What makes goal-setting hard and how to get around it

Setting goals is not about setting in stone where you will be in 5 years. And, planning is not about creating 10-page detailed descriptions that will never map to reality.

Try looking at it this way instead:

Goal setting is about holding yourself accountable for where you want to be

The purpose of setting goals is to practice specifying what you want. Setting good goals is a skill. It involves having honest conservations with yourself so that you’ll practice and learn what it is you actually value (and desire).

Planning is about holding yourself accountable for how well you’re moving towards your goals

Planning is similar to goalsetting in the sense that you have to consider and specify what you will get done. This means evaluating both your internal resources (time, energy, attention) as well as external factors (other people’s schedules and other (un)foreseeable dependencies). You’re honing your estimation skills.

The two areas where it often goes wrong

Wrong fidelity (detail)

When you’re determined to make something work, you often cope by simply throwing more at the problem. In the case of planning that can take the form of a highly detailed multi-page plan. That’s actually counterproductive. Not only does this cost you an unnecessary amount of effort, but it also leads you astray. The future is unpredictable and you can’t outwork it by creating super detailed plans. You’ll just be proven increasingly wrong in unforeseeable ways, and likely get demotivated as a result.

Wrong timescale

Not only is the “external” future unpredictable, but what you will want is in the future is unknowable. Would you want your two-year-younger-self to decide what you will aim for this year? Probably not. You must focus on appropriate timescales. Far enough in the future for it to be a certainly desired improvement, and short enough to be able to realistically guesstimate your efforts.

How to do it right

You approach it as a skill that you’re developing. You only improve it through repetition. To set yourself up for succes you’ll want to make the repetitions of high quality by choosing the appropriate fidelity (detail) and horizon length. The key is to also set-up the supportive processes like check-ins and wrap-ups from the get go. You need to stay engaged with your goals throughout the quarter.

I’ve applied these principles in a Goal Setting guide which I call Life Goals OS. It’s part guide part product. Learn how to come up with, and define killer life goals. You manage your goals in a clean Notion dashboard based on the OKR framework.

It’s currently live on Product Hunt:

And, available on Gumroad:
(free version available, 50% off the full version with code ph50)

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