A letter to someone on the internet who is getting old and feels lost

I am turning 35 years old soon and I feel like I haven’t achieved much, both personally and professionally. I have held jobs in small and big companies for mostly for 1-2 years each, traveled and lived in different countries, had 2 failed startups, and have about $500k in savings. I am single and haven’t had a serious relationship for many years now.

As time went on, I started feeling less excited about everything, personal or work related. I used to be excited about new technologies, but not these days. I feel like I’ve seen most things before, and it’s all just different iterations of the same. I increasingly wish I could go back to my 20s. Now I feel too old to go to festivals, bars and clubs and make new friends that way.

This has been a recent change for me. When I was ~30 I still considered myself young and able to do anything I could do when I was in my 20s. But not anymore now. I feel like my time for everything is running out. Have you been through a similar thing? How did you deal with it?

– Anonymous Hacker News contributor

I came across this Hacker News submission under the heading “How do you deal with getting old and feeling lost?”

I and many others could relate to the author’s feelings  so I want to share some ancient wisdom that could address these problems in the form of a letter to trendingwaifu, our lost 34-year old HN submitter.


Dear trendingwaifu,

I read your Hacker News submission about getting lost and feeling old.

You may think that the opinionated techish readers of Hacker News have all the answers and maybe some do, but you might be better served by looking for advice in sources of wisdom that have survived the test of time.

In that spirit, I want to share a few pieces of ancient wisdom that have helped (and continue to help) me as a fellow 30-something navigate the same problems you are going through. 

“I feel like I haven’t achieved much”

Achievement is tricky. You’ve actually achieved quite a bit but the thing about achievements is that once you have one, you’ll move on to the next one. 

If a friend tries to comfort you and says, “but you’ve done so much already! You’ve done X, Y, and Z!” You will respond with “Yes but that was a fluke and actually it didn’t really help with my newest important goal and so I’m a failure.”

Hearing a list of your achievements from a friend is nice but doesn’t solve the problem of always feeling like your previous achievements are not enough.

I want to give you some new frameworks for thinking about goals and achievements that I hope can help you navigate this problem.

Who are you?

First, I’d like you to think about “who” it is that wants these worldly achievements.

You may have tried meditating at one point but if you haven’t, try it out.

Breathing meditation asks you to do something simple, to pay attention to the breath.

But this simple task is incredibly difficult. You’ll try to focus on your breath but you’ll end up thinking about chores, your plans for the weekend, your job, your middle school crush. 

Then you remember “oh yea I should be focusing on my breathing” and then the cycle continues.

Do this a few times and you may get the sneaking suspicion that this brain of yours is not really “you” per se, but rather some buggy program that attempts to integrate your experiences into something coherent.

It is at this point that you realize your desire for achievements, professional or otherwise is not some deep seated, immutable part of your character. It’s part of the artificial construct called your ego.

And instead of a coherent personality that stretches back in an unbroken line to a first memory and looks forward to an indefinite future, we discover a self ridden with gaps and ambiguities. Who “I am” appears coherent only because of the monologue we keep repeating, editing, censoring, and embellishing in our heads.

Stephen Batchelor, Buddhism without beliefs

Your ego helps you navigate life but the construct isn’t perfect as you’re finding out. Acknowledging and observing the ego in a detached manner will help you let go of the need for achievements because you realize the “you” that needs achievement is not “real.” 

Your ego is software and you’re not the software.

Let go of results

But you shouldn’t run off into the woods to become a monk. You don’t need to renounce the world and all worldly pursuits once you realize that there is no real “you” to speak of.

What you can do instead is to continue to explore professional pursuits that you find interesting or useful to the world.

But, the trick is to work at these pursuits without worrying about the outcomes.

No, I don’t mean do your work in a stupid way. If you’re not getting results at work and you have some ideas to get results, make the changes.

But you’ll never have 100% control of the outcome of your efforts.

The startups you worked on failed despite your best efforts. I don’t know anything about your startups but from what I know about starting your own business, it is about putting in your best efforts against what you believe the world needs and hoping for the best.

Sometimes that results in success, but more often than not it fails.

The Bhagavad Gita is an ancient Hindu text about a young warrior Arjuna who feels internally conflicted about going to war against his family. Krishna, a Hindu god, gives him advice about handling this complicated situation.

Krishna tells Arjuna that those who are truly free perform their duties in this world without regards to the outcome. They do their work as offerings to the gods, not so that they can get rich or become famous or get a million twitter followers.

They live in freedom who have gone beyond the dualities of life. Competing with no one, they are alike in success and failure and content with whatever comes to them. They are free, without selfish attachments; their minds are fixed in knowledge. They perform all work in the spirit of service, and their karma is dissolved.

– The Bhagavad Gita

I’ve been trying to do this with my own work. Before I write a blog post I light some incense and recite a small prayer to Ganesh (another Hindu god). “Ganesh, I offer my writing in service to you and I ask that you help me continue to perform this work in that spirit.”

I’m not Hindu or religious nor do I really even “believe” in God or gods.

But this little ritual reduces the anxiety of knowing that very few people will ever read my writing. It helps me be okay with the writing simply being an act of service to the universe.

So whatever it is you end up doing next, perform your work in the spirit of service and let go of your attachment to results. It is quite liberating.

“I used to be excited…”

Despite the previous point that you should be detached from the results of your work, I don’t believe you should just randomly choose a pursuit and then try to be detached.

You are in a fortunate position to have options and you should take advantage.

Excitement is for your 20s, meaning is for your 30s

First, you shouldn’t feel bad that the things that excited you in your 20s no longer excite you in your 30s. 

If we swapped out 30s for 70s, you wouldn’t find it weird that a 70 year old is not interested in music festivals and new technology.

You just happen to be at a transition point where you’re searching for “what’s next.”

But, I don’t think excitement is what you need. Excitement about anything can and will fade. What you’re looking for is meaning.

Though I drew on Eastern philosophy when discussing your feelings towards your achievements, I believe good ol’ Western Catholicism has more to offer here.

And don’t worry, I’m not making the case for conversion. I just think Catholicism is smart about navigating your desires.

Pay deep attention

James Martin, a Jesuit priest, writes that everyone will experience a deep emptiness and longing for something “more.” Naturally, as a religious man, he makes the case that this is a longing for God.

Feelings of incompletion may reflect dissatisfaction with our daily lives and point us to something that needs to be rectified. If we are trapped in a miserable job, a dead-end relationship, or an unhealthy family situation, it might be time to think about serious change. Dissatisfaction doesn’t have to be stoically endured; it can lead to a decision, change, and a more fulfilled life. 

Yet no matter how happy our lives are, part of this restlessness never goes away; in fact, it provides a glimpse of our longing for God.

– James Martin, The Jesuit Guide to (Almost) Everything

You don’t need to believe in God to understand the feeling.  But you do need to take this longing seriously, and to do that, you need to pay deep attention to your life.

The Jesuits have a practice called the daily examen. Is is basically a detailed reflection of your day. It is designed to help you look at your day to appreciate the good thing that occurred, reflect on your “sins,” observe where you had opportunities to be more loving and whether you acted on them, ask for forgiveness, and  ask for help to be better.

The beauty of this practice is that it is “spiritual data.” By forcing a deep reflection of your day, you notice the small things that made you feel good, the ways you acted poorly and would like to rectify, and the moments where you felt strong feelings of consolation (yes I want more of this in my life!) or desolation (this is soul sucking and draining).

If you do this on a consistent basis and take action on those observations, over time you’ll create a life that is deeply meaningful to you.

“I am single and haven’t had a serious relationship for many years now.”

I started dating my wife in college, so I don’t have much practical advice to give you here on how to optimize your online dating profile or whatever.

But I do want to point that out that friendships and romantic relationships are cultivated over time. While you meet everyone for the first time somewhere (such as the bars and festivals you mentioned), the more important piece is spending time with those people on a consistent basis AFTER you meet them.

You ever wonder why many people get their friends in school or at work? It’s because they spend so much time with them.

Make time and space for relationships

Judaism takes Shabbat very seriously. It is a day of rest that has quite a few restrictions. Shabbat starts at sunset on Friday and ends at sunset on Saturday.

During that time you are not supposed to do any work, which means you can’t use your phone, conduct business or make purchases, drive, cook, write, etc.

But by subtracting the work and distractions from your life for just 24 hours, you are truly creating time and space to be fully present with others.

Enjoying uninterrupted good conversation with friends for an evening without anyone checking their texts will do wonders to deepen your relationships with them.

I’m not saying you should do Shabbat specifically, but rather, find something that allows you to spend consistent time with others on a regular basis, outside of work.

I’m in a running club that meets once a week and have made friends that way. Running for one to three hours together is an opportunity to cultivate relationships through conversation and in this case, commiseration.

If you joined a club of some sort and then offered to host a regular lunch or happy hour at your home every week or every other week I don’t see how you wouldn’t deepen your existing friendships, make new friends, and perhaps find a romantic partner.

Shabbat thus seems to increase the chances of I-Thou—rather than I-It—encounters with others, when we see them for who they are, rather than what they can do for us. It gives us some time and space to experience the Divinity between us.

– Sarah Hurtwitz, Here All Along: Finding Meaning, Spirituality, and a Deeper Connection to Life — in Judaism

That feeling of connection you’re seeking with friends and a future romantic partner at best can only be kindled at the first encounter; what is most important is that the fire is stoked consistently over a long period of time.

“I feel like my time for everything is running out.”

Everyone’s time is running out. You still have a long time to live (if you avoid riding motorcycles and smoking and such).

But this feeling comes from the false notion that there is some deadline to achieve something and that if you don’t, your life is a failure.

The late Allan Watts, a hippie popularizer of Eastern philosophy, said it best:

For unless one is able to live fully in the present, the future is a hoax. There is no point whatever in making plans for a future which you will never be able to enjoy. When your plans mature, you will still be living for some other future beyond. You will never, never be able to sit back with full contentment and say, “Now, I’ve arrived!” Your entire education has deprived you of this capacity because it was preparing you for the future, instead of showing you how to be alive now.

– Allan Watts, The Book: On The Taboo Against Knowing Who You Are

This is not just some trite piece of advice to live in the moment.

To internalize this insight that the future is a hoax will require serious cycles of study, contemplation, and action.

I wish you all the best.