Many people are afraid to run their own WordPress plugin and theme updates. That’s simply because they don’t take WordPress maintenance seriously. You don’t need to be an expert in WordPress to feel safe running updates. You do, however, need a plan and a commitment.
It’s true, sometimes things break when updates are installed
WordPress is a living thing. WordPress plugin and theme authors can not accountant for every possible combination of how you’ll use their products. However the alternative is also not a good idea. The longer you hold off running plugins and core updates the worse things get. As they say it’s not a matter of if something will happen, it’s a matter of when. The good news this these situations are rare and can be easily resolved with a simple plan.
Plan for the worse case
The worse case is you update your website and everything breaks. To detect those, use Jetpack Monitor which will send you an email if the website is down. I recommend having a web developer connected to Jetpack Monitor who can hop on the website and fix the problem should they receive a down notification.
Even in these worse case situations a website can typically be restored by examining the error logs or debug errors then deactivating/roll back the offending plugin. Just by having that as a plan is generally all you need to begin doing regular updates. I’ve also found people who have a plan very rarely need to act on that plan.
Commit to regular updates
Being proactive saves you time. The amount of times things go wrong during an update are very rare. The amount of times things go wrong by neglecting to do your WordPress updates, given enough time, is 100%.
Create a schedule to run your updates and stick to it. I use ManageWP and deploy WordPress core, plugin and theme updates at minimal weekly. I’d recommend sticking within the weekly or monthly schedule. If you can’t do it regularly then find someone who will :).