The value of planning is the process, it’s very rarely the plan itself.
An effective planning process drives out the complexity of what you are trying to achieve. It shows you the priority, who needs to get involved and where the difficulties may be. You also get to say what you aren’t going to do, which is especially valuable before you’ve invested a lot of effort.
One quick test for effectiveness, check the level of detail you are working to, and measure it against the scope and duration of the plan. If the scope is more than a couple of weeks, then anything talking about specific days or people is too much detail to be useful. By the time you are looking at a year, then the plan is more of a strategy, and you are better placed to think about a focus of effort and the outcomes you are chasing, rather than the specific things and order they will be done.
Once you’ve built a plan, get ready to rip it up. Things change, and the only thing that’s uncertain is how quickly they will change. If you stick dogmatically to the plan, you’ll quickly find yourself chasing dates that don’t make sense, or pushing for features that are no longer needed.
The most painful failed projects are those that treat the initial plan as a rigid structure, rather than a guide towards a potential future.
Still, keep cycling through the planning process. Take in what you’ve learnt, what’s been completed and consider what’s changed. This means you are not starting from scratch each time, but course correcting with more information.
Iterating is key, especially in a fast moving environment. If you find planning a chore, then doing it little and often should cure this feeling. If you plan by six-month cycles, try cutting it to three and I’m sure you’ll get a better outcome.
Create your plan, throw it away when it’s no longer helping!