It never is! And, many times, it's best if you can think even farther ahead & have a few plans going at once.
I would also recommend sharing those travel plans here from time to time as it can help to write things out & read over them. You might also be able to get good advice from someone who sees a better way to do something or knows that something won't work as you intended!
So, here are mine, updated.
2019
May: Versailles/DL Paris/WDW - Flights were booked before I started in this hobby but our hotel in Versailles was paid for almost entirely with the Aspire... will elaborate at some point in case it can help someone. Reading "how I did it" posts from others definitely helped me a lot.
August: London - Got the flights with points at 11 months out. My first flight booked with points I earned here! But, we but did not book a chain hotel for various reasons (location & history, nothing to do with property quality or anything like that)
September: Kyoto - I have a conference here & the museum is paying for the hotel so not really relevant. We were going to go in March but decided to tack some leisure time onto the conference instead since I'd be there anyway. I don't usually count domestic trips in my plans but this is a "bigger" one so I decided to make sure I have enough time blocked for it.
October: Maldives (honeymoon) - Wedding gift from parents but the Aspire is ready for the resort charges. Originally we wanted to go touring around South Korea & we are really into Korean food/cooking at the moment but, well... honeymoon. Maldives. Must-do
2020
January: Using our winter break to go to South Korea now (& you should see my restaurant list) - using either Hyatt or Bonkyvonk points. Probably Hyatt bc I can pair points with the free anniversary night on the CC as Grand Hyatt Seoul is only Category 4!
April/Golden Week: Disneyland (CA) - Hoping to rent points at VGC from a kind owner I found on the boards. Already paid a partial deposit for that & we will see what happens at the end of the month. Flights will be with points and I think I have those squared away!
July-August: OLYMPICS!!! I'm not going anywhere, I'm just excited. (Well... hopefully we will see some cool events. We had better hit that lottery)
October: Vienna/Prague/Budapest - I'm currently working on the "point plan" for this one & it looks like we will be staying at IHG properties. We wanted the
ABD Danube Oktoberfest but timing didn't work out & we wanted to change the itinerary a little bit.
2021
Unknown but it will likely be somewhere AA flies since I'm on the train & packing away points already
- contenders include Madrid & Dubrovnik. Copenhagen is also a possibility but not via AA. And, I think we will do a WDW/short
Disney cruise combo in the fall or winter. I'll be in the second year of my PhD program so not sure how much time I will want to take off then but I will definitely need a break at some point. I won't be booking anything far ahead of time, though, so this could be a lean travel year.
2022
March-May: ABD Egypt (this is when we think we will feel comfortable going but we will need to decide for sure at least one year in advance) - I am going to start working on these flights as a "just in case" as soon as I have the October 2020 trip squared away, since I need to be booking those flights in about 4-5 months. I try to collect Disney GC year-round but for this trip, a CIC might be a good idea. I'm thinking about going for CIP #2 next month & PCing CIP #1 to a CIC.
So, at the moment, I am planning 3 years out for multiple trips at once. I quickly learned that spreadsheets are your friends. I think it's also important not to put all of your eggs in one basket when it comes to loyalty programs. If you have a few programs to choose from, you can rotate the program you use & give yourself time to build up a stash again after each trip you take.
For airlines, I work with JAL, AA, Delta, JetBlue, United. (JAL is AA's partner & keeping points with both is not necessary for anyone who doesn't do Japanese domestic flights. The reason to do it then is because JAL blocks AA & other overseas partner awards out of J/F on domestic flights. You can upgrade for a fee, but I don't want to chance not getting the upgrade when I really want it. I don't want to pay the fee, either.)
For hotels, I have Hilton, Hyatt, IHG, Marriott. I use Hilton most because the Aspire is amazingly lucrative in terms of picking up points. Hyatt is a better brand overall, though. (IMO)
Thanks to everyone here I am always refining my strategies, picking up new ones, etc. I love this thread
You can move them to another card
Yay Baby steps.
and Congratulations on the wedding...I’m assuming that’s before the honeymoon 
