Milestones > Timelines

Angelo Alessio
2 min readDec 16, 2021

This is essay #3 of 7 as part of the 7-day Tech Progressive Writing Challenge. Join the discussion with build_ in the Discord.

With everything seemingly moving at the speed of light in web3 (and arguably the tech sector at large), it’s important to periodically step back and assess the larger situation. And not only stepping back periodically but also ensuring there is a constant pulse on the operating environment.

This is especially true as it relates to DAOs that rely on being community-driven. One method that can help with ensuring you are operating sustainably is to think about community goals in the terms of milestones rather than timelines.

Milestones represent concrete outcomes to anchor against rather than timelines that are subject to planning fallacy. Milestones account for a broader array of solutions that go into achieving the outcome versus timelines that can sometimes force groups into tunnel vision.

A mountain climber is more concerned with the milestone of reaching the top and measuring altitude rather than time.

Long Horizons

One way to help think about milestones rather than timelines is to focus on long time horizons and working backward from there. Where do we want to be in 20 years -> 10 years -> 5 years -> 1 year -> 1 month from now? There should be a logical chain of events that flow from one to another and it can help decouple teams from pursuing unsustainable optempos and rather focus on making incremental progress towards milestones.

Situation Dependent

There will always be situations that demand nothing but urgency such as a security vulnerability, hot fix, or essential uptime requirements.

In other instances there are developments to be done that demand strategic urgency such as outmaneuvering a competitor or completing a dependency that is holding up the rest of the community’s work.

In some cases it even makes sense to go backwards and unwind some of the work towards a milestone because there is a path that may prove to have a much higher ROI, although these cases should be rare.

Regardless, setting clear milestones for the community/team to strive towards allows enough breathing room for a comprehensive solution and incremental progress towards a clear outcome rather than an arbitrary deadline.

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