When you make a mistake and it costs you, the worst thing that you can do, in my opinion, is to fail to learn from it. If you can learn from it, and even help others learn, the cost can become well worth it.

This week I made such a mistake, and it cost me a bit of money, and a LOT of time to clean up. And while the end result is not perfect, it has some added benefits that make up for its shortcomings.

This week I will try to give you a quick “Reader’s Digest” version of the events, and next week I will cover the lessons learned.

I have been working with a Hotmail account since before Microsoft bought them, literally in the last century.

Nowadays you can use their Outlook service with any email address using an “alias”, and I wanted to make my sl@stevelegler.com address the primary one, but I went one click too far, and accidentally deleted my old Hotmail address.

“Ooops! I better put it back”. But it was not possible to do so online. Aaaargh. After a few hours on Monday evening, I gave up and went to bed, figuring I would try to call and speak to someone the next morning.

I could send emails out, but I couldn’t receive any. A few years ago, this would not have bothered me, because when you run a family office, you usually don’t want to be found. But now, as a family business advisor, building a client list, this was a problem.

At about 4 AM, I woke up and could not get back to sleep. Was it because I was “off the grid”? Or was it because I was trying to figure out how I was gonna get back on the grid?

On their customer support website, it is nearly impossible to find a phone number, because it costs them a lot of money to help you that way. They prefer to minimize those interactions, but I was hell bent on calling someone, because I was hoping that they could revive my old email address, and that was the simplest solution.

So I googled “hotmail support phone number” and just like that, I came upon an answer with a toll-free number. I called, and “Jessica” told me this was a “paid support” line.

Now I had a live person, and I just “knew” that my problem only required a quick fix, so how much could that cost, I wondered. But I had that live person and did not want to let go, so I said OK.

Half an hour later, she was finally at the point where she understood my problem almost as well as I did. Another 20 minutes or so later, her tech friend, to whom I could hear her speaking in another language, had supplied me with a new hotmail address, which I could have done on my own, had I concluded that this was my best choice.

Oh well, we are almost done, so I let them finish up. Another 10 minutes with “Harry” to give him my Visa number to cover the $149.99 to pay their company, not Microsoft, but some randomname-noname.com service company.

I felt like I had been had, but at least I had something workable, and they did spend time helping me, and I had agreed to pay.

But my fun was just beginning, as I now had a new Hotmail account that could receive and send emails. However, my other account, where I had all my contacts and dozens of folders of saved emails, could only send emails.

I still needed to somehow “fuse” them together.

So do I call them back, or try another solution?

Next week: How Microsoft saved the day, and how I learned that you don’t need to actually speak to someone to get things done.