Making and running good sidequests is a bit of an art. They take
emphasis off the main story. If the adventure your players are going on
is time critical, a side-quest doesn't make much narrative sense in
most cases. However, they provide an opportunity to try new things
and mix the situation up. The trouble is fitting them effectively into
a session. With that in mind, I'll be sharing my thoughts on the matter in the hope that it helps someone out there.
Do Your Players Even Like Them?
Sidequests are a tool. Some groups might not want any at all.
They'd prefer a narrative tight story and want to go towards its end.
However, I've also seen situations where people prefer to jump around
more often. Each session was mostly self-contained and allowed for a
wide variety of different types of quests at the expense of a greater
narrative. This is quite similar to the different styles of television series.
A Break
Sometimes players want to take a small break from the main quest and
do something new for a little bit. They don't want to abandon the
main story but just want something different. Often it is something
lighter and more relaxing. I most often see this kind of thing in
horror heavy and/or high casualty games. These two often go hand in
hand. It can also be a chance for the players to see how far they've
come. An adventure that would have killed them earlier is now
something they can breeze through in their spare time.
Time Gap
There are some adventures where there may be a more relaxing period.
Things take time even in a fictitious world. If your players found an
item and it'll take time for learned people to research it, you have
options. You could skip past all of the uneventful things and go
right to the point the story starts up again. However, you could also
use the chance to mix things up with a sidequest. Some players
prefer to have an interesting though less important adventure in that
time instead of skipping past it by using the downtime rules or hand-waving it away. The
rewards for this kind of thing are better than the downtime rules in
Dungeons & Dragons 5th edition as well. Another way is to have a main story that is composed of multiple stories that intersect. In such a case, it's not just a sidequest but an important task related to the story that needs to be dealt with sooner or later.
Part of the Design
Having multiple quests that on the surface have nothing to do with
the main goal could be part of the design of the adventure. A
classic example I can think of is needing to raise money for some
purpose. In this case, the results of the quest influence the main
story but the story of the sidequest doesn't relate beyond the
monetary factor. Trying to find items or equipment is similar but
material instead of monetary.
If the basis of the campaign isn't a story but instead the adventures
of a group within a particular faction that gets different jobs, the
campaign is kind of a collection of sidequests already. You might
have the equivalent of a season finale or a special, just like a
television show might, where there is a larger story that takes more
time than your typical story. Multiple ones might be related and become the biggest story of
your campaign, but you'll still have other more disconnected adventures.
How Related?
There are degrees to how closely related a sidequest is to the
events of the main story. It can be completely or nearly completely
disconnected. Helping someone you ran into on the streets is one such
example. Sure, maybe the party has some connections with some temple
of a good aligned god that helps people who need it, but that's as
closely related as things are. Another situation is where the party
will need to help a faction that one or more members of the party
belong to and are aiding the party in their goal. In such a case
helping the faction is also helping themselves, but the connection to
the story isn't as clear. It is still present though, since there could be consequences to not helping.
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