Hacking Vacation Time

One of the big themes in The 4-Hour Workweek by Tim Ferriss is the concept of mini-retirements: taking extended vacations as a means to recharge as opposed to delaying gratification until the magical age of 65.

While I think delaying rest, relaxation, and travel until retirement is a sucker’s game, I’ve never been all that interested in the type of mini-retirements that Tim proposes. In theory it sounds great, especially if you’re young, single, and can work remotely, or if you’re between jobs. But for most of us it’s impractical, or at least difficult enough that the ridiculous work involved isn’t worth the payoff, regardless of cost.

Over the years I’ve developed a similar, more realistic, strategy that has worked really well for me. I feel like I get most of the benefits of mini-retirements without compromising my involvement in our business or putting extra stress on others within the company.

And, even though everyone doesn’t have the type of schedule flexibility that I have, I think this translates really well to the vacation time that most people have to work with. We’re still small enough that one person being gone has a tremendous impact on everyone else, which is one of the reasons why I tend to be strategic with my time, similar to someone who does have a set number of vacation days.

Day Trips

I love day trips. Anything further than a 40 minute drive and less than a 2 hour drive makes for a great day trip. There’s a huge variety of options within that radius around here, from the Adirondacks to Vermont, Western Massachusetts, Hudson, and a dozen more escapes. I’ll also include NYC, which is about a 2.5 hour train ride right into Penn Station. A few times per year I’ll take the early train into Manhattan, arrive before lunch, spend 6-8 hours in the city, leave around dinner time, and be home at a reasonable hour.

The beauty of day trips is that you can disconnect and get the feeling of being on vacation, without ever having to pack, book a hotel, or use any vacation time (assuming you go on a weekend). There’s very little effort upfront in terms of planning, and requires almost no time to get back up to speed when you return.

The Long Weekend

This is the sweet spot for me. Getting away for 1 – 3 nights allows me to really unwind and escape without actually spending that much time away. A 4 day, 3 night trip feels like a long time, but it only involves taking 2 days off from work.

By spending a few nights, you can travel a bit further. Long weekends are perfect for 3 – 5 hour drives or flights. As long as you keep the travel to a half day or less, you still have plenty of time to do things on the arrival day and departure day.

One of the best parts is that you can hit the ground running when you return because you only missed a day or two, compared with the buildup of being gone for an entire week.

Longer Trips

Since starting the business I’ve taken a few longer trips where I’ve 100% disconnected for a week or more. To be honest – and maybe this is just me – I tend to see a diminishing return after a long weekend length trip. Anxiety starts to set in, and my mind starts to wonder about what might have happened while I was gone.

I’ve never taken a month or more off, however that’s probably what would be needed to see any real benefit beyond the long weekend. That’s something I would like to do at some point, but isn’t super practical and doesn’t interest me at the moment.

Making The Most Of Your X Days

Let’s assume for a second that you get two weeks (10 days) of paid vacation, not including other PTO like sick and personal time. This is about average in the US, depending upon where you get your numbers. I think the best way to “hack” the time so that you get maximum benefit is to take a bunch of day trips on Saturdays and Sundays that use no days, and then use your vacation days exclusively for long weekends.

Those 10 days can be split up into three four day weekends (2 vacation days each) and four three day weekends (1 vacation day each). That’s seven(!) pretty solid vacations. Seven trips to look forward to. Seven chances to get away from the day-to-day grind and recharge your batteries.

This is effectively how I’ve been structuring my vacation time. Personally this is much more desirable than taking one two-week vacation. So while I’m not taking mini-retirements by the Tim Ferriss definition, I am getting a lot of mental breaks and plenty of travel in without being away from the business for very long. The same concept of not delaying gratification comes into play, it’s just mini-vacations instead of mini-retirements.

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