Digging Builds Character

I've never heard anyone say, "I like small talk." This is probably because small talk sucks. Bringing up boring things like the weather, talking about sports, or the latest hit HBO show is done because it's easy for other people to relate to, and sharing your Opinions™ about more polarizing things like money, religion, and politics isn't. But mostly, I think small talk is frowned upon because we can't form lasting relationships based on small talk, and we're all just a little bit lonely.

Ok, maybe a lot lonely.


I think the reason most people are lonely nowadays is that we don't know how to connect with people. Not that I'm going to lead everyone through my Masterclass™ on How to Deal with Loneliness By Connecting with Everyone You Meet By Avoiding Small Talk right now, but it seems like a good service to share some reflections on how to deal with being alone.

The obvious solution when being alone is the problem is to be around other people. But this doesn't always work because it's perfectly possible to be surrounded by people and feel more isolated than you've ever felt in your entire life. When we feel lonely, what we crave is a sense of connection.

Small talk has this well-deserved reputation for being too fake, too superficial, and not stimulating enough for good conversation because it prevents us from having deeper connections with people. Small talk is by nature temporary, the kinda quick conversation you'll have with your barista or the weird guy at the party who would charitably be described as "eccentric." Lasting connection occurs when we take the time to nourish our relationship with others: not enough time, and it just becomes an intriguing memory. But as with teleportation, the place also matters: not the right place, and it turns into oversharing.

One of the many annoying things about modern life is that we've built up a highly compartmentalized society. How am I supposed to make deeper connections when I can only talk about work with coworkers, groceries at the farmers market, and books at the book store? None of those places are very suitable for deeper connections because chances are there's not enough time to really get personal.

The opposite view is that compartmentalizing your life can be helpful as you're able to choose what parts of your personality you show off to different sets of people and reveal your deeper heart accordingly. But this sucks because the different parts of our personalities aren't distinct entities; they bleed together and influence each other.

Compartmentalize your life: the slightest bump makes everything fall apart.

Choosing to remain at the small-talk platform may keep our compartments intact (there's no risk of the relationship ending if all you do is further the status quo), but this will inevitably make those relationships fizzle out. Not actively growing a relationship means neglecting it and letting it shrink, just like the roots of a plant shrink when it's not watered.

But how do we grow these roots in the first place? Is there a limit to how deep the roots of a relationship can grow? How much of our inner world do we reveal to the different circles of our life? This is the art of connection, and it's fundamentally a spiritual question.


Spiritual life is primarily marked by connecting internally to yourself, with "yourself" being understood in various traditions as the soul and/or God within. This connection brings out various internal feelings, values, and realizations, like springs of water seeping out of the ground.

These feelings, values, and realizations are the water of our inner world, and the more we dig for it, the more will flow. This water nourishes the roots of our connection with ourselves, and it's naturally going to ground us and keep us stable, just like a tree relies on roots to stay firmly planted. Initially, the water that flows will be murky because all the dirt contaminates it at the surface, but the deeper we dig, the purer the water we'll find. The purer the water, the more easily the roots will grow. But what do we mean by digging?

Digging builds character.

The digging is the work we do to understand who we truly are when everything that is not ourselves (our jobs, our hair, our opinions, etc.) has been stripped away. In essence: who am I?

I should mention here that contemplating this isn't easy! In the early days of the pandemic, it was super popular to summarize everything I've just said by saying something like, "If you can't go outside, go inside!" That hasn't worked for most of us because inside is a dark, dirty, dangerous place we don't particularly enjoy. So here are some tips on how to do that internal excavation:

  • Make a habit of meditating, so you set aside time every day to look inward
  • Journal your emotions, so you can understand that you're not your emotions
  • Be human. It's ok to struggle some days, don't beat yourself up about it.
  • Find some people who already do this work. Talk to them about your reflections and struggles.
  • Read something contemplative and philosophical. Bonus points if you do it regularly.

Remember that there's a time and place to share your reflections on all these things and that not everyone deserves to know your most profound realizations. A good rule of thumb is to only share with the people who value the internal excavation; with the rest, you can talk about the weather.

Happy because I wasn't expecting to make it to week 2 yet here we are,

-Sid