It's incredibly hard to let go of something you built from the ground up and hand it over to someone you trust enough to run it the exact same way you did.
The idea of hiring somebody to run the day to day operations of the business is financially sound.
Finding, incentivising, managing, monitoring and collaborating with that person/people is a separate set of challenges most solo/bootstrapped people do not possess the skills to undertake. Moreover, their business is their "baby" and letting somebody else take the reigns is emotionally difficult.
landing page does a decent job describing what we do. we're a general purpose analytics app tightly integrated with other SaaS apps.
I won't get into specifics on MRR, but we currently have thousands of users and hundreds paying
I never hired. I should have hired. I had alerts waking me at night dozens of times as well. I planned family trips around internet availability. I thought I was needed to solve any problem. That's why I never hired. I thought it would be too much effort to train someone.
Selling the business resolved all these issues at once. Hiring someone to take care of these things for you will allow you to have time to yourself and wind down. I trained my replacement. Turns out other people can do this job.
You don't have to start with the sale. You can start with delegating.
Whenever I consider entrepreneurship as an option for myself, it is always the customer-facing sales part which leaves me feeling like I would struggle.
You want to sell to a party who will run it as if it was their own product (or who will hire a capable team to expand it further). That is possible for a $400k ARR product, but much harder for a website doing say $50k through one-off sales.