes through a break-up, and the default response is “I’m here if you need to talk”, but I rarely follow up on that. This may be the excessive planner in me coming out, but wrapping up conversations with next steps (either with the person, or on my own) can be helpful.

#4 Cadences

It’s tough to keep in touch with people, so why not plan it out? Building on my obsession with Google Calendar, I’ve started scheduling recurring ‘catch-ups’ with my friends. They can last 30-60 minutes, and range from as often as weekly to monthly. Some are structured, but the majority are open-ended — with the goal of voicing anything that’s on our respective minds. I’ve pushed them back, had conversations earlier than planned, etc. The goal is just to get into the habit.

Conclusion

Life is too short — every interaction should spur feelings, questions, and overall just feel worthwhile. I believe this begins with shrinking your ‘network’ and support base, making it exclusive to people you want to engage with and develop a deeper relationship with. This is followed by being intentional with vulnerability and taking a genuine interest in their respective lives.

This is not to say that networks and acquaintances are not important. A lot of relationships will continue to be functional in the context of work, sports, etc. However, as long as I’m being intentional with the close relationships that I’m fostering, I think I’m on a path to living a good life.

This post was inspired by The Art of Happiness, a gift I received from my friend Steeve, and from starting a 5-Minute Gratitude Journal (adapted), which my friend Kanwar told me about.