Friends and Relationships ft Valentin and Cliff

In this episode we chat to Valentin Perez and Cliff Weitzman about friendships, relationships, and the our ideas of the good life.

Some of the highlights from our discussion:

People usually underestimate how easy it is to help friends come to visit who you value the most. If there is something blocking someone, who you really like spending your time with, from coming to visit you, Cliff argues that you should take it upon yourself, as your responsibility, to unblock it so that you can benefit from their presence. Taking the initiative and making the first step will make it happen – otherwise these interactions may slip past very easily.

Junto – together in Spanish – are groups of people brought together to have discussions about matters of particular interest or intellect. Cliff came across this idea in Benjamin Franklin’s autobiography as the American statesman made a junto with the idea of bringing all the most ambitious and intellectual people together at the time and have them sit together once a week and talk about the matters of the world. The ideal size is around 12 to 15 people with only one main rule which is that there is only one single thread of conversation. With the same set of people every week, the junto creates more connections and can build on ideas from previous discussions.

When it comes to stepping outside of our comfort zone, especially with socialising, it needs to be intentional. The more you practice socialising at the boundaries of where you are comfortable, the more you expand the range of your comfort zone. If you don’t practice making yourself uncomfortable in order to make more social connections and interactions, you’re relegating yourself to live a limited life for the rest of your life.

You want to find people who give you energy being around them. A good heuristic for who is a good friend for you is who can you talk to indefinitely and it’s important to recognise that this is different from person to person – it’s based on personality, interests and a host of other factors. When expanding his own network, Cliff discusses how he asks his friends to identify the 5 most exceptional people they know. He says that this puts the ability to define exceptional into the other person’s hands but you always get people who they really value.

Any framing that implies a game of human top trumps can be unsettling and problematic. In life there is no winner – there are a million different categories and we are each running our own race, thus resorting to a game of ‘top trumps’ is a fruitless exercise. Cliff draws on a quote that “you cannot be jealous of someone – if you want to be jealous of someone you have to consider their entire situation, not judge them based on one lane”. Even if you judge them to better than you in all the lanes, you don’t know what is going on behind the scenes in lanes that you cannot even see. The key is not to make a value judgement of that specific person as an individual but rather to consider the interaction effect of the two of us and how that would work.

Whilst we all know that friendships and relationships are the most important things in life, we rarely monitor them as closely as we should. Beyond putting someone’s birthday in our calendar or sending a Christmas card, we don’t treat them with the same level of measurement and management as we would tracking our macros for our physical health, even though relationships are more important.


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Not Overthinking is a podcast about happiness, creativity, and the human condition. We talk about things to help us think, do, and be better. Things like social interaction, lifestyle design, mental models...things that are hard to examine, but important to explore. And hopefully, things that make for a fun and interesting chat every week.

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Ali is a junior doctor and YouTuber working in Cambridge, UK. He makes videos about medicine, technology, productivity and lifestyle design. His links: YouTube, Blog, Newsletter, Instagram

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