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Working for someone vs. doing your own thing (tik.dev)
339 points by thakobyan on Jan 14, 2020 | hide | past | favorite | 222 comments



There's a pretty high correlation between parental wealth and success as a startup founder. I assume it's because of the safety net.

My friends who have been successful (and who had blue-collar upbringings like me, and all in mid-40's now) all worked full time jobs until their side projects were self-sustaining. None of them hit unicorn status, but I think all of them have lived healthy, fruitful lives.

Also note by "sustainable" I mean they had contracts worth substantially more than their salaried job. Because to transition to that completely, you've got to set aside time and money for so many things: insurance, legal, hardware, whatever corp infra, recruiting, etc, as well as offset the risk. So I'd not jump ship too soon, until you have a real plan on how to get your company from A to B. Especially these days when tech salaries are so high, it'd be a mistake to opt out of it too soon.


Given the research on adverse childhood experiences, there's likely a subtler advantage too, for founders who were raised in more stable and secure environments. Growing up under greater pressure (violence, abuse, trauma) leaves you less resilient, more risk averse, more at risk. I'm not saying wealthy families don't have this, or that poor families can't be stable and secure. But on average it probably makes a difference. Call it an emotional safety net.


That's a great point. I can only speak for myself here, but I can 100% confirm that having been raised in a loving, secure, and stable home has probably been the greatest contributing factor to my career success and having a major inclination in life towards optimism.

The gratitude towards my parents alone has driven me to push myself harder in my career.


Maybe the best way to look at this kind of environment is that it's a different form of wealth. Correlated with money, in the sense that poverty brings stress and often many forms of brutality, but definitely not identical with it.


> Maybe the best way to look at this kind of environment is that it's a different form of wealth.

Absolutely love how that was phrased. I couldn't agree more.


I like this a lot too. And, turning it around, a big motivation to gain wealth for many people is exactly because it's a means to provide that environment for their children.


I would say I had a great childhood in general, but also with some major stress factors—I feel I can safely say that those stressors don’t leave you on their own so organically. And that kind of stress, even if it’s not conscious all of the time, can colour one’s perspective in an impactful way. Sometimes for better, funny enough—but also for worse in others.


Absolutely. It's impossible to bring yourself to take risks and leave your comfort zone if the outside world is a terrifying and malicious place.


What I personally experience is that whenever I'm in a verbal fight with my SO (for example), I'm physiologically ready to physically fight (though I never actually fight, I'm simply hyper aware and prepared for it, it's an automatic thing).

I've learned that there are people who don't have this response, they simply keep it on an emotional level. These people also never experienced or saw any physical fight during childhood and were never really bullied.

I saw fights pretty much daily as a kid and experienced them at least once per month, winning about 50% of them. So I've experienced both sides quite a bit.

I've noticed that kids who fought daily have this much more in their physiology than I do.


Yeah I'm almost the exact opposite. I did a lot of martial arts when I was younger but never had any actual fights. Not serious ones. By the time I reached adulthood I had no idea how to act in either verbal or physical fights and was avoidant of confrontation. It's hard work but I'm gradually getting the hang of being present and holding my own in tough conversations. It's still very rare for me to get angry rather than just irritated, defensive or passive aggressive. When I do get angry it simmers in the background without any outlet, and either dies away or eventually explodes in a weird, unexpected way.

I was thinking more about people who grow up with very little, i.e. aren't sure if their parents are going to put food on the table that day. If you start out like that but manage to get a steady job etc..., I think it can be much harder to take risks like changing career or being assertive in certain situations.


I wouldn’t say that’s my experience, though I’m sure that’s true. I’m referring more to the stresses imbued to a family from something like lack of money.

It’s more of an internal preservation thing than a fear of externalities.


If it was measured as part of GDP our priorities might be different (better).


Gross Domestic Parenthood?


Nice ;)


Exactly same here and really grateful to be so lucky, especially when I compare with my less privileged friends.

It is a factor often missed in outcomes and sometimes wrongly attributed to persistence.

It is always easy to be persistent without any economic pressure or financial liabilities, even more so when your family ensures that for you.


Incidentally, I just got back from the annual checkup with my 7yo, and the doctor mentioned that the strongest indicator of kids staying on a good path through adolescence is whether they regularly have dinner together as a family or not. That surprisingly exceeds any other socio-economic demographic indicator.


I’ve thought about this metric, a lot. There is no doubt that having family dinner has a lot of benefits. But I can help but ask myself - is family dinner a silver bullet, or is it that families who are holistically “doing it right” also make family dinner a priority?


I have a theory on this and can speak from my experience.

The problem I think with NOT eating together is that it sews disharmony in the machinery of the household.

If everyone DOES eat together all the work related to it happens together as somewhat of a team. You do the thing once. Everyone is in a shared state of being. Specifically being satisfied in appetite and social interaction and ready to do there own thing after.

Otherwise Billy is hungry at a different time than Sandy and Sara wasn't hungry until it was time for bed. Dishes have to be re done for each person. Billy made a better dinner for himself and left none for his sister. Someone ate in the bedroom and left a glass of milk out over night and mom was angry in the morning...

I am rambling and maybe it's obvious but ultimately I don't think it's just the act of eating together I think it's the reduced friction and increased cohesion of the household that shared dinner causes.

To answer your question, Maybe family dinner forces you to be "doing it right" just by the act of having the family dinner.


I also wonder about whether there is a quality criterion there or is quantity all that's needed. For example if most dinners consist primarily of yelling at kids to sit down, eat vegetables, quit playing with food, just hurry up and swallow it, small bites, not that small, no poop talk at the table, inside voice, quit dropping your spoon, feet off the table, no kicking, don't annoy your sister, STOP SHOUTING.... Does that count?


Actually, almost definitely yes! Those things you mentioned, despite being friction areas, are actually loaded with all kinds of cultural and class norms, and the fact that you have parents who care enough and are around enough to be able to set those boundaries is a major selection criterion for success in other areas.

That's not to say you can't screw it up. If family dinners are spent in silence with the kids praying they get through the dinner without setting dad off again and watching him beat their mom to a pulp, or hoping that they don't get sexually abused later that night by one of their family members, etc. Then yes, maybe there are some quality issues, but I'd argue even in that extreme case, it might still be a positive indicator against the base cases of abuse without that element.

I was a paramedic. There is a massive fraction of society with upbringings like you wouldn't imagine. That's what you're up against. When people say they have a dysfunctional family, it's often pretty mundane. Especially compared to people in that class that didn't realize until they were an adult that things like getting raped by all of their mom's boyfriend's isn't a normal thing everyone deals with as soon as they start puberty.


That sounds outright terrible. Yes, it's not as bad as being beaten or raped (as mentioned by Enginerrrd in a sibling comment), but that's a really low bar.


I see that spending 30/45 minutes as a family is very important for communication. It helps understand daily life with its joys, issues, milestones. It helps bring peace in the family, and emotional support as well as practical planning. It helps to know each other. It's a no pressure situation, whoever wants to talk can talk, it's the best way to open up.

I've done it all my life, as a child and a parent, I have no idea why people would not want to enforce this.


This is a question of the causality between the family dinners and the socio-economic indicators of a kid. Just like most of similar questions, it is healthy not to assume causality until proven there is.

IMO, having regular family dinners is just one of many characteristics of stable and healthy families.


This is probably related to the general 'people bond over a shared meal' thing.

As you have more meals together, you are (they bond to you) and feel (you bond to them) more loved by the other people at the table.


Damn this hits too close to home.


>> Growing up under greater pressure (violence, abuse, trauma) leaves you less resilient, more risk averse, more at risk.

Speaking from personal experience, I have to disagree. I was raised in Baghdad by a single parent, my mother. We lived through three major wars, almost never had a steady income till after 2004 when I was 19 and started working for the US military as an interpreter. I believe growing up under great pressure (and violence) has made me more resilient and increased my appetite for risk.


Absolutely that can happen as well. But the research on adverse childhood experiences is pretty compelling. Sorry I don't have links handy.

Also, if your relationship with your mother was strong, that counts for a lot. I'm glad you survived and are thriving!


Possibly interesting, a behaviour I used to see from people with "bad" upbringings is a desire (or requirement) for chaos.

eg they get their life on track, but it seems to be "too boring" (or similar) for them, so they start creating chaos with the people around them to get things "back to normal"


N=1 “ What doesn't kill them doesn't make them stronger: Questioning our current notions of resilience.” https://www.ncbi.nlm.nih.gov/m/pubmed/29254696/


Right. However, I think the study you're referencing is mainly concerned with parental and physical abuse.


This is somewhat of an aside, but it's been interesting watching the constant debate about the direction of causality between financial and emotional stability in a family.

I think when I was younger I tended to see financial success and stability as a downstream effect of other factors, but I can't help but now see that viewpoint as naive. Economic pressure alone is sufficient to create severe emotional stress and instability (which probably creates a feedback loop that makes it even harder to recover from).


I've seen this personally. I happen to know people from all backgrounds in The Netherlands. While I myself am middle class, I know people who almost died from hunger (in The Netherlands, yes) up until people who know the king and prime minister in a professional setting. Let's just say I have a diverse family and group of friends.

My conclusion is: when privilege is applied well, there is no competing it. And the stable and secure environment that you're talking about plays a role in that. As I've noticed that I'm lacking it a bit (just a bit) and I am seeing its effect. The issue is that this type of stuff is mostly automatic behavior, so it's hard to flush out.


This is really related to the audiobook I'm currently listening to (Reboot) and how this CEO coach works through the childhood problems of different C-level executives like he had to do himself first.

Imagine not having to deal with that during entrepreneurship, without the issue wealth of contacts and money, what an advantage it is.

Sure, you can have more grit if you come from a more constrained background, but I would not know what I would choose between the two.


Pressure can also make diamonds and I know a lot of people who have become incredibly driven and successful precisely because of what they went through, while others who have had it easier tended to coast through life.


I don't think it is possible to separate out all the individual parts that go into making someone driven and successful, especially not with only anecdotal data


In that case then both perspectives are equally true and false.


They aren't equally true and false... the truth value is just unknown


Reminds me of the line "The sun can either come up in the morning or it doesn't. Therefore there is a 50% chance the sun will come up tomorrow"


I see privilege as both a head start and a multiplier to your individual effort. People who put in no effort will still end up nowhere unless they have an absolutely enormous amount of privilege that allows them to succeed on a head start alone.

Someone with little privileged who puts in a huge amount of effort can overtake someone with a high privilege who puts in a normal amount of effort.


Sure, same goes with luck, skill, natural abilities, etc. It's all an outcome from several major inputs.


> Growing up under greater pressure (violence, abuse, trauma) leaves you less resilient

Is this a thing? I thought the common wisdom was that you gain resilience once you get past hardships, not lose it.


It's possible for past hardships to leave you emotionally messed up for years, which could make it harder for you to deal with future hardship.

I don't think there's a hard rule on this, and it depends on the mentality of the individual. It's possible for people from rich and poor backgrounds alike to be resilient.

But I do think emotional security helps you deal with challenges in life. It's not the only thing and it's possible there's other ways of dealing with it. But growing up in a secure environment makes a difference (note, this doesn't necessarily mean rich. It means stable. If you're rich, but a close family member dies when you're young or some other hardship occurs, you can still be emotionally hurt despite having an otherwise secure environment -- that's why it's a bad idea to judge people on their backgrounds, you never know the full picture)


There are different levels of hardships. Having to work hard and sometimes having less to eat or winning some easy fights with bullies may make you more resilient. Being mugged every month, beaten and abused by parents every week may break you.


I don’t think it’s possible to make any causative statements about complicated, undefinable terms such as resilience and hardship.


As a startup founder with wealthy parents, this seems likely. Not only can parental wealth serve as a safety net, but you might also get direct investment from your family, have a safety net if things don’t work out (enabling you to take more risks), not have to exert as much effort taking care of sick, old, etc. family members because you can hire people, get access to powerful family connections, and learn from highly educated parents.

What’s weird to me is that I don’t see more successful founders mentioning that having economically well-off parents being a factor in their success. I’ve long since accepted that any success I’ve had or will have will be, at least partially, a result of my privileged upbringing. I used to be a bit bothered by that, but now I’m happy to give tons of credit for any of my own successes to my parents. And anytime I hear about startup founders achieving success despite coming from poorer families or even hostile environments, I’m super impressed.


I think it's a very common thing with success that people want to attribute it to their skills and not factors such as pure luck.

Might also be a cultural thing, in many societies there are myths of equality and everybody having a chance.


>What’s weird to me is that I don’t see more successful founders mentioning that having economically well-off parents being a factor in their success.

It's not just people with rich parents. I've noticed people tend to dismiss parental help they get even when it's just a few hundred every once in a while. They don't connect that vacation they just took, was paid for by that Christmas present they got, or that they're able to save because they're living rent free with parents.

It's like people see money from their parents as non-existent and don't count it in as 'extra' money they've received. Meanwhile, they've never actually had absolutely no money, because their parents never let them reach that state.


I wonder networking has to do with any of it. If you're poor you'd be very lucky to have connections that matter, whereas if you're born into a wealthy family there's likely to be somebody of value either of themselves or somebody they know and can introduce you to.


I would say it is not so much the connections you have but the connections that you can make. Growing up wealthy gives you the background to connect with unknown wealthy people easily. There is no need to be introduced because you can be familiar immediately.


I wonder how much of the correlation is dollars, how much is attitude toward wealth and money, and how much is entrepreneurial exposure.

If you come from a “the pie is fixed size; gotta fight for your share” mentality, you might have different propensity to succeed as an entrepreneur. Likewise if you never saw the real good, bad, and ugly under the covers.


Yeah, exposure is important too, both to people and concepts. Beyond the tech work, you've got to deal with legal, HR, accounting, etc. Coming from a background where all that is everyday life is a big advantage. And if you can get actual references on who to talk to about these things, even better.


> There's a pretty high correlation between parental wealth and success as a startup founder. I assume it's because of the safety net.

Could also be genetic. You'd have to design an experiment (or, more likely, find a natural experiment) that controls for genetics to know.


Are children adopted into wealthy families disproportionately start-up founders? I'd probably guess so, relative to the overall population.


> high correlation between parental wealth and success as a startup founder. I assume it's because of the safety net.

Supporting a few sibling commenters here. I believe it is more nuanced than a safety net provided by parental wealth.

I definitely come from a background of privilege. My grandfathers were both high status professionals. My parents were a combination of high-performing professional and Ph.D. I have pursued several ventures. I have no major success to report from a startup perspective, but plenty of professional success. I have certainly taken risks in my career.

I have never consciously planned risks around the thought that my parents could provide a safety net. I have always had backup plans several layers deep and my parents have never factored into those plans. I cannot rule subconsciously banking on their support. Luckily I've never had to fall through all my backup plans.

Like I said, I certainly come from privilege. I'm not trying to say I did it all on my own. I am not trying to say my parents had nothing to do with it. Just that my safety net has not been planned around any parental largesse. I built it on a foundation provided by them.

I like to put it this way: I am a self made man. I made myself and achieved what I have on my own. I have achieved it with skills and a mindset that I learned from my parents. That I learned from the high quality education that they directly gave me and that they made sure I got in my schooling. I have achieved it with a confidence borne of an upbringing that tells me I deserve success and should expect it if I work well. I have achieved it in an economy that is supportive of professional development. I have achieved it by working hard - and being lucky enough that my work got to start at 0 instead of in a socioeconomic hole. I have achieved it by being lucky enough to live in a society where I am not discriminated against. I have achieved it by being lucky enough to be born in a time and place, and to parents, that were conducive to my hard work and to my success. I am a self-made man, but I don't think that's too much to brag about given the privilege I was born to.

So, there was never any direct safety net from my parents, but the safety net was there d/t the circumstances of my birth and life and luck. These things enabled hard work to pay off. Unfortunately hard work is not enough on its own. Luckily for me, I did hard work in the right time and place.


I agree that there's more to it than growing up comfortably well off. Among other factors there's the mindset; I grew up in a professional family with deeply working class roots, and was raised with the idea that the way to get ahead in life is to get a good education so you can get a good job. The prospect of owning a company or being an employer rather than an employee was never even acknowledged. It took me a long time to break out of this mindset despite always having a general feeling that owning a company was the only real way to get ahead.


I think this is a valid counterpoint. I didn't mean for it to sound like "silver spoon" kids get their success given to them, and debated deleting the assumption sentence after posting. The intent was just a note for OP to factor into account. But it sounds like a lot of others read it the first way.


I get what you mean. And I agree. It's a huge impact. I am incredibly lucky, as are others with similar backgrounds.

In hindsight, I'm honestly not even sure that the nuance matters. The effect is largely the same whether there is truly a "safety net" of any sort, or whether the circumstances of birth and raising eliminate the need for a safety net.


Yes agreed - it was luck that you gave you the ability to then become a self-made man.


I know someone who fits this bill. They grew up in a well-to-do household and quit their high-paying job to travel and build a startup. They had enough money to quit, but even if they didn't they'd still live comfortably.

They're also at a big advantage because they used to work in Silicon Valley and have a lot of connections in the industry.


> There's a pretty high correlation between parental wealth and success as a startup founder.

I'm not disagreeing, but is there any research to support this that you can share, or is it based on your personal experience?


There is plenty of evidence supporting positive correlation between parental incomes/wealth and the child’s success in academic and commercial endeavours, but little evidence either way relating to success at starting a new business.

But given that the secret to successfully launching a business is to have enough resources to fail many times, it stands to reason that successful startups are highly dependent on founder funding (and thus, parental wealth).


Yes, this makes sense, but hard data would be much more compelling.


This article links some studies related to entrepreneurship and risk taking based on family wealth, but I haven't dove into them thoroughly. Worth checking out:

https://qz.com/455109/entrepreneurs-dont-have-a-special-gene...


Thanks!


I wonder if there’s a concentration of poor founders and rich? In my small high school, the people who were poor and succeeded all started businesses (not startups).

The “smart” kids, myself included mostly had middle class backgrounds and all became professionals, there’s only one that I know of who is a business owner.



In addition, there is a ton of knowledge and social capital that you get from your family. Case in point, Bill Gates mom when he was a young man negotiating contracts with giant IBM.


Worth noting that working on the side writes you out of most possibilities to get investment from VCs. (not discouraging it, in fact I'm doing the same)


I would assume not; most people have this safety net. Having one or two parents with a couch you could sleep on is standard.


Sleeping on a parent's couch isn't an option for many people for a wide variety of reasons, and it's certainly the very minimum bar for a safety net. For example many people I know live thousands of miles from their parents. Sure it's an option, but it would be truly a last resort before homelessness.


Yeah well a lot of people envious of success act like having parents with a spare bedroom is some sort of elite privilege, and not the norm.


I like Austin Kleon's insights here [1]:

"A day job gives you money, a connection to the world, and a routine. Freedom from financial stress also means freedom in your art. As photographer Bill Cunningham says, 'If you don’t take money, they cant tell you what to do.' Because the real truth is, once you start making money doing what you love, it BECOMES A JOB. And with it comes all the hassle of a job."

It's why I've personally decided to work for someone else full time and then use any time I can get outside my day job to do the things I really enjoy (which are very profitable). The full time job enables me to be more "creatively reckless" in my side projects, which in turn allows me to learn a lot and stretch creative muscles I might not otherwise get "working for the man."

1. From: https://tumblr.austinkleon.com/post/69005574484


I would like to try that approach but I just don't have the energy after working all day to come home and start investing time chasing wildly creative projects.


A hundred years ago a wonderful slender book was written, "How To Live On 24 Hours A Day" by Arnold Bennett. He suggests getting up early and doing your passion projects before work.

https://www.amazon.com/How-Live-24-Hours-Day/dp/1603863680


But I get up at 4am already


That works well if you don't go to work on your full-time job before 9am


I'm trying to do a bit of that, but it's understandably difficult. I have an easy day job time-wise, but even then I feel like I rarely do my best passion project work at home. Lately I'll wake up at 5 and work, go to the office from ~8 to ~4, and then get a couple more hours done at home afterwards.


I keep explaining this to my kids. They are still refusing to let me sleep. Why do they treat me this way?


I would say that this also depends a lot on how draining and intense your day job is. Some jobs require too much of you to be able to do anything once you are done - or do so in periods.

You will probably have to decide what is most important to you. You cannot chase and strive for promotions, extra responsibility etc. on your day job while still wanting to do your own thing in your spare time. Perhaps you need to look for a job that has less pressure and perhaps less pay, but which does not drain you.

I have just had to go through the same realization myself that I cannot chase on both fronts. And my priority is my own projects, so I will have to course correct.


I would argue that _most_ full time jobs probably require too much of us than we should be willing to accept, regardless of if we have energy left over to do anything else outside of those hours.

40 hours per week is more than half of most people's waking hours. That's a terrifying amount of my life to have to spend on something I don't _absolutely love_ doing, and I sincerely hope I can find a way out of it sooner rather than later.


What? Assuming you sleep 8 hours a day, your waking hours per week would be around 112.


not counting that 40hrs weeks accounts just for working hours. You should add 1hr per day for lunch or equivalent pause, and often 2hrs\day for commute. You easily end up to 55 hrs that is ~50% of your waking time. You should add all is needed to sustain a full time job that requires you to be conscious of what you're doing, so I'd add some routine habits that make this possible, like maybe time to readapt your consciousness from work environment where you just lived and focused thoughts the last 9 hours, as I feel to need. You sell your life when working full time for someone's(something...maybe) else enrichment. Those 40 hours a one give to someone else are the most profitable hours a one have


I agree and we cannot do anything about the hours apart from perhaps trying to find some part-time job, but that is probably not easy either.

So my point was just to not bet full-on on two horses at one. If your priority really is your side-gig or starting your own business, then do not run too fast in the hamster wheel also. Put yourself in a position where it might not be the most fulfilling work, but it serves the purpose of giving you economic room for pursuing your own business.


I agree with you 100% that it's on the individual to find a job which is most suitable for them.

Interestingly, for myself the more intense the day at work is, the more energized I feel when I get home to work on my own passion projects and businesses. Since my role has been relatively autonomous, I'm the one setting the intensity level and if it's a high pressure day it means I bit off more than I bargained for.

To avoid the after-hours productivity slump, I try not to let work get "slow" by taking on new projects, asking other teams what problems they're encountering, and finding new tools to add to my arsenal. That being said, there are still days that seem to crawl by and very little is left to be done. Those are the days that drain me mentally and physically. Some of the people I've worked with have talked about how they spend their workdays pretending to work while actually playing mobile games or whatever and how it makes the day go by faster. I'm genuinely fascinated by what I perceive to be their complacency and lack of ambition.

As background, this is my first role at an organization I'm not a founder of and I started there three years ago at the age of 27. Starting at age 14 I had my website network which was racking up $500+ a month in server bills, so the entrepreneurial lifestyle (rollercoaster ride) is my definition of normal. As a first-time employee, I've had some embarrassing moments while learning the rules and etiquette which is probably common sense to everyone else.


I’m writing a book on how I do this! I’ll be sharing here on HN once it’s complete.

But the TL;DR for the chapter on motivation and energy comes down to: work on things that improve your own life, set clear objectives, and work in small chunks. The book itself is being written in 30 minute chunks throughout my week because that’s all the time I can spare.


I found that back when I had lots of free time, my style when doing projects was: I start where I left off, I get engrossed and code late into the night, repeat that one or two more days, get bored and "burned out" from the project, don't touch it for a week or so (sometimes I work on some other projects), repeat.

Of course, that's not really sustainable. But 30 minutes does not seem feasible for me.

It's not like you're going for a 30 minute jog where you just run without thinking. Don't you need to take time to "warm up" until the project you're doing starts being fun? And how does stopping just when you start enjoying yourself not kill your motivation? And don't you think about the project throughout your day job (instead of whatever problem you're supposed to be working on)?


Agreed, 30 mins is not enough time to get into "deep work" for programming. At best you could do some business-y tasks.


I reckon TDD would get you at least part of the way there, because it enforces a discipline of making smaller, meaningful changes. Hard to learn though, and some things genuinely do need longer.


on the contrary it can make you more productive. for one it forces you to take a step back regularly instead of blindly going down a potentially wrong path.

https://en.wikipedia.org/wiki/Pomodoro_Technique


I’ve found 30 minutes works just fine for programming as well as the more mundane tasks. Primarily because it’s not always 30 minutes, that’s just the minimum I can get away with on a regular cadence.

Then a spare weekend will finally come around and I’ll have made enough progress that I want to spend an hour, or three, on the project.

The purpose is to make progress however you can. This is also why my other points are so important: work on something that will directly benefit you (scratch your own itch) and have a clear objective outlined.


In 30 minutes I can pick up where I left off and write most of a blog post so i can definitely see it working for writing or the like but I'm gonna get much less programming done than if I worked continuously for a while.


Then don’t work so much. One can live comfortably doing freelance programming for 3 months a year and spending the rest of the time on creative projects.


"It becomes a job" doesn't really satisfy me as a description for what occurs when you strike out on your own. Running your own business is much more intense and engaging than having a job. Now, it's important that you see it as multiple jobs, and not just one job. Whatever your day job is you're going to have to wear multiple hats in a startup and it's going to challenge you in different ways than a corporate job will. In a corporate engineering job, it's likely that you're working on a small subset of features of a broader product and of a broader organization. As a founder of a company, you'll be coding, promoting, designing, innovating, QA, customer service, sales, and more.


...bookkeeping, reviewing contracts, managing insurance and licensing requirements, networking, the list goes on. You can farm this stuff out when you get big enough, but in the beginning you need to rapidly learn a lot of business skills that you may have only passively come into contact with prior. You will be better for it, even if you decide to go back to corporate at some point - you'll be relieved you don't have to do all the bootstrapping, but you'll appreciate what really goes into a business operation in a way you never did before.


The key is to have a high-paid part-time job.


And in what universe would one find such a thing?


Working remotely from a cheap place for clients from expensive places, charging expensive place market rate.


Contract work is not the same as part time work.


It's up to you to skip over clients who demand full-time commitment.


Or low outgoings.


Yes, however if you can figure out a project that pays your salary and is low maintenance (very hard) you can have even more time for your art :)


Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument. It's also rife with dubious claims:

> I’ve been working remotely for four years now, and I know that working alone can make you lonely..

I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex-coworkers (that may also be fully remote), etc. I hear it a lot, but this argument honestly falls flat on its face as long as you're not a weird hermit that only works from your house. In fact, that main reason I wanted to work remotely is because I get to meet people (particularly women, as I'm getting to an age where marriage is starting to become a priority) that I'm more interested in than in the myopic circles that are commonplace at large tech companies.

> I like the idea that you can earn money while you sleep, but are those businesses fun?

Yes. Because it gives you the freedom to do whatever you want. And freedom is fun. I mean, passive income is basically free money -- I'm not sure I'm getting what author is saying here.

> I imagine working on your own thing full time and on the side are definitely not the same; it’s scary, to be frank. If my side-project became my full-time work, might my passion for my project dwindle and become yet another job? How would it differ from my current job?

I don't see how working for your own business could ever become "just another job" -- you're acutely invested in the venture, your strategic decisions guide it's success (or failure). Working for a corporation is the definition of "autopilot" for most above-average employees (engineers or otherwise). This could not be more different when doing your own thing.


>Not to be dismissive, but this post feels a bit like rambling without a clear thesis or main argument.

The post opens with:

>This is more of a brain dump or an internal monologue. I don’t intend to prove any point or convince you to start your own thing. Neither do I want to reassure you that working for someone else is the best option for most people. My goal here is simply to get my thoughts out so I can think clearly again and rationalize this thing that’s been nagging me.


Missed this, mea culpa. Speed-read through the first few paragraphs, as they seemed to be an extended introduction.


"When people think you're dying, they really, really listen to you, instead of just waiting for their turn to speak.”


I didn't actually read the article too thoroughly so I missed that quote, but that was essentially my thought when I read the other poster's complaint. "why is that a bad thing?".


When I told people I took a full-time remote job at my previous company, they all asked me if I was going to miss seeing people.

And that just confused me - I do sports so I hang out with people, I take language classes outside of work, and on top of that I am married and we have a pretty active social life.

If you only see people at work - I think that's a red flag. Get a hobby where you see people, it's good for you. :P


I hear it a lot, but this argument honestly falls flat on its face as long as you're not a weird hermit that only works from your house.

Having worked remotely for close to five years now those who worked in coffee shops and not from the comfort of their own homes were usually the weirdos.


I work in an office currently but did the coffee shop thing in grad school. That would be my work environment preference honestly; something about the ambient background noise / environment and knowing none of those people will interrupt you. (Actually, my office has a coffee shop within in and that is indeed where I sit most of the day when I’m not in meetings.)

I am an extreme introvert though and could go just fine for weeks without interacting with anyone, so if that’s what you mean by “weird”, then yeah, I guess so.


As a near daily regular of a cafe to work on my own projects, I’m curious why you think that. I won’t take anything personally. :)


This is just my experience so far.

For some reason those whom I worked with who were choosing to work in such places usually were also not overly sociable. I have, of course, at least one example of a person who works at home and is self-admittedly antisocial, but the correlation is still there.

I have this one friend who only really uses his tiny apartment for sleep and other basic stuff. He works at coffee shops and doesn't cook even though he's good at it. Getting to know this guy was a lengthy and laborious process.


I think the rambling was basically the point. He wasn't sure. I found it kind of refreshing.


Paraphrasing, but he said early on that he wasn't trying to convince the reader of anything and that it was just a brain dump of his thoughts.


I thought that was a bit odd. If it was for the author's own rationalization and is not trying to convince the audience of a any kind of point, then why is the author publishing this publically? Why can't the author write this out in notepad or on pen and paper(Like I do.) and leave it at that? Vanity?


His brain ramblings may be useful to someone else out there having similar experiences or thoughts.


Well as for entrepreneurs, limited ability to meet people is a common complaint. There's even a TED talk about the issue. We had a successful founder speak to my class when I was in school, and this is one of the downsides they discussed. Most people meet friends through work, and meet significant others through friends.


I think his points are valid. Speaking as someone who has spent the past 18 months doing my own thing.

> I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex-coworkers (that may also be fully remote), etc. I hear it a lot, but this argument honestly falls flat on its face as long as you're not a weird hermit that only works from your house. In fact, that main reason I wanted to work remotely is because I get to meet people (particularly women, as I'm getting to an age where marriage is starting to become a priority) that I'm more interested in than in the myopic circles that are commonplace at large tech companies.

It shouldn't be controversial that if you decide upon a path in life where 8 hours of it you spend by yourself, you're going to meet less people than if you were working in a team at a company. Also, some people do not live in the same place they went to school and/or university for example (unlike you).

> Yes. Because it gives you the freedom to do whatever you want. And freedom is fun. I mean, passive income is basically free money -- I'm not sure I'm getting what author is saying here.

If you want to make money, you cannot do whatever you want, you have to do what earns you money. And sometimes what makes money is not what is fun.

> I don't see how working for your own business could ever become "just another job" -- you're acutely invested in the venture, your strategic decisions guide it's success (or failure). Working for a corporation is the definition of "autopilot" for most above-average employees (engineers or otherwise). This could not be more different when doing your own thing.

Passion can dissipate. Doubts will set in as you question yourself whether it's all really worth it. If you want to make money you will inevitably have to start doing things which you would rather not do (because you would rather do something else), and that's when you start to question the whole project, because if success is in doubt then why spend your time doing stuff you don't enjoy if you have the freedom to do something else [which is fun]?

That all sounds quite negative, so let me balance it out by saying I really enjoyed working autonomously, but if trying to create a business with a product I would definitely aim to do it with a cofounder or two. Consulting by oneself is fine though.


> I also work full-time remotely. I built a community around myself, made new friends and regularly hang out with people I met at coffee shops, at startup meetups, old classmates, ex-coworkers (that may also be fully remote), etc.

This reads like “I have a social life.” I’m sure the author has a social life as well, but it’s way harder to casually chat to people throughout the day when you’re working on your own. (Source: also self-employed/solo for four years.)


Probably the biggest hurdle is dealing with healthcare on your own, it's just prohibitively expensive to deal with alone in the US. Multiple incomes is where it's at, at least until one of the projects takes off to cover cost of living and healthcare nonsense.


What is your definition of prohibitively expensive?

I've bought a gold plan off the exchange in California for Kaiser and it's $530/mo with no deductible. That's lower than I expected.


$530/month sounds insanely expensive to me as someone outside of the US. My private health insurance costs me approx $100/month. 530 is over half my rent (outside of a major city though, in the major cities rent is much higher)


Your insurance is probably heavily subsidized by government from income tax.


Yeah, and? It's not that the US has one of the lowest income tax rates in the world (in fact, it's one of the highest, especially to their citizens that work abroad).


It's prob important to know level of coverage and % of income it costs vs absolute numbers which is fairly meaningless.


how much do you pay in taxes though?


I've recently moved to the US from Australia. The amount my employer and I pay for my healthcare is significantly more than I paid in Australian taxes for healthcare. And that's before including my deductible, things my insurance doesn't cover and the amount I pay in US taxes for healthcare.


In Australia, the government spends over $70B on healthcare, but collects only around $10B through Medicare levy surcharge. The only reason your healthcare spending in Australia seemed so low is because an overwhelming majority of the cost of healthcare in Australia is covered through general taxes, and not through the Medicare tax. Even if you focus on Medicare benefits only, the Medicare levy surcharge only covers less than half of the Medicare benefits.

That said, healthcare in Australia in fact is cheaper than in the US, but not as much cheaper as you think it is.


The US actually spends more per capita on health care than Australia both public and private https://www.healthsystemtracker.org/chart-collection/health-...


Yes. And US doctors make more "per capita" than Australian doctors. About twice as much. If they continue making more, I don't see how paying their billing rates from the taxes addresses the "affordability" problem. If you were to fix billing rates at a lower level (through single payer and such), you wouldn't really have any doctors to begin with, at least not for a while.


Doctors' wages aren't the biggest cause of higher spending. Admin costs and pharmaceutical spending are the largest (unnecessary) cost centers.


Citation needed. Most of _my_ medical bills go to the doctors.


I live in Australia and that doesn't seem out of the ballpark. I pay the equivalent of USD$1.3k a year in levies and USD$100 a month for health insurance. Australia doesn't have access to the same level of care either (for example, bleeding edge cancer treatments or experimental medicine).

I also pay substantially more in other general taxes (compared to the US), which ends up funding healthcare as well.


For healthcare? In my case much less because the system feels a bit like very regulated competing non profits with a public option available and defined minimum service.

I've heard we've been paying more and more for certain types of medicine as far as subsidies go and although i haven't looked into it enough i can't help but look with distrust at recent governments over it.

https://translate.google.com/translate?sl=nl&tl=en&u=https%3...


Approx 35% in income tax (which includes social security etc).

Note that private health insurance isn’t a necessity, public healthcare is generally ok here, but I choose to go private for comfort and additional peace of mind.


I was looking last year in Washington. Cheapest option for my family was ~$1800 / month, and that had a 14k deductible and ~20k max out of pocket. It also couldn't be used outside of Washington state (which sucks).

Went with the health ministry route because we align with their principals already, plus we can visit family out of the country and be "covered".



That’s because health ministry isn’t ACA conforming health insurance. It’s ridiculous the law had to allow those stupid plans to exist to be passed.


Can confirm similar prices for a family of 3, no prior health issues.


Since 2010 and ACA, health insurance companies are not allowed to factor in pre existing conditions for premium costs.

When you search for health insurance, you’re only asked for age and location and smoking. Basically, nowadays in the US, your health insurance premium is simply a function of age, and the premium for oldest person at 65 is limited to be a multiple of youngest (healthiest).


$530 a month is like 85% of rent where I live in the midwest. I mean if I could only get healthcare through the marketplace, I would be better off working part time or not at all collecting unemployment and food from pantries than I would be essentially putting all my extra income toward health insurance.


Mine is 275/mo for Kaiser at a high deductible but still gives me the amount of coverage I basically used when I was employed (Physical + maybe one additional visit per year). Single person, 26, no kids.


yeah...for me one expensive drug a month (truvada, which is ~$1500 out of pocket) means it makes no sense to buy a high deductible plan.


> $530/mo

Wow. Just wow. As an Australian, I cannot fathom having to include $530 into my monthly budget just to ensure I don't end up homeless (or heavily in debt) if I get really sick. I'm not a socialist (I'm quite a centrist when it comes to economic policies), but something about the US system absolutely must change.


Not sure how it works in Australia, but if i break down my salary by taxes in Eastern Europe, I'm paying 33% "social tax" which comes out to around 1900€/month. This breaks down further to 2 groups. One for pension and the other for healthcare.

Pension is 20% from the total. (used to pay the current pensions)

Healthchare is 13% from the total.

This comes out at around 990€/month for "health insurance". There are advantages and disadvantages to both systems, but I'm pretty sure you're paying something as a tax for you health insurance and it's probably similar to what they're paying.

To be fair, i'm well paid and a person with an average salary would pay around 250€ monthly. It's just the way our system is setup with a fixed % which automatically creates tax brackets.


The healthcare costs for insurance in the US don't include the costs of actually visiting the doctor or getting medicine. You still have to pay for those, amount dependent on the terms of your plan.

For example, a routine doctor's office visit can cost hundreds in addition to the monthly fee you pay.

Last year I paid $300/month for my medicine, in addition to other costs.


Wow, you earn a lot for Eastern Europe. What do you do if I may ask?


Probably a software engineer. If you're a little above average, salaries are very high. Most software engineers I know in Romania make at least 5 times the national average. Good ones make up to 10 times the national average.


Still, according to his numbers he makes about about €70k/year. That's more than me and my friends make in Germany and Austria. Either Eastern European salaries took off like a rocket or Germany heavily underpais.

Really curious what his job and location is, maybe I move there :)


That's before taxes I believe. So after income tax and social contributions, you'll have paid 40-50% of that. Doesn't sound off to me. At least, that's the case here in Romania.

Another interesting fact is that in Romania the tax system is simple enough to always negotiate in net salary. Your employer takes care of paying taxes and social contributions etc.


So €70k/year before taxes is a normal dev salary in Romania? Are you sure, since that's basically German level of salaries but with much lower COL. Do you have any sources for this?

Because if that's the case I'm coming over to join you. :)


we compete on the same market, so we have the same salaries.

But the rest of the country doesn't, so we have the lower COL.

Give me a private contact and I can give you some concrete answers and tips regarding the area.


Cool. Drop me a line at the email in my profile please. Thanks


software engineer/manager with (bigger) international projects. This is on the high end for such positions.

I can't complain :)


Wait until you hear what we pay for child care on top of the cost of insuring a family (I suspect that $530 is just for a single individual, or maybe a couple at most). Let's hope your student debts don't put you in the poor house too. Oh btw, that $530/mo for health insurance really only matters if you have a serious illness. Needed to go to the emergency room for some minor injury, or perhaps want preventative care? Be prepared to spend thousands every year.


That’s actually on the cheap side. If you have say a wife and 2 kids, you pay around $1500 a month on the health exchange.


I don’t know how you guys do it. With the exchange rate that’s probably close the my rent each month!


1500/4 = 375, which is significantly cheaper than 530.


The person that said $530 said no deductible, and they’re probably a young person. $1,500 family of 4 insurance will have at least a $5k deductible and $13k oop max I would estimate.


my wife and i are in our mid-50's. Here in NM, we have $1095/month with a $6600 deductible each. I'm happy paying 10 of our income for health insurance, but only if we actually get health coverage without that kind of deductible.


My parents at a few years older than you get bronze HSA PPO at ~$2k per month for both with a $13k oop max and a $5k or something deductible.

The thing about health coverage is that you either pay via your premium or via deductible/oop max, but there is no escape. The health insurance is there to protect you from losing your assets from costs over the out of pocket maximum.

Since you’re in mid 50s, even the astronomical amount you pay is actually being subsidized by younger people, since your premium is capped as a multiple of someone in their young 20s.

Otherwise, you’re real health insurance premium would be even higher. That’s just how expensive healthcare is in the US, and how guaranteed you are to needing it as you get older.


Keep in mind Australia has ~40% more doctors per capita than the US [0]. And the supply/demand curve is not linear, so physician shortage alone can account for a significant part of the price difference (note that Singapore and Japan are noteworthy exceptions to the doctor/quality ratio). As for why there are fewer doctors in the US than most developed countries, there are a number of potential reasons, and there is no reason to believe that any of them would be solved by the government subsidizing healthcare. You might just get long wait times like Canada and the UK (with comparable, but still higher physician counts than the US), which are sort of the jokes of socialized medicine countries.

[0] https://data.worldbank.org/indicator/SH.MED.PHYS.ZS


Let's do the math.

Someone making 100,000

On average you pay 2% of annual salary to health levy which gives you medicare 2000.00

If you are over 90k you pay 1.5 unless you have private insurance On average $2000. Plus on average $800 in extra like someone driving you to the hospital

$4800 aus to usd = $3312.41

It looks like you are paying half.

But the government is spending 7800 a year per person. So the additional cost comes from general tax revenue which you pay.

On average you are paying an extra 10000-15000 in taxes on that 100,000


Given the context of this conversation... How does the math change if you strike out on your own, earning nothing for a year?

I think it suggests that the healthcare barrier to entrepreneurship is much higher in the US than in Australia.


I pay $15K/yr for a family of 3 for health insurance. Where I live it costs $95K/yr post-tax for a family of 3 to maintain middle class lifestyle (verified by not working for a year), including about $3K/mo mortgage, $1k/mo real estate tax, $1K/mo groceries, and a modest vacation in the tropics in December. So while $15K is clearly expensive, it's not dominant in the grand scheme of things. Of these numbers, BTW, it's the real estate tax that pisses me off the most: I have to pay the government to live in my own goddamn house, WTF.


Try changing your viewpoint on real estate taxes. I assume you live in a city (or else you wouldn't be paying much). By allotting your parcel of land for private use, everyone else's destination will be just a little bit farther away on average when a trip from A to B takes them past your land.

(Ref: why were medieval cities so dense despite their low populations and plentiful surrounding acreage? Everything had to be walking distance, so a big manor in the middle of the city would place a major burden on everyone's commute whose destination was not that manor).

So the tax is what you pay for the burden that your exclusive hold on the land imposes on others.

Or, you could think of it as what you pay to maintain the right for it not to be paved over as a superhighway, plus what you pay for the government to agree to keep other people from trespassing.

Not the fee for living there -- the fee for not letting others live there.


Medieval cities are dense because they had walls outside for protection. It's not like the US has insufficient acreage. I kind of got why the real estate tax was so high when my state wasn't charging sales tax on internet purchases out of state, but now it does, and yet the tax just keeps going up every year, and they also pile on the levies to boot.


I think you are missing the point of the system: you pay the difference in general income tax now so when you are unable to pay such levels the state (and those still paying income tax) take care of you. If you are always able to pay for private health insurance or are always being taxed highly on income you are very lucky and should have no problem kicking in for public health.

There is no minimum tax payable before accessing healthcare services: if you have no income, or are unlucky, you won’t die or be debt ridden for the rest of your life.


And in the US the Affordable Care Act means that if you don't have much income the government will pay for some (maybe all?) of your health insurance premium.


$530 a month would be amazing. I have a wife and 3 kids and we are looking at closer to $1200-$1500 a month for decent health insurance.


I'm confused. You're currently paying $300 pp pm. That is much better than $530 pm.


the per person amount hardly matters for a family's budget...the fact is you're paying far more than a single person


Of course per person health insurance costs matter when discussing health insurance costs. Why would one compare the cost of one apple to the cost of a bag of apples?


"I'm not sure why I can't afford to feed my children, I only have 12 of them."

Children are getting covered just like adults are. Just because they aren't/can't earn an income to cover it doesn't mean it doesn't cost just as much to the insurance provider. In fact, children tend to go to the doctor more, so...


Medicare and Medicaid provide free healthcare to many Americans. Obamacare subsidizes health insurance for many additional Americans. For the most part, you only pay full cost for insurance if you can afford it.


You don't qualify for medicaid if you have any assets. You'll have to spend down to you last $2k in assets before you qualify for medicaid. So... someone in the middle, who perhaps has some savings, can still be ruined if they have one moderate incident which would force them to spend down all their assets to poverty level before receiving any assistance.


For the record, if you live in CA, I don’t believe this applies to Medi-Cal. Unless you’re a “Medi-Cal individual who receives long-term supportive services or who enrolls in Medi-Cal through certain disabilities”, I believe only income is tested.

(Not that this is enough! I am absolutely on the side of everyone having access to good public health care.)

https://ca.db101.org/ca/programs/health_coverage/medi_cal/pr...


well... certainly in NC, it's 'assets' (although house/car don't count, but any savings/investments do)


the difference is probably negligible when you sum up taxes

and like others said you would qualify for either free or subsidized insurance if you were low income


I don't think that's the case. $530 is nearly 10% the median household income. And that's just healthcare. Keep in mind countries with higher tax rates aren't just getting socialized medicine but vacation days, parental leave, cheaper education, and usable public transit.


Germany's system is generally liked, and "the public option" is ~15% of income (but we "split" it between employer and employee so it doesn't look as grim, which means you get half of that less in salary, but only pay half yourself). 10% seems reasonable, and is something you'd only achieve in Germany if you have a high income (because the total amount paid is limited) or go for private plans (which you can if you're self-employed or in some special cases, or if you have a high income; caveats apply). The public insurances also provide a much lower level of service than the private entities (e.g. you're paying for glasses yourself unless you're basically unable to function without them). That's on top of having income tax on the higher side and a high VAT, and high rents. From that perspective, 10% seems great.


Not at all! Using some simple online calculators, assuming you earn $125k in San Fran, your take home pay after tax is $85k. In Australia, your take-home pay after tax is $88k (and that includes the medicare levy deduction if you don't have private health cover).

So not only are you being taxed more in the US, you also have to pay for healthcare on top of it. Insane.


if you're working a regular job then that's not true because employers heavily subsidize your premium or pay for it in full if you're working full time.

if you're self employed then your health care premium is 100% tax deductible


Half of Americans don’t have employer sponsored health insurance:

https://www.kff.org/health-reform/press-release/coverage-at-...


I think most people don't know that. I didn't know that.


Speaking from experience, this is true. You should be comfortable with going without insurance for a while if you're going to go out on your own. Or consider alternate programs (health ministry, direct primary care subscription, or use 2020's new ICHRA options to route employer pre-tax expense to employee premiums). Lack of health insurance is a large barrier to starting your own business.


If you don't have a family and have a remote gig lined up move to low cost country for a bit.


Wouldn't that imply startup rates to be much higher in countries with national healthcare? But I don't think that's borne out in data.


There are many confounding factors there. Countries with government-provided healthcare also have many other differences that contribute positively or negatively to entrepreneurship.


It isn't, and it is a known enigma. That said, I'm inclined to think our entrepreneurship rates would be even higher in this country if we had a non-employer based health care scheme. I base this on the anecdata of having met easily dozens of people over the years who wished to be entrepreneurs but stayed in job because of the health care benefits. Would love to see further studies of this correlation between health care costs + entrepreneurship.


Entrepreneurship in Scandinavia is higher than in the US.


Was just looking at this out of curiosity the other day and in California the equivalent plan to what you’d get from employment to cover a family is $1,500/month from anthem. This is the platinum ppo from the exchange. $15 doctor visits, $9,000 yearly max, no deductible, $30 tier 3 drugs.

The price is similar to what you get from an employer, except the employer pays most or all of the premium.


That doesn’t sound right at all. I just searched on coveredca.com and anthem platinum ppo for 2 40 year olds with 10 and 15 year old children is $3,600 per month.


I graduated the same time as you & had a side project that I handled for about 2 years at bigger co before making the transition to running with it full time (now ~3 years)..

I can tell you the points that stick out the most for me:

- i've learned a HELL of a lot. I've learned so much running through the hustle life that comes with making these projects work & handling life around it etc there couldn't really be a price tag on that. At first I was more or less a hacker w some sales skills. Now I feel like I could handle ceo-coo-cmo-cto type things all because I had too. These are lessons & knowledge for the rest of your life. Even a generalist will be thrown constant challenges, I guarantee it.

- I had to make big adjustments to my social life. It's good you have some remote experience because this one was a challenge. Deciding what to go to and trying to spend time w/ community is difficult when you are trying to get it all done. Spend energy and time in places you enjoy & appreciate. When I worked at big co I would go to things all the time on weeknights and throw it on the weekend but you cant really afford all those peaks as much when youre on call as the boss. It's too taxing.

- Self Care: Could really go a long way with this one but damn.. This is the most valuable lesson I have learned. You have to watch over yourself. Like Marshawn Lynch put it this past weekend.. "watch over your mentals, your emotions, your chicken (i think he was talking about the body." Take some time off to relax when needed, keep tabs on your body and mental well being & keep close community who can help and support you when needed. It will go a long way to have someone who can help you when you just need to vent or maybe have a glass of wine ~ ~

- I'm happier - I do a little bit of work just about every day but I'm also spending a bit more time in creative areas that really make me feel good that I coulnd't seem to get time for at a big co. I make less money but I can't really seem to put a price on that "hey i'm gonna go surf cos waves are crushing right now.. will do this when I get back" option. The ability to control my time in life is one of the most valuable assets I have.

There is something about humans and how we think about what it is like on the other side. Is the grass greener? Only one way to know ~ ~ good luck xX


Funny they compare working at a big tech company vs starting a business as dichotomies. I actually think there is a lot to be said about saving up a lot of liquid investments at big tech cos, then using that as personal runway/seed capital for your startup. That is my plan, anyway.

Having a project that already has ARR is a massive headstart over most people too. Especially if you are close to ramen-profitable, then quitting to run it full time only requires sacrificing relatively assured opportunity cost.

I don’t know how it works when you’re on a visa but since I’m not, I know I would probably just quit as soon as I had enough liquidity. You don’t have to be married to your first business for life. It’s an amazing opportunity, not only necessarily financially, but also in terms of learning potential.


> I know what most people’s heuristics is when they face this uncertainty: think about ten years from now and figure out where you want to be. And do the thing now that gives you more options to get there. I wish it was as simple as most people claim. Looking back to the twenty-year-old me and the person I’ve now become, I see almost no similarities, interests, or passion. I was a completely different person back then and the only thing that has stuck with me after all these years is my love of soccer. How do people predict the future? Clearly, I’m no good at it.

This is actually the primary focus of a book I just read [1]. The author's primary thesis in this book is that that there are some very interesting reasons why we completely suck at imagining what a future life will be like.

This isn't really a book recommendation - the author took a single idea and chewed it in 20 different ways to make a larger book. However, if this is something you are struggling with right now, you might benefit from it a little.

[1] Stumbling on happiness - https://www.amazon.com/Stumbling-Happiness-Daniel-Gilbert/dp...


"and I know that working alone can make you lonely. ... If I work on my own business alone, I won’t have co-workers until I hire them."

In 1999ish I was approached by two chaps that I worked with and one of whom I worked for (he was my boss.) Would I fancy being the Managing Director of a new company thing they'd dreamed up? Nothing too grand, first customer was where we worked already etc etc. Times have changed a bit now and we have some customers that most people in the UK have heard of.

Our triumvirate has worked out really well over the years. We will never set the world on fire but our little business keeps us and our 20 odd staff pretty comfortable. Three directors has worked out very well for us. Two stops one being a twat for example!

My advice is that you might consider finding and attracting a few allies but you must position them carefully. Fill in the bits that you are shit at. For example, if you can't be arsed with accounts then get someone in who will and pay them properly with shares if they are an early appointment and you can't give them readies now.


>> If I work on my own business alone, I won’t have co-workers until I hire them.

There's another, more subtle issue. If you aren't sitting on a million-dollar seed round, there's a _huge_ energy gap between working alone and hiring someone, even for a consultancy, never mind some kind of product effort on which you work for a year before you get any revenue.

This is in part because of the additional taxes you have to pay if you're no longer flying solo, and in part because of demands on your own time. Say you're doing something solo and you're super strong technically and can do what you do very efficiently. It's pretty easy to generate a ton of revenue working in this way. It's also much easier to tolerate gaps or reductions in revenue - you could just work on your own stuff and continue to pay yourself from past revenues. Say, now, you want to grow, and hire people. But you can't just hire people. Now you have to pay for their benefits, pay unemployment insurance, etc etc. Moreover you have to manage them, which will reduce your own "technical" throughput to basically zero. I've done a back of the envelope, and for me it doesn't make sense to have fewer than 10 people in my employ, since I can't skim enough off the top to justify my own loss of productivity. And 1 person solo LLC vs a 10 person company are vastly different companies in terms of business operations (especially bizdev and sales), taxation, and regulation.

I'd theoretically like to grow at some point. But I don't know how to do it in a sustainable fashion as a consultancy.

Being (overly) fiscally conservative, I would not feel comfortable hiring for a more product-oriented business either unless it demonstrates traction and upward trajectory. $1k/mo is not what I'd call "traction".


Partnering informally with a "collective" of like-minded independents is one way to thread that needle.


Those independents are few and far between in my field, unfortunately.


A day job doesn't have to be your side project's enemy. If you do web dev at work you get paid to do something that makes you efficient at web dev. Then you go home and work on your side project and you don't need to spend hours struggling with webpack or why str=((num || fallback) + '') works, so your side project is done more productively too.


Come home at ~6pm, make/have dinner ~7pm, exercise ~8pm, get home and shower ~9pm. At this point there's not much time to do work, especially if you have to go grocery shopping, do laundry, clean, have a family, or any number of other misc things like get a haircut or have clothes dry cleaned.


It's so funny to read stuff like this from people who don't have kids. I remember thinking the same. Now I look back and realize with horror how friggin much free time there was and how much more I could have done with it!


A side project can be 2 hours a week. You can optimise making dinner so it take less time (cook in bulk, make some meals salads). Exercise can be done at home, probably 30 minutes in the morning and evening is more than enough.


As with everything else, you have to prioritize - there will never be time for everything. Meal prep and home exercise alone can cut that schedule down to 60-90 minutes, so you can begin on the side project at 7.30 pm.


7.30-9.30 would give you 2 a day. Say 2 nights and then on the weekends. 8 hours a week. That isn't much but the trick is to do something quite focused.


I personally just get so drained after a day of work, on top of exercising, and some sort of recreational activity would be nice. The work isn't hard. It's the thinking that goes around the work that is the draining part. Especially if you want to keep a job. Others can perhaps compartmentalize a bit better than I can.


It depends on what you do at work a lot I think.

Working on greenfield projects is so much less mentally draining than working on some old thing with only 10% of its functionality encoded in tribal knowledge that interacts with like a 100 different services that you need to constantly be learning about.


Definitely. Greenfield is rare in my experience though. And there is greenfield solo (awesome) and greenfield team of 20 all chucking code in (instant legacy!)


Most of the time I'm doing nothing at work all day, yet I manage to pass out for 3 hours of exhaustion after I get hone


I need to meet this guy. It sounds like I wrote this piece. I have exactly the same thoughts and I also love soccer...


Wondering how many other people are beginning to consider their future in this way. It's interesting that he linked to the a16z post on Passion Economy. As opportunities for remote work where each individual charts their own course increases, the future of work could change significantly.


I don't see this work for everyone. In the HN discussion[1] about Passion economy, someone mentioned that industries with the most creative and "passionate" people, the distribution of rewards follows the power law. Only a small percentage of the total industry will be able to capture the profits that is sustainable.

So yeah, I am skeptical that this is the "future of work".

[1]https://news.ycombinator.com/item?id=21200795


I have nothing to add that hasn't been said in other comments, so I'll comment on something that surprised me a bit:

> Looking back to the twenty-year-old me and the person I’ve now become, I see almost no similarities, interests, or passion.

Comparing the me of now with the me who graduated college almost seven years ago and I... am essentially still the same guy, only with a lot more money to spend.


Funny to read someone else's musings on this as I've been working through many of the same questions for a while. I started full-time in the tech industry before I was out of high school, then went corporate, then got out for a while, then back in, then had my own business for a while, sold that, got a job for a few years, and recently left that job and went traveling for a bit to think about things and consider going back to full-time employment or work on a project and hope it makes enough to survive on.

> Do I have to choose it now, or can I do what I’m doing now and decide later?

If you're thinking about it now, then you should start figuring it out, or you're postponing the inevitable and these questions will be on your mind every day.

> If so, why are these questions disturbing me now and not in the future?

Possibly because you are dissatisfied in some way with what you're doing now. A good chance that you're finding it comfortable but not stimulating.

> How do most people work out what’s the right path for them to take?

Most people don't, and don't believe the ones that say they knew in advance what the right decisions were. None of us can see clearly into our possible futures; we can't see in advance the successes we'll have or the mistakes we'll make. The best we can do is to understand our motivations when we do make a decision, and then at least be at peace with that decision no matter how it turns out.

> Does it have to be either or can you do both things together—have a full-time job and do your own thing?

If you want to live a balanced life -- i.e., without all of your waking hours behind computer screens -- you should choose either/or. Working full-time and trying to put real energy into a side project doesn't leave much time for anything else, and it will cause both your full-time work and your side project to suffer.

This isn't to say that people never manage to pull this off. Some people make it work out. They are the exceptions that prove the rule.

> Looking back to the twenty-year-old me and the person I’ve now become, I see almost no similarities, interests, or passion. I was a completely different person back then and the only thing that has stuck with me after all these years is my love of soccer. How do people predict the future? Clearly, I’m no good at it.

Congratulations, you're a normal, healthy person that's still growing and maturing. Keep doing that.

> I wonder whether, as we grow older, the rate of change in our interests slows down too?

It hasn't, for me, and I think I'm at least 10 years ahead of you. Nor has it for any of my more interesting older friends.

What does change is the gradual realization that you won't have time for all of your interests. Being a dilletante is a lot of fun while in your 20s and 30s. Some manage to have fun continuing to dabble in a bit of everything for many more years, even into very old age. Other folks start to feel like they might be missing out on something by just grazing the surface of their interests, and start to consider whether their time might be better spent focusing more intently on just a few.

> I imagine working on your own thing full time and on the side are definitely not the same; it’s scary, to be frank. If my side-project became my full-time work, might my passion for my project dwindle and become yet another job? How would it differ from my current job?

Your project should become your full time job. You should maintain the discipline you have in your current job and resist the urge to fritter time away here and there.

But it will be different, because you'll be investing in your interest, and despite it becoming your job, you'll still feel an ongoing sense of satisfaction at being solely responsible for your success or your failure. If you wake up one morning and have a great idea for your project, you won't have to convince middle or upper management, or enlist a sales team, or wait until the next company all-hands. You'll just do it.

And that can be really rewarding, and it can also be a great big trap you fall into, without anybody else holding you accountable or challenging whether your next idea is a good one or not.


Thank you for your insightful answers.


Doing your own thing often means working for clients which means working for someone .


Being alone is easily fixed by a coworking space


Not speaking from experience here, but I don't think it's the same. I'm guessing there's a churn of people, so no long-term relationships, also since you're not working on the same thing you have less of a connection with them.


Cached Version: http://archive.is/vgHTv


These days, you either work for a company as an employee, or you work for cartel as an entrepreneur.


Why not both?


I never use term "working for someone". I can work "with someone" as a part of the team. In my native language (Polish) "employer" could be literally translated as "workgiver", which is a complete bullshit, because "work" is not a social construct, but kind of relation between living organism and nature (and only because of that it is derivately social).




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