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Baxter State Park, ME<\/p><\/div>\n
The Small Business IT Questions Nobody Asks Out Loud<\/strong><\/h2>\nIt was somewhere in the middle of one of those games that the questions started. Someone asked me about setting up a home network, and then another question followed, and then another. Backups. Wifi. Whether a particular password habit was actually a problem. None of it was complicated by the standards of my day job, but every question was genuine, and every person asking it was sharp, capable, and running a business or a household competently in every other respect. They just did not have anyone to ask.<\/p>\n
None of this is unique to one mountain shelter. A recent analysis of the small business technology gap<\/a> found that most owners are not short on ambition. They are short on access to the kind of expertise that closes the gap between what they own and what they actually understand about it.<\/p>\n![\"\"](\"https:\/\/cmitsolutions.com\/wilmington-nc-1168\/wp-content\/uploads\/sites\/158\/2026\/08\/20260806_TheRainStoppedTheHike-Leanto-300x226.jpg\")
Chimney Pond Shelter<\/p><\/div>\n
The next morning the rain finally broke, though the wind never really did, and we made the climb to the summit anyway. I wore a CMIT shirt under my jacket, not because anyone up there would notice, but to remind myself of what other CMIT owners around the country were building while I worked my way up that mountain. Katahdin is not an easy climb, and reaching the summit at sixty one felt like its own kind of greatness. Standing up there, I kept thinking back to the shelter the night before, about how much of what I do for a living gets explained to strangers on a mountain and how little of it gets asked by the people it would actually help.<\/p>\n
Twenty Issues of Managed IT Services Questions, and Counting<\/strong><\/h2>\nTwenty issues in, I have covered phishing and business email compromise, backup and redundancy, off-boarding, legacy hardware, business continuity, AI governance, vendor contracts, and the mechanics of passkeys and multi-factor authentication<\/a>. Somewhere along the way, I started assuming I knew what business owners and office managers actually wanted to know. That night in the shelter proved otherwise.<\/p>\nWhat Small Business IT Questions Are You Still Sitting On?<\/strong><\/h2>\nSo I am asking directly. What is the question about your network, your backups, your security, your servers, or your computers that you have been meaning to ask someone but have not gotten around to? It does not need to be sophisticated. The best question I got in that shelter was one of the simplest, and it told me more about what people actually worry about than the last several issues combined.<\/p>\n
Reply to this newsletter, or send me a message directly. I will build a future issue, maybe more than one, around whatever comes back.<\/p>\n
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The Gang<\/p><\/div>\n
Until next time, keep IT simple.<\/p>\n
Dave<\/p>\n
Chimney Pond Shelter<\/p><\/div>\n
The next morning the rain finally broke, though the wind never really did, and we made the climb to the summit anyway. I wore a CMIT shirt under my jacket, not because anyone up there would notice, but to remind myself of what other CMIT owners around the country were building while I worked my way up that mountain. Katahdin is not an easy climb, and reaching the summit at sixty one felt like its own kind of greatness. Standing up there, I kept thinking back to the shelter the night before, about how much of what I do for a living gets explained to strangers on a mountain and how little of it gets asked by the people it would actually help.<\/p>\n
Twenty Issues of Managed IT Services Questions, and Counting<\/strong><\/h2>\nTwenty issues in, I have covered phishing and business email compromise, backup and redundancy, off-boarding, legacy hardware, business continuity, AI governance, vendor contracts, and the mechanics of passkeys and multi-factor authentication<\/a>. Somewhere along the way, I started assuming I knew what business owners and office managers actually wanted to know. That night in the shelter proved otherwise.<\/p>\nWhat Small Business IT Questions Are You Still Sitting On?<\/strong><\/h2>\nSo I am asking directly. What is the question about your network, your backups, your security, your servers, or your computers that you have been meaning to ask someone but have not gotten around to? It does not need to be sophisticated. The best question I got in that shelter was one of the simplest, and it told me more about what people actually worry about than the last several issues combined.<\/p>\n
Reply to this newsletter, or send me a message directly. I will build a future issue, maybe more than one, around whatever comes back.<\/p>\n
The Gang<\/p><\/div>\n
Until next time, keep IT simple.<\/p>\n
Dave<\/p>\n
What Small Business IT Questions Are You Still Sitting On?<\/strong><\/h2>\nSo I am asking directly. What is the question about your network, your backups, your security, your servers, or your computers that you have been meaning to ask someone but have not gotten around to? It does not need to be sophisticated. The best question I got in that shelter was one of the simplest, and it told me more about what people actually worry about than the last several issues combined.<\/p>\n
Reply to this newsletter, or send me a message directly. I will build a future issue, maybe more than one, around whatever comes back.<\/p>\n
The Gang<\/p><\/div>\n
Until next time, keep IT simple.<\/p>\n
Dave<\/p>\n
The Gang<\/p><\/div>\n
Until next time, keep IT simple.<\/p>\n
Dave<\/p>\n