It depends on the circumstances and how you want to prioritize things. Generally I'll take on the 5 easiest tasks across all my 'active' projects.
I feel that as engineers we generally react negatively to the idea of bike-shedding or "building cathedrals" but the reality is that there is always a bike-shed. The question we should be asking is not should we deliberate over the design of the project, but rather to what degree does this project (and consequently the business in paid situations) benefit from deliberation.
In the case of personal projects, I am far more concerned with the process then the outcome and will allow myself to indulge in bike-shedding maximally.
Otherwise I find so much time is wasted on tiny details that don't matter, and the overall picture still fails to emerge (aka a definitional bike-shedding session).