Why you should set clear limits on free advice

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I’m in a dispute with my accountant. We both feel wronged. And it’s all because of the way they treated free advice. My accountant is part of a mid-sized local accounting firm. He prepares my taxes, which are complex, and also advises me on tax strategy. With a few exceptions, I’ve found the tax prep … Continued

Self-employed and moving to a new state? Good luck with your medical insurance.

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The state lines in the US might as well be national borders if you’re trying to change your health insurance. I recently moved from Massachusetts to Maine, a total distance of 100 miles. I am self-employed and was paying the usual insane amount for my own health insurance in Massachusetts, including coverage for my spouse … Continued

The glorious freedom of starting over

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Sometimes losing everything is an opportunity. Forty years ago, in late December, I broke up with my wife. After years of unhappiness, it had become clear that the we didn’t belong together. She requested that I leave the apartment the next morning. I had a small suitcase full of clothes and nothing else. I called … Continued

Why I’m moving to Portland, Maine

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Yesterday my wife and I bought a house in Portland, Maine. We’ll be moving there soon. I thought you might be interested in how we chose Portland, after 40 years of living near Boston. Why New England? I moved to New England — Cambridge, Massachusetts — in 1979 at age 20 and I’ve been here … Continued

Buying a house? Where’s your imagination?

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My wife and I are preparing the house we’re selling for buyers and an open house in a month or so. We fell in love with the house almost immediately. It’s on a beautiful piece of ground in a nice part of our town. It’s big but 100 years old, with personality. It has four … Continued

The blogging streak

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Every once in a while I begin to wonder if I am crazy. Why bother blogging here every week day? Since this blog began in March of 2015, I have posted on it every weekday. In six-plus years, that has added up to 1,700 posts and 1.5 million total words. These posts have seen 3.5 … Continued

How I got (moderately) rich by investing in myself and my family

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Fair warning: this post is all about decisions I made and why I made them. If you don’t want to hear about that, skip it. I just agreed to purchase the home of my wife’s and my dreams in Portland, Maine. And pretty soon we will move there and own it, free and clear. This … Continued

Fastly crippled much of the Web, then issued the perfect apology

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Fastly runs a CDN — a content delivery network that makes delivery of Web pages faster globally. Due to a bug, major Fastly clients including Amazon, Reddit, Spotify, eBay, and Pinterest were unable to serve pages to customers for about an hour Tuesday. Fastly apologized — and its apology is a clinic in how to … Continued