Lifetime friendships and mid-life reinventions

Christian Hernandez
3 min readOct 15, 2023


A long-needed weekend getaway made me realise how little we invest in finding outlets for our vulnerabilities

This post is not about tech, the climate crisis or entrepreneurial advice. It’s about a very personal experience this weekend which made me reflect on friendship (especially the male kind), solitude of careers and midlife reinventions.

First some data: In our modern world of fast paceed careers, child taxi driver on weekends for activities, attempts at trying to be a present partner to our wives, men have lowered the number of “close friends” with a significant increase to “No Close Friends.”

Social norms (or false assumptions about social expectations) also lead to many men (🙋🏻‍♂️) repressing the sharing of emotions, which leads to the already shrinking friendships mentioned above leading to very different levels of emotional engagement even with close friends. (And no, sitting together at a pub or the stadium watching Arsenal and feeling the emotional rush of that late goal against Man City does not count as emotional openness… but it is a cool shared experience).

So, we have less close friendships and those that we do have, we leverage less to share and build our own emotional resilience. My own close friendships (some going back twenty to thirty years) are not helped by the geographic dispersion, time zone differences and fake/real/perceived “busyness”. This is a group that shares a very active WhatsApp group, ocassional calls, ocassional overlapping business trips, but limited continued dialogue with our sometimes very similar lives happening in parallel across time zones.

So, for my birthday this year I decided to change that. We chose the dates and venue (Miami, where several of us had had *many* a fun weekend getaways in our “youth”). I had a secret agenda to forego hitting the SoBe Bars or Coconut Grove Michelin starred restaurants and instead making the space for us to truly catch up on life.

My “hack” was a suggestion that each of us choose and prepare dinner each night and putting an agenda item for each dinner: work, kids, partners. Indian Daal, spicy Ceviche, California-inspired fish tacos served as the convening table fare for what the French would call sous table.

As my wife will attest, and I will confirm, I am not very comfortable in my own head by myself. It turns out, neither are they! But this safe place of comfort allowed us to open up about vulnerabilities, fears, anxieties, concerns that I have not voiced to others…ever!

My reason for sharing is not to celebrate a successful weekend with dear friends, but to call out the challenge many of us face. Regardless of gender, the feeling of not having a trusted peer to speak to exacerbates as you progress through your career. 70% of new CEOs according to HBR feel “loneliness.”

Each of us in Miami this weekend have taken *very* different career paths over the last decades, but we each felt comfort in having started our professional life alongside each other (or at least our University journeys). Some of the challenges were universal, some very specific to each of us. But a trusted friend providing active listening gave us the comfort to share thoughts and emotons in a raw format that none of our peers, colleagues or therapists might naturally hear.


AI gnereated picture given the social media shyness of some in the group :)

I write this post to also call out the vulnerabilities many of us hold and the need to find an outlet. A trip to Miami or a walk in the park might solve the same unlock… but boy did it feel good and boy did I not know I needed it!

(Thankful to my friends who cashed in social capital with their kids and partners to spend the weekend together and thankful to our partners whom well agreed without whom we would not be where we are today in the broader sense. Kids… we all struggled with how the heck to make Screen Time work properly ;)

Flying home surprinsgly rested, peaceful and hopeful and hoping others will be inspired by this to plan their own time with those you trust and love.




Christian Hernandez

Partner at @2150-vc backing technologies that make our world more resilient and sustainable. Salvadoran-born Londoner. YGL of the @wef Father ^3