I've been happily self-employed (freelance web development) for two years. Last year I took about 2.5 months off to work on my own project. It goes like this:

- start saying no to everyone

- spend about a month winding down existing projects

- enjoy your break, do something you love for a while

- when you get below $X in savings, ask around for work

Basically, there is a one month spin-down period and a one-month spin-up period. You have to have pretty good deal flow (i.e. you are already telling people no most of the time) to try this, and it's still stressful when you start to worry about whether your savings will last. But as long as your work doesn't inherently require you to be on call, you can wind things down and shift responsibilities around. As long as you're considerate of your customer's needs when doing this, they'll be willing to accommodate you. And you can practice this whenever you wind down an existing project in order to switch to a more interesting and/or lucrative one, a skill you ought to be practicing at least a couple of times a year if you're an excellent programmer.

I think this works if you're a one man shop...once you hire employees, though, things change. A lot. You have to keep your business running because your devs have trusted you with their family's financial well-being; you have a responsibility to keep the business healthy.

How much "keeping things running" is actually needed? I'd imagine disappearing completely for a couple months wouldn't work, but what about a couple months of signing on only on Monday mornings?

I think that's contingent on your business model and the maturity of your company.

I can only speak to my biz: most of our revenue is service (although we're trying to migrate to product). So we have three primary "departments," if you will: sales, production, service/support. I've chosen to staff out "production" first with kickass developers. But somebody has to take care of sales and service. Service/support, we've automated that pretty efficiently and only bother devs with processed support issues.

Sales, however, still requires the cultivation and management of client relationships. You can't just phone that in, and the way we've grown our business has been via relationship (i.e., referrals and word-of-mouth). So even if I was 100% out of production (which I'm not, yet), there's still the bizdev side.

At least that's how it is now; two years in the future I'll probably have a different answer and perspective. A lot of this stuff you just figure it out as you go; there's not a book out there that tell you how to run your biz.

You know your manager is sleeping with your wife, too, right? That bastard.

I never considered that before - how DO entrepreneurs take time off? Is this done post-post-/Ramen profitability? Never? Just for a day at a time? Or does the flexible schedule prolong burnout?

You don't.

This is one of the first things you'll notice being in business for yourself. It's hard to arrange time off. One of the benefits of working for a company is that there's a team in place to make sure the train stays on the rails while you're gone.

You also don't get sick days.

This may be the median startup behavior, but I've seen plenty of counterexamples, at some quite successful startups.

>You also don't get sick days.

That's one of the hardest parts of running your own business IMO. I had to have an op, recommended recuperation was 2weeks of bed rest, I was back working the next day; yes there were deleterious effects on my health.

And yet, you'll probably find as I did, that if you disappear for a week or so, nothing really terrible happens. With clients, it's easy - tell them you're gone. When you run an SaaS, it's not as easy, but I became so ill I wasn't able to do a thing… and we lost maybe one customer.

The others who were waiting on my emails got a very sincere apology and explanation, and we were all good.

This goes to show that you only think you have to be there all the time.

Automate everything that can possibly be automated, and when one goes on vacation, check email a few times a day. Might even be able to get some work in during the evenings.

Also, the flexible schedule allows for mini vacations whenever you need it, which helps a lot. It's great to be able to blow off work whenever an opportunity to do something great comes up, as long as you're disciplined about getting things done other times.

If you're checking email a few times a day, you're not on vacation. You're just working remotely.

You can look at it that way, but not so much true. The great thing about being a self employed is that it doesn't matter where you work.

I take my computer with me everywhere I go, even on vacation. I've had conference calls in the morning and hit Disney World in the afternoon. Usually my customers don't even realize I'm out and about.

So while you could say that your not really on vacation just remote, you could look at it the other way and realize you could spend a month in Florida on vacation and still make a few bucks in the process. I've been on vacations that have paid for themselves simply by putting a little work in for half a day here and there.

This is basically exactly what I was going to say. I'm currently spending a week far from home base wind and kite surfing. Once in the morning and once in the afternoon, I answer customer questions/suggestions, and after dinner I spend 4 or 5 hours fixing bugs and working on implementing something.

It feels a lot more like vacation than work.

It's really hard, especially during the first couple years, but my only perspective is as a bootstrapper, I think funded people maybe have more flexibility (or maybe not? I dunno).

My experience is that you just have to force yourself to stop working. It's terribly easy to let your business tak over your life. Me, I just force myself to forget about everything but the bat-phone on Sundays.

I can't reply as a funded person since I'm also a bootstrapper, but having done work for some startups they typically have directors which work for the funding group that sit around and make sure their money is working hard. So I imagine they have less flexibility.

Time OFF?!? HAhahahha!