This is what I do, with the exception that I use google maps to create my route after studying the life map. I think it’s a good brain game too to memorize routes every day.
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I kind of turn that on its/my head—sitting down with the map and cup of coffee to attempt to design the most efficient route like I’m solving a sudoku puzzle or playing a game of chess. I’ve spent some serious, serious time working this out (sometimes, even longer than it takes to run the dang thing)—but I enjoy it. Then, my reward for designing such a route is being able to run it with my brain turned off—just following whatever instructions the Komoot turn-by-turn navigational voice pipes into my Shokz headphones. 
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This is much closer to what I do: study LifeMap, make a rough plan, drive there and “wing it”. I really admire all of you who create routes and copy them to devices–that seems like the right way to go about this. I did find early on that I often change my planned route based on what I see when I get there. As a walker I probably have more time to do that on-the-fly.
Not sure if anyone mentioned it but I try hard to pick a route that circles back around to my starting place so that I minimize having to rewalk a long street. Just a series of loops every day!
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I look at Wandrer’s* big map on one screen to easily identify new roads and paths to walk and make 3-4 mile paths in Google Earth Pro on another screen; I currently have ~250 routes in Google Earth Pro. I make my routes so they loop back to my starting point. The night before I review the path on Google Earth Pro and memorize it. I pull out my phone a lot while walking to make sure I’m following my route.
This process has worked for me so far, but I’ve been walking older urban/suburban neighborhoods around where I live, which are mostly on a grid plan. In a few months I’ll start walking a suburban city with lots of cul-de-sacs, windy streets, and no sidewalks, & I’m not looking forward to those streets.
I track my activities with my Fitbit (or Strava app when I can’t connect to GPS on Fitbit), which sends it to Strava, which sends it to CityStrides & Wandrer.
*I’m not a CityStrides subscriber, hence I don’t have access to the route builder.
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I’ve found that the Footpath app is a great alternative. It’s what I use simply because I was using it a year or two before I ever found out about CS.
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I often will build a preliminary route in CityStrides. However I find that it’s hard to transcribe that route because the route builder in CityStrides covers all the street names so it’s too hard to write them down.
Then I’ll go over to dynamicWatch’s Route Planner and build the route there as it offsets the street names from the road itself. Then I write turn by turn directions on a post it note that I have folded in half, so I can get up to 4 pages of turns. I also carry my phone with me in a running vest, just in case I misinterpret my minimalist directions and need to check on google maps or City Strides where I am.
I’ve tried printing maps and sending turn by turn directions to my Garmin watch, but I found the map too bulky and the watch directions too annoying.
Try this again - I recently updated the map style to push the street names off a little bit. It helped me see the street name while creating/viewing routes.
You may want to try exporting route files as a GPX Route file to an audio turn-by-turn navigation app that’s connected to some headphones—preferably some open-ear headphones like Skokz bone conducting headphones so you can be aware of your surroundings. I started doing this when taking turn cues, paper maps, or watch navigation proved to be cumbersome. I export my GPX Route files to an app called Komoot for turn-by-turn directions pumped into Shokz, so I rarely have to look at my route map unless there’ something unexpected. If you do this, I would recommend turning off the “Automatic Replanning” setting so it doesn’t recalibrate your route if it thinks you’ve missed a turn.
Whatever change was made has very much improved the readability of the map using route builder. I don’t need to use an external tool any more to build my route, I can do everything directly in CityStrides.
This is how I did all of Seattle. I keep my LifeMap up on my phone (vintage 2016 iPhone SE) while running and periodically check the map to make sure I’m hitting all the un-run streets. If a section of the map looks tricky, I’ll use Node Hunter mid-run to make sure there aren’t any sneaky nodes in unexpected places. I just run till I’m out of time or mileage for the day, trying to loosely plan to the point where I’m not replicating already-run streets as I return to my starting point.
When I’m trying to do speedwork during a run on new streets, I try to pick sections where I can run without making very many turns for the duration of the speed intervals, since it’s really hard to run interval pace and look at your map simultaneously, lol.
I track my runs using Strava on the same phone. No wrist device, no advance planning, total setup (old cheap iphone + free Strava + CityStrides supporter) is cheap enough that I can afford to stop for coffee on the way home 
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My methods have evolved over the years. With better tech and features from James things have gotten much easier.
I use the route builder in CS to build numerous routes. New roads are all 15min+ drive from me now so its nice having routes built from different areas in case I find myself that direction. I export my routes and save them in Strava which will sync directly to my Garmin Epix (If you dont have strava you could import them into Garmin Connect directly instead). I will also sometimes confirm looking at a Strava heatmap of my route area if there are any discrepancies or interesting trails.
From there its pretty simple. I start up my Garmin, load the route and glance at my watch for whenever I have to turn. If I get off route you can always stop the route and restart it and it will pickup from wherever you are. When Garmin created watches with maps it made things so much easier than before when I was always pulling out my phone.
When you start spending more time just getting to new roads the idea of “winging” it isnt very attractive. If I drive 20 min each was to get new roads I want to make sure I’m efficient as possible and not miss things.
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I’ve spent many years orienteering, so holding a paper map is 2nd nature. I print out a map of a decent size area and then use citystrides routebuilder to draw routes that I transfer to the paper map in highlighter as I am going to run them. I use different color highlighters and aim to have 4 or 5 runs on each map before that area is covered. It keeps me from having to keep pulling out my phone. I use plastic page sleeves if it’s rainy.
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This is why a watch with maps that you can import routes to is so great! A literal glance will tell you everything you need to know.
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I use CS to figure out where to run and ridewithgps to plan out the route. I used to force myself to memorize my routes and do it all from memory, even forcing myself to leave the phone in the car. I did that for my town, but now that I have moved on to others, I will try to memorize 1-2 miles at a time and break out the phone after each section to try to memorize the next.
The memorizing did lead to some missed streets, getting lost a bit, etc. But, always fun
I also tend to do large loops and end up going through areas many times to finish streets, so re-running streets doesn’t bother me!
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Here’s what I used this morning.
I work out the route using route builder, print out (reusing the blank side of any other print outs) and then mark the turns I need to make. I’m in a constant plan, run, review on CityStrides, and plan again cycle.
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Here are a few examples of the “street cheat sheets” that I take on my runs. I’ve used this patented text-based method over the past 4(?) years and nearly 6000 streets. PS: I carry a phone as backup in case I need to get a better visual on an area, reorient myself, find the shortest route back to the car, etc.
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Love to see a thumb compass outside an orienteering meet!
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