Thank you! It’s taken a lot of time and work for him to find something. Frankly, I think he’s a little overcommitted at college - he’s a double major in Mechanical and Civil Engineering, plays a club sport that is both a fall and spring sport, has a position that takes a lot of time in the fraternity and, as mentioned above, he works slowly due to the LDs. But he likes to be busy and he’s found that as long as he schedules, he can make it work. The frustration for him is that now that he is used to being scheduled, it’s hard for him when other people are more haphazard. It drives him bonkers that he can’t get his friends to commit ahead of time to a specific day for dinner or going out or whatever. So we’re working on making sure there’s enough flexibility in there that he can have fun too. I worry that he works too much (this is the opposite of my younger son, who never met an assignment he couldn’t put off…)
I like the idea of a monitor with the calendar constantly open. As many people have pointed out a smart board, which might be what I am envisioning, is expensive. But maybe if there was a way to just have a digital version of a calendar with his assignments and stuff open on the desk all the time, that could work. I say digital because my teen is not likely to sit down with a marker and fill out a paper calendar or white board. Question, though, wouldn’t the monitor have to be hooked up to something with the calendar in it? Wouldn’t it have to be hooked up to a computer or something?
Yep, the monitor is hooked up to his computer. Maybe because he’s kind of a STEM dork, but he’s got multiple computing devices. At his desk is a big desktop that he built himself. It’s got the three monitor set up, all hooked up to the computer.
He’s also got a laptop and an iPad. His first two years no laptop, he only used the iPad and the desktop. The iPad can’t run some of his engineering programs, he basically just uses it for note taking I think. He brings the laptop with him if he knows he’s going to be working on homework or problem sets somewhere other than his apartment, so like if he’s going to be on campus for several hours, and it’s what he brings home over breaks so he doesn’t need to bring the whole big desktop home if he wants to be able to work on stuff. The desktop is by far the most powerful - it runs the engineering programs much faster and has a lot of gaming functionality, but it’s a pain if that’s ALL you have and you are going to study groups or something.
Anyway, you didn’t ask about all of that. If your kid is going to have a laptop and not a desktop, I’d suggest getting a second monitor regardless - I use the laptop screen and the second monitor for work, and it’s really helpful. I like to be able to see multiple documents at once to be able to research on one screen and type on the other or whatever. You can either plug the monitor in to the laptop directly, or get a little hub thing that can have monitors, laptop, mouse, keyboard (or dongles for wireless versions) attached. You can really add as many screens as you want, provided you find enough outlets to plug them in. So he could use a calendar function like my guy uses his Outlook calendar, or google calendar, or whatever. And just put it up on a monitor.
Interesting to read the various perspectives on this topic. I hope OP is able to help their child.
My wife is a techie, and one you would expect to use a digital planner, but she swears by the paper planners. From posts in this thread, I wonder if it is more common for females to prefer this.
I now use a digital personal calendar that I find useful. Initially I tried to plan everything, but it quickly became overwhelming. So now only big events or non-regular events make it into the calendar. Dental appointments, one or two of my favorite team’s games that I may attend (not their whole schedule), family visits, etc.
Trying to project how I would have used something like this in college… Homework assignments, group meetings, class schedule in the planner? No way. Project due date, semester breaks? Yes.
I never used a calendar for 45 years. That is not to say that anyone could/should do the same. I only say this to echo the sentiments others have posted to start small / simple.
I use Google Calendar and MS OneNote. They are free, they work on my existing devices, and work well across Mac / Windows platforms.
So there is this device called an IPad. Lol. You can do I think everything your wanting.
Your child is doing what is in here and it’s great for kids with ADHD. The strategies can be very similar.
https://altair.pw/pub/lib/How%20to%20Become%20a%20Straight-A%20Student.pdf
My daughter, now in graduate school uses paper, pen, colors. Just what works for her. She used to get black board paint. Paint her door to her room inside. And make like every reminder on there. She also had a paper planner that worked for her well.
The point is creating a system that he will stick to and following through with it. If the has something that works, that’s fantastic!
I do and think differently. The way I accomplish things and the way my wife does are totally different.
Just have a system that is logical to him.
I agree. My husband is a digital junkie. He actually has our computers connected so I am notified of his events, which I hate. I will stick with my Blue Sky paper planner. I’ve just been busy erasing stuff, in fact. Long live the pencil!!!
So did my son in engineering. Working on 3 devices at the same time lol.
After rereading your post. I am confused what the problem is? Sounds like he’s doing great actually unless I am missing something. He sounds rather organized.
I use my Google phone for everything and have access to the calendar for like everything. It works for me well. If I know I need to get something done but eh, just don’t want to, it goes on 3 days in a row. I will it go during that time. Lol.
I think just finding something that works is the hard part. A digital version of the book I posted that I know you know about is just talking those paper methods and using a phone or computer to accomplish.
Anyone remember the Palm Pilot? My husband used that for years, and synced it with my computer which I really didn’t need!
First digital calendar device I remember…
I’m not the one looking for help. 
I told the OP what my son does and then expanded on it when I was asked some questions.
My older boy - the one in college who does all this - is super organized. My younger boy, currently a HS senior, just doesn’t do the work. It’s not that he doesn’t know what’s due or isn’t organized about it. He just procrastinates forever and a day. It’s a different problem and not the issue of this thread.
The high school he attends probably uses a system like Canvas, and (nearly?) all colleges do as well. This is a blessing, as everything he needs to know—assignments, due dates, communications from teachers, syllabi, materials, etc…are all pre-filled for him in Canvas.
It is also a curse, because it means there is no need for teens to learn how to keep track of these things during high school, as it’s already done for them. 
There’s no need for them to write down their assignments in class, or to put test dates on calendars…it’s all filled out for them. Sigh.
So, speaking from experience, you won’t be able to get him to create and use a planner, when he doesn’t need one. What you CAN insist on, however, is that he starts keeping track of his own calendar. You’ll stop keeping track of his life, and transition him to keeping track of it (and then following up and informing you as needed). I strongly suggest using Google Calendar, as most places use that these days, and he will be able to add and share calendars easily.
Now, to help this transition with a resistant user, this is the part that you will need to jump into as well. You will need to have your own Google Calendar, so that he can share his calendar with you, and you can see that it’s being used, and you can “invite” him to events, and he can do the same with you.
And he needs to start making his own dentist, doctor, and all other appointments, and entering them in his calendar. He needs to enter his reoccurring events such as play or sports practice, or lessons or tutoring. He needs to put in games and performances, concerts, shows, birthday parties, school breaks…all of it.
When he makes plans with friends, put it on the calendar. A job? put it on the calendar.
When he wants you to do something with him, or you need to be present in some way, e.g. drive him, etc., or he wants to let you know about something like a dentist appointment, you need to reply: great - share a calendar invite with me and I’ll check.
In other words, you’ve got to reinforce with him that things go on his calendar. (And after you get his shared event, then you can put it on your paper one!)
He will also be receiving google calendar invites through high school and beyond. He’ll likely meet with college professors by booking time slots via google calendar, events will be listed on different calendars that he will access…he needs to build his skills with using it now, as he will need to use it in college.
Now, he won’t have it “out” on his desk all the time, but he can always have a tab open to his calendar in his browser, and he’ll always have it with him on his phone. He needs to get used to checking his calendar and using it until it becomes a habit. Plus he can also add “Tasks” to his Google Calendar which is very useful; everything is in one place.
My ADHD kid who’s in his second year of college needed a lot of pushing to use his calendar; it is hard when there isn’t a need to do it (because of Canvas), but over the years it’s taken hold. I still ask him to send me calendar invites when he wants something from me, rather than me writing it down myself. And he now uses multiple Google Calendars so he can see things in different colors, and show and hide different things like his sport club calendar, or his classes calendar, and just see his appointments.
Good luck!
These are good poimts. I am interested in knowing a bit more about the part about having the calendar out. Because I think even now in school teen has his stuff already populated by the school in Google classroom calendar. But I feel like he needs some kind of system where the Google Calendar is always visible. Sort of like a wall calendar where he can see what’s coming up in the future and not just check the Google classroom each day and figure out what to do the next day. You know what I mean? So the part you mentioned about having the browser open to Google Calendar I think should be a part of his organizational plan. And even though the school does do most of the work even now as far as putting things on the calendar, I feel like teen needs to have set, blocked scheduled time for studying and breaking up projects and things like that. He just got an iPad. It’s our first Apple device. We’re not part of the Apple ecosystem and are mostly Android/Wndows users. But I wanted him to have an opportunity to at least try it out and see if the features on it would be useful to him as far as creating an organizational plan and for potential note-taking in college. My main goal is for teen to figure out an effective organizational system prior to starting college but also have some part of that organizational system be visible to him daily without him logging into a program to check his upcoming events.
Also thank you all for your suggestions. I really appreciate those of you who took the time to respond.
He may want to start developing a habit of checking his calendar on set days.
For example - 1st of the month, review what the month looks like as a whole.
Sunday night - do a deeper dive for the week ahead.
Every morning at whatever o’clock - deepest dive for that day.
He can set up a digital calendar to remind him 5 minutes before he needs to check until he’s in the habit.
I totally agree. This is pretty much what I do as a paper planner.
This is true. But both of my kids used their planners to note when sections of longer term things needed to be completed.
I think that is important to have too. Breaking up big projects into smaller units so there is no last minute rush to get it done. Also, I feel teen needs to plan his study times which would be easier to do if he can see what blocks of time are available.
We have the Cal Newport book. Haven’t done a deep dive yet into the book but will. Thanks.
@NewtK, another app you/your kid might want to try out is “My Study Life - School Planner”
It’s specifically designed for students.
I talk to you good amount of college student’s. Many are using AI apps for lectures. They get approval. It’s for note taking. Many products can even test you on the lecture notes. They swear by it. I know some light like it but the students I talk with really like it. They can then hone down on the important parts for the test /knowledge. I am a auditory learner. I didn’t take notes really in Med school but I listened to the tapes later and then took notes. This is way better in my opinion… Just another tool in the toolbox