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Comment by buf | Hacker News Reader

I moved to SF in 2008 as a poor college grad. Since then, I've spent all of my time in startups. It's an unhealthy addiction and it's going to kill me.

I was the third engineer at Eventbrite, and I spent years working many extra hours. After 4 years, it felt like I worked 10 years.

I quit and moved to Europe to try to leave the startup scene, but a month later, I found myself the CTO of a startup in London. The addiction continued. Eventually I found myself back in SF. I'm on my 3rd CTO role now. We're about to raise a series B.

More than I'd like to admit, I want to stop this madness and just enjoy life. Hang out with my family. Perhaps move to Denver or Austin to maintain some semblance of tech life, but get out of the madness. I've been looking at houses in Denver for over a year. And it depresses me.

I know that it can't happen. I know that I'll be working like this until my health prohibits me.

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There's a term for this called "revealed preferences." If you keep saying "I wish I could work sane hours" but actually keep making decisions to work insane hours, chances are you actually really just want to work insane hours.

I spent a lot of time being confused by this, listening to perfectly healthy young people with good paying jobs and no attachments telling me "I wish I could just drop everything and go traveling for months on end like you do" and then just sort of trailing off. "But You Can!!!" I always wanted to shout back. You just don't actually want to do that. Or you would. What that person really wanted was what they had: a stable comfortable job and a nice car and apartment, practicing for the day when they had a wife, kids, lease & mortgage to solidify that reality of "can't go traveling". Sounds pretty comfy, actually. If only they could come to grips with what they wanted and be happy with it.

It might be worth stepping back and looking at what you actually want. You just might find it's what you already have.

These people may also be stuck in a local optimum, though. There are plenty of examples of people that finally do drop everything and go traveling or make some other deep change in their life, and end up much happier. But making that kind of decisions is not easy.

"Revealed preferences" used to be called "unconscious compulsions."

The phrasing is revealing, because "revealed preferences" suggests that your actions are somehow in alignment with your true core values, while "unconscious compulsions" suggests that your actions are destructive to your true core values, and you could consider doing some psychological work to realign them.

Psychology suggests the latter view is more realistic, especially if you're not getting any genuine fulfilment from a situation.

It also suggests that unconscious compulsions can be the result of external influences, particularly in childhood, and may not be true preferences at all.

People can want more than just one thing. It might be fairer to say that they want all the things they say they want. But they want this other thing the most, and since this other thing isn't compatible with the others (can't travel the world and also be CTO) it wins.

I think that's fun to say but isn't really. The reason people don't drop everything and travel is not because they really don't want to, they have other fears and obligations. Perhaps some of those fears are not as justified as the person thinks and perhaps the barriers are more illusory than the person thinks but I don't think it is that really just prefer working for "The Man."

There is a danger to armchair psychological terms but it is extraordinarily fun to use them. :)

Similar story here, been doing the crazy startup founder hours for half a decade now, haven't really lived much outside of the office in that time. Feeling also trapped: if I drop out, then I'm somewhat giving up on all of the people who over the years I had to convince to join me in a vision that I'm becoming tired of. It'd very likely lead to the collapse of a source of fulfillment, purpose and income for many people, but at the same time I suppose I have only one life and don't have to be a martyr.

What's something someone with a strong entrepreneurial, technical and managerial background (and very good pedigree) can do for maybe 20 hours a week and still pay the bills? I would love to drop out of the race for a few years and smell the roses.

> What's something someone with a strong entrepreneurial, technical and managerial background (and very good pedigree) can do for maybe 20 hours a week and still pay the bills? I would love to drop out of the race for a few years and smell the roses.

Consulting. Small business. Almost anything really.

How hard is it to make some $5k per month if you have a skill that you can charge $100+/hour for! About a week and a half of work per month.

Plus taxes.

What's something someone with a strong entrepreneurial, technical and managerial background can do for maybe 20 hours a week?

Exactly what you're doing now. But only 20 hours a week of it.

You can spend today having the talks you need to have to make this happen, then start your first sane work week tomorrow.

There's a documentary ("Some kind of monster") on Metallica's creative process for the St Anger album. It shows James Hetfield (arguably the band's leader) wanting to have a more balanced schedule, and adapting the band's process to fit to it. The result was a very mediocre album.

All else being equal, you should consider stopping the madness, it will probably better for everyone long term than more and more years on the same path.

Of course it could happen - there's nothing inherent that keeps you from downshifting and enjoying your life more. Even if you're truly addicted to work, addictions can be beaten.

I have to admit I find articles like this completely perplexing. As soon as I achieved a little bit of professional success, I dropped full-time work like a hot rock, and I don't miss it at all.

What do you do now? Part time contracting?

I'm at a place where I don't really need to work full time either, but I haven't figured out a plan for getting out of it.

Would also love to hear the answer to this.

Not the GP, but I took a bunch of time off work, traveled with my wife for a while and then hacked on fun things until I found one I could make into a product. I'm now living off a bootstrapped product, and I couldn't be happier.

Ditto here but it took me a lot longer than I expected it would.

How did you escape the cycle? Or are you living off of a big exit?

The vast, vast majority of people cannot simply "drop" full-time work. If I dropped full-time work, I'd have to move myself any my family away from the Bay Area, where all our connections and friends are. That's kind of an unacceptable lifestyle change for my family.

I was like that and it did catch up with me when I was doing that for around 11 years. I still work in startups but no longer the crazy hours and to my continued surprise: we get everything done still while no one works crazy hours.

It's 2016 and I feel like I'm going to become like this. I have a case of insomnia and drive to just work. I'm soon to graduate and the idea of working at a large company seemed nice after I applied, but when the offer was there I had to turn it down because I didn't want to be comfortable. I feel like start ups have so much to offer in terms of personal growth and I don't want to miss it.

Let's chat by email. Maybe talking to another CTO who is running a post-Series A startup and who is roughly your age with a similar background (and who has the exact same concerns) will let us figure out a plan out of the madness.

http://pixelmonkey.org/contact

The way I see it, this is great. Start up success means you get to live a lifetime of working in X many years instead of Y like everyone outside of tech, where Y >> X. You have the freedom to direct that energy towards family, yourself, and charity when you want to call it quits. Most people don't get that luxury. You also have the freedom to look back at a short, but intense career of (hopefully) successful products that you were a core part of. Even fewer get to experience that.

Don't assume your health will be good forever.

Id bet E(X) >> E(Y) though.

I think the OP perfectly reasons through your situation.

Perhaps the real madness would be trying to change something that is obviously very important to some part of your soul.

Have you been able to "cash out" enough to do what you want?

Technically no. Eventbrite still hasn't gone public.

Well having done a few conference and course registrations through it, it works very well. Just don't let it turn into a Ticketmaster.

If you're interested in selling a few shares now, then I would recommend EquityZen. The process is very simple.

Fwiw I grew up in Colorado and love it so much but live in Bay Area now. I too am trying to get to back to Denver. If you want to start a company there let me know! :-)

I'm in the Denver area. I just left a startup here to become an independent consultant. There's a really solid tech community in Denver/Boulder.

Maybe you could stick CTOing but slack off a bit as the company becomes prosperous?

That's not me.

I don't know you, but you get my respect for that statement.

Maybe it should be?

Don't see it as 'slacking off' though. See it as establishing a mature work/life balance.

The problem is that as a startup founder/CTO type the way you work sets the pace and culture for your entire company. And not everyone will be cool with that approach. You could miss out on experienced, senior people who just want to work normal hours and not feel like they're letting the side down.

This is the core of the problem: 'slack off' is actually 'having a life' but you yourself and everyone in the ratmill finds it slacking off. Maybe you are lucky and will realize that this is crazy before your health catches up.

Funny how that works. I'm a soon to be college grad, born in Denver (currently in Boulder,) looking to move to SF and get into the start up life. Want to switch places?

BTW: I love Denver, just want to see what's up with SF.

A sense of purpose is a burning fire. Stroke it as best you can. Take care of your health, but also your beckoning. You sound like you're on your happiest path. :)

Why is "looking at houses in Denver" depressing?

To me, it represents a slower pace of life.

EDIT: trust me, I'm not bored.

Are you sure it isn't just boring, vs. depressing? Maybe if you find a hobby or side project, it'll counter the boredom.

But..isn't that what you just said you wanted?

Is big city life that fulfilling? For me all the high end cuisine and art galleries started to blur into each other. It was like constant stimulation, very sugary, and I got burnt out. So I quit my job, moved into my truck and will just ski/climb/hike for a year.

I moved from cities to a mountain village where 40 people live at the high point of the year. Best thing I ever did. I still like some cities but the different pace made realize we are just winding ourselves up needlessly. It is indeed an addiction which you do not need to achieve what you want (exceptions aside ofcourse).

A slower pace of life allows a person to focus more, in my opinion. I've lived in SV but I live in Tahoe now and get way more done programming from the mountains.

You might be thinking about it the wrong way. It might be a slower pace of work, but certainly not a slower pace of life as that will always be what you make it. I think the problem here is what you've defined as life.

Slower pace from where exactly? SFBA?

I couldn't disagree more, if that's indeed what you're saying.

NYC, yes. SF - absolutely not.

Here's a crazy idea: stop overworking. Being a CTO doesn't mean you have to work long hours.

In fact, I'd go as far as to say that he has a responsibility as a CTO to maintain a clear, balanced head to delegate and make decisions and working long, hard hours is the antithesis to that.

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