Resistance to Planning

Structuring my time to enjoy spontaneity.

Hey friends,

Lately, I've been trying to plan more.

See, I was never a fan of planning. I had no plan for life in school and ended up studying CS in college because my classmates did it and my mom told me to do it (thanks, mom!). And because I liked computers more than people back then. I quit my first job because I didn't feel like combining it with studies, I quit my second job abroad because I got bored (and homesick), I ended up freelancing, then business, then product management, then consulting.

I also didn't plan to get a rescue diver's license (I just said yes when I wanted to say no), a skydiving license (it just sounded like fun), a motorcycle license (it felt like a cool idea), and I didn't plan to do a whole bunch of other stuff that I ended up doing. A lot of it was fun, some of it wasn't, but most of it wasn't part of my plan for life because I never really had one. The idea of having a plan felt boring so I went with spontaneity and a general direction for life instead.

But there's a drawback to this approach. Spontaneity is great for discovering new things, staying alive, and living a more creative life, but it's not great for maintaining a specific direction, seeing things through, and achieving bigger goals. As Antoine de Saint-Exupéry apparently said (according to Google), "A goal without a plan is just a wish".

And lately, I've been feeling like a lot of my goals are just that – wishes. I've repeatedly found myself having not enough time for all of my priorities while simultaneously procrastinating away whatever free time I did have because there was no specific, actionable list of things I could be doing next.

It made me feel terrible, so I finally decided to do something about it. It's now been about three weeks since I started turning my idea checkboxes and Someday Things into projects and tasks, splitting them up into finishable chunks, and dropping them into my task manager (it's my version of a calendar) with timeframes attached to them.

The result?

My brain's having mixed feelings about this, but it's totally worth it. I still don't enjoy planning, but I love getting things done – and having a bit of a structure and an actionable plan allows me to get SO. MANY. MORE things done.

Counterintuitively, structuring my time gives me more freedom, not less. Plans and retrospectives made me better at estimating how much time things take (who'da thunk!), and having an actionable list in front of me makes it easy to jump right into doing without thinking too much. This cuts down on procrastination, which allows me to enjoy spontaneity that much more.

And spontaneity still happens. After all, my plans are designed to be broken!

Sensibly, of course.

Have a sensibly structured week,


A few thoughts

Leading the conversation. It's not that hard to assume an active role in a conversation if you practice it deliberately. How do you practice it? Actively think about the things you can say instead of staying quiet or going "aha" and "yeah" – and then just say them without thinking too much. Dumb jokes work great. I've been practicing feeling ok about looking stupid in conversations and it helped make my conversations that much more fun.

A fallback routine. You can plan all you want, but life doesn't always care about your plans. It helps to have a fallback plan or a routine you can gracefully fail back into when your main plan doesn't work out instead of failing with abandon.

Socialization without procrastination. I love hanging out with people, but it often puts my mind into a relaxed and procrastinative state afterward. Lately, I've been trying to decouple these two things by socializing mindfully and staying sharp in the process. Too early to judge yet, but I think it's paying off!

Loved this

It's been a couple weeks since I last spent quality time reading, so I'm sharing some of the older stuff I liked. That's one problem with being "too productive".

The man who walked around the world: Tom Turcich on his seven-year search for the meaning of life "He started to make plans. He didn’t want to just see a bit of the world: if possible, he was going to see all of it. “Because the world is complex and vast, and because my general temperament is pretty timid and more towards the shy side, I wanted to be forced into adventure. The point of adventure is it’s uncomfortable and you have to grow in it."

Incompetent but Nice "It’s that fourth quadrant that I keep coming back to, and have trouble with. What do you do about someone who’s really nice but can’t seem to do the work?"

The fun part

I just can't for the love of me decide what to do about this section. In the meantime, here – have a dog (her name's Odi and she's a good girl):