Several things worked for me:

• At the beginning of my work day, I have to login to Jira and view my tickets. I visualize myself doing that, and then creating my to-do list for the day from org-mode. It brings forward unfinished tasks from the previous day, so there’s a process or workflow: log in, open Jira, start new to-do file, compare file with Jira, update either Jira or the to-do file or both. I guess it works because it’s not just the to-do list, it’s several other things happening at the same time. So you’re not “updating a to-do list” you’re “starting work for the day”. Reframing the action can sometimes help.
• Gaming it. If I get asked for a status update, I get “points” if I have the information I was asked for already in either Jira or my to-do file. That’s enough for a little dopamine reward because I was prepared. This follows a thread in my life where I really value being prepared ahead of time. Like anticipating cars ahead of me and braking before they do. How much of the future can I predict and adapt to with the minimum effort?
• Visualizing. This is a bit woo-adjacent. I picture myself sitting down at my desk and remembering my to-do list. It works for me, but most people look at me like I’m a Sasquatch or something! Visualize doing something the next time you sit at a particular desk, or when you enter the office. I hope it works for others too!

If I think of more I’ll add it in other comments. I really hope you can find some tricks that work for you!