Reddit reviews Build a Business, Not a Job!

I realized a few years into my business that:
-I was not able to grow the business because it seemed I was always dealing with emergencies.
-I was not able to fix things right first time because there was another emergency
-I was spending lots of my time doing entry-level tasks
-I was getting older and my marriage was suffering because I was doing 100% of everything in the business.
-I was not performing preventative maintenance because I was swamped with "real work" to do.

I was 40 - still crawling around under desks, still doing 100% of the work, on call 24/7, not able to go after better business and not expanding margin. I was EXACTLY what I swore I'd never become.

Here's what I did:

I started by documenting and defining several easy-to-replicate procedures - software installation/update, new PC setup, disk usage clearing, backup troubleshooting, You should have ticketing, admin, and billing systems that work reasonably well. It can help to track your time accurately in a PSA tool so you have some idea how much time these tasks take.

I hired a good, trustworthy local kid with interest but no experience in IT. Started him part time "we'll try this for 30 days and see if it's a good fit - either of us can walk away with no hard feelings if it's not working out" - on some CompTIA training videos and working through the documentation I had made up. At first he was doing a lot of software installs, new PC setup, and very basic troubleshooting. Kind of like a doctor/resident relationship, I would explain my process and talk through every step I was taking and why...and I'd ask him to talk through his through process when fixing issues and guide him to the way I'd do it.

I also grabbed many of Karl Palachuk's SOP guides as a foundation, and the Best IT Service Delivery Book Ever by Simpson for him to go through.

He picked it up very quickly, and started spending some time fixing our automation and integrations - making us both far more effective. He started working with our backup vendor on fixing backup alerts, then patch management, etc.

A couple years later, he's had a couple raises, we're looking at hiring another 1-2 techs this year and an office admin. Cash flow is better, I've been able to land bigger clients than I could as a Single Point of Failure consultant.
Took a vacation last year for the first time in forever. The business continued to operate.

It hasn't been painless, but it's been pretty smooth and a great opportunity for both of us - I get part of my life back, he now has a career doing work he enjoys, and I have time for some of the higher-level work, like security architecture discussions with our bigger clients, and determining our path for more security consulting work.

What would I do differently?
I would have started sooner. I would have hired this guy back when I was working with Continuum and taught him to manage our interactions with their NOC. I would have had more processes documented and emphasized his role in maintaining and expanding those docs.

I did try working with a couple outsourced helpdesks but my clients wanted me or someone directly under my supervision - the outsourced helpdesks had too many exceptions and limitations for us to go forward.

I highly recommend David Finkel's "Build a Business, Not a Job"
https://www.amazon.com/Build-Business-Not-David-Finkel/dp/1450709842

and Chris Ducker's "Virtual Freedom: How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business" - most of his concepts also work with an outsourced NOC, SOC, or helpdesk.
https://www.amazon.com/Virtual-Freedom-Become-Productive-Business/dp/1939529743/ref=sr_1_5_twi_pap_2?s=books&ie=UTF8&qid=1519146561&sr=1-5&keywords=virtual+assistant