Doing a 1 year strategy before a 5 year strategy is harder than the reverse.

(This is only true for post-PMF companies)

A 1-year strategy needs to wrestle with quite a lot of rich detail about specifics.

A 5-year strategy is allowed to (and should!) elide a lot of details to focus on the core narrative arcs.

If you do a 1-year before a 5-year, you need to somehow retcon all of the messy real stuff into something that sounds like it's intentional, and it has to stand on its own.

If you do a 5-year strategy first, and you do it rigorously, then you can focus on the most important throughlines which is much easier to rationalize.

The future obscures lots of details, so you shouldn't have unnecessary details or precision in your very long-term strategy.

A lot of day-to-day trade offs simply evaporate over sufficiently long time horizons.

Then, when you do the 1-year strategy, you don't have to make it make sense on its own.

You can simply point at the 5-year strategy, which does make sense, and show "this is our incremental step from where we are today towards where we're going".

Many orders of magnitude easier!