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Ask HN: How Did You Escape 9 to 5?
226 points by vi1rus on Aug 31, 2016 | hide | past | web | favorite | 172 comments
Title says it all.

How did you escape your 9 to 5 job to start your own business?

I am curious about how you effectively spent your time while having a full time job and a side business and at what time did you decide to take the full plunge.




My story. I worked my ass off for 10+ years, saved a little bit of extra cash after paying off most loans and then bought an online business that I was interested in.

I tried doing both for 2 months in parallel. One day I woke up and said "F*k this. I am done. Gotta quit". I then went to my boss and gave him the notice. I did calculate my risks as the business was just bringing in enough to keep me floating (with 2 kids and a wife). However on Day 1, my income was down by almost 75% (ouch, wifey was not quite happy but she supported)

Been 2 years since then and never been happier. It is tough, income is still less than I what I made in my cushy job but I will not give it up for that 9-5 bullshit. No more traffic to deal with (I hardly drive during rush hours now), no more commute (I work from where ever i want, mostly home office), I can take time off if I want or I could work on weekends if I want. The business runs 24-7 but I Don't have to.

Of course, not everyone is in a similar situation but we all have a path if you really want to do it. Bottomline is that you have to really really want this. It is almost like an addiction to do your own thing and not work in a shitty (Even if highly paid) 9-5 job. My job was so easy barring the shit commute. I could go in, talk to users all day, run projects, write some code and at the end of the day, I will get a big fat paycheck. People loved me at my job. I loved them back. Easy as hell. But I didn't want that anymore. I was not up to it anymore. I wanted to quit my "cushy" job.


Very cool! I quit my cushy 9-5 about a year ago and have been contracting off and on since then. It has been amazing and I realized I can never do the 9-5 thing again. I hope to start my own business at some point. The problem is... I haven't had a good idea yet...

I have been thinking about buying an existing online business if I can't think of anything. When I look into it though I am completely in over my head. Do you have any recommended resources for learning about that sort of thing?


Same boat as you. I think this could be the key:

https://www.coursera.org/learn/startup-entrepreneurship-disc...

I can't recommend it highly enough.


Thanks! Definitely gonna check this out! Out of curiosity did you do the 'paid' or 'audit' version of this? I can't really tell if the 'paid' version is worth it. I can't imagine the certification being useful.


I always just audit the courses. I'm doing them for my benefit, not for a certificate. I might buy the lecturers' book though as a thank you.

Pro tip: Use the mobile app, download the videos and watch them at 2x speed to save time :-)


Pretty easy to download on a desktop as well: https://github.com/coursera-dl/coursera-dl


Can creativity be learned? I feel like I've been cursed with a stellar memory, which people often perceive as intelligence, but I see lots of my coworkers come up with great ideas for new tools and processes that enhance our core business. Some of them even seem obvious after the fact (not that it discredits them at all), but I seem to lack the creativity and confidence to build anything on my own. Do you think this class would help?


I have done the first week since estefan suggested it to me. After week one, I will say this: It has definitely been helpful.

It gets a little too philosophical at times in a "you need to want to change the world sort of way" but the professor really emphasizes that you need to become aware of your own strengths and suggests different ways of utilizing your particular skills to discover and solve problems. He provides concrete examples of how others have done this which I have found useful.

If you lack confidence and creativity I think it might help you out. Of course there are no silver bullets for this sort of thing but I think I have already learned something from it.

If you would be interested in taking the course in sync with me and discussing the various lectures, let me know. I find that to be helpful when MOOCing. My contact info is in my bio, hit me up if that sounds appealing to you.


They're trying to teach creativity, so you sound like their ideal participant. Give it a go.


feinternational.com has some really good articles on buying/selling online businesses. But most importantly, you need to also create your own criteria first. I also wrote a blog post on this topic with my thoughts. Feel free to take a look for some pointers.

http://yashchandra.com/2016/04/17/how-to-buy-an-online-busin...


Great post. Thanks for sharing man!


Same here.

I quit my cushy office job 2 years ago to start my own company. This year will be my first time posting revenue over $1 million. :) Needless to things, things are going very well for me and I am much better of now than when I was grinding away hating life.

Good on ya!


Do you have a link to your website? I'm interested to see what you do.


Interesting story, codegeek. I'm curious as to what type of business you bought, and how you discovered it. A website of businesses for sale? Is it in your same field which I assume is coding?


Yes, my field which is tech (duh!!). I am actually an addict when it comes to sites like flippa, feinternational etc. Both are mostly useless but every once in a while, you get a real gem there. I found one. It was funny because I was accidentally browsing flippa that day (labor day weekend and I had to stay home which was not the plan originally). I liked what the seller described and the way the seller described it. It seemed genuine and was a real product business. So I got up, spoke to my wife (you def. want that blessing :)) and then said, can we do this ? I was like "hell an MBA will cost me more than this and what is the worst that can happen?". I lose the money but I learn doing something real that I want to do. So I saw it as a win-win situation and went for it. In hindsight, it was the best decision of my life. Survivorship bias may be, but who cares.


Do you have any more information on how you filtered business and what made the one bought stand out?


No specific information but I have written a blog post on this topic and some general guidelines that I followed. Feel free to read the post (linked in my profile)


I've heard Health Insurance is pretty expensive if you are self-employed. How did you deal with that? Is your wife also employed in which case you are just able to share hers?


I did buy obamacare for a year or so but now my wife works and we use her health insurance. I will be in deep shit if I have to buy out of own pocket (family of 4). So yes, that helps a lot as well.


Yes. This is common (in the US) for solo business people with families. When I talk to self-employed people, few want to discuss health insurance. The topic seems to be taboo. Maybe some are going without insurance? Obamacare does not address the issues of a solo business owner. As far as friends who run solo businesses, those who would discuss the topic all said that they had their wives get random corporate jobs (e.g., at a retail bank location) to provide health insurance.


Germany calling in. ;-)

This is a big business stopper in Germany, too.

Health insurance is a must here and can easily add up to 500 Euro or sth. like that per month when you got a wife (not working full time) and children.

So getting ramen profitable is possibly much harder.


Not OP but self-employed going on a decade. Have high-deductible (intentionally) insurance covering myself and wife along with tax deferred Health Savings Accounts. In our mid-30s. Insurance runs $400/month and gets a tax deduction. Covered at 70% for just about any procedure/medicine. Not sure of what's typical. We have this done pre-Obamacare (grandfathered plan), but prior checks show within ballpark if not grandfathered (assuming HDP/HSA that is).


"... and then bought an online business ..."

Where do you find businesses to buy? Is there a site for this or is it just a word of mouth thing? I'm curious.


Feinternational.com has been recommended here often.


Also flippa.com


Check out this thread, has a bunch of online business brokers mentioned in the comments and the OP article: https://news.ycombinator.com/item?id=12254484


How does wife like it now? Is she happier despite the income disparity, or has it been a permanent sacrifice she has made for your happiness?


It is mixed feelings. She is happy that we are now close to the income we wanted even though progress has been slower than expected. Every once in a while, she does question if I did the right thing. Mind you though. Our expenses were very high when I quit. We got accustomed to a certain lifestyle back then and never had to think too much about money. That has changed but it does not mean we are poor. She is practical and smart and sees the long term benefit for all of us, not just me. Without her support, I would not be able to do it easily. No questions about it.


I am preparing myself for a deflation of lifestyles as well. Once my loans are completely paid, my basic needs (food, shelter and related, public transport and internet access) will be covered by 40% of my income. The rest, currently, is spent on accelerating payment towards loans from friends and establishments. Will be done in 3 more months at most, which feels great. Though my closet could do a bit of a refreshment, I have put together an inventory which I will tick off and be done with it for the next couple years. My early next year, 45-50% of income should be able to go to savings.

What I have found most useful is to create a list of NEEDS and WANTS. Need is what is essential to your mental well-being. Clothes, good quality coffee (though this is a luxury for most, i count it as food and do not cheap out on it. I just don't like bad quality food nor coffee), shelter, a basic telecommunication device.

Wants are stuff like a certain kind of telephone beyond the basics, a certain kind of earphones, -sunglasses, -mechanical keyboards, etc. You see the sentiment.

Make an inventory of what you actually need, and what you desire. Then temper your desire. Sure, I do spend money on this or that once every little while, but that is a treat and a gift now, not the baseline.


I'm curious to know which expenses you found you were able to live without easily, and which cuts were actually hard to bear, and why. Thanks for telling your story!


> It is tough, income is still less than I what I made in my cushy job

But you have more ways to avoid taxes (both legal and not so much). If you get paid cash for anything, you may be able to conceal the income. You can creatively shuffle losses into the limited liability corporation, to avoid being personally affected, and basically just sock it to whomever the corporation owes.

Self-employed people typically have way more ways to write off expenses.

In Canada, if you're an employee, you don't get to write off anything. Drive to work? Can't write off gas or car repairs as a business expense. Work from home a lot? Sorry, can't write off any portion of your rent or mortgage. All that changes if you're self-employed; you can write off every this and that: transportation; the proportion of your home that is your office. On the yearly tax return form, all employees can claim a meager little "employment amount": a token sum compensating them for their inability to write off anything.


I think you are being downvoted because of the "you may be able to conceal the income" part. You don't want to do that specially when running an online business (which is never cash based). Everything has a trail and you need to try and manage all records correctly.

But yes, you have some ways to get some deductions for your business and write off a few things like meal expenses for client visit etc. But you cannot directly conceal income. That is almost a sure way of inviting the Tax Police/IRS.

At the end of the day, it is not so much about deductions for me. I still make less cash than my job (so far at least) even after deductions. It is more about the freedom of doing what I want to do.


While you cannot simply "write off" your drive and mortgage [as an employee in Canada]; depending on details, you CAN mitigate some of the taxes through your home office etc if your employer fills out t2200 in a way that benefits you.

(I am completely NOT a lawyer or accountant; but an IT worker and this is what my accountant does for me; your milleage and circumstances may vary :)

See sections 7, 9 and 10: http://www.cra-arc.gc.ca/E/pbg/tf/t2200/README.html


It was just brute force.

I worked every evening, every weekend, on the tube on the way to and from the office. During my lunch hours. My coworkers knew not to interrupt me during lunch, because I always took a sandwich to the same desk, put my headphones on, and worked.

Have you seen that comic "You must burn", that's exactly it. It's painful, there's moments of crippling self doubt, there's moments when you'd rather be doing literally anything else, but you must burn through them. https://startupiceland.files.wordpress.com/2012/01/you-must-...

I had several failures. I launched an iPad app that failed. I launched several webapps that failed. In total, 4 "product launches" that failed and crashed and burnt, and countless more mini-projects that never finished or caught traction.

It took me years to get my first B2B client, but once I got it, I didn't have to work ever again, now I have 5 clients, and am concentrating on launching new products and growing and partnering.


Is this the article you are referencing?

http://www.feld.com/archives/2011/10/be-on-fire.html

Cause that picture is now my new wallpaper...

Also it sounds like you have a similar path to mine. Launch stuff, fail, launch again stop mid way when no traction, launch, fail.

Mind if I ask what you are doing that having 5 clients is all you need to be self-sufficient?


Yes that's the article! I love that picture too.

I am doing media monitoring, I collect vast amounts of data on social networks, p2p, rss, webscraping ... then built reporting tools on top of it - high level trend reporting, customer segmentation for acquisition and brand targeting, planogram computing based on collaborative filtering, an entire media and brand intelligence platform.

I also do Forex trading with TensorFlow, but that's only making about 70-80k a year, which is probably a living wage, but not if you're in London and have an insatiable appetite for GPU's like me ;)


I feel like calling out the humblebrag, but that's just impressive man.


> I also do Forex trading with TensorFlow

This is the second time today I'm reading about "solving X with TensorFlow", which I find very interesting. It's not, "solving X with machine intelligence/AI/an application I wrote". I don't really have a point, just thought it was interesting!


> I also do Forex trading with TensorFlow, but that's only making about 70-80k a year, which is probably a living wage, but not if you're in London and have an insatiable appetite for GPU's like me ;)

Please teach me how to do this. I will pay you for your time.


I'm developing a Deep Learning platform that helps with rapid data ingestion and model creation and training, all with a web GUI. It's intended to be an "accelerator" to take all of the boring engineering out and allows you to focus on the data science.

I'm about 1-2 weeks away from launching into beta, if you're interested I can provide you with a machine, a license for the platform, and consulting on how to search for profitable strategies.

My contact details are in my profile :)


Great thanks so much for sharing. Here is video version I found in the comments https://youtu.be/z1x3BZjU5Pw


Brute force describes it well. At some point you have to take the plunge. You will likely learn fairly quickly if it's for you.

Expect to fail. And while it shouldn't be a goal, my failures have always been more beneficial, more productive than any success. Success always has the risk of promoting complacency. Failure will test your character and grit. In the end you will know more about yourself having tried than not. I also recommend doing it as young as possible. It helps to teach you the possibilities. If you decide it's not for you then you have time to start over and rebuild. Maybe with maturity and a different perspective you have the opportunity to pursue it again later on.


Quite a few people just are not comfortable taking this high risk (way higher than just investing in risky startups) with their own money, time and often health. Those unslept hours and stress are not negligible.


I agree, and I think that is a great reason to not "escape 9 to 5."

Much to my point about doing it young, if you are unsure, but you are tempted by the siren song of startup fame and fortune. The hype, glamour, fame and fortune is largely the exception and not the rule. The hard work and the hard lessons are much more the norm. The benefits you might receive are earned, and they are paid for in sweat, stress and sleepless nights.

The bottom-line is that it comes down to knowing yourself. You make a great counterpoint to those that are certain working for themselves, or starting a startup is their path.

If you are uncertain, the best way to confirm it is to test yourself, take the risk.


Good for you and thx for sharing. I like the "brute force" aspect. That is what I tell a lot of my friends as well who really want to do it. There is no formula. There is never a right time (except some basic planning). JFDI


Put simply: Being in control of my own time, day rate, and outgoings.

I grew up in a very entrepreneurial environment, so after university I took a full-time job for 12 months (as a junior dev) then went freelance. I started cheap and upped my rate by £50 for every new project I took.

During the 10 years I've been freelancing I also came up with my quality of life ratio, which is: How long does it take me to earn a month's rent? This balances both increasing my day rate with reducing my outgoings. It currently takes me 4 hours to earn a month's rent.

I currently work for around 3 months per year, which gives me cash to spare. I also live in a communal warehouse. I had to build my own bedroom (which now looks awesome), but rent + communal food + bills comes out at about 1/2 - 1/3 what most would pay.

I've also spent a few years running my own startups during this time. None were what I would call successful, but neither did any afford me the quality of life that freelancing does.

I loose around 50% - 75% of prospective work because I'm too expensive, but that is fine and something I account for. I also have a number of more junior developer friends I can field this work off to.

With my free time (and funds) I'm currently working on setting up a community in rural Portugal.


Since you're only working 3 months per year & assuming those are consecutive, how much time/effort do you need to queue up another 3 months of work after being out of the game for 9 months? Having to keep your profile/reputation fresh and letting existing/new clients know seems nearly impossible.


I tend to take on one significant project per year, i.e. on that looks good on the CV. Generally work comes along through word of mouth, but if I'm getting itchy for work I'll start mentioning it to old clients/colleagues etc.

I generally also spend some time off working on my own open source projects too. Reading HN helps me stay up-to-date too :-)


Thanks for sharing. Sounds like you have a very solid reputation and network. Nice job!


You don't happen to be related to Stephen Charnock the puritan minister of London are you (b.1628-d.1680)? He's one of my spiritual mentors I look up to.

That communal warehouse community sounds cool! What's the name of that place? I sometimes think about finding a place like that to do work in, but we don't have anything like that in Southern California where I'm from.


Ha, quite possibly. We have an interesting family history, but it all went wrong sometime around the War of the Roses. I think we picked the loosing side.

I probably shouldn't mention the name of the warehouse on a public forum. Happy to talk about what makes it work though (tl;dr: A varied range emotionally mature people!).


How did you get started with this? Especially being so junior?


After college I spent six years working at a good tech company. In addition to a lot of great learning, it allowed me to build a big financial cushion. I continued living on a graduate-student-like budget with a software engineer salary, so I saved about half my after-tax income.

This generates one year of runway for every year worked. But my savings also grew thanks to some solid investments, so after six years I had ten years of runway.

Over the subsequent four years I spent down about 30% of my savings while working on startups of my own (I made some revenue, I took some small angel investment). Relationships and expertise that I built in the process allowed me to pivot into running a lucrative consultancy.

Before somebody says "you can only do that if you're young and unattached", I will add that I got married before I finished school, and our first child was born the same year I quit my tech industry job.


That is highly impressive. I would like to be able to save 50% of my net income, but I have found that I have very little control over spending and end up saving only around 20%.


That means that for each five months working, you build up reserves enough to last you one month without working. It's not a lot, but it's something. Now make some effort to push it to a 33% savings rate, and for each three months worked, you'll have one month of expenses saved. And so on. At some point, it becomes a game of cutting expenses and raising income.

If you get to live on 20/25% of your income and invest the rest, in 5 to 6 years you should have enough invested to pay your expenses for the rest of your life, assuming an yearly average return of 4% over inflation. This formula was made popular by Jacob from Early Retirement Extreme blog/book/forum/wiki: http://earlyretirementextreme.com


What would happen if you just moved 50% of your monthly income to a savings account and convinced yourself that it's going to stay there because it's for savings?


I was employed by a big US tech company in France (8+ years). I left a few months ago to grow my own startup.

I've been working on the side project for 3 years before that. It's a SaaS web + mobile app. I worked on this project in my spare time (nights and sometimes during weekends). It was solving a problem that I was dealing with personally and I bet I was not the only one. The great thing with a side project is that you have no pressure and you can code features fast at the beginning. It was still a lot of work though but you don't feel it when it's your baby.

When it started to get traction (feedback from users is critical at this point) and some healthy revenue, I decided to take the plunge. France give you the opportunity to continue to earn something like 70% of your previous revenue (estimation, there are calculations rules) for 2 years in the case you create a new business.

I believe I found the motivation because my daily job was project manager but my side project was more of a developer job. Coding your own product without all the pain that a PM needs to resolve was a breath of fresh air. Combining the two competencies was also an advantage for learning to be an entrepreneur (even though I was more of a newbie as a developer compared to the devs I was working with in my previous company).

Now I'm enjoying it, I hired a few interns and joined an incubator in Paris.


Whoa whoa whoa, tell me more about the thing with France and collecting a percentage of your previous salary. How does all of that work? Who pays for it?


It's paid by the state while you look for another job (national employment agency). If your plan is to create a new company instead of looking for a new job you can get the aid as well. They'll usually leave you (almost) alone as long as you prove that you created a company and that you're not getting any salary of course.

It's great and something that doesn't make the news so much. It could be viewed as a state funding program. The state will get back much more in taxes and employment when and if the startup takes off.


Wow, that's neat. I'm assuming there are regulations around it, like being a French national or something along those lines?

Either way, thanks for pointing this out. That's an incredible benefit.


> France give you the opportunity to continue to earn something like 70% of your previous revenue (estimation, there are calculations rules) for 2 years in the case you create a new business.

lolwut, that's pretty awesome.


Yes. I know a lot of people who were able to launch their company thanks to that.


Personlly, I have a family, mortgage, and full time job as a developer. I did an hour a day of 'car coding' with my laptop tethered to my cell phone, an hour here or there in the evenings and weekends. Took about 6 months to build an MVP and launch. Still working 9-5 though, and tweaking the product and message. I wrote up some details below.

https://medium.com/@m.taylor/zero-to-mvp-thirty-minutes-at-a...


Almost all of these replies involve growing a side project at home while remaining employed. I was under the impression most employers (at least in tech) do not allow this. Aren't you worried that your former employer will come knocking when your successful, asserting ownership over what you built? Where do you find companies that are cool with this? I've asked about tolerance of side-projects during interviews and have always got very clear, unambiguous "Work on only our company's stuff or GTFO" responses.

Also curious about how many of the "saved <double digit> percent of my salary for years" stories happened in the Bay Area with its impossible cost of living. And if so, did you do this with a family? How? I consider my lifestyle extremely frugal, yet I couldn't imagine saving enough capital to start a business in 10 or even 20 years.


EDIT: I realized your question is probably about running a business on the side, not just writing code. My reply pertains to writing code.

I have been working at startups for a few years. I have made this work and been able to open-source both projects I do in my own time, and projects I built at work. Here is how I do it (note I am not a lawyer and not qualified to give legal advice):

* First step: always read your employment contract--the whole thing--before signing. Ask questions. Ask them to explain how software IP works in plain english (and in writing). All companies have lawyers, that's what they're paid for. I've never had anybody mind that I asked.

* Second step: do not sign a contract that grants IP to your company for software you wrote, on your time, on your own hardware, that is not directly competitive with the business. If this is the contract they give you, don't join the company. It's likely not enforceable, but you don't want to be in an IP lawsuit someday.

* Third step: list anything and everything you have on Github (public or private) in your exemptions. Contracts usually allow you to exempt anything you worked on before you joined.

* Final step: Write code! Do it on your own time, on your own hardware, and don't create anything that could be perceived as competing with the business. As a rule, I generally notify my boss (in writing) of _any_ side project I start working on, whether it's public or private. All he has to do is CC the lawyers, and they say "All clear, the business does not own that IP".

I may have been lucky in finding so many places that are "cool" about this. But mostly, I think it comes down to screening companies by talking about this up front.


I've refused to sign employment contracts which push all "IP" into the employers ownership saying things like "You don't get to own my graphic-novel or my band's songs or whatever just coz you pay me to write some web-app"

I've never had them refuse to amend that clause in the face of that. Maybe it's different outside the UK.

If they did refuse to amend, I'd continue the job hunt basically. I probably don't wanna work for a company that inflexible anyway.

Also, contracting works well for owning your own IP. Contractor clients appreciate you have other clients too and don't usually even try to demand exclusive ownership of the product of your mind.


I once had an employer try to get me to agree to let them use my name, voice, and likeness for any purpose whatever (including specifically for marketing purposes). I told them I refuse to let them use those things for any purpose outside the company and I got an amended contract that same day.


Noncompetes are illegal in at least one state (California), difficult to enforce elsewhere, and usually severely limited in scope. For example if you worked for Uber, you could be barred from starting your own taxi or rideshare app on the side, but not from starting a healthcare services business or game studio.

I did have one company try to get me to sign a 10-year noncompete, upon pain of having to pay twice the market cap of the competing company. I am not shitting you. I tried pointing out why this was outrageous and unenforceable (what if I worked for PayPal?!) and they didn't seem to get it. So I told them to gtfo.


Beyond just echoing the sibling commentors RE: don't sign a contract with such a clause (I've personally never even been asked to sign one, out of 4 professional jobs post-university), I'd like to point out that there are much cheaper areas than Silicon Valley with bustling tech scenes.

I myself work in the Research Triangle Park in between Raleigh and Durham, North Carolina. The cost of living is low, and the starting salaries are slightly higher than what I've seen in the Northern Virginia / Washington, D.C. area. I was also able to climb the pay ladder fairly quickly in my so-far short career, and I'm making way more money than I need to facilitate my (admittedly rather humble, but comfortable) lifestyle.

Similar things can be said of the San Antonio, TX; Burlington, VT; even Fayetteville, AR; Fargo, ND; Twin Cities, MN; and many other places in the country you wouldn't necessarily associate with tech. One thing I learned the hard way is to always consider the cost of living when considering a job offer. $X is worth far more in Raleigh, NC, than it is in Washington, D.C..


Employees don't have any control over what you write on your own time. I think some older IBM contracts claimed they did, but if you sign one of these today, you're an idiot (and they're not enforceable).


I don't think this is entirely true, at least in most states in the USA. It's called "duty of loyalty" and it basically means you can't compete with your employer. Whats competition is gray but I'm sure you can imagine examples of shades that are clearly competition, shades that are clearly not, and all kinds of shades in the middle.


I think a lot of people renegotiate that clause so that they continue contributing to open source etc. I think companies are open to it as long as you do not use company resources to build what you are building.


I essentially used the 4 hour workweek script and am somewhere in the middle of that timeline, setting up my business now. 1. Figured out how to get all of my work done super fast 2. Started taking days off and working remotely using my above efficiency skills to put more and more time into my side project while still meeting all of my deadlines and obligations 3. Negotiated a remote and part time contract that only has me in the office 3 days a week. 4. Grind.

I'm still in the setup phase of my business (a hydroponics farm/green wall installations) but being able to devote entire days to getting going has been immensely helpful.

I started working the new contract about a month and a half ago. It was hard staying focused at first and I was a little too happy - go - lucky with my newfound freedom (Overwatch). So, while I was getting everything done for my 9-5, I've been moving slowly on the farm. Things have been better these past two weeks and I'm excited to get cranking in a serious way.

I should note that before I had even considered building a business or taking this step, I'd been doing research for the past 4 or so years that started my last semester in undergrad. I'd also done many small scale, non commercial projects for different clients in the evenings/weekends before I made the jump. Like another poster, to me, this is the equivalent to grad school. I could spend a bunch of money on an MBA and learn some things, or I could start this business, learn hands on, and potentially walk away with profit instead of debt.


>> 1. Figured out how to get all of my work done super fast

I always assumed that, as developers, we couldn't afford to automate writing code (as Tim's proposition is originally to automate the income), and so you do your work faster. Can you comment how you do that, how did you buy your remote time from that, etc.?


I'm not a developer, I'm a researcher. However, a big take away from the book for me that I'd imagine would apply to developers as well was not answering emails or going to meetings. He get's into how to do this politely and gradually, and it's definitely saved me time.

The gist of it is, generally, no matter how huffy the person at the other end is, what they're sending you is probably not an emergency. That being said, you can afford to batch your emails so you are only going through and responding to them once or twice a day as opposed to constantly losing your train of thought to reply to them or read them. This might not exactly apply to you, but reading 4hww got me to consciously think what sorts of things I might be able to cut. Actually taking the time to notice what those things are could help anybody I'd guess.

I got my remote time from that because I've been working at the same org for 2 years and have kept track of my wins/successes. I've gotten a lot of those because I've learned to be more efficient using ideas like the ones above. Over those two years, I've also noticed that our org has a problem retaining mid level employees and so I was able to leverage that when talking about remote time as well.

So I'm not automating my income, but I am saving time by cutting unnecessary tasks.


I left my cushy job two months ago. For years I tried to build various products (SaaS) on the side to facilitate the move. I was never able to get enough traction mostly because I wasn't able to devote enough time. I realized that I'd be never really be free unless I took a leap.

I'm launching my first official product in Sept. and have been consulting to pay the bills. The consulting has been good...perhaps a little too good as I feel myself getting pulled away from the product as I'm still busy after raising my rates a few times already.


Wow that sounds familiar. I'm consulting and trying to launch a product in October, while realizing I've kind of stumbled in to my own little software consultancy. I just had to hire a guy to keep up with the consulting load, and I've raised my rates a few times.


How's that (the hiring) going? Are you subcontracting?


"unless I took a leap."

Yes, exactly. Kudos to you for doing this. Taking the initial leap is the hardest part. Good luck!!


What kind of consulting do you do?


Web development consulting. Basically what I did at my previous job but now I have to get my own clients. I never really liked the pitching part of my old job but find it easier now that I'm basically selling myself and believe in that "product" more than what I had to sell before. Making this part more of a company is my fallback if the product side of things doesn't work.


A viral video (https://youtu.be/rNu8XDBSn10) that turned into a whole career.


Are you really CGP Grey? If you are, it is amazing that I run into you on HN.


Yup it's me. Not a frequent poster on HN, mostly a lurker.


Ain't HN grand?


So you make a living off of publishing on youtube? I was always fascinated by this model.


Yes: the ads you see on YouTube are split between the creator and YouTube. Now that I'm a larger channel there is patronage and sponsorships as well, but it all got started with building an archive of popular videos.


Can I ask how many videos you made, until you started to make enough cash, for example to pay the rent? Thank you.


I don't remember the number of videos, but my goal was 200,000 subscribers before leaving my day job. Subscribers aren't views (and they mean less now than they did when I started) but that was my estimate on how big of a base I needed to be confident it would work. 200,000 subscribers wasn't paying me as much as I earned as a full-time teacher but I knew the lines would cross.


Just curious, how many videos do you upload? From what I am seeing, maybe 5 minute video 1 per month? How long do you spend on this in total (research, sponsors, video editing, etc...)?

Again, this is amazing to me that people can make a living off of youtube.


It's about a video every six weeks, but I am not a typical YouTuber in this regard.


I did remote contract front-end development for about 3 years. Working contracts gave me a TON of flexibility to work on my own projects on the side. I also tried to take high-paying contracts and save as much money as I could. When my last contract ended, I had enough money in the bank to survive for ~18 months without another paycheck, even while paying rent in SF. Currently, I'm about 9 months into that.

I've worked on several projects since then, one of which (TaskforceApp.com) is making $500-$1500/mo. The other I just launched on HN about 3 weeks ago: http://www.IndieHackers.com. It's gotten almost 300k pageviews since launch, and I've lined up some awesome sponsors who combined are contributing about $1000/mo. My plan is to keep growing the site by adding interviews, writing more blog posts, and adding forums/AMAs.

If you're interested in hearing lots of other stories similar to this (most of which are more impressive), I recommend checking out Indie Hackers. I publish average monthly revenue stats in addition to interviews with the founders behind all these companies.


I have been watching indiehackers since you shared on HN. It looks really good and high quality stuff. Another bookmark for me as I obsess with the various products being shared and their stories. The revenue transparency is an icing on the cake :)


Sweet, I'd love to hear your feedback/ideas sometime! @csallen


Super cool! I used to use Taskforce and actually cold emailed you way back in the day (4 years ago?) back when I didn't know much about web development!


IndieHackers looks really nice, although it would be useful to have the interviews dated to see how recent they are.


Good point, will add dates soon!


I didn't escape my 9-to-5 job to start my own business (hoping to, eventually) but I did become full time work-from-home which is about 75% as good.

I pretty much set my own hours, start work between 8am and 9am and end between 5pm and 6pm.

Some days I really get nothing done -- right now we're in the midst of buying a house, and I must confess I'm spending lots of time communicating with the lender and broker, packing, etc.

Other days, I work until midnight to get stuff done. It feels a bit like being self-employed, but of course you still take orders. But you also have the backing and resources of a larger organization. Kind of a transition to self-employment, you might say.

I do have a side business of playing music for weddings and other occasions, but that's pocket change and will never turn into full time.


I can also work from home pretty much every day. I avoid it because I have 4 kids at home, and it's kind of a zoo.


Yeah, we have kind of a strict rule here that during business hours I'm not to be disturbed. Luckily, my daughter's in school 8am-3pm now, and then she often is ferried around to after-school activities, so the house is pretty quiet during the school year. So you have something to look forward to, hopefully :)


I'm just opting in the 9-5 :) Not everybody has what it takes to run a business.

I'll do two things:

- Build and MVP and try to find paying customers. Once the money is flowing in, I might take a venture again into the startup world.

- Use a few hours / day to build the thing and start to look for a business co-founder.


Agreed - I actually _like_ 9-5. It's nice to have a break now and again, but I like daily routine of going to an office, seeing colleagues, etc.


Exactly. And I read earlier on here that for lots of companies, for each year you've been at a company you can do a remote day a week. Sounds perfect to me.


I'm on my way out. I had a break in a few years back and lost everything. So I sold what I had left, took my savings and went backpacking for a year:

http://khanism.org/perspective/minimalism/

I had dreams of getting into grad school, but that didn't work out and I ran out of money ($20k NZD) so now I'm back in America working software. It's soul draining.

I'm not an entrepreneur. I have no desire to start my own business. Right now I'm saving until my lease expires. Then I plan on selling everything and doing something crazy again.

I might look for writing residencies. I have a film I'm self-funding a demo for in order to crowdfund the rest. I'm looking at fellowships. I'd like to get the film started while still employed and quit work once it's funded and I'm over 50% done with its development.

If all else fails, I'll buy a car and live of my savings, driving around America for a year or so while perusing some of these things mentioned. The 2nd major option I'm thinking of is getting another Australian work visa and taking another dev job or finding a writing residency there.

The thing is: I have no kids, family or debt. My parents came from poverty and my father spent ever dime on making sure his kids had a debt free college education. I feel like these things artificially limit others, but they shouldn't.

If you're religious (I'm not), missionary work is something you can do with your family. I also have a close friend teaching English in Germany and just allows her college debt to grow (we'll have forgiveness eventually. Either that or she'll eventually get her German citizenship and renounce the American one).


I think the key is to have a Safety Net. If you're lucky, you get one for free at birth. If not, you need to build it yourself during the first several years of 9-5ing.

Once you know for a fact that you can coast along for an entire year if things go south, life gets a lot better. You can start consulting and not have to sweat the occasional dry spell. You can build income generating products after work or during those blessed dry spells. You can do all that stuff remotely while dialing up your leisure time activity of choice to whatever level feels the most comfortable.

Better still, with a bit o' Safety Net, you'll be able to demonstrate to yourself that you can quickly pick up contract and full-time gigs when you need them. And you can emit artifacts that demonstrate to prospective employers that they should grab on with both hands if you happen to signal availability at any point. That helps a lot towards being able to bootstrap a product business on the side.

Eventually, after much trial and error you'll find something that sticks. I think for me it was something like Job Quittin' Side Project #6 that finally started bringing in enough profit to replace the day job.

Finally, make sure you're having fun along the way. It's not supposed to be a grueling heads down slog for however long it takes before you finally "win". It's life. And it's most enjoyable if you actually take the time to enjoy it while it's happening.

All the best! Let us know how it turns out.


Curious why people here hate 9 - 5 so much. I can understand starting a business if you have an idea you're passionate about and you're confident you can make you more money than you can make working for someone else. But most software development jobs actually allow you to have a lot of autonomy (flexible hours, work remotely, etc), a place to socialize with people who are likely going to have a lot in common with you and good pay with a nice safety net. Venturing out on your own and starting your own business has none of these things.. at least in the beginning, you are likely going to work more, for less money, by yourself. I understand why the small subset of business owners start their business for the reason I mentioned above, but I get the impression a lot of people working 9 - 5 are just assuming the grass is greener on the other side...


Well here's why......

The benefits you listed, "flexible hours, work remotely, etc"

Are, indeed, nice, but they are actually far more rare than you'd expect. Many places still require 100% "facetime" despite being able to commit & deploy code and take calls remotely, and some that don't require "100%" still will hem and haw over days that you are not in the office.

Not everyone is sitting in an (over)funded startup with foosball tables, a fridge full of beers, young & eclectic coworkers, and happy hours with the coworkers every other day - where as long as you complete your projects by/around deadline, you're happily well-employed.

And most are not in an area that complains over a "dearth of tech talent" and have the liberty to hop from job to job without actively searching, taking the time to interview several rounds, and locking in the second job before leaving the first.

Labor Supply and Labor Demand have upmost influence on these factors, and with thousands of intelligent people finishing coding bootcamps every day, Supply is far outpacing Demand.

The other key (and probably the biggest) benefit you're missing is legitimately coding for yourself with your own. You want to develop a "Slither.IO" type game by yourself with PhoenixOnElixir as an un(der)employed coder? Go for it. Because most of us aren't getting jobs at Blizzard or Riot. You want to build a fitness app in a city with only financial/legal/logistic coding jobs? Go for it! It's an unparalleled learning experience.


Thanks for your response. I guess I've been coding long enough now that I just view it as work and not fun (although I do enjoy other aspects of my job). I do remember when I enjoyed coding just for fun so I can see the appeal of your argument there.

I'm surprised to hear that supply is outpacing demand where you are. Where I am (in Toronto), we always have a hard time hiring good people and it seems to be getting more difficult.


Thank you too. I agree that as I get more jaded, I consider it more "work" than fun in C#, but at home when I get my webscraping/scripting jobs in Python or even my front end styling working, I still get the thrill of achieving. From what I've heard, even more jaded devs than myself enjoy it when the work they produce is going to their own/their future employee's own benefit than when they are working for someone else, underpaid.

Question for you: Is hiring good people refer to hiring good people, or hiring people who pass your exams and interviews?

I'm still recently out of college, but when I first joined a company, our interview questions were more along the lines of Palindrome/FizzBuzz and being able to write good, simple SQL queries. We found out relatively quickly if you were competent for the job, and if not, you were gone.

Now, even MVC/CRUD Apps are asking interviewees to complete Google coding interview questions such as "Implement a Binary Search Tree" - which most of us even just a few years out, have not done for quite a while.


Yeah I would never ask anything crazy like "implement a binary search tree" in an interview. Our hiring is more like, look at someones resume, and if their skills generally fit what we're hiring for and they actually know the things on their resume and they don't seem extremely lazy/arrogant/(whatever personality flaw that is hard to work with), then hire. A lot of the time we bring them in to the interview and they don't actually know the things they say they did on their resume. For example, if you claim to be experienced in object oriented programming but have no clue what i'm talking about when I say words like inheritance or polymorphism, you do not actually know object oriented programming. You should also know how to do it in one of the languages you say you know on your resume (I don't care if it is the language we're hiring for, syntax can be learned quickly enough).


I am not familiar with the industry at all, but my understanding was that there weren't enough programmers to fill the demand. So it turns out to be the exact opposite?


I don't have an issue with 9 to 5 if the time is used wisely. You're paying me a salary per year. Is that salary to get a product out of me, or to fill a seat? My issue is the time waste. It's been exacerbated recently because of having too move and my daily commute going up from 20 minutes to 5 -> 5.5 hours. I work on the transit as much as I can.

My current contract I was hired to create a new software team, but research wasn't fully scoped out. So the project isn't feasible, and scrapped. I'm now primarily idling, and sitting here just collecting a pay check. I'm looking but the travel time is making it difficult to apply properly.

My last contract I worked 80 hour weeks for five months until I burned out. I loved it. I had a team I loved, a good challenge, remote work etc. I quit that and tried boot strapping a business but my savings were obliterated by an unforseen expense.

So why the hate for 9 to 5? A majority of the jobs I've worked there is so much time waste. Time I can be doing something else, I have a plehtora of hobbies and no time to indulge them. My current contract has no work for me. Two contracts ago I was set to do a python web service slated for a year to a year and half. I finished it in a month. I'm not a rock star or 10x, just it was not scoped out or understood how easy it was to implement. If you're going to have me sit in a chair for 9 - 5, make use of me. Please for the love of all that's holy make use of me. I will work my tail off, and do over time, but let me do in on my terms. Give me something challenging, and let me learn. Now not all 9 - 5s are like this. But I've had more difficulty finding an interesting 9 - 5 versus starting my own venture. Also it seems alot of the roles I've worked projects are no where near properly scoped.


Ugh, that commute sounds rough. Good luck with the job search.


Work on your own business during those hours. They are paying you to sit there, so sit there and create.


Since I am the one that made this post, I will answer you.

- If I work at my 9-5 8 or 12 hours a day it makes no difference in the money I bring home. You can say that theoretically I will get promoted but there are limits.

- I do not control my fate. Case in point today AFTER I made this post the company I work for laid off 16 people, it's a company of 180 so close to 10%

- I don't want to have an expensive house / car. I just want to financial be able to support myself and my family

- Freedom. Freedom to not work for a day and not have to explain myself. Freedom to travel somewhere and not have to worry about it. I realize the contrary to this, perhaps having my own business is not really freedom. I will still have clients, or people that need things from me.


Thanks for the response. So in my view, all of these points can be resolved by simply having more money in the bank and it is much easier to earn a decent income by working 9 - 5 as a software developer right now (at least where I live) than it is to start your own business. Having a decent amount of savings/disposable income allows you to:

- Feel less pressure to work longer hours. Worst case scenario, you work 8 hours a day, your boss fires you because they seem to think you should be working more and you find a new job within a few months

- Allows you to take some time off work unpaid if you wish and travel wherever you want

Of course this all relies on your take home pay being greater than your expenses, but this should be possible if you have no aspirations to own a fancy home/car (I don't really either). If you want a lot of money at the expense of taking on higher risk and likely working more hours with more stress and you think you can achieve this with your idea, then I think starting your own business makes sense.


I quit my day job back in 2008 and it's probably the best thing I've ever done. The first year or so sucked in terms of work hours and financial security. I had to drop all my day job income to scale up the non-job income and my income and credit both took a hit in the short-run. Today, however, life is amazing.

1. Security - Over the years, I've built up a nicely diversified stream of income. Sure, some of them slow down or disappear from time to time, but the odds of me losing even 50% of my income overnight are so low that if it happened, it would likely correspond with some kind of catastrophic societal collapse. On the other hand, I've watched several good friends (and my dad) lose their jobs with no notice this year - and often, no severance. If you're like most single people, losing your job = losing 90% or more of your income.

2. Task flexibility - If I start to hate a part of what I'm doing, or if there's a segment of that income stream I don't like doing, I don't necessarily have to keep doing it. I might decide it's unpleasant but worthwhile, or I might decide to move in another direction or outsource the task. There's no boss to say I have to stick with it or personally complete it.

3. The "work in your pajamas" factor - I usually don't, but it's not uncommon for me to work in a golf outfit, yoga pants, or a bikini/swimsuit coverup depending on what I intend to do that day. Depending on the dress code of your day job, you might also save a lot on work clothing.

4. No artificial caps on income - Instead of relying on a boss or HR department to give you raises (often limited by what everyone else there is getting, or some annual percentage cap), I can work harder/smarter and increase it indefinitely. This has worked out very well.

5. No coworkers - Some people would call this a drawback, but I love it. I'm an introvert, and I get more than enough social interaction by joining clubs or taking classes (and I've met a very diverse and interesting group of people in doing so).

6. You can do things when it's most efficient - I do my shopping on weekdays, I drive mostly outside of rush hour, and I tend to vacation mostly in the off-season and shoulder seasons. In doing so, I save an incredible amount of time and money.

7. Greater control over your priorities - Let's say something happens and if you don't take action RIGHT NOW, your company will probably lose money, a client, an opportunity, whatever. If you have a boss, that boss is going to want you to deal with it immediately. If you work for yourself, you can decide whether it's really that important, or if you'd rather enjoy your evening/vacation/etc. and let things fall where they may (and most things aren't as urgent as they seem, so it often works out anyway).

8. Flexibility in terms of hours worked - Yes, some jobs really do offer this, but they're few and far between - and in many cases, a job billed as "flexible" just means the boss wants to be able to use you at any hour of the day. Similarly, most jobs do want you accountable and at a desk SOMEWHERE for at least 40 hours/week and some portion of the business day. Working for myself, I can get my work done in a few hours and then go do something else. Yes, there was a time in the beginning when I worked insane hours, and yes, I've had occasional bouts where procrastination allowed 3 hours of work to swallow an entire day - but on the whole I work much, much less than almost everyone I know (while earning more). Sometimes I feel guilty about it.

9. So much free time - Working 40-60 hours/week, commuting, and getting ready for work takes up a lot of time (slightly more if you're female and you have to dress up). I sometimes go back home to the Midwest for weeks or months at a time and my grandma and I do tons of stuff together because my free time approaches that of a retired person. It's not automatic with self-employment, but it's certainly more possible than if you have a day job.

I'm sure there are other pros I'm not thinking of at the moment, but I get bad feelings just thinking of what it was like to have a day job. It's not for everyone, but for me it's a night and day difference in terms of quality of life.


Thanks for your response. I think everyone can agree that your situation sounds much better than working a 9 - 5 job :). I'm a bit more interested in the year or so that sucked, though. My main concern is for the few people I know who are thinking of quitting their day jobs to start a business, but whom I feel are not going in to it with their eyes open (in their view, everything about starting a business is better than working 9 - 5, whereas in my view you're giving up quite a bit in the short term in hopes to gain in the long term).


I was very interested in consulting after reading about it from Patrick McKenzie and others. I especially loved the idea of having a choice of when, how, on what, and with whom I work.

When my 9-to-5 job became unbearable (long hours, bad management, high stress, etc), I finally decided to resign and give consulting a try. I didn't have a specific plan, and I spent the next 3 months figuring things out while living off my savings.

My backup plan was to return to 9-to-5 if I ever depleted all my savings without getting any traction. Fortunately it never came to that (although it got very close). Three years later I'm earning a very comfortable living consulting and I get to work on super interesting projects with super interesting companies.

I've written more about the experience here: http://www.gkogan.co/blog/how-i-learned-to-get-consulting-le...


I'm in the process of getting ready to make the plunge.

Right now doing 9-5 on top of part-time software consulting, mostly WordPress sites with trendy front-end stuff, but with occasional custom-backend and mobile app projects. I've partnered with a local design firm that outsources development and they provide me a steady stream of projects generate a majority of my side income). So far no marketing except for word-of-mouth advertising from happy clients.

I'm on track to do over $50k this year, but I don't think I can scale this any further without quitting my day job. My plan is to score another $XX,XXX project in the near future, stock up on cash and health insurance for my family, and finally take the leap.

My biggest concern is that we're dreaming of building a house in the next 3-5 years and how that'll affect my ability to secure a loan. We're planning on having the land paid off before we begin construction, but I still need to learn more.

Anyone have experience here?


I was already doing some side-project while employed and my contract was not renewed.

I took a 30% cut on my unemployment benefits so I had no obligation to find work for 6 months. After unemployment benefits ended, I tried to find a bit of investment and also did a KS. Both failed, so I started to eat a retirement plan I still had.

Then I applied for another 3.5 months employment benefits ( was my right ), and I simulated trying to find work.

Then it got really ugly and did some parttime barista work. Sold some belongings.

Then the product got traction: https://mecoffee.nl


With the consent of my employer (another startup) I started in the mornings, evenings and weekends with a very supportive partner.

The aforementioned employer then began to fail, and so I was extremely lucky to be able to devote more and more time to my business as the aforementioned startup started to ask people to work fewer hours.

Once I hit a revenue target agreed with my wife, I jumped ship: http://www.elstensoftware.com/blog/2011/01/21/going-fulltime...

To lower the target required, I cut pretty much everything apart from the mortgage and taxes.

In some ways I miss the constraint of working fewer hours - I think I had better focus then; these days I do make a few mistakes with where I spend my time.


Left my last full-time job in early 2014, jumping into freelancing with both my old employer and past colleagues-turned-founders as my first clients.

The first year was insanely though - trying to find clients that would pay what I desired - and I went through severe bouts of depression when Canadian Winter hit. My close friends who knew about the situation told me to go back to employment, I wasn’t cut out for this.

But I went through that trough of sorrow and hit many breaks in 2015 with clients that valued me enough to more than make up the losses I had the previous year. Fast-forward to today and I earn enough from consulting that I spend more time on personal growth and working on my own projects than I need to work with clients to sustain my living.


I work full-time on my website since 6 months, after two years of development and growth when I was an employee. At first, it was only a little side-project so I haven't done anything to prepare my exit to entrepreneurship. I've quit my job when my partner and I we have felt a real potential for our website. I guess it's less stressful in France than in other countries, because we have in France the possibility to terminate the employment like a resignation, and then receive comfortable unemployment benefits during two years. There is no need to save money, and no pressure at the beginning of the startup.

Everyone has its own way to work on a side project. Personaly, I worked every mornings, before work. Why ? Because my brain was fresher, my spirit less crowded by external thoughts. I could go to work without frustration, with the satisfaction of having worked on my own website. And at evening, I could hang out with my girlfriend or friends without feeling guilty.


I haven't fully done it yet, but am on my way. About 2.5 years ago I left my 9-5 career (about 8 years into it) to become a contractor/consultant, basically continuing to do the same type of work, but for multiple clients, with an hourly rate. This was at the same time that our first child was born.

It's probably the best decision I ever made. I'll make about 1.5x what I did as a 9-5er this year while I probably worked less hours overall. I work from home 80% of the time. No commute, so much less stress, I'm lucky to have great long-term clients (who I wouldn't have been able to acquire without my previous 9-5 time).

Eventually I want to bootstrap a startup - that's phase 2. I've built up enough of a cushion, even though child #2 arrives in a month. I've got a side-project going on that will hopefully turn into a business. I'm still figuring out how to best transition, because right now the $ is good and difficult to voluntarily turn down.


I woke up one day and realized that if I had to spend another day commuting for nearly 2 hours a day to sit in an office that I hated, I would lose my mind. So I quit and found a remote job. There are lots of remote companies out there, find one


Do you know if many remote companies offer part-time work?


I escaped my nine to five years ago... I'm now at a startup and I'm 6am to 10pm ;)

Mostly a joke.


I had much the same comment, but less joke :)


Not quite answering your question, but I quit my great tech job and decided to burn my savings and go into debt by going to law school. At least consider that maybe it's not the 9-5 that's the problem, but the line of work itself. Being good at something doesn't mean you're passionate or motivated for it. Depending on the kind of person you are, lack of passion/motivation can be an insurmountable obstacle to being the best you can be, to being fulfilled by your work.


I actually agree.

I have come to realize that 9 to 5 is not horrible, the key is self-fulfillment and happiness. For most people they will be unhappy regardless of the state of finances or work they do.

I realize that even if I have my own business it does not mean I won't have to deal with things I don't like. What attracts me though is the financial independence, having control of my future instead of someone else having control of it.


For me, it's control. I cannot stand idiot managers making decisions that have such a significant impact on my life. Everything from major, broad issues down to where my desk is located and the temperature of the office and when I have to be in. You will still have to work everyday full-time, probably more, and have different stresses, but I cannot fork over my autonomy to others in exchange for a paycheck.


I am very similar. I recently started a cushy dev job at a big company, and the micro-management, bureaucracy, and office politics drove me into a pretty deep depression, to the point where I began to utterly dread coming into work. I quit after two months and now I'm taking two months off to work on personal projects...

I haven't truly escaped 9-5, but I'm finally excited to wake up in the morning again.


I just decided I wasn't happy at my 9 to 5 job. What followed was a deduction that unhappiness means there's an opportunity I'm missing. So I started observing and found what I wanted at the moment--I started working part-time at a small software organization doing systems integration. The transition was flawless--I didn't need to stay at my corporate job.

Of course, such undertakings are a bit risky. After a few months I found my money starting to melt as I wasn't receiving stable income from the new place I enjoyed working in. Doing a bachelor's degree while teaching and working quite prevented me from seeing how this money meltdown would shortly lead to some uncanny situation of mine. So, with about 3 months delay I understood that I'm in another unhappy situation and I should start observing for the new opportunity I was missing.

Here comes a time for some background. For about 3 years I was living with a close friend of mine who is involved with an organization called Camplight--a digital cooperative working in the web outsourcing business. Things were quite great in this company and it was a bunch of sustainable, playful and hard-working people. I wanted to join them since I heard about it, but the lack of experience prevented me from doing so. However, during the years I worked a 9-5 job and switched to doing systems integration, I got quite experienced. Also, I loved to talk with my flatmate about Camplight and the challenges around being a part of a cooperative. And it started to click that this was the opportunity I was looking for.

And that's how I escaped a 9-5 job in about a year and am really happy about it. I'm doing quality software, communicating with valuable people and helping the cooperative grow.


Diligent savings over many years combined with low-risk investments. The stable income it generates now covers all living expenses for my family. I'm still part of the 9-5 crowd by choice while I search for my next calling in life. However, the main job is now more of a training ground and networking center than a primary source of income.


Can you share what sort of investments drive the majority of your income?


Mostly fixed income securities and fixed income-like assets (like real estate, asset-backed loans, etc.). $10,000 invested at 4% brings in a little more than $1/day.

Yes, the market value of the securities and assets may fluctuate day-to-day, but the income doesn't. As long as the borrower is of sufficiently high quality, then there really isn't any concern about the principal getting paid back.


Thanks for sharing. Mind if I ask what your cost of living looks like? Seems like it would take a large amount of capital to get a livable income off conservative incoming-paying investments at 4%.


My cost of living is about the same as the typical family with kids attending good public schools along the SF Bay Area peninsula, but the approach should be repeatable in most places. My expenses over the years has stabilized at less than 50% of take-home salary (not including bonuses, equity grants, etc.) for my main job, in line with a previous post of 30% of income. So the absolute worst case scenario for a 4% return is 25 years.

In my particular case, I had saved all my bonuses (both cash and equity) and most of the income from the aforementioned portfolio. I was also fortunate to have held a consistent side job for most of my career.


My 9-5 job got a bit boring after 5 years so I decided to work on an idea I already had in mind for a few years. With the help of my co-founder (which I met in the meantime) the business got serious and I noticed that I'm way to busy with the 9-5 job. So I got the opportunity to work 24h/week at a local startup which also shares our technology stack. I usually split the week in 3 days on the paid job and 3 days (w/ one day of every weekend) for our own startup. Now we're one year later, still having 2 jobs as the income is not sufficient enough to pay for life.


I started my own software consultancy: we mostly focus on web applications, and we've had awesome experiences helping many startups in the NYC area!

Lots of times startups have a good codebase, but they are having hard problems with just a few parts of the product: they don't always have a lot of funding, but it's fun to make connections and help them succeed.

Though, it isn't so much "escape from the 9 to 5" as it is "now you work all the time."

Not that I always work more (some weeks are slow, others very busy) but I do find myself having to be available more.


> Though, it isn't so much "escape from the 9 to 5" as it is "now you work all the time."

Hah, so true. Although I find working for my startup more rewarding than trading hours for money.

My path is similar to yours, I quit my 9 to 5 job in 2007, started a software consultancy than moved to building my own SaaS in 2009. Since than, that's the only revenue for my family (2 daughters, wife, doing home school).

The stress and lower money at time for sure, but like others said, would not trade this to return in enterprise job.


Ask HN: How did you try, but fail to escape 9 to 5?

(to fight the survivors bias)


I was working 9-5 for five years as web app developer which allowed me to create financial buffer to live for several years without work if needed. I live in a cheap country.

At the end I actually took one year off, and during that time I learned to code mobile apps and then successfully joined Toptal and work as freelancer. And since I am in Toptal I receive also many freelance job offers from other sides, just because I mention I am their member in my linkedin profile. I was surprised that they have such a good reputation.

Anyway, I credit my success at joining Toptal mostly to the amount of free time I had during the hiring process (which took cca 1 month), so that I was able to fully focus on it.


Rather than artificially avoid 9 to 5, I am now in a job where 9 to 5 makes a lot of sense (for worldwide 24/7 coverage) I clock out at 5ish and I don't worry about work until next day or after the weekend. No such thing with a business.


For the first six years of my professional career I worked for a combination of small design firms, web dev firms, startups. Averaging a year at each. All, essentially, were client service companies. From that, I learned how to pursue, land, deliver, and re-land projects across a bunch of different industries. Then, I moved to a new city and found working out of my home office more enjoyable than being hired. Once I realized I could land projects & get paid w/o being an employee - I stopped interviewing for jobs and started pursuing project I found personally interesting.


I worked for about a year and a half after college and then quit to do my own thing (autodidacting -> startup). At each job I was frugal and saved over half the money I earned. I also accumulated money by working small jobs in high school and college, and some from my grandparents. It I'm frugal, the money I saved should last at least 5 years or so.

While working my full time jobs I spent as much time as possible improving myself, rather than succumbing to Sucker Culture. The same applies to high school and college.


What is Sucker Culture?


Sorry I was on my phone and couldn't link - http://www.daedtech.com/the-beggar-ceo-and-sucker-culture/.

In short it refers to letting others take advantage of you.


I did something like this early on in my working life. I got to the point where my side business had repeat customers and enough of a portfolio where I felt confident that I could bring on more customers. It wasn't a full jump, but the side business became the focus and I took on different side gigs to supplement income. I went back to a 9-5 after a few years, but during that time I did see consistent growth in the business.


Lived in parents house while working for a few years to save on rent. Kept expenses vey low.

Saved enough for business school tuition. Hated business school and dropped out. Was left with a wad of cash. Started business since I'd learn more from starting a business than staying in school.

Best decision of my career by far.


Is your business profitable? If not how much longer can you sustain yourself?


Started working remote.

Now people only look what I accomplished, not how long it took.


Well, I started my own business. Now it's 24/7.


Biologically impossible


You must be fun with to hang around.


I put the fun in endofunctor


Who works 9-5 anymore? The factory jobs are all gone.


Just about everyone in IT. The (software) factories are thriving the world over and despite what StartUp people and various other revolutionists will tell you, hardly anyone is even trying to disrupt this. Because people (both employers and staff) are mostly happy with the status quo. You'll hear a lot of talk about reduced office hours, flexible office hours, working 4 days a week, "commuter revolution", etc, etc... those things are statistical outliers that haven't really affected the large picture. Leaving your job to build a business is probably the _least_ statistically significant factor in all of this.

So yea, factories (and factory working hours) are here to stay for the foreseeable future.


I actually just quit a factory job to start software dev. The conditions and pay were terrible at my factory gig so I started learning to code in my spare time. Probably few people on this forum would be connected with people who recently have worked in factories. But those jobs do exist, and man do they SUCK!

Especially when the people in software aren't developing products for you because they have never met you, i.e. don't believe you exist. There are good things and bad things about the homogeneity of SV culture, and outside perspectives, especially from the working class, don't often make it past a seed round.


It's always interesting to hear another person talk about this. I've seen an article or two talking about how under served the working class is in regards to software.

Makes me wonder how much of it is economic, and how much of it is social.


A tremendous number of large corporations in North America have a traditional "butts in chairs" mentality/approach.

I'm a consultant but many clients, and especially government ones, in large enterprise IT, insist on seeing you in the office 9-to-5 (well... 8am-to-6pm really, but I digress).

While in the news and especially Hacker News, we hear more about the startup-type businesses, majority of people are employeed in big traditional corporations.


I don't think I've heard of a '9-5' factory job.


I had an 8-4 job one summer, when I worked temp jobs for an agency at various factories.

But the rest were 7-3, 12-8 or something in order to make multiple shifts fit.


Men are just machines. Most factories want 24 hours of production, some 7 days a week.

It's almost always rotating 3 shifts of 8hr(days, afternoons, midnights) or 2 shifts of 12hr(days or midnights).


Well, I work 9<something> to 5<something> most days and so do most of my colleagues - employer is very sensible, nice office, interesting varied work....


You mean 9 to 6


I'm in France, and doing 9-7


italy, IT sector, 9-13;14-18 minimum


what?


9 to 6, unpaid 1h break. Been there just after school (but mainly to be able to say I did stuff for BMW).


by working from 10 to 6....




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