The Middle Passage

Imagine a cold winter night. Your kids are in deep sleep upstairs in their bedroom. You are sitting under a blanket with your partner sipping wine and watching a movie. Tomorrow is Saturday and there is no school or office. You are in good health, financially well off, have good relationships and no real worries. You have made it.

Isn’t this a beautiful image. Isn’t this image worth striving for? The first time I read this, it stopped me on my track and got me thinking. While I loved this picture, I wondered, ‘What will I do when I wake up the next day? What are my goals? What am I striving to achieve next in life?’ I realized that while a good family and financial freedom are great to have, I will still always need the next goal.

Most of us live the first half of our life following a path specified to us by our elders and the society stereotypes. Kids are told that they have to study and acquire skills. Then get a job and start making money. Then find a partner and get married. Then have kids and raise them. Buy a house. Safe for your future. Our parents and other elders constantly look over our shoulders and monitor our performance on this path and give us constant feedback. However, for most of us, this stops happening at some point. Either parents grow old or we don’t allow them this role anymore. For some of us, the constant striving from one goal to the next one slows down at some point in life. We start to question the value of goals ahead of us and whether they really mean anything. While we still need to get up and go to work, take care of kids and deal with day to day life, the uncertainties of future are gone and life is on a set path. A sort of boredom and directionless-ness starts to set in during his phase. A sense of lacking purpose and lacking excitement. This is often termed as midlife crisis in pop-culture. Midlife crisis happens to a lucky few — those who don’t have to keep their mind busy fighting for survival. It often happens to individuals who are actually able to find relative success in most dimensions of life creating a vacuum of targets.

There is more than lack of purpose behind midlife crisis. There is also the shattering of naivity of thoughts, feelings and relationships. As a kid, we are constantly stimulated through novel experiences. Over time, novelty starts to become rare and by the time we enter midlife crisis, most experiences don’t feel exciting or novel anymore. In early stage of life, it is easy to fight with someone and then go back to playing with them the next day forgetting all about the fight. It is easy to fool ourselves into thinking of summer friendships are bonds as strong as sibling bonds. By midlife, our ego functions are mature creating shield in relationships, we are smarter and thus more easily able to see the flaws in others and independent enough that our expectations from relationships are way higher than what they used to be in early life. This makes it harder to find and maintain deep connections. By this time, the honeymoon phase in our relationship with our partner is over. The one relationship that we had deeply believed to be the answer to every single hole in our life is most likely bogged down by the weight of unreasonable expectations. In fact, many of us are already divorced. By this phase, the realisation of the frailty of own’s body has landed with the signs of chronic diseases, wrinkles and balding.


How do I know all this? It’s because I have been through the journey of my own midlife crisis. It might be foolish and premature of myself to claim that I am out of this crisis, but I definitely feel that I am in a better place than I was when the crisis had started. In the rest of this post, I will share how my thoughts have evolved as I went through the middle passage.

My first and most important learning is that we need to allow ourselves to experience this phase of life. It can be scary and confusing to be in this state, often also be angry at and blaming others for it. However, if we allow ourselves to experience this and try to imagine a better future that awaits us beyond it, we may actually give ourselves a better chance of exiting it successfully and as a better human. For better or for worse, most of us lived the life before this crisis on a pre-set path. In some sense, we were not being ourselves at all — we were merely playing roles that others expected us to play. With most expectations either being fulfilled or having become immaterial, we have the rest of our life ahead to lead being our true self. This journey very well might be about finding who that person is, hidden deep in the layers of roles, personas and expectations.

During my early life, I used to think that there are things that need to be done — a checklist of sort. Education. Career. Money. Relationship. House. Kids. There was a subconscious thinking that once all the things are done, I will get to chill out for the rest of my life. My friends and I used to discuss how it will be cool to be able to retire by the time we are forty. Then we can spend our life travelling, pursuing our hobbies, doing social work, focusing on our health etc.

During midlife, the desire for early retirement was replaced with anxiety of becoming irrelevant. I love travelling — but can I just do that all the time? I don’t think so. I have a lot of hobbies, but they feel good as a way of getting away from my day job. If I had to fill my entire time pursuing hobbies, I am not sure I will find them as fulfilling. When I think of social work and the best way to have an impact on the society, I keep coming back to the things I know I can do well, which, in my case is around technology. My reflections over the last several years have led me to believe that I now feel that I never want to retire. I love my domain. I feel that it provides me with the potential of making the world better — just like with any domain, we can use our skills either to make the world better or make it worse — I strive to work on problems that will help make the world better. Thus, now, I don’t see a reason to really leave it and find something totally unrelated to do to spend my time.

Maybe I am in the set of lucky few, who are in the domain they love. Even if you fall in the bucket where you don’t really love your domain, the answer to what you should do with your time will not come to you if you sit and think — I have done that a lot. I now realise, the only way we will get that answer is by going out and trying different things. Give them enough time to learn the basic skills and go past the initial friction — don’t judge too soon. If you go out there and try different things, your callings will find you. Calling is not about doing things for others — it is about doing things for yourself. When I had enrolled in computer engineering course, I had done that merely based on the recommendations from my seniors. Now I love this field.


While I have a great family, through the midlife, I had started to feel a void of deep friendships. I have thought hard and deep about why it was so easy to build deep connections in the past and not so much now. The big realisation, the obvious realisation — people were the same back then as they are today. Just as selfish, just as flawed. Then what has changed? The thing that has changed is that now we put on masks of egos, we judge and we expect. I have spent a lot of time yearning for connections and yet not finding the time fulfilling when I do hangout with people. One of my mentors told me, if this is happening, it means that you are not looking for connections in the right place. If you look for connections amongst your clones, you are likely to find the ego functions to dominate. I now try to put a more conscious effort in making time to build connections. Given that the bar is now higher than it was when we were younger, a wider net needs to be cast in our attempt of finding connections. I am also spending more time nurturing the old connections that have fizzled out for no reason other than time and distance.


Through my middle passage, for the first time, I started grappling with the idea of end of life. Image of a frail old person who is in constant physical discomfort, who has nothing to do with their time and who is lonely is a scary image. This is not a hypothetical image. I know a lot of seniors living the last phase of their life this way. These were people who were smart, active, connected and respected in their youth. They are on anti-depressants now. Could this be the future for many of us as well?Unhealthy food, improper sleep, stress, frequent parties with alcohol, exposure to plastic and cellular radiations — who knows what their impact will be on us as we grow old. Many people in our generation keep relocating for work and have very few, if any, kids. We are likely to not have strong network of family around us in our old age.

I have started taking extra care of my health now. I do moderate workout regularly. I have adopted healthy and sustainable eating habits. I am consciously changing my mindset to reduce stress at workplace. I now call or meet with my elders frequently with the desire to give them company. When I started doing this, the intention was to give them company. What I realized is that I actually love spending time with them. They love sharing their wisdom and through their conversations, make me feel young. In fact, I realized that if we let them, they can still play that parent role for us which kept us driving through the first half of our life. Engaging with them and seeing them go abot their last phase of life also gives me hope that when its my turn, things will somehow work out for me as they are for them.




I work @Google leading teams on hard data problems. In personal life, I am an armchair philosopher. This blog shares my thoughts and experiences — Ashish Gupta

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Selfish Altruist

Selfish Altruist

I work @Google leading teams on hard data problems. In personal life, I am an armchair philosopher. This blog shares my thoughts and experiences — Ashish Gupta

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