About a month ago, on ReadWriteWeb ran a link to a TED video about learning from failure. It spoke to me and I started thinking about some of my failures in my professional life over the past years. I have had more of them that I initially thought of, and while that was a little depressing, it was instructive to collect all of them in one place. So why not share them with you, dear reader? After all, I usually tell you about my insights. Here goes.

I have written three books, with two of them actually published. While you may think of that as a success, in reality neither of them made any real money. My last book came out the week before 9/11, and that was a dark period for so many things, including trying to sell any books. With each book that I wrote (the first one was never published), I learned more about that business. Now I know enough to skip finding a “real” publisher entirely, if I ever have another book in me. There is still a lot I need to learn about the self-publishing industry, but that seems like the way to go in the future.

One of the most important decisions about a book is its title, and typically new authors don’t have final say-so on their titles. I was working with an established author on my first published book (which is always a great idea anyway, because you have much to learn). But our proposed title didn’t grab the publisher’s attention, and we ended up with a real dog that didn’t do much for sales. Oh well.

How not to run a website. Over the years I have worked on the editorial content for more than a dozen different websites involving technology information. Some of them have done better than others. But one thing that I have learned is you need the right balance between content, sales, and page views. All three (and in the right proportions) are important: if one is lacking, your site is doomed. If you have more content than sales, you also aren’t going to get very far. Having too many chiefs or people that think they are in control and not enough worker bees is also a recipe for disaster. On one site, we had an experience imbalance: we had very experienced editors but very inexperienced sales people. That wasn’t good either.

Another way not to run a website is to have quirky analytics which are giving you poor visitor information. At one place, we had one guy who had built his own custom stats package to collect our page view numbers. Trouble is, no one actually believed these numbers, including some of the advertisers. Do yourself a favor and get in bed with Google Analytics or some other commercial product and understand what they are telling you.

Not having the right mix of authority and responsibility. Many of my jobs I started out with a lot of responsibility but not actual authority to get things done, hire the people that I needed, or be able to spend money on contractors or freelance help to fix things. Again, not a good sign. Coming into one job, I was told that I would have a certain budget only to find that each purchase required a near papal authorization. Authority and responsibility need to be in balance too.

One of my biggest success stories was starting up Network Computing magazine back in 1990. I made my boss show me his proposed budgets, and he wasn’t comfortable about doing it but I said that I wasn’t taking the job without seeing the actual numbers. I think he brought me into his office over the weekend and wouldn’t let me leave his sight while I looked over his spreadsheets. We went on to have one of the fastest growing magazines for the parent company, and many of the staffers whom I hired back then are still associated with the magazine (although in its online form now).

Some of my failures come from being part of volunteer organizations that suffer from a lack of quality leadership. It is easy to spot these organizations: the people at the top don’t do a good job of delegating tasks. Or they don’t know how to develop new recruits, because any good volunteer outfit demands a fresh supply periodically as the old hands burn out.

Every job has its natural rhythms and ups and downs. Part of being successful is in keeping in tune with what is going on in your organization, and as the song says, “Know when to hold ’em and when to fold ’em.” Sometimes I have stayed longer than I needed to with a particular job, or passed up opportunities because I still had unfinished business. Or been fired because of whatever the circumstances that made me and the organization incompatible.

As I said, I have had lots of success in my life, and I am grateful for that. But it doesn’t hurt to look back and review some of my failures too, and hopefully I can avoid repeating them in the future.