There's a story idea I've been playing with for years now but I feel like I need to do two time skips one after the other which may be weird for readers. I have a prologue where she talks to her father who's in prison (death row) for the murder of her mother, which he denies commiting. I feel this scene is important as it explains a lot of her situation and I'm a sucker for dramatic scenes. The next chapter takes place a year and a half later. Trying to simplify things; she meets these people who reveal a whole new world to her and ask her to join their group. I want to jump forward two years after that instead of spending the time on her learning and training as I think that might be kind of boring. Would it be better to have her meeting the guys in a flashback? I've been holding off on this story for years since I just can't think of how it would be best to handle these two time skips.
Would it be better to have her meeting the guys in a flashback?
Yes. Or if it's possible, mention the meeting in at most two or three sentences.
All stories revolve around events in a character's life. And while a character may have experienced many life-shaping firsts - the first meeting with a vampire, the first kiss, the first Tae-Kwon-Do lesson - not all are interesting to us as a reader. No matter how exciting the first adventure of a rookie vampire hunter is, if the story as a whole revolves around the same hunter (but older and more experienced) infiltrating a vampire clan to take down their big bad, we can assume the first adventure happened and move on.
Does this sound wrong? Well, as human beings, we subconsciously cut out a lot of our 'firsts' all the time. A person pushing fifty interviewing for a job is unlikely to mention that one summer in '86 when he went door-to-door selling vacuum cleaners. An Olympic swimmer appearing on a talk show isn't going to talk about the first silver tri-state championship medal she won. Unless, of course, these events are immediately important to the present. For example, if the company the middle-aged man interviews at makes the same vacuum cleaners he used to sell back in the day, or if the swimmer's coach who helped her win the Olympic medal is the father of the girl she lost the gold medal to in the tri-state championship.
The same should go for your characters.
Normally I don't like giving this advice with regards books (and, indeed, would tend to give quite the opposite), but in this case I feel it's warranted:
Think of it like a TV show for a moment.
This can be done in 2 ways: Either think of it as a single episode, where your prologue is the brief "stinger" before the title sequence starts (which represents your timeskip), or think of it as an entire series, where the early episodes are setting the scene and worldbuilding. If you have a timeskip like this, it would usually be at the end of the first episode (or, perhaps, a two-parter), and then get to the main story. In this style, having multiple timeskips won't work, and will leave the story feeling disjointed.
However, that brings us to the other way in which a TV series can build the world and expectations: a series of self-contained episodes which prime us on the world in which the story is based, before throwing us into the first lengthy 'arc'. This is, perhaps, something to play with: Instead of having 2 timeskips, have several, and make the skip shorter (both in the scene itself, and the amount of time skipped) each time - show snippets of the training, glimpses which also serve to teach the reader what the character is learning, introduce us to the characters, giving us chances to see "the rookie" failing through inexperience (at first), and gradually overcoming those mistakes. Rather than a montage of lots of very brief snapshots, you give fewer, longer scenes.
Don't overdo it though - this should probably all add up to the first couple of chapters, ending on an indication along the lines of "and that brings us up to today", letting your reader know that things are about to settle in for the long-haul.
- Start with the Prison scene (T-18 months, start of story)
- Push onward to her introduction to the hidden world (T±0, ends the first chapter)
- Add an event about 9 months into her training - perhaps a test or dummy mission? (T+9 months, starts the second chapter)
- Another 6 months, another event. Make it mirror the first in some way, to show the character's development. Perhaps she's now the one mentoring a fresh-face? (T+15 months)
- 3 more months, time for a 'graduation' of some sort. She's still a rookie, but now at least she's competent in the basics, and ready to properly participate in the hidden world (T+18 months)
- For the next 6 months, consider a few (very few) callbacks to the earlier events, and allusions to other events that have happened in the time we skipped, which might be referenced in flashbacks later on - a paragraph - or less - for each, to give a flavour of her new life.
- Chapter 3 starts the main story (T+24 months)
An important thing to note here - you need to make the scenes short, and (ideally) you need to make subsequent scenes even shorter. This then means that Chapter 3, drawing the story out at length, will more obviously be the start of the "proper" story. It's a bit like a circling a drain: every loop brings you slightly closer to falling down the plughole, and every loop takes less time to complete.