Ask HN: How do you deal with entrepreneurial obsession?

40 points by throwaway-001 a year ago

Two years ago we me and my partners got an acquisition from a startup we created in the previous 2 years, while having a full time job, my background is software engineering. Since then I couldn't stop thinking on my next "idea". Rationally I know there is nothing that kills creativity like trying to be creative, one of my reference on the topic is Why Greatness Cannot Be Planned: The Myth of the Objective That being said, this entrepreneurial goal has polluted everything in my life and the way I see the world. I stopped to genuinely enjoy experience since everything became a potential problem to solve, I started to be less present during interaction with other people and I pretended to have less time for things that I like because of some phantomatic idea I had to test. I recently started meditating with Sam Harris's Waking up, which is really helping on bringing more awareness in my life, not solving my problems but at least acknowledge those are there. My goal is to understand if I still really want to be an entrepreneur or I'm just projecting expectations from the shadow of the past success, if the answer is yes I want to keep my exploration in a more sane journey. I don't believe I'm the only one experiencing what I described, did anybody deal with it / are you dealing with this? What was your experience did you find something that worked for you?

mdorazio a year ago

Here's what worked for me: stop fantasizing and actually go try to start another business around one of your ideas. In my case (and for most people) it failed and cured me of this mindset. Ideas are easy and problems are infinite. Execution is hard and unless you're really in love with the problem, it's usually not worth it.

  • ransom1538 a year ago

    "Ideas are easy"

    I know this attitude commands HN. However, I just never understood this comment. I have seen MIT grads, with millions in funding fail because their idea was horrible. I have seen non tech - was working in fast food grads pull off a company because their idea was not terrible. As I got older, I realized, its ALL the idea. It has to be an idea you would give up 5 years for, your friends for, and your excess time: shoot me over that idea.

    • inconfident2021 a year ago

      It is not ideas are easy, it’s just they are cheap. At a given time, multiple people may be having the same idea. So, only the speed of execution differs. I have seen horrible ideas get leverage because of execution.

      You can see this prevalent in indie game industry. If you talk with designer’s everyone has their next big idea that can change gaming. But the industry is so unforgiving, any bad implementation or execution is severely punished. For example, see Dwarf Fortress. Stellar idea, awesome execution, but it took them really long time to hit mainstream. It is because the graphics wasn’t good enough for most mainstream people. Likewise, you see something like cookie-clicker going viral.

      There is no not one single dimension to starting up. You need to be furious in all matters. Ideas are just multiplier’s. Good idea will give you enormous leverage but poor implementation is instant death. Even horrible idea when well executed can bring values.

      It might be case they failed because they are MiT grads who most likely have a huge ego problem.

      • 6510 a year ago

        > At a given time, multiple people may be having the same idea.

        Ahhh, now I get it. What you describe here is not an idea at all. It is just something to do. (We could also disagree how to measure quality. I can imagine great ideas that cant possibly work or just cant be profitable.)

        In the games industry for example a real idea might look like Pong or table football but one could also argue those are just iterations of croquet. Maybe the real idea was the Mayan ballgame of Pitz and everything after it was just a slight modification.

        Ideas range from bad to good but we each make our own definition.

        Personally I'm looking for an idea similar to camp fire. The execution of a camp fire is cheap. Or take grilled meat or alcohol those are not cheap ideas!

        Colonizing mars or a fusion reactor, those are cheap ideas. If you have ideas like that you need to do better.

    • xwdv a year ago

      The idea should be easy, if it isn’t, it is a sign you are trying way, way too hard or you are reaching too deep into a domain you don’t understand and isn’t easy for you.

      The idea should be easy.

    • MarcoSanto a year ago

      I will humbly give my POV on this. I also never understood the VC verbiage until after I “launched”. Now here is what I understand after coming forward with a business idea: the formula for “success” is being able to “uncover” a market request for a product/service and SELL that product/service to them. In this regard idea = market_need = make_something_people_want. Therefore, to me ideas AND execution are EVERYTHING. I think what people mean is that “talking” about an idea is not sufficient. I strongly disagree that ideas are cheap, as I disagree that execution is a given. I believe ideas are oxygen, execution is hydrogen, what you want is water…

    • throwaway-001 a year ago

      You are getting closer. I think what making it even hard is, money is not an issue right now. My search and hesitation has been my mental projection of seeing myself doing that one thing in a 5 year span in a complete loss just because of my love for it. Maybe I'm looking more for this more profound target where to focus my attention and energy in a more romantic way that just purely money making. Or am I just delusional in seeking this?

      • jrumbut a year ago

        Have you considered starting a family? All these ideas about love and romance might be better expressed outside a business context.

        • throwaway-001 a year ago

          We do have a family, but again that cannot be all. I do want a deeper sense of purpose in my life knowing that I did something for somebody else, doing through a business would allow me to do it in a sustainable and focused way (not volunteering). Historically I always struggled not giving all myself towards an objective and that is how I operate the best of myself.

          • robofanatic a year ago

            Have you considered philanthropy?

            • throwaway-001 a year ago

              No I haven't, I wouldn't even know where to start.

        • the_only_law a year ago

          Unfortunately the job market seems less vicious than the dating market.

          • licebmi__at__ a year ago

            I believe the set of people who complain about the “dating market” and the set of those who believe dating is a market is the same set.

    • wnolens a year ago

      It's still not about the idea.

      You're assuming that the idea is going to make you give up years and friends for. It's the person that does those things. Personality traits are much more important here.

      And if you've ever seen an idea through to successful conclusion, the end state always looks different (sometimes vastly) from the initial seed. So the idea wasn't important except to charm the person into going through the process.

    • lhnz a year ago

      You are right and you will be more right in a few years once AI is better integrated into our tools and good execution is even easier.

  • throwaway-001 a year ago

    > unless you're really in love with the problem

    You touched a neuralgic point of my experience that for some reason I omitted in my original post. One of my biggest source of frustration and sense of inadequacy is not feeling (or not seeing myself) that strongly passionate about anything/anyone specific. My last iteration of this concept was to fall in love with a specific group of people and explore the problem they encounter day to day.

  • VoodooJuJu a year ago

    >Ideas are easy

    Good ideas are extremely valuable and once they're found, they are (and should be) guarded. Oftentimes, the only reason a business is able to take off is because they've discovered a blue ocean (a novel idea) that no other fishermen know about. But once the word is out, party's over.

    You can observe this implicit understanding by founders whose lips stay sealed when asked about the details of what they do [1].

    It's harmful to the success of an entrepreneur to treat ideas cheaply. For many businesses, the idea is their sole competitive edge.

    I like to joke that the reason most people here treat ideas so cheaply is because they're conspiring to get others to spill the sauce - so they can lap it up for themselves!

    [1] "That project has now turned into ~$30k/mo profit..." -

  • pier25 a year ago

    Execution and setting up a business always takes much longer than you expect.

    I started working on an audio hosting project that I thought would take me a couple of months. A year later I have a decent mvp and I'm starting to get my first beta users. I haven't even implemented payments yet. My marketing is crap. Etc.

marban a year ago

I've 4 exits and ~25 failures under my belt, and I'm dealing with the exact same problem; However, over the years I've come to enjoy every single project that didn't work out more and more because failure is the default, and valuable information for the next attempt. And as long as you keep the surface area for luck to strike wide enough at any time, you're gonna make it through somehow.

Can't agree that loving the problem is a prerequisite, but more of personal trait. If you work on something that's boring AF and still can deliver best-in-class because the result ($/fame) is what you're ultimately after, there's no need to get high on your own supply.

goodpoint a year ago

You are asking in the wrong place. HN is filled with the idea that every moment of waking time should be dedicated to hustling, doing startups, being productive... in short, work.

Unsurprisingly people here are telling to double down on following your ideas.

Such attitude is very effective at creating burnout.

  • shrimp_emoji a year ago

    Yeah, I have no idea whether it's because I'm not American or just a lazy loser or something, but the manic "how do I make more $$$$$$$?!?!" mentality is alien and repulsive to me lol.

    I do work because I like it (and, unsurprisingly, the things that are most likeable are the least profitable or practical). And I don't do it at an unsustainable pace, which anything you're trying to profit from inherently demands. And the only way to profit in software is to pin your users down to a table and give them a night of value extraction they'll never forget. You also have to work with cringe technologies, like web tech. Money is the root of all evil to me, and being obsessed with it seems unhealthy af and a disgusting basis for technological curiosity/craft.

  • throwaway-001 a year ago

    I do not mind work a lot, usually I don't experience burnout if I'm working on something that I'm profoundly interested into it. My sense of exhaustion comes from not knowing where to focus my energy. I guess HN could be a good place where to have this conversation since feel like the best place to find people with a similar experience/feeling to mine.

    • goodpoint a year ago

      > usually I don't experience burnout

      Are you sure you understand what burnout really is?

      > My sense of exhaustion comes from not knowing where to focus my energy

      Yeah, that sounds like burnout all right. But don't ask HN, ask a therapist.

ianzakalwe a year ago

For me : stop living in fantasy and start taking actions, getting other people excited about the idea and asking them to join me. It’s too comfortable to never let fantasy get in touch with reality. And once you do let it get out there I know what needs to be worked more on.

  • throwaway-001 a year ago

    Don't get me wrong, I do had a couple of ideas and validate with rigor, some of them really had a little traction. But when I think, do I want to dedicate my soul to this problem for the next 5-10 years I think is not really worth it or I'm not impacting people life in any major way.

chenxi9649 a year ago

I don't think you're the only one who's experienced this, but I think you're in the minority in realizing that you're experiencing this.

This thread has a lot of gold nuggets, but most seem to be focused on how to successfully start a company/follow through with an idea. While the more critical question seems to be your first question, whether you still want to be an entrepreneur.

For myself, I think it was important to realize that at the end of the day we are just all a bunch of monkeys who gained the ability to experience things, along with the illusion that we can alter this experience. That's all this is. We are just all trying to tickle our brains to feel better in one way or another.

Everything we are doing is for our own "experience". Some of us wants to make the world better because it makes us feel better that others are living a better life. Others might want to create impact because it feels good to be someone who've created impact. There is no absolute truth/reality. We are all just trying to make our experiences better.

All of this might sound obvious and even a little cynical. But it's given me a strange sense of comfort and helped me find "myself".

Also curious to konw if you've found the answer to your question since the time of this post!

  • throwaway-001 a year ago

    > All of this might sound obvious and even a little cynical. But it's given me a strange sense of comfort and helped me find "myself".

    I don't think is not about being cynical. We are what we experience and for me at least is the only existence that matter. I want to make my day to day on this earth relevant and enjoyable and as for now entrepreneurship checks a lot of boxes, I also revisit this belief very often.

    > Also curious to konw if you've found the answer to your question since the time of this post!

    No, and I wasn't expecting/hoping to (probably only 1% of my was). What I was able to do today was to do more writing exercises using some of the content that was posted which lead me to:

    What do I regret not doing? - Learn how to play music - Why am I not doing it? Because I feel I would take time from something more important?

    Today I booked a music tutor. I guess I consider this as a win.

vhiremath4 a year ago

I like to think about my long pursuits as achieving a kind of purpose at a certain point in my life. What is the purpose of me needing to be working on my own thing? If I execute against the idea with that in mind, I usually go further. Once I’m done with a given purpose layer, a new purpose emerges (not always right away).

I’ve been working on my current company for almost 8 years. At first mine (and my co-founders’) purpose was to just give it a go. We expected it to fail and for us to have to go back to our jobs. None of us actually cared about the idea we were initially working on (thank god it shifted and pivoted to something more personally fulfilling). We cared about trying it for real with our best friends (quitting work, working long hours, etc.).

When we hit our first real wave of traction, the purpose changed to “let’s take this thing as far as possible from a scale perspective”.

Basically, I’ve never thought about doing something because the idea itself is what’s carrying me especially for a company where pivots are necessary to increase my chance of success (almost all software companies). Not prescribing this way of thinking to anyone else. Putting it out there in case it resonates.

  • throwaway-001 a year ago

    Thanks for sharing.

    > Basically, I’ve never thought about doing something because the idea itself is what’s carrying me.

    On the opposite spectrum, I don't think I can do something unless the idea itself is what’s carrying me.

dpkirchner a year ago

I have a lot of ideas for things I think I want to build, that might make a useful amount of money, however when I examine my thoughts more closely I realize that in nearly every case I merely want the things to exist. That forces me to come to terms with facts like:

- I only have so much time and skill

- Most ventures fail and I need to be cautious about using others' success as inspiration

- I place a really high value on free time (extension of the first point)

Since I started thinking this way, I've stopped feeling (as) guilty that I'm "wasting" time on things like being social or reading or playing video games instead of chasing dreams.

I haven't had entrepreneurial success yet, like as a founder, so I guess that probably taints my view here a bit.

mejutoco a year ago

> My goal is to understand if I still really want to be an entrepreneur

I do not have a solution for you but it seems you currently identify as an entrepreneur. I think if you want to stop this "obsession" you will need to stop identifying with it.

I would give it a defined time to obsess about it. During that time you can do something specific about an idea (not just daydreaming). The rest of the time you let the thought pass without feeling guilty, since you have a time slot later.

My recommendation is to do something physical too: swimming, pottery, walking the dog, weights...

surprisetalk a year ago

I tend to obsess over ideas too. Ideas are so much fun!

Don't feel ashamed over dreaming about Changing the World or Becoming a Billionaire. Dreams are delightful.

But you have to keep your dreams at arms-length. I wrote the following essay as a playful reminder to myself to stop taking my ideas so seriously:


I highly recommend Derek Sivers's book on entrepreneurship, Anything You Want.

As I'm on my own business journey, this tiny book keeps me grounded to a mission of truly helping people and enjoying the process.


You might also need to change how you interact with people. How to Win Friends and Influence People is the magic guide on talking to people:


Another possibility is that you need to find fewer people to talk about your "ideas" with. Not everybody is interested in this stuff. But I am!

Feel free to schedule a chat with me anytime:


If you're coming up with ideas to avoiding doing work, remember that "Everybody wanna be a bodybuilder, but don't nobody wanna lift no heavy-ass weights".

Everybody wants to be an entrepreneur too.


Above all else, you are not your success. If you're 30 years old right now, you've only got ~2,500 weekends left. Spend that time intentionally.

ydnaclementine a year ago

I've read it on here, but the act of thinking about doing things and fantasizing about all these potential accomplishments is a dopamine trap. Create a list of things you're "constantly think about", and start one. Then at least you have the ideas written down, and you're not constantly spinning that ideas plate in your mind. And just like others say here, actually implement something. Even if you don't get very far you'll learn something for the next idea, and you can always come back.

aww_dang a year ago

Shoot for low hanging fruit first. Build up a passive income stream. Once this is in place you have the freedom to explore, or if free time is as valuable as you say it is, just enjoy that.

ravenstine a year ago

I dealt with entrepreneurial obsession by failing enough times that reality communicated to me that I don't have what it takes to be an entrepreneur.

  • throwaway-001 a year ago

    That's what I'm terrified of. Was my previous success purely just based on luck and I don't have what it takes to have business born from my creativity?

    • fuzzfactor a year ago

      What if you were a down & out blues musician and all you had left was your creativity?

      It doesn't make very much difference what you do, it's going to take 5 to 10 years just to get back on your feet enough to even consider the opportunities ordinary people have the whole time they are less unfortunate.

      So it's a toss-up, you can use your creativity very heavily and allow it to direct your rise, OTOH you could drop everything and gravitate toward something different that might be more promising once the difficult-survival period has beeen overcome.

      It can look a lot different when you consider the points of view taking action for survival purposes versus to achieve prosperity.

      If you're going to survive on your creativity, you may need to double down on both the survival activites and the creativity.

      If not, you may need to become stabilized or even prosperous in some other way before you can indulge very much creativity in the long run.

      There can be quite a valley between those two extremes.

crosen99 a year ago

I learned long ago that if the focus of my obsessing is on some future state or accomplishment then I will be anxious, miserable and not at all creative or productive. But if I can direct the obsessing to actual activities I enjoy in the here and now, I find my sweet spot.

I forget this constantly, and have to bring myself back to it repeatedly. But whenever I do, I find I’m home again.

kordlessagain a year ago

It's about building something, so I just allow myself to obsessively build things. Starting something may result in what is built being marketable, but it may also be a market "failure" or not stand up to innovation in the market over time. It's a good way to channel obsessively learning how to do new things!

andrewfromx a year ago

This is for you:

"After a high flying 20+ year career in tech, Philip Su burned out. He found solace in an unexpected place: a retail Amazon job."

  • throwaway-001 a year ago

    thanks for sharing, I'm not sure how I feel about that experience. That first thing that came in mind is, I don't want to end up to be so burnout that I need to drastically compensate in a similar. I believe I'm trying to prevent something like that to happen in the future.

nvartolomei a year ago

> Two years ago we me and my partners got an acquisition from a startup we created in the previous 2 years, while having a full time job, my background is software engineering.

What did your employer think of that? Wondering about your experience in balancing day job/startup.

  • throwaway-001 a year ago

    It was never been a problem, everybody in the company knew I was running a business on the side, and I was still being recognized for my day job accomplishments, even got a promotion. I guess I made myself very efficient in getting things done, actually building things never provided any burden.

garrickvanburen a year ago

Try imagining you’ve just a few moments left to live.

What one thing do you regret not doing?

Do that.

I once had a sheet of paper completely filled with new ideas to work on.

I didn’t even know where to begin.

I went through this death bed exercise eliminating all but one of them.

I’ve since completed it, and continued to judge potential projects against that criteria.

pg5 a year ago

I cured mine by replacing it with a music creation obsession.

HopenHeyHi a year ago

  one of my reference on the topic is Why Greatness Cannot Be Planned: The Myth of the Objective"

  I recently started meditating with Sam Harris's Waking up, which is really helping on bringing more awareness in my life
Rolls up newspaper.. thawack

Stop that. You don't need that shit.

Listen to Ze Frank about Brain Crack (he is a very nice man from a long ago interwebs where people didn't try to sell you self help bullshit):

  • garrickvanburen a year ago

    Thanks for the Ze Frank pointer. I was continually inspired by his work.

    Merlin Mann’s “Make Believe Help” is similar, both in vintage and in message.

  • surprisetalk a year ago

    Why don't you think his methods are useful?

    • HopenHeyHi a year ago

      Self help genre nerd snipes a lot of otherwise intelligent people. It is a bottomless pit.

      Vaguely useful is reading biographies of interesting people/companies like John Carmack or the Chucky Cheese dude, and so on. Gives you a bit of color on their experience, look at that crazy journey, sounds wild, I want to have a life like that..

      Think of it like Harvard business case reviews but without the just-so tea-leaves retroactive nonsense - that path is for consultants. A mind is a terrible thing to waste.

      If you have a cool idea just chase it down and see what happens, figure out the rest as you go. :)

    • goodpoint a year ago

      Meditation can be good, Sam Harris and the rest of the are not.

      • throwaway-001 a year ago

        oof, had no clue about it. Probably mistake not researching it. By my experience so far I haven't seen any trace of such philosophy in the App I'm using, I guess is very well packaged for a mainstream consumption.

        • HopenHeyHi a year ago

            Individuals and publications associated with the term reject what they view as authoritarianism and ostracism within mainstream progressive movements in Western countries, especially within universities and the news media. 
            This includes opposition to deplatforming, boycotts, and online shaming, which are seen as threats to freedom of speech. Those who have been labelled as being part of the IDW come from both the right and left of the political spectrum. The validity of the term is contested by some it has been applied to due to the range of beliefs it encompasses.
          Me neither, this is some unspeakable evil. Meditation apps should be about authoritarianism and ostracism. These people just don't know how to be mindful and chill.

          If you haven't found traces of their bad philosophy in the app you're simply not looking hard enough pal. They might be subtly influencing you to think incorrectly.

          Please make sure to watch out for these things next time you meditate.