Summary: Humans don't always take the time to think and plan very well. That does not mean we can’t think about our goals and how we want to go about achieving them. This meetup is an attempt to prompt strategic thinking. 

Tags: Repeatable, Investment, Highly Experimental. (Highly Experimental here means that things like this have been run, but I haven’t actually ever run a meetup following these exact steps. Lots of variations on it exist and I don’t have any strong opinions on which is best.) 

Purpose: Humans are capable of strategic thinking and problem solving, we just don’t do it automatically. The purpose of this meetup is to prompt people to actually think about what they want and how to get it. 

Materials: Some way of keeping time is required, such as a kitchen timer or a smartphone with a timer app. Having a bunch of pencil, paper, and writing surfaces may be useful for the participants and is recommended. Some people might want to use devices like laptops or cell phones; I suggest if you want to use one that you turn the wifi off. 

Announcement Text: Humans are not automatically strategic.

We do not always take time to think through what we want to achieve and how we plan to achieve that. It isn’t a factory default setting in people to consider how our plans might go wrong, or whether this is really what we want. That can work out for us, especially when what we want to do is a normal, expected thing that most people set out to do and succeed at.

Many of us aren’t living normal, expected life paths. Today, we’re going to take some time to sit and reason about our goals and do deliberately what we might not do automatically.

Description:

Explain the following steps to the group, then run the timer as everyone goes through the steps. (If you want to adjust the questions asked or the way people group together, go ahead! Just plan that beforehand and have a different script to read off of.) If someone is unsure what time span they should be planning for, the recommendation is to plan for the next quarter, aka the next three months. That said, if it makes more sense for a participant to plan around the next ten years or the next two weeks, that’s fine.

1. First, what do we want? What are the values we want satisfied, what do we feel is missing? Take five minutes, by the clock, and just list out what it is you want. You might say rough categories like “Health” or “Friendship.” 
2. Second, no really, what specifically do we want? We’re going to take five minutes again. If you said “Health” before, try and drill down to something like “able to run a 5k” or “able to bench press a hundred pounds.” Ultimately it’s fine if you’ll know it when you see it; if you said “Friendship” before then something like “At least two people I have meaningful conversations with every day” is fine as long as you know what you mean by meaningful. Still, try for clarity. 
3. Third, how are we going to get what we want? Take ten minutes this time. What steps need to be carried out in order to make that happen? Once you have those steps, consider if that’s the only plan you need, and if it isn’t (it probably isn’t! There’s no reason to be confined to only one plan!) come up with additional plans or angles of attack on the problem. 
4. Fourth, what might stop us? Take ten minutes again. If you knew for a fact that you failed, what is the most likely reason you failed? What’s the second most likely reason? Look for flaws, oversights, and issues in your plan. Come up with fixes for those, and then come up with problems in your fixes. 
5. Fifth, peer review. If you’re comfortable with it, pair up with someone else. Take turns explaining your goals and plans to your partner, and let them make suggestions or ask clarifying questions. We’ll spend ten minutes one way working on one half of the pair’s plans, then switch and spend ten minutes on the other half. 
6. Sixth, announcement. If you’re comfortable with it, we’re going to go around and briefly state what we’re trying to achieve and if we have a target timeframe in mind, when we plan to achieve it. Just say the goals from step one and step two, trying to take maybe half a minute per person. If you have more than fifteen people, consider breaking into smaller groups of roughly equal size.

All told, this should take you a little over an hour to go through. Expect sorting, getting people's attention, and "one more minute" requests to add very roughly around fifteen minutes.

Notes: Lots of variations on the questions, groupings, or time scale are worth trying. In general, this is a pretty personal exercise and it’s fine if different people at the same meetup are doing things differently. I do strongly recommend sticking to the timers though. 

Credits: This is transparently inspired by “Humans are not automatically strategic” by Anna Salamon.