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When I first started as a contractor back in 1847 I steadfastly refused to take any time off; reasoning that time off == money lost. The most I would do was a week and then only if at least one of the days was a public holiday that I didn't get paid for anyway.
But then I realized that time off == better work. Besides, I got to the point where I had an annual budget which aimed to work at least 44 weeks in any year; more if possible but I would be okay at 44.
So started to take more time off; first 2 weeks, then 3 then 4 at a time and it made no real difference. I still made the money I wanted to and had some great vacations.
Moral of this tale: take time off: it will make you a better worker. 
"If you think it's expensive to hire a professional to do the job, wait until you hire an amateur." Red Adair.
Those who seek perfection will only find imperfection
nils illegitimus carborundum
me, me, me
me, in pictures
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I'm there. It's taken a while, and its eerily similar your thought process to mine - 1 week off == expense of paying for the vacation, plus the loss of billing time.
I live near a large lake, and I love to sail. I'm at the point now where I happily dream of taking a week or two or three off and just sail back and forth.
Charlie Gilley
<italic>You're going to tell me what I want to know, or I'm going to beat you to death in your own house.
"Where liberty dwells, there is my country." B. Franklin, 1783
“They who can give up essential liberty to obtain a little temporary safety deserve neither liberty nor safety.” BF, 1759
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I'm exactly at that point. Started early February last year. So far I managed to take one week for christmas and new year's celebrations. But I don't see taking another week any time soon.
But I do plant to get where you are, eventually.
To alcohol! The cause of, and solution to, all of life's problems - Homer Simpson
----
Our heads are round so our thoughts can change direction - Francis Picabia
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It's pretty easy. I tend to work by front loading my hours so that I ramp up a couple of months before a holiday so that I can clear off my desk and get rid of a lot of the crap work. Then I mark the time in the schedule and make sure that this is down as "Do not disturb time". For instance, I'm off to Tenerife this Friday for a week - I have one more reasonable task to do this week and then that's it - I log off on Thursday at 5PM and any issues can wait until the Monday I get back to work.
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Every hour spent not making money is a wasted hour.
I have my main day job, and run two personal businesses, a stationery company (although it now has 60,000+ lines of products including PPE, Security Equipment, Site Materials, Tooling, Janitorial and Premises Management Supplies and more), and a CCTV and Premises Security Company.
I also have investments and rental properties.
I realise at the moment I cannot take any time off, and it is likely to be that way for at least another couple of years.
Once I get to >£1,000,000 I shall start motioning toward winding down the hard work and taking it easy.
Until then it is Work Work Work.
---------------------------------
Obscurum per obscurius.
Ad astra per alas porci.
Quidquid latine dictum sit, altum videtur .
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I used to think more like this. But life is very uncertain. What you put off may never happen. With that in mind I'll be on vacation in Aruba 10 days from now
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Have a great time, Aruba is fantastic.
---------------------------------
Obscurum per obscurius.
Ad astra per alas porci.
Quidquid latine dictum sit, altum videtur .
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I work straight for 6 months then take 3 year vacation 
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6 months planning the heist.
3 years in prison when it goes wrong?
---------------------------------
Obscurum per obscurius.
Ad astra per alas porci.
Quidquid latine dictum sit, altum videtur .
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I've done something similar a time or two. Course the state called it unemployment.
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You have to be looking for work to be unemployed
and most unemployed are not worth a couple million, and have multiple 1000+ acre properties
I own three companies
My companies are setup so I only need to monitor them
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Colborne_Greg wrote: You have to be looking for work to be unemployed
Well by that definition I was only unemployed for about 2 weeks then.
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That is the definition is which defines the unemployment rate
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Colborne_Greg wrote: You have to be looking for work to be unemployed
and most unemployed are not worth a couple million, and have multiple 1000+ acre properties
I own three companies
My companies are setup so I only need to monitor them
Skite...
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I get a high hourly rate but works at irregular interval. (.NET certified trainer)
So most of my time is free. I also have my economies in front of me so I can refuse work if I don't want to work.
In fact, I forgot what a vacation is, because this is a concept that only people with external time constraint seems to have. (It can be the boss, the business, customers, or social pressure like wife, kids and friends)
Except to go out during summer with friend, I don't have any of those constraint. (On the short term, sometimes, but never on middle and long term)
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When I had a family to support holidays were a very precious luxury, we would try and get 2 weeks away in a year but not always. The time off == lost income is certainly a driving force when the finance is tight but if you get to the point where there is more incoming than expenditure (this happens when the kids leave home) make the time to take all the breaks you can.
Never underestimate the power of human stupidity
RAH
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You take your laptop with you.
Easy Peasy!
cheers
Chris Maunder
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righhhhhtttttt 
Charlie Gilley
<italic>You're going to tell me what I want to know, or I'm going to beat you to death in your own house.
"Where liberty dwells, there is my country." B. Franklin, 1783
“They who can give up essential liberty to obtain a little temporary safety deserve neither liberty nor safety.” BF, 1759
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Based on the replies, I have concluded that there are a number of people I would love to interview and understand the business decisions they have made. Some of us became employees and then got a wife / family, and have been trying to bust free financially ever since. The best thing I have ever done is to start my own business.
I appreciate the feedback except for Chris'. I took my laptop on vacation once. I have never eaten so many <****> sandwiches I my life. I can still see my FIL looking at me with concern, telling me I needed to really go on vacation and put the laptop away. I still recall paying for all of them to be at the beach. I think there is something wrong there, but I'm not sure.....  never did figure out how he said that with a straight face.
So, how many of you do working vacations?
Charlie Gilley
<italic>You're going to tell me what I want to know, or I'm going to beat you to death in your own house.
"Where liberty dwells, there is my country." B. Franklin, 1783
“They who can give up essential liberty to obtain a little temporary safety deserve neither liberty nor safety.” BF, 1759
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Have a life 
Seriously, I do not force myself to a either-solution. I did in the beginning (home office for the last 25 odd years) but it didn't really worked and I got grumpy  Nowadays, if a idea / thought for solving some work related problem raises it's head I'll deal with it. Often by writing it down on, preferable, a post-it note (my memory haven't gotten any worse but I do not trust it as much these days  ) and returns to vacation.
rgds /Jonas
ps during the dark hours of the moon-less nights the Masked Dark Programer returns ...
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The short answer is that I don't get away as often as I should.
The main thing is keeping on top of any queries that come in. That imposes a constraint in that you can't go anywhere "off the grid" - a reasonable data connection is essential (and that's a pain, quite frankly).
When I'm away I always have an ultrabook (with a 3G card), and a 7" tablet with me. The former has a full set of dev environments on it and is fully equipped to build our products (but not sign them - the code signing cert stays back at base on the CI server). We use TrueCrypt to keep the code etc. secure.
That means that I can investigate bug reports and put together a patch for a customer if need be.
In practice, I can't think of a time recently when I've had to do that. Mostly it's just email (but that in itself can be quite a drag - at a conference last year I had a chatty dev sending me several tech queries a day!).
As a case in point in the last week while I was at the ACCU Conference[^] I wrote about half a dozen emails (a mix of sales/reseller enquiries and tech ones), but never fired up a compiler once.
Anna ![Rose | [Rose]](https://codeproject.freetls.fastly.net/script/Forums/Images/rose.gif)
Tech Blog | Visual Lint
"Why would anyone prefer to wield a weapon that takes both hands at once, when they could use a lighter (and obviously superior) weapon that allows you to wield multiple ones at a time, and thus supports multi-paradigm carnage?"
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Hey Charlie - I think that's like the "Holy Grail" question for contractors or business owners. I've had the same question myself for years and have some thoughts that may help but no perfect answers - part of the reason for that is that it really depends on the individuals circumstances (we don't all have multiple businesses with millions sitting in the bank and multiple employees that can handle things when we step out of the picture for years at a time!).
1. Goals. How much money is "enough"? If you have goals, as some of the other people have responded indicate that they do, then it's easier to define when it's ok to take a break because you've "earned it" and you won't associate the "another hour = another $" as much (or at least that's the idea). If you're really ambitious that can make this difficult because you're always striving to get in just a few more hours. The other issue that many of us have dealt with personally (at least when you first start out) is the concern that if you don't do this work now then the work opportunity may not exist tomorrow - that's lost income, right? The truth is that may in fact be the case and you'll have to make a judgement call on that based on the other factors - do you have other work lined up in the coming months, how marketable are your skills, how big is the opportunity, etc.
2. Productivity. Some people "need" vacation more than others and, as others have commented, that a vacation will make you more productive in the long run. It can be hard to be convinced when you have a s**tload of work staring at you that the fastest way to get through it is to take a week off! I really think that comes down to the person as some people need a break more than others and some need different types of breaks - a night out playing pool once/week vs. a vacation away for a week. Only you can answer how your productivity is affected by taking a break - just don't ignore the fact that it can be affected and don't ignore that your "break" choices impact your family.
3. Community decision. As you have already commented, bringing work with you everywhere will not make your wife a fan! I've been there too, more than once! Unfortunately if you're the only person that can deal with a particular part (or all) of your business then it may be unavoidable to bring a phone/tablet/laptop and be accessible in case of emergency, but do your best to separate the emergency situations from planning to "get a bit of work done at night while at the resort" or "pulling out your laptop at the beach or poolside while the kids are having a swim". Ultimately if you're in a family you are one member of the decision making team (unless you happen to run a dictatorship) so be sure to involve your family in your goals and vacation plans. The more they know the better they can support you and help you to help yourself ("Dad, you said we could go camping this weekend after this project was done") - some times we need those little reminders to stop us from being workaholics.
I can also tell you that having been involved in a number of entrepreneur groups that this is a common theme across any self-employed discipline - and I've heard very successful entrepreneurs stake the importance of making that time (and that includes both from those individuals who have families and personal lives AND those who had "lost" their families because of their focus on work) and also people that sincerely believe that being an entrepreneur means you don't have a personal/family life (which really sounds sad, especially when you consider that many of us are doing this, at least in part, for our families).
Sorry for the long response. As I said at the beginning, there is no perfect answer. My suggestion - get input from everyone here, talk to your family, and figure out what works well for your situation. *edit - for the record, I can't remember my last real vacation so feel free to ignore all of my advice! *
Cheers
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I was self employed for about 6 years. I usually took a few weeks a year of official "vacation". I would plan to do no work, but would still respond to some calls and emails sometimes for emergency fixes, sometimes to just say I was on vacation and I would get to it the following week. Most of my time off would come in the variety of a few days here a few days there kind of thing. That plus the ability to take a few hours off in the middle of the day to go for a hike or whatever kept me sane.
It was only later that I realize what a horrible job I was doing at taking vacations. My first vacation after I started as a full time employee again was a real eye-opener. I literally didn't think about work in any serious way from when I left early on Friday until I was walking back in the building 10 days later. I felt so refreshed.
It really made me value vacation time much more highly, and I'm much more willing to trade salary and other benefits to gain more vacation time. I highly recommend you do your absolute best to fully shut down work for a few extended stretches (1 week minimum) a year.
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Budget appropriately. Know how much you are likely to make in a given week (or however much time you wnat to be able to take off), and then know how much the vacation will cost you, and then save that amount. Put it into its own savings or money market account, or even just a jar in your house.
Then when you have enough and aren't in the midst of a project that mustgetdonenow, you take your vacation. A portion of that amount will be giving you 'paid vacation' and the rest will pay for your vacation.
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