Vacations for bootstrappers?

It’s kind of summer (it’s been a very wet and rainy one so far) here in Italy, and the talk turns to vacations.

I’m curious what kinds of things you guys do, especially those with families. How do you balance the need to get away and spend some time with your loved ones, with the need to stay in touch with your business?

What I’d like to do is rent a house somewhere, and maybe spend mornings out with the family and afternoons working.

Earlier in the year we (me, my wife and 8 year old son) did 2 weeks in a hotel resort in Thailand. Then a week travelling around the UK. Later we are going to drive around Ireland for 2 weeks.

I just need a laptop and an Internet connection. I just do the minimum to keep things ticking over on holiday. I can usually get away with working an hour a day (mostly customer support).

I would take more holidays if my son wasn’t at school. ;0)

Tip: Never release major changes to your software or website a few days before going on holiday.


Just take the vacation and spend time with your family.

Nobody regrets “spending too much time with family” on their death bed.

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I used to ask a friend to keep an eye on things; they’d act as my level 1 support, handling the quick easy day to day stuff when they had time, and forwarding complex stuff on to me. I’d spend the day on holiday as normal, then when my girlfriend went to bed I’d work from my laptop - there were a few late nights, but the rest of the time off was undisturbed, so it still felt like a holiday. Never do any work in the morning though - if there’s something to deal with you will probably either end up leaving late, or worrying about it all day.

I’m hoping that when I complete my move from running client websites to selling software that there will be less to go wrong and that I’ll still be able to handle the support load by checking in at the end of the day.

That said, I often think the ideal situation (until you can afford employees) would be if you had a good professional relationship with another person or two who run similar businesses that are at a similar point; you could become familiar with each others’ products, then have a reciprocal arrangement to help each other out when necessary, keeping track of the hours you each spend, and settle the balance at the end of a year.

Very good advice!

Of course it all depends on the kind of business you are running. Last year my wife and I spend 3 [months traveling][1]. To make this possible I documented everything necessary in detail. For general customer support I hired a part time help (yep oDesk) but the most work was still done by me using a laptop in the tent (or hotel room). There the documentation payed off because I could just get things done in a small amount of time without thinking to much.

Biggest problem was the blocked internet in a few countries (like UAE or Iran) which can slow you down a lot. We don’t have kids yet so this may not apply to you in the same way but still :smile:

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I agree with the sentiment, but the devil is in the details. Also, there are a lot of people who regret not having “enough” money. Indeed, it’s one of the primary causes of family strife. Also, I was curious what kind of arrangements people make that work for them.

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About a month ago we did a 2-week motorcycle trip to Lofoten, Norway with our baby SaaS. It was definitely needed, as I had drifted into a workaholic mode.

We had a software bug that required us to check on the product 2 times per day at minimum. But then, we had the customer support too so we needed to find an internet for that anyway. But I tried to keep working at minimum and most days spent just 1-2h working.

So I did customer support in a fishing hut. I did customer support in a tent. I did customer support in a camping site kitchenette. And as I clearly communicated that I was on the road, my customers were very understanding.

At first I was a bit stressed for not being able to work more, but then the vacation just took over :slight_smile:

Being able to travel with my work is something I’ve aimed at from the moment I left my day job, so it was an awesome experience. And it will be easier next time as the SaaS is getting more stable and mature.


Sorry for the off topic, but there’s a really fascinating story about a shipwrecked Venetian captain that was blown way off course and ended up there:

I guess we have it pretty easy these days!

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Fascinating story! Thanks for sharing :slight_smile:

Interesting! I’ve been thinking about this (running a startup from a motorcycle). I’m not a motorcyclist yet but am considering becoming one - dual sport bikes are very compelling. I’m building an application for a client that connects motorcycles to freelance tour guides (shameless plug:

This might be called cheating but I chose to let my mother and father watch our kids, then flew our team for a business retreat to portugal and took the wife along for a week. 2 days of meetings, 3 days of fun. Win win.

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If you must do support or work an hour do it in the early AM when they won’t notice. I don’t want my kids to remember “Dad used to work on vacations”. I used to work a little on trips but now I leave everything (even cell phone) at home. It still takes 2-3 days to stop reaching for my non-existent cell phone.


Being a bootstrapper means you do have freedom and latitude in where and when you can work. Technically you can probably work from anywhere, but should you? Everyone needs some down time and if you have a family they especially need you to have downtime with them. My wife and I have four kids, we do two one week trips a year where I’m “offline”. My wife keeps an eye on emails for me in case any emergencies pop up but otherwise I try to stay away from any electronic gadget. It gives me a chance to totally unwind and be totally engaged with my family. If I need to do a little work (which has happened) I try to schedule it in the evenings so it’s not cutting into family time. For a few weeks that’s probably an ideal setup, for more than that it would probably be hard to stay almost completely offline, but it would depend on the situation. I would love to get to a spot where an hour or two a day is all that’s required. On the SAAS I could see it happening, with my consulting work, not so much.

Just remember to have backups of everything and if you need to access anything remotely from a different computer, make sure you can get access (I found out the hard way about our home firewall settings once when it was not convenient).

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I’m just out of 2 weeks of vacations with 2 kids. We basically remained in our house because we like the area, and moved around in the countryside.

What really refreshed my brain was: full days out of house (beach, lunch outside etc). I only handled rare support request and a little bit of writing, but nothing heavyweight.

For longer sessions, I keep a 3G connection handy and a very small laptop (MBA 13") but definitely allow myself to go offline.


We usually would spend time at one of our family’s places. We found a compromise that I would work 1 to 4 hours each morning, in exchange we would spend 4-5 weeks vacationing. Since we spend the vacations at our parents’ places, it’s quite an easy setup (we’d have internet and I usually find a small room where I can work semi-undisturbed).

Since both our parents live in different countries than us (they’re in Lithuania and Indonesia, while we live in Germany), vacation time is pretty much the only time we meet them.

I try to automate what’s “automatable” (I run a job board, so I just need to click a couple of buttons each time a job or event is posted on the site and write the invoices once a month), keep the 1-to-1 stuff at a minimum (e.g. answering personal emails) and just work on some code maintenance.


I have found that the more frequently you take vacations, the more leeway you have with getting some work done while there without it being an issue with your spouse, or guilt for not spending time with your kids. Of course, I’m talking about the 2-3 hours in the early morning (or during naptime) type of working arrangement. We usually mix up weekend family getaways, staying with relatives, group beach vacations, couple-only getaways, etc. peppered throughout the year. That way we never build up to the point where “we need a vacation”, since there’s usually something refreshing right around the corner.

Note: learning to vacation on the cheap (like sharing a place with family/friends) is what makes this possible.


I often fantasize about how local businesses just put up a sign that says they’ll be back in 3 weeks. We should be able to do that as internet companies :smile:

Now that we have employees it’s easier to disconnect while away, but I often still need to do a little bit of work on a few days of the trip. Before the employees was impossible not to.