“Be More Productive.” Should I Plan My Weekends?

It’s Saturday afternoon, and my one-year-old woke up from her nap early. The plan was to write during this time, and so now I’m trying to draft this post and watch Pinocchio at the same time.  But I’m not complaining – she seems to be enjoying the movie, and it feels like I’m watching it for the first time because I’ve forgotten everything about it (like the terrifying “donkey transformation” scene, for example).

Sometimes it’s nice when plans go off-track. In my interview with Scott we talked about how uncertainty and spontaneity aren’t just fun, they’re essential to the human experience. We can’t control everything, and that’s OK. Some of the best moments are the ones where things go sideways.

Still, I’m a big advocate of planning. Last year my goal was to plan my day 183 times (over 50% of the year). I came up a bit short, only planning 171 days. But I was happy with the results, and wanted to set an even loftier goal this year of 300 days. That’s almost twice as many days as I did before, but I have some plans for closing the gap.

For one thing, like any other habit it got easier the more I did it, so towards the end of the year I was doing it a lot more. But still, even if I kept the pace I had in Q4 2019, I wouldn’t get to 300 unless I made one, big change: I would need to start planning on the weekends.

In 2019 I viewed my planning exercise as a “work” thing. It started as soon as I got in the office, and helped me plan, prioritize and execute my tasks for the day. But when the weekend came, no more planning. Planning is so rigid, so restrained – it makes the weekend sound like work. And after all,


But as I look back on what I did in 2019 and what I hope to do in 2020 I have to ask myself: is planning my weekend really such a bad thing? Does applying plans to my “time-off” take all the fun out of it? I think about when my wife and I went to Italy and how we took pride in the fact that we didn’t have “plans.” A good chunk of our time was just spent wandering, and some of our best memories stemmed from completely unexpected events (like getting robbed).

But still… we had plans. We booked flights which established a time-frame, identified cities that we wanted to see and planned to visit them in a logical order. We determined how long we wanted to spend in each city based on things we wanted do and how long we thought those things would take and we booked accommodations. We got advice from friends and family which resulted in two guided tours both of which were highlights of the trip.

We stopped there, but we could have gone further. We could have picked a few restaurants beforehand, established specific routes for site-seeing. If we really wanted to, we could have planned every single step of the trip. Is that “doing it wrong?” What if we’d taken the opposite approach? What if when we first came up with the idea, drinking jalapeno pale ales beneath the low lights at the bar in Alexander Michael’s restaurant, we’d just bought one-way tickets and taken an Uber to the airport?

When it comes to your free time, what’s the “right” way to do it?

I think the answer is that it’s different for everybody. For me personally, I like a little structure. The balance we struck in Italy was just about perfect for me, so why not take the same approach with my weekends?

I’ve been experimenting with this; I’ve planned 28 days through February 8th, and three of them have been Saturdays or Sundays. Weekend plans might not be terribly detailed, but they do help. Today for example our girls had swim lessons in the morning and I was meeting someone for lunch after. As we were leaving for swim Liz got a client call she needed to take. Aware of both our commitments, I simply texted Liz that I was going to go ahead and put the girls in the car and take them. She could drive separately, meet us there and I could just leave from swim directly to meet my friend for lunch. No rush, no stress.

And everything was fine until I started driving and the car’s Bluetooth picked up Liz’s call and suddenly she couldn’t hear the client and all her client could hear was me giving my girls a pep-talk about keeping their goggles on.

The best experiences might be the ones where things go sideways – but paradoxically, having a little structure can actually give you the freedom to have those experiences in the first place.

2 thoughts on ““Be More Productive.” Should I Plan My Weekends?

  1. Your “thinking out loud” seems to be a good way to consider the merits if structure versus spontaneity. But I hold to the adage “failure to plan is a plan to fail”. Of course plans go awry, as you pointed out with swim lessons, so, having the mental and emotional agility to “roll with the punches” is necessary to maintaining good humor. Another fine post.

    Liked by 1 person

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