Working for someone vs. doing your own thing

by thakobyan • 7 years ago

339 222 7 years ago

tannerc3• 7 years ago

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

winrid• 7 years ago

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 :)

chrisco255• 7 years ago

"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.

aksss2• 7 years ago

...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.

kentrado• 7 years ago

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.

tannerc3• 7 years ago

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.

spir• 7 years ago

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

q-base2• 7 years ago

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.

akvadrako• 7 years ago

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.

zerr3• 7 years ago

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

tonyedgecombe• 7 years ago

Or low outgoings.

AnIdiotOnTheNet2• 7 years ago

And in what universe would one find such a thing?

dvt2• 7 years ago

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.

daxfohl7• 7 years ago

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

hunter-gatherer• 7 years ago

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.

just_myles• 7 years ago

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?

iherbig• 7 years ago

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.

celticmusic• 7 years ago

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?".

dvt2• 7 years ago

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

Tade02• 7 years ago

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.

whytaka• 7 years ago

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. :)

Xcelerate• 7 years ago

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.

Insanity• 7 years ago

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

Nimitz14• 7 years ago

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.

unishark• 7 years ago

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.

archagon2• 7 years ago

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.)

daxfohl7• 7 years ago

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.

neonate3• 7 years ago

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.

daxfohl7• 7 years ago

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.

complianceowl3• 7 years ago

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.

Yabood2• 7 years ago

> 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.

manigandham3• 7 years ago

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.

aledalgrande2• 7 years ago

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.

mettamage2• 7 years ago

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.

mehrdadn• 7 years ago

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.

minism• 7 years ago

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).

sokoloff• 7 years ago

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.

daxfohl7• 7 years ago

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.

hanniabu2• 7 years ago

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.

toohotatopic• 7 years ago

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.

toasterlovin2• 7 years ago

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.

ForHackernews• 7 years ago

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

BlameKaneda• 7 years ago

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.

bpt33• 7 years ago

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?

jameslk• 7 years ago

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...

manicdee• 7 years ago

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).

ppeetteerr• 7 years ago

Are you referring to this? https://qz.com/455109/entrepreneurs-dont-have-a-special-gene...

Spooky23• 7 years ago

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.

aledalgrande2• 7 years ago

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)

greggyb2• 7 years ago

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.

taneq• 7 years ago

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.

daxfohl7• 7 years ago

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.

discordance• 7 years ago

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

SamReidHughes2• 7 years ago

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

throwaway1777• 7 years ago

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.

pinky1417• 7 years ago

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.

steve19772• 7 years ago

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.

grawprog• 7 years ago

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.

huherto• 7 years ago

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.

overcast• 7 years ago

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.

glfharris• 7 years ago

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.

poulsbohemian2• 7 years ago

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.

simple_phrases• 7 years ago

Entrepreneurship in Scandinavia is higher than in the US.

JoshTriplett• 7 years ago

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

tempsy6• 7 years ago

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.

moretai2• 7 years ago

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

Thorentis2• 7 years ago

$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.

dkersten2• 7 years ago

$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)

racketracer• 7 years ago

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.

camhart• 7 years ago

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".

LeoTinnitus• 7 years ago

$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.

aksss2• 7 years ago

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.

qaq2• 7 years ago

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

davidjnelson• 7 years ago

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.

lotsofpulp8• 7 years ago

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.

JoeMayoBot• 7 years ago

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.

arvinsim• 7 years ago

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

thaumaturgy• 7 years ago

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.

thakobyan• 7 years ago

Thank you for your insightful answers.

hownottowrite• 7 years ago

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

mc34• 7 years ago

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.

moretai2• 7 years ago

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.

opportune2• 7 years ago

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.

hanniabu2• 7 years ago

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.

mc34• 7 years ago

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.

daxfohl7• 7 years ago

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!

opportune2• 7 years ago

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.

j45• 7 years ago

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

dilippkumar• 7 years ago

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...

gerdesj• 7 years ago

"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.

tinyhouse• 7 years ago

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

m0zg6• 7 years ago

> 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".

chrisweekly• 7 years ago

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

m0zg6• 7 years ago

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

h00dui• 7 years ago

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

r34• 7 years ago

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).

trumbitta2• 7 years ago

Being alone is easily fixed by a coworking space

posedge• 7 years ago

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.

cryptica• 7 years ago

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

cfontes• 7 years ago

Why not both?

luord• 7 years ago

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.

Working for someone vs. doing your own thing

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