Ask HN: I’m Lost. Help?

38 points by lost_founder ↗ HN
Hi HN, long time reader and commenter, using a throwaway for fairly obvious reasons.

Context: Grew up (very) poor, but in a loving family. I’ve been a programmer since I was a kid, went to a top3 CS school, worked at banks, large tech companies, and in the intelligence community for a few years. I founded a company, raised, ran it for about a decade, and sold it just before the pandemic (good timing).

The acquirer was a shitshow, and the two years I was there was a massive mess, especially during the pandemic. The transition from in-office work to remote work was also hard, as I’m definitely an extrovert and missed… people. Granted, remote isn’t the same as “forced to stay home and everything is closed due to the pandemic” but still.

So now it’s been a year since I left the acquirer, and I feel … lost. I was definitely burnt out both by the startup (cofounder issues) and by the acquirer (see earlier description of it being a poorly run shitshow), but I find myself passionless and sad.

I have an incredible wife, great home, etc., and generally am happy with life most of the time, but I’m having really bad trouble figuring out what I want to do, even though seemingly every option is available - starting something, finding a job, etc. I’ve spent this year getting married and then traveling, which was fantastic, and I definitely feel less burnt out - but how do you get to the point where you find a passion again?

Is this something anyone else has faced? It feels hard to talk about with friends because it can come off as bragging; financially, I’m well set, and I love my family / relationship and my friends, so it almost feels unfair for me to be passionless and lacking the desire to do… anything.

How do I get back to who I was, in terms of feeling driven to solve problems and make impact? I feel like I’ve lost who I once was and don’t know how to get it back.

Open to any and all advice, and happy holidays. Thanks for reading my missive. <3

54 comments

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I haven't been so successful like you at business, and faced same situation of lack of passion. I realized that in order to be passionated again, I should try new things. I found new niches like listen audiobooks, hobby rc cars, life optimization, learn new web frameworks... And feeling really passionate about some of them right now. Sometimes you have to be open minded and just try new activities. It helped me a lot.
Helping others seems be something people have found rewarding and motivating for a long time and across cultures. There might be something to it.
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It seems like you've 'made it', so why aren't you taking a step back to gain some perspective and try out things you haven't been able to?

Also, make peace with the fact you won't be able to get a drive similar to your youth due to the amount of responsibilities you have now. I've accepted that, and you're likely financially better off than me.

I am trying to take that step back, actually. I’d never really traveled, so I made that largely my focus this year. That was great.

I guess I’m referring to it from a work perspective; without moving to a different state/country (which is a possibility but my family is all here) I can’t retire where I’m at now given what I have. Moreover, I’m not even sure what “retirement” means; I feel like I’ll have the same feeling I have now, without knowing what drives me.

I guess I’m missing my “drive” or “mission” I once had; is that a thing you lose from youth? I’m 35, so not exactly old, but I’m not 22 anymore either.

34 here, got the same issue you have with the drive I had from my earlier years of an unprofitable project.

One thing I'm trying to do is keep up the consistency with searching for whatever fancies my interest, and let it come naturally as I dive down the rabbit hole on whatever topic I am interested in. Eventually I reach a point where I can see a path to setup something that requires substantial effort and commitment (usually a job or a project). So it's like an interest transforming into a mission and therefore leads to drive. Maybe that's the flow you need.

> How do I get back to who I was, in terms of feeling driven to solve problems and make impact? I feel like I’ve lost who I once was and don’t know how to get it back.

This is an interesting statement. I feel the same, but I wonder how much of the optimism and motivation I had in my 20s was unfounded and naive, stemming from a lack of experience. Having seen stuff play out multiple cycles has made me more pessimistic (realistic?) This makes it harder to become motivated, at least about technology. I guess that's a good thing to some extent, but it's also sad that I can't go back to that old naive self who blissfully worked on stuff without questioning. I think you need to deal with the fact that you can't go back to that old self because you have more knowledge that inhibits the naive optimism.

Maybe try something other than technology? How about working out? Playing an instrument? Art?

Fair point, and very interesting. I did pick up fitness as a hobby, but maybe I need to double down on it… or play more ukulele.

Thanks for the advice.

Maybe a museum. Anything that resonates with you. You get to choose where to go from where you are.
Yeah I felt the same way about 18 months ago. I took a contract gig (hybrid) that pays well, lets me pick up some new skills, but limits me to 40 hours a week, isn't that hard and I'm not emotionally invested since I don't even work for the company.

It's been a nice way to get some space and figure out what I actually want

Has it been helpful? Have you figured anything out?
Yeah, I got some hobbies. Reconnected with old friends. Starting working out and taking care of myself a lot better. I was way too emotionally tied up in my job when I was working for big corporations. I got kind of lucky cause I work with a good group of people and even when we're remote we interact all day long-I do wish we went into the office more though

Nice thing about contracting is the hiring process is a lot more streamlined, and there's no expectation you'll stay for years. So, when you're feeling better, you can move on to a regular job again

I have no advice, but I sure wish I had your problems.
:(

I really don’t intend this as a brag, I promise. I’m also well aware that there are people struggling with much “worse” issues than me; I grew up with a lot of them, lost multiple friends to suicide, and so forth.

But if there’s anything I’ve learned, it’s that depression and/or unhappiness does not care about your wealth.

When I feel that I have climbed to the highest peaks and I now stare into the limitless and desolate void, the choice is now whether or not to rejoice in the dance of life.

Many have walked the same road and many plunge into the abyss of despair. For many others, including myself, it's a landmark or the continual scenery.

For me, I don't believe there was a way back. I think it made me a different person. It was and is great, but I am lonelier than ever despite being surrounded by wonderful friends and family. And that is probably for the best. Lonely is probably not the right word for it.

Why is it for the best? Lonely feels right, even though by all objective measure I’m definitely not.
It sounds like you’re describing loneliness, and objectively you mean aloneness. You can be lonely without being alone.
I have found myself as a new person with a new system of values and new interests and a great new outlook on life, yet the world around me has not yet shifted. It's my imperative to communicate my values with others and find others with common interests, and I either haven't done a good job of doing that, or my values and interests may be incompatible in general with others and society at large (or at least with my current social circle).

I value the existing people and relationships in my life, and that keeps me from changing too much and grounds me in reality and society, which is probably good for me and for society at large. I think that this sort of thing happens to everyone.

Maybe we strain against our harnesses and the web that we're in, and sometimes the web holds fast, or sometimes the network shifts and comes into new, better and more harmonious alignment.

I went through some of what you’re writing about: start-up, acquisition, handcuffs, sabbatical-mode, and now newco.

Feel free to email me, happy to chat it through.

Thank you! Expect an email in the next day or two. <3
help me build my business as an mentor/advisor? Not kidding here.
I invented a product and founded a company and after a similar length of time sold it during the pandemic. It's a wrench. My older child will be leaving home fairly soon. That's also hard to absorb.

I've almost by accident arranged to start a part time research / academic role (PhD student) in January. I can also manage financally. This work will help fix an urgent practical problem in my country and wider.

Am I burning with passion and leaping out of bed each morning? Not yet.

If I took a wrong turn here would it be disaster to change my mind? No.

Give it time. We're both making a big change after many years and I think that amongst other things the supertanker in our heads takes time to change course. It may not be enough, but I think time is necessary.

(Feel free to drop me an email - see my home page - if you wish.)

You don't sound lost, but you do sound bored. Dive into a non work related hobby. If I was rich and married I'd do as much as I can to learn, teach, and collect art. None of us would be able to tell you what is important to you.
Since no-one's mentioned it yet: you should see a therapist, feeling lost like this is an excellent and common reason for therapy. Happy holidays, g'luck.
Do nothing. Binge tv shows. Go on long walks. Hit the gym. Your mind will pull passion out of boredom and restlessness. Lean into it.
10 day (free) vipassana meditation retreats will fix you right up. Don’t get caught up in the dogma though.

dhamma dot org

If you want to have kids, now is the time. Seems like you’re in a great position to do it right and it will almost certainly fill the hole you’re feeling.
Just install Blind and start complaining about your TC
Hahaha thanks, this made me legitimately laugh out loud
Legit, TeamBlind is full of crazies (like myself) but it's a great source of entertainment and ideas. It also gives you a good insight on what's going on in the market, and to see other high achievers also feel the exactly same as the OP; PhDs earning 600k for Google complaining about their work or thinking they need to do a startup, etc...
The men who walked on the moon faced a terrible challenge: what do you do afterwards? Surely, everything else won't stack up to... Ya know. Walking on the moon. (You can read their biographies. It was a struggle for them.) Perhaps you might relate -- successfully selling a business is a significant life achievement. But... What next?

Personally, I've observed a lot of people here at HN invest a significant portion of their lives and significance into their careers and companies they found. But then -- a story similar to yours, their career or company is taken from them, and an existential crisis hits.

Speaking as Christian and an engineer -- Paul made tents for a living, but Paul did not live to make tents. Paul lived to share the gospel, something of eternal significance. I've found, as he has, that this investment is far more worthwhile than anything else I've ever done with engineering. I hope I won't lose my job any time soon. But even if I do, it's not my life's work. The book of Ecclesiastes is a magnificent read in this regard.

Congratulations on your wedding, and sale of your business! I'm sorry to hear the acquisition didn't go as well as it should have. Hoping the best for you in 2023, my DMs are open on Twitter if you want to chat!

Don’t try. It will come if you just follow your whims and don’t commit to anything. You’re not burnt out from programming. You’re burnt out from delivering, which is a totally different and much more demanding framing of the activity. When you have to stay laser focused for so long, it takes its toll. It’s the opportunity costs. You don’t get to do what you want, and your body and mind are not ready to go through that again.

Don’t try. Just do what interests you until it doesn’t anymore. There’s nothing wrong with that.

I think what you're going through right now is a lack of meaning. You had a clear meaning, purpose, and drive when you were working on your startup. All of that gradually dissolved as the startup was acquired, the pandemic started, and you got more isolated from the things you care about doing and the people you care about working with. A messy cofounder relationship doesn't help there, either.

I'm not unfamiliar with this feeling, actually. I've had occasional stints of depression and one of the biggest hallmarks of feeling depressed is a total lack of meaning. Nothing seems interesting. Every idea I come up with feels shallow and lame, or feels like it won't make a difference in the way that I want. If I can actually come up with any ideas at all. You mention a lack of passion as well, but I feel that they kinda feed off each other - finding meaning means finding passion, finding passion means finding meaning, etc.

I say that two emphasize two things.

First, I don't believe your current state of meaningless-ness is permanent. Nor is it impossible to control. It is illusory, and if you work on the root cause, then you will find that you can in fact control how meaningful you find things. Meaningless-ness will fade away. So how do you do that?

Well, second, I suspect you might be mildly depressed. This is not actually too surprising to me, though I can imagine it would be surprising to you since you illustrated a lot in your post about how outwardly good your life looks. It does look good from the outside! But really there is a good deal of change and upheaval there, and it wouldn't surprise me at all if it took you some time to process it.

I would encourage you to go talk to a good therapist. You sound exactly how I sound when I get mildly depressed, and, to put it mildly, therapy is awesome. It's made a big difference in my life. If you are already seeing a therapist, perhaps it's time to switch it up?

Therapy is the high order bit towards resolving this, but there are a number of other smaller hacks you can do. Start an exercise routine (if you don't have one). Spend time with people you care about and who like you (if you aren't already) - I know the pandemic certainly wreaked havoc with my social calendar. Walk outside in nature. There are many more things you might like as well. In my case, it was often unclear to me which activities I actually liked, and it was useful to do things and then study how I felt afterward, to see if I actually liked them or if I was just telling myself I did. (I found out a lot of surprising things this way, like I didn't like some friends, but I was undervaluing others, for instance. I also found that I really liked going outside, even though I never realized this was the case before!)

Anyways, hopefully that helps a bit.

You have lost your appetite after the exit. Exercise, travel, meet new people, have kids, start enjoying your time on this rock and you will find new passion. I doubt you started your business out of despair 10 years ago. Fix despair and your new passion will be readily meet you. Other commenters advise therapist. That’s not a bad advice. I wish you luck on the path.
You have played and won the available finite games, now maybe look for some of the infinite ones?