Ask HN: Who here struck out on their own without a plan?

I kind of did, about a year ago - http://news.ycombinator.com/item?id=941417.

I didn't exactly have no plan whatsoever - I had a consulting company, and another side business, but I was kidding myself when I thought I was "ramen profitable". A few projects done for a couple of grand is NOT "ramen profitable". But I was so sick and tired of burning away at Wall Street that I just said "fuck it, I'm gonna do it".

After a year of working harder than I ever did at a Big Soul-Sucking Corp., I'm finally making some money. I experienced a situation where I didn't know how I'm going to have rent money for the first time in my life, but that's turned out to be not that bad.

I'm still not where I need to be - my main business is still working on custom projects for clients, but I have a few sources of income, some more passive than others, working on a startup, and definitely on the right track. But I've learned more in the last year than at last 7 years spent at BigCo, having a lot of fun, being my own boss, and it's awesome.

If I knew how hard it was gonna be, I probably wouldn't have done it. So my advice - just dive in, you'll figure out a way to float somehow.

I had a decent job -- reasonably good pay, decent benefits, good people. But I wanted to work in software and that just wasn't the role there. I was also living in Orlando, which is a shithole, so something had to change.

I saved up $12,000 and quit last year, despite the terrifying economy. No real plan beyond "do something interesting." Moved across the country, built iPhone apps, had a good time. After about eight months, got bored, money got tight, but no biggie -- I got a job at a startup. I couldn't have landed it without everything I learned during my little adventure.

It's an amazing feeling – it's freedom. No one expecting you at any place or any time. Just you, your motivation and whatever you're able to imagine.

If you've been working for the man for awhile, having 100% control of your time can be weird. My advice would be to establish a routine and stick to it like glue. If you've got a specific working space, make sure you're in it each day at the same time. Eventually you'll be able to fully enjoy the flexibility, but at first productivity will require you sticking to what you understand as a working schedule. Modify this as you learn your natural rhythms throughout the day. (ie: maybe you're a night owl, so you enjoy a bit of work in the mid-morning and then a six hour burst later in the evening.)

Working at home is fine and all, but you might want to find a quiet, productive place away from where you live. If you're near a nice library, this is ideal. The change of scenery will help you stay sharp.

Give yourself a break, if it's at all possible. I used the flexibility that self-direction bought me to go to Europe for a couple of weeks. It recharged my soul. Some kind of adventure will do you good if you've been following other people's rules and direction for any lengthy period of time.

Most importantly, set clear goals for yourself when you're ready to get down to work. I didn't always do this and my work suffered. Even if you're working by yourself, a little scrum action might do you some good: plan weekly sprints and do a little standup with yourself each morning or evening to review your progress. You're your boss now – no one else will hold you accountable.

Good luck. It's a bit risky, sure, but a great feeling.

Oh, coincidence. I did this about twelve minutes ago.

Yes, I've just tendered my resignation. I work in a large, large company. The place is okay, the people are good, the code is fine I guess. I just wanted a change of direction. I started in videogames, and compared to that, this job feels far more... stuffy. And boring. Anyhow, I wanted a shot at starting my own business writing web apps. I literally do not know: javascript, ruby (therefore rails), much of linux, or webservers (well, I've heard of a whole bunch).

But hey, I have good savings, I have low rent, I have a nice computer, and in addition - unlike when I was working in videogames - I have a sleep-cycle that has me up at 8:00am every day.

As for the actual experience, I've just informed my direct lead, and we'll have to talk to the head of our department later today. I guess I'll let you know how it goes!

Good for you.

8 years ago. I had a 1 year old son. Just married. Wanted to be my own man, run my own company, do my own thing. I wanted my son to see me as a man who goes after his dreams.

So, I just did it. Took on some consulting work, and then spread the word of what I could do. Gets better every year. Not so much consulting now, more residual income from software and hosted services, and android game development, but it's a living and a lifestyle.

I have. Depends on what your goals are when you quit.

For me, it was to do a startup, but I made some fundamental mistakes along the way.

I spent a good chunk of time learning how to build. Before then, I had never built something from the ground up. So that was good.

However, there's a bunch of stuff outside of coding that I didn't know. The biggest thing was I didn't know anything about customer acquisition. Once I built something, I had no idea how to drive people to it.

The others are usual mistakes. Not finding another cofounder sooner. Not moving to Silicon Valley. Of course, you'll have people that say you don't need a cofounder or that you don't need silicon valley, but I've found both to be tremendously helpful. So, know yourself and what you need.

As long as you know what your goals are when you quit and work towards it, you'll be fine. If anything, it'll give you time to build skills or notoriety.

I've never been in the situation you're in, so I can't say my advice is particularly worth much.

But don't make important decisions based on emotion. Especially if you don't have something lined up (unless you're good for cash). In your described situation, it doesn't look like the benefits of quitting immediately outweigh the cons. The weekend is coming, why not use that time to think about what you really want to do?

I did, however you never really "quit", especially if you are at risk of going broke. I went broke about 6 times after quitting, however if you are a developer (like most people on here), then you probably have a skill that you can use to get work on the side. That side work is critical to getting your business off the ground. That's because most businesses you start won't be paying the bills in the immediate future.

Even worse, they need money! I actually successfully managed to get to an exit, however I now advise other people to work as long as they possibly can before they quit their job. I know how lucky I got and I also know how many times I literally was days away from being completely broke.

Then again, perhaps those moments are what makes the entrepreneur. I do think that having a plan would be useful. While your plan won't be accurate, at least you can think through all the steps you need to take for the foreseeable future.

Also ... try to have 6 months runway if you can (I know, that's a luxury).

Create a plan, begin executing and then go after it. The worst case scenario, you have to get a job again. The last thing you want to be is in a position 10 years from now asking yourself "Why the hell didn't I do it?"

The only other thing is to make sure you take care of your basic needs (health, etc). I've made the mistake and have met others that have put their business before themselves and it helped nobody. Aside from that ... best of luck!! You're in good company on this site!

Any other rules I try to artificially create can instantly be broken so I'll stop providing advice

I did this about 2.5 years ago: I was just totally drained I figured I knew enough to get something else started, I was pretty much prepared to sleep on a friend's or family member's couch until I could make money doing some online marketing. I had no money but I couldn't imagine another year in the office. When I walked in to quit my job my boss wasn't expecting it (tad different from your scenario) so started to drill down why I was leaving-- for me it amounted to not being able to have freedom of movement and work when I want etc. The office was killing me. We ended up hammering out a remote working arrangement that has served me well and allowed me to get a bunch of other projects off the ground. I wouldn't have predicted this opportunity to come up, so I guess I benefited from a classic case of "you need to close one door to open others..." Not sure if that's helpful, but I find when you are done emotionally in a job or project compromise can be a killer especially for people with the creative entrepreneurial spark.

I did it.

I was completely burned out. I had actually had a hospital visit due to stress, and ended up still working another 5 months after that (3 of those after I told the company I was quitting and converted to a consultant, working just as many hours but getting paid hourly instead of salary).

The good part there is that I had a nice cushion to land on and do nothing for about a month. At the end of the month I had a little bit of ambition back, and decided to do some small consulting gigs to make the cushion last a bit longer while doing less than full time work. This lasted far longer than I wanted, but unfortunately, I hadn't gotten enough of a client base to kick back into gear when I needed it. Luckily, a long term client showed up right when i needed it, otherwise I'd probably be back having a real job again. I'm much happier with my current arrangement, in that regard.

The lesson to be learned from me? You can head out w/o a plan, but you should probably form one and execute on it while your surviving on your savings.

I quit a job of 7 years with no plan of what to do next. My wife (but wasn't a wife yet) had a reasonable job, and we figured if ever there was a time to take a risk, that was it.

For three years now, we've lived on the philosophy of "if we stop making money today, we have X months left before I have to go get a job". At the end of each month we reassess that, and fortunately we're still doing ok. If nothing else, my work is a hobby that makes us money. I doubt I'll ever get rich from fivesecondtest.com, but it's something to be proud of, and that's more than you'll get working for someone else.

If you think you COULD get another job in a pinch, then really you have zero risk providing you have either a decent amount of money saved or have few financial commitments.

http://usabilityhub.com/account/logon/ is unstyled right now (no css), btw.

I quit my job without any plans last July.

I had a conversation with the CEO and the company environment he wants to build is not what I wanted to be in. I gave my two weeks notice the next day.

I had no idea what to do but it just happens that a good friend of mine is looking to start something. I asked him to be my cofounder and now, I'm finally doing what I have always wanted to do.

I still work part-time just to pay the bills. We're building the product and trying to find customers. Once I put more money in the bank, I'll be full-time on the startup.

Do what you need to do, just don't burn your bridges.

I graduated from college, sold everything I owned, and drove across the country to San Francisco.

Months later, I have advertising income from www.ThatHigh.com that generates enough money to pay my rent and food. I now spend all my time working on Djangy.com - private beta invites coming very, very soon!!

I ended ten years of employment in July. Burnout was killing my motivation to code at all and I gradually came to realize how damaging this could be.

My plan is to take a sabbatical, travel a bit, and recharge my intellectual batteries by learning a new language and a new problem domain. So far the hardest part has been sticking to my guns and turning down new job offers.

This TED talk makes a good case for this: http://www.ted.com/talks/stefan_sagmeister_the_power_of_time...

I haven't viewed your video yet (bookmarked it) but I am completely on the same page as you. I am soooo burned out, have worked 11 years. In short, something isn't right and I'm not happy. I'm out of here in November.

Think about it this way. As a programmer, the future of your career depends on your ability to keep learning new things and to stay on top of new technology. Anything that threatens your ability or motivation to do that is very dangerous.

It's easy to get comfortable in a good gig, particularly if the pay is high and the work isn't too onerous, but this is a trap if it means you wind up doing the same thing for too long.

I've been doing that constantly since 1999 when I quit a job with no safety net other than being only 17 years old and still living at home.

Since then, I've rarely any medium or long-term plans, just flitting from opportunity to opportunity as it presents itself. I'm here, doing well - now married, have child, have a mortgage, and still as aimless as ever ;-) If you're self motivated and a little hungry, things stick together.

Right now!

Only possible because my wife saved up a bunch of money while I was working. Now we're burning through that, I'm updating my portfolio, blowing the dust and cobwebs off several startup ideas I had shelved for so long. No income yet; I'm going to start aggressively looking for consulting work as soon as the portfolio is up. I've had a couple "fell in my lap" job leads from friends but none are in my area and I can't move right now.

I'm hoping to hit some kind of rhythm where I'm able to stay just afloat with a part-time contract work, and the rest of my time I can spend time 1. with the wife and 2. exploring my experimental software ideas.

My mantra and rationale remains unchanged: even if I fail at this little adventure and go broke and have to panic and reorganize my life, that in itself will be a lot more fulfilling and exciting than the burnt-out, depressed place I was in at my former job.

I've heard that when skydiving, once you reach terminal velocity it's becomes less frightening. So it doesn't feel too bad right now. But I'm entirely aware that the ground is quite hard and only a few thousand feet, er, dollars away.

Best of luck to you!

IMO, for most people, having an expensive lifestyle is not worth working at lot. Just save money, quit and live cheap for a while.

It seems to me that most people are happy to put up with long hours at a stressful or boring job in exchange for a cushy lifestyle. If you're willing to forgo the big house, nice car and 42" plasma screen you can buy yourself some extra freedom though.

I don't think they're really happy. Some are; lots aren't.

Just because they keep doing it doesn't mean they're "happy." Lots of folks never realize that they, yes THEY, could do something different.

All that you have to consider is how much you burn on a monthly basis and how long you can sustain to focus on your endeavor without any stable source of income.

Having full-time to focus on your plans will help, if you can afford to not be making money for some period of time.

Some of you already mentioned it in their posts, but for those who didn't: Who did it when you were in your 30s? 40s?

Striking out on your own is a lot easier when you're leaving your first or second job. When you've got family and/or are on your way up the "corporate ladder", the incentives for swallowing your ambitions and sticking to your current job seem bigger.

Which is kinda sad, as by then you should have a bigger appreciation of time, and what it means to waste it.

So, as someone who has his first 10 years of corporate work under his belt and doesn't want another 10 of working for someone else: Who's a late starter, too?

I actually did that a few months back, but got a counteroffer I couldn't refuse (a really awesome deal).

"the obvious need to immediately produce revenue" -> so no savings at all?

I would make a flowchart but here goes:

Are you a good engineer? If yes you can work elsewhere.

Do you have good rapport with your managers? If yes you will have decent references.

Are you well known or popular? If yes most people will applaud your courage.

Do you have money saved up? If yes you have a small runway to figure out what you really want.

Life's too short to hate your life.

I think this is well said and summarizes the main things to think about.

I've quit a job twice without an official plan or offer in hand on two occaisions. The metric for savings I used was 6 months living expenses.

The main reason I was comfortable with doing this is that I'm confident I can get a job to feed myself whenever I want.

I think the last point is the most important and the main reason I quit my jobs.

So as I've mentioned, I've done this before without the "work for myself" part. Twice actually.

One of the contacts I made today was the only technical recruiter I've ever met that understands the industry he caters to. I'm looking on my own, but he has a nose for finding much better than average gigs. I'm not relying on him, but he has exclusive access to a fair number of decent companies which quickly broadens my search.

Managers can't complain. Heck, one of the partners went out of his way to write my review. Partners don't write reviews. He did it to make a point. However, constantly going the extra mile has me physically and emotionally exhausted, and I see no chance for relief until mid-2011.

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I keep my foundation expenses to a minimum, and normally save 30-40% of my paycheck, but numerous mishaps this year have effectively wiped out most of this year's efforts. My health is currently of concern (despite being in my late 20s and reasonably good physical fitness), so that's what's giving me pause as I investigate those options. That and sacrificing my bonus and 401K match (7% of compensation), though at this point I'm willing to eat that.

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The intention is mobile games. It's something I can do entirely by myself, save for paying a college student for help with the first year or two of getting my tax nonsense in order. No direct customers to deal with. Tools and hardware that doesn't suck. Development costs are negligible. I have a detailed concept, and overall complexity isn't much more than something out of the NES era -- much of the effort will be re-learning my drawing skills, and incessant polishing. The overall scope is very realistic for a single person to push out in 4 months.

Originally the plan was to release on the side with the hope of eventually covering most, if not all, of my foundation expenses so I can save more aggressively. However stress has me past my breaking point -- I'm already broken. I doubt more work is an ideal solution, but a relaxed pace and being able to release something that meets my standards is a change of pace I sorely need. So either I continue to crank for the office while cranking for myself, or I tell them I'll build my own lunar lander... with blackjack... and hookers!