There’s a lot of value in automating things in your life — making things automatic or easy to keep happening. Ramit Sethi has a great concept of automating your finances, where you design your budget and have the fundamentals of your personal finances automatically happen (e.g. You build your budget, and then you have your rent/mortgage, your credit card statements, your savings, etc. all auto-deducted from your checking account). Scott Adams has a great blog post about how you should focus on building systems, and not goals, in order to create sustainable routines.
Sometimes people need to focus on automating things, making them easier/more automatic, but sometimes people over-automate — they set up their system and they rarely check on how things are progressing. There’s a balance here — John Bogle (founder of Vanguard) has a great quote “Don’t peek”, meaning you shouldn’t obsessively check your investment accounts, as that leads to you making poor, emotion decisions, but people can over-automate things, leaving them on auto-pilot.
For example, with your personal finances, it’s good to get things automated (I love Ramit’s recommendation), but I also carve out a few minutes each month (with a reminder from a recurring calendar invite so I don’t forget) to check on my accounts to make sure there’s no fraudulent transactions, no balances are significant ‘off’ from where they should be, etc. When you’re managing big, complex initiatives, there’s again this balance of not asking for so many In Progress Review (IPR) check-in/sync-up meetings that people don’t get any work done, because they’re always updating the status slides for you; but you also don’t want to so rarely check in that your team/colleagues are spinning their wheels or they’ve veered far from the vision or haven’t gotten the feedback they need to go in the right direction. This is why the concept recurring meetings like sprint planning, sprint reviews, and sprint retrospectives are so powerful in Agile Scrum — they force teams to stop, step back, and examine and validate what they’ve accomplished and where they’re heading.
Find that sweet spot in the systems of your life, both personal and work!