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Tell HN: Turned 44 today and I'm lost

332 points by 0414throwaway ↗ HN
Been professionally developing since my teens. Was the first person in the history of my university who was both a fulltime student and full time employee. Exceeded in all expectations at every job. Became the founding CTO of a start-up, put my heart and soul into it, and we sold for low 8 figures. Started a second company with some of the same people but directions started to diverge and I left. I moved to a different state for another job. Became a freelancer for a while. One of the guys who was at both start-ups recruited me into his current company with a total comp far exceeding what I asked for. All mortgages, car notes, and credit cards are paid off and our investments are enough for our day-to-day. I’m really only working for the health insurance.

But I've never been more unhappy and lost.

I used to joke that I would be dead by the time I was 40 though stopped because The Wife hated hearing it but I do feel like I have no plan past this point. Being in pandemic lock down during this time hasn't helped. I told my therapist that I feel like I've hit my mid-life crisis, though not your typical one as I'm not going out and buying a muscle car to cruise high schools. I know I'm depressed and have been for the majority of my life. Been in therapy for a while and tried various pills (didn't help), TMS (somewhat helped), and thinking about trying Ketamine.

I feel like I've hit my zenith already and it's just a slow decline from here on out. I’ve been dreading this day because it’s a sad reminder of that.

451 comments

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yuppie_scum
You should go on a nice vacation somewhere. Consider doing some volunteering as well.
fermigier
Peter Drucker has a chapter on this in "Managing Oneself".

In summary:

Second or parallel careers

It’s relatively common for people to pursue second careers after their fist has peaked, or because they want to try and find success in a different area. This is especially true if your first career is in an area that is not the optimal environment for your performance – a second, or parallel career can offer the chance to make a difference somewhere else. A second career also creates options; you are less restricted when you have something else to work on.

Drucker identifies three ways to develop a second career:

- Start one – move from one organization to another, different sizes, different industries, or something else altogether

- Develop a parallel career – something on the side, or a part time job

- Social entrepreneurship – spend less time on the main job, and work on another activity (usually nonprofit)

(Abstract copied from: https://willemharmsen.com/notes/managing-oneself/ ).

codegeek
It seems like you have accomplished a lot and now you are in mid life crisis of what to do next. I would say if you have financial freedom already, why not do some things where you help others like volunteer etc ? I mean serious work and not just a weekend thing. We tend to live for ourselves so much that we sometimes forget we could give back to this world in our own ways. May be that will give your life some meaning ?

I say this because I am myself sometimes feeling lost even though I haven't accomplished as much as you and one thing that puts a smile on my face is when I help someone else, someone who is less privileged than me. I am now trying to find ways to really help others directly (not just donating etc but doing actual work).

quantified
Life is, or can be, about much more than work. You could be at mid-life crisis, it’s real and you’re exactly the right age.

Exercise, make sure your needs (quality time, intellectual engagement, emotional connections, nutritional, family quality) are being addressed. If you’re burnt out, take time for you. As codegeek wrote, consider volunteering. Making a meaningful difference, even small ways, to others is way more important than making bank once you’re adequately set.

If you can live a reasonable quality life without employment for the rest of your days, you’ve hit the lottery. Be totally psyched, and use your freedom. Wish I was in your shoes.

incanus77
When you sold the first company, how did you pick the subject of the second company? Was it an opportunity, or was it something you really loved? Is there something you are really passionate about now? Could be anything… hobby, travel, certain pieces of tech, whatever. Think about it and try lots of things out. Maybe go back to things you enjoyed when you were a kid. In my experience, you need something, or a series of somethings, that really interest you and drive you. They might seem silly. They might seem dumb or done already. See if you can find something that you like to play with. Really play. Go from there.
djohnston
Tangible recommendation, if slightly biased to my own interests: find your local flight school and take your first lesson.
lbriner
None of us live forever but I think for many people, the ultimate hope is to make a difference, to leave the world slightly better than we found it, to invest our skills into progress and removing some of the evil we find around us.

If you can find what you really enjoy doing and turn that into an investment into the planet and its population then you get to arrive at your death bed really believing you did something valuable with your life.

As they say, few people wish to have earned more money or spent more time at work, they wish they invested in people, in communities, into the less fortunate etc.

Good luck. I'm two years older than you and still feeling like some of my best is yet to come!

hluska
I started my forties with a major health crisis and I can relate. If you want to talk to someone, my email is in my profile.

Ultimately though, I had to find other things and live a more balanced life. In my case, my health scare was such that fitness and nutrition became passions. I hope you can find a passion that works for you. It's okay to discover new things, rekindle old hobbies and do things that don't make sense from the outside.

Good luck friend and I'm sorry you're going through this. I can completely relate, it sucks and there is quite literally nothing I can say. :(

JMiao
Did you go through it alone?
Bud
If it helps at all, my 40s were my favorite decade so far. You sound like a person who really has a tremendous amount to offer. You just need to figure out what you want to do and what gives you joy. I am not a magical genius who can figure that out for you, but since you can definitely afford it, I'd agree with the folks who are suggesting a vacation or some kind of volunteer work.

You mention how much of your life you have devoted to your professional development. Perhaps it's time to be selfish and think just about you and your personal development.

I also don't think ketamine, or psilocybin, would be a bad idea. Many people have gotten lasting benefit, and relief from depression, out of those substances. If you do try one of them, do so in a peaceful, controlled setting, with a very trusted person around. And a lot of art materials! ;)

throwawayboise
40s were the worst for me. Marriage fell apart when I was 39, and my 40s are sort of a blur of just getting from one day to the next.
geoffbp
Sorry to be nosey but what was the cause for your marriage falling apart? Just interested, thanks
artemonster
You have to re-evaluate how you measure your self-worth. When all you have done in your life is climbing some imaginary „ladders“ to „success“, then suddenly you will feel empty, if you have no other ladder to climb on.

And why do you think you have hit your zenith? Because you will not be able to redo the success that you have had and climb another ladder? But who have said that you should?

Beware, NO wonder pill or wonder drug will suddenly make your life easier, because (I suppose!) the issue lies with the purpose of life, not with some other biological reason. What is the purpose then? Well, there were a lot of smart people trying to think about this topic, you can start by studying them.

gxs
OP is in therapy, where you learn various techniques to manage whatever specific issues you're encountering.

What the meds do is make it easier to employ those techniques.

So while there is no wonder pill that will solve your issues, in certain cases if used properly they will definitely help.

I say this so that OP isn't discouraged from taking drugs because of comments of this variety that say true happiness comes from within - while it does, there are certainly things (like therapy and medication) that can at least put you on the right path. Like everything else, there can be a lot of trial and error to find the right ones.

artemonster
I see this as a pure existential crisis and for that you don't need medication (IMHO). A lot of personalities tie their self-worth to an external measure (like some sort of "success" or whatever) and that could work for almost your whole goddamn life, heck, people can become aggressively successful, feeding that trait, BUT until this external measure dissipates. In case of OP they have admitted that they won't be able to repeat this mode of success: maybe too old, too tired, whatever. Suddenly, this uncovers the original issue of tying your self-worth or finding your existential purpose in this process of having/doing X. If you are measuring some X, and, objectively X is good, but you measure shit and are unhappy, clearly, the problem lies within the measurement system :)
gxs
Fair enough, but by the same token OP mentioned that he is sure he is depressed.

Depression can get in the way of finding joy in things, even things you once found joy in. This on top of other symptoms that can contribute to OPs feeling of dread so to speak, such as a lack of energy.

In therapy, you learn techniques to learn to manage this, and meds can help with this. They can have a number of different effects, and some can definitely have a positive effect.

Successfully managing symptoms can free up mind space to actually take action to alleviate the issue, such as your proposal to take inventory of what's actually important and carefully reanalyze and reassess how you're measuring success in life.

I'll end this by making sure it's understood that I'm not saying you can find a magic potion that will cure all your woes. Rather, medication is one weapon in the arsenal that can sometimes work successfully.

Anyway, this is all complicated and evaluated on a case by case basis, so I'm glad OP is actually in therapy.

artemonster
I completely agree with you on all points you've said, especially the last one.
nvarsj
I think you hit the nail on the head. A good therapist will point this out as well.

The OP's entire self identity is wrapped up in their career - which explains, also, their great success. It's a common ailment in high pressure, high money industries, and especially common in tech. And now, the inevitable existential crisis when that is over - what now? They spent 20-30 years doing nothing but focusing on their job, and tying their self-worth to external validation.

I think what a therapist would say is to focus on yourself rather than extrinsic rewards. You need to learn to be happy with yourself and not rely on validation of others or society to do that for you. Finding a hobby that gives you a lot of personal satisfaction is one approach.

goatcode
There are probably a lot of parameters to a solution that will work for you. Having had similar periods in my life, while I'm waiting for a resolution I've always found small physical projects that I see through to completion to be a great way to wait. When you complete something, it provides something positive to you, neurologically and thereby emotionally.

It may seem silly, but at least for me, tilling a new garden, building a small physical thing, doing some task that's physically taxing and I can see through has been great while waiting for the end of my larger difficulty. It won't solve all your problems, as implied above, but it could be a good stop gap while you're looking for solutions. Your therapist (or a new one if this one doesn't work out) could provide long-term solutions I'd hope.

You're not alone, friend. You will get there -- I've done it a number of times (though in my case, without the money part figured out; well done in that regard!).

arisAlexis
Existential posts are the majority on reddit r/fatfire, check it out and the answers
Maxburn
Fortunately you are in an excellent position to be able to just stop everything and think long and hard on what will make you happy.

Myself personally and I imagine a lot of other people out there are in the same boat, minus the money to be able to stop and reflect.

Make some changes. Maybe some will be the wrong ones, fine, keep doing it.

jvalencia
One of the hardest lessons I've been learning is that I need to "choose" what I want to be and then do it. When the responsibility fades a bit after hectic decades, it can feel pretty empty. Do you want to become really awesome at DnD, woodcrafting, body building, church service, etc?

Pick 1 or 2 and double down. Choose what you want to become and give yourself a goal rather than inheriting one.

mooreds
First off, sorry to hear this! It sounds like you're really having a tough time.

Second, I think that this search for meaning is not unique to you, nor to modern people. We've been doing this for millennia. Religion, philosophy, stoicism, psychology, they all try to answer the question: how do I live a good life?

I don't know you, but I'll give you the answer that I'd give a friend who came to me with this question.

* Find a therapist who works for you. This may involve trying many different ones. If you try 10 and none work, maybe therapy isn't for you, but having someone who is paid to listen to you can be very helpful. Since you know you have depression, find someone to help you with that (which may involve trialing different medications). This is foundational and none of my other advice will be helpful if you don't do this. This post from a leading VC may prove helpful: https://feld.com/archives/2015/04/bringing-depression-shadow...

* Find something bigger than yourself and your achievements to work for. Sibling comments suggest volunteering, I'd be more specific. What are you interested in? Coding?: volunteer at a school or bootcamp and teach folks to code. History?: volunteer at a museum. The outdoors? volunteer at a park. Commit to the volunteering for at least 6 months and treat it like a job because it will be providing what a job might have done in the past: a firm sense of purpose.

* Find some non-work groups to hang out in. This could be sports clubs, civic groups (Odd Fellows, Elks, Rotary Club, etc), book clubs, etc etc. This regular, non work focused socializing will help give your life some richness. I just saw this video and one thing that stood out to me was how relationships with others can give our lives meaning: https://www.youtube.com/watch?v=r6WZuLKOa6k

greenhorn123
You probably won't like this answer, but most people are lost in one way or another, they just put a brave face on it and pretend that they know what they are doing and why they are doing it. Find some older people to talk to and see how they managed getting through this phase, that will get you a lot further than talking to peers or younger people.
tasuki
> You probably won't like this answer, but most people are lost in one way or another

The alternative is having lots of problems and being in an objectively bad situation. If you're just feeling lost, it means you have solved most of your problems - congrats! I find it never really gets much easier, or much harder.

mostertoaster
Seems like you need to find some higher meaning in your life.

Ultimately at some point do you live for yourself or do you live for someone/something else?

King Solomon was the richest wisest man alive and yet in Ecclesiastes he seems to despair and says everything is meaningless.

hpkuarg
If you don't need to work for money and are able-bodied, go build something with your hands. Buy a remote plot of land and build a cabin. Buy an inner-city plot and build an affordable house that you could rent out at below-market rates. Do Habitat for Humanity. The list is endless.

That's what I would do in your boat.

whiddershins
Do you have kids, and if not, have you considered it?
markus_zhang
I'm far less successful than you but on the same "slow decline" boat.

I still don't know what to do but I sent questions here and on reddit. What I figured out is that I need to find a different set of values that grow, not decline when I grow older, pass 40. I have yet to find anything that fits but hopefully you can find something soon.

Good luck!

jimiray
I've been giving the advice for years that actually planning for what you'll do past retirement is as important than having all the money you'll need. I've seen my parents and in-laws struggle with mental health issues and boredom more than they have ran out of money. I'm refusing to do that, I found 3 things that I really love and working on turning those into third careers go keep myself busy. The 3 things are teaching yoga, personal training for people over 50, and becoming a divemaster.
markus_zhang
Absolutely. I'm reaching 40 this year and people around me always get surprised when I told them I'm making plans for retirement. For most of them planning for retirement is just financial, and many of them do have a solid plan.

But I'm mostly worried about the mental/spiritual part.

whiplash451
In a similar situation as yours. Not a magic pill, but I found a couple reads very useful:

A Guide to the Good Life: The Ancient Art of Stoic Joy, by William B. Irvine

The subtle art of not giving a f*ck, by Mark Manson (the book is a lot more interesting than the title suggests)

troglodynellc
Drop the therapy and start lifting weights. I'm not kidding.

If the problem is that you feel things are gonna be a slow decline from here, then fight it. Make that your new goal, even if you know it to be a losing battle. It will focus your mind on demonstrable milestones like hitting new deadlift personal best.

Even if you do something else, at the very least recognize that you've gotten to the point where you don't need to focus on the "work" and "money" part of life; as such treat this as an opportunity to focus on something new. After all, we only have a limited time on this earth to experience the things you want to do. This crisis is your mind's way of saying "I haven't done something I wished I had done." It isn't bad, it's just cognitive dissonance. Find the root of that dissonance and do that which would resolve the problems keeping you from finding fulfillment. This process will be emotionally painful but also cathartic.

Best of luck; know that every man has it within them to pull through this and come out the other end happy and fulfilled. So long as you are willing to question everything about why you are the way you currently are, you will eventually seek out the truths you need to proceed.

JMiao
Yes, but the thing is, the right therapist might help with the self-reflection you're talking about in paragraph 3. "Therapy" isn't one thing.
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weego
Absolutely never under any circumstances attempt to take people away from their safety net, therapist or otherwise.

You have no understanding of their wider life and concerns, and people asking for big life change help can be surprisingly susceptible to advice.

Trasmatta
Every couple years some new trend pops up that people start claiming will fix everyone's mental health issues. One of the current ones seems to be weight lifting. I have no doubt it can be massively helpful for mental health for a lot of people, but it's awfully condescending and detached from reality when people show up say "lmao drop therapy, all you have to do is pick up heavy things".
NhanH
Does your statement apply to “get therapy” itself?

I’m not trying to be snarky, I’ve seen way more advices on getting therapy rather than start lifting weight. I don’t have an opinion one way or another, but when I read the GP advice, I thought it was the one being unusual rather than common

Trasmatta
If the claim is "just go to therapy once a week and you'll be cured", then I would say yes. Depression is multi faceted and there's no single solution. It would likewise be ridiculous for somebody to say "stop weight lifting, all you need is therapy".
weakfish
Absurd to ever suggest to a stranger that they stop therapy. You don’t know them. Awful, awful thing to do.
throwaway13575
If you do start lifting, I would recommend Starting Strength (Rippetoe). The 3x5 squats, deadlift, press routine got me out of a deep depression. It gave me life. I saw that the mind is supported by the body, and without health the mind is a turmoil.
_Microft
> Drop the therapy

NEVER, EVER, suggest dropping therapy to someone with depression.

svmegatron
Better yet: keep going to therapy and start lifting weights!
blipvert
Woah, toxic masculinity alert!

By all means give weights (or running, cycling, whatever) a go, but stay with the therapy.

Better to listen to professionals rather than some rando on the web.

aarpmcgee
Not sure about the suggestion to "drop the therapy"—if op's current therapy isn't helping so much, a different therapist/approach can make all the difference in the world. It took a lot of time for me to discover that kind of therapy worked best for me, and it also took some determination for me to find a therapist with whom I could really connect. My current therapist has helped me so much.
getlawgdon
Terrible suggestion. Full stop. OP: Do not stop therapy.
vvvcccvvv
No no no. Never tell someone you do not know to stop going to therapy. Please be careful
jawerty
Ignore the other commenters this is good advice to give a man in a tough spot. If you find it yourself you'll be stronger. That's it. Life is tough and not fair, sometimes the people you rely on won't be there. The less dependent you are on others to get yourself out of a hole the better off you are.
howmayiannoyyou
Not reading that you have kids. If not, that can redirect focus off yourself to something more worthy IF you can maintain SOS as a parent:

S = Selflessness.

0 = Objectivity.

S = Self-awareness.

We tend to feel lost when were aren't challenged or we're hyper focused on ourselves. We tend to feel a level of contentment when we are helping/mentoring others, interacting socially in a positive way, or learning.

Hope that helps.

throwawayboise
44 is pretty old to start having kids, IMO, and I would not advise having kids as a way to try to fix your own mental health at any age.
photochemsyn
Finding something new to strive for is not a bad idea, but it should be orthogonal to your past interests. Something you have to come in at a relative beginner level. Of course you're never going to be as good at it as people who've been doing it for 20 years plus, but that's OK. Think more in terms of self-development rather than winning a competition with others. I've had some limited success in regaining a positive outlook by diving into programming and networking at a similar age over the past few years, coming from a background of academic benchtop lab researcher who never wrote a line of code (maybe an Excel macro) before.

For a chuckle about the inevitable decline as we age, see this quote from Trainspotting:

https://www.quotes.net/mquote/1200371

u2077
It seems like you have experienced a lot and that the field you are passionate about has nothing left to offer. Just because you’ve reached the top and there’s nowhere left to go, doesn’t mean that there aren’t thousands of interesting opportunities elsewhere. I would love to say that traveling and doing all these new things would be helpful, but at the same time, chasing a checklist will just leave you unsatisfied. Maybe move somewhere else? Meet different people? Live slow and relax?

Other people can give you their advice, but you know yourself best.