My biggest mistakes

In a series of posts, called readers choice, I write on whatever topics people submit.

This week’s reader’s choice post: My biggest professional mistakes.

I’ve been thinking about this post for weeks, as I have many mistakes to pick from.

I do try very hard to learn from them, but the ones listed below have stuck with me more than others. In some cases they are mistakes I’m likely still making now.

Here are my top mistakes:

Not staying with the same boss/group. When I was there (’94 to ’03), after a long stint on the IE team, I jumped around Microsoft every couple of years, putting my curiosity and passions ahead of climbing ladders. I wanted a diversity of experiences – I had four job titles in nine years at Microsoft – but this made it harder to get promoted and, in some cases, to earn respect in the MSFT culture. The advice I give people often is pick your manager first. A great manager will negate most other work problems, whereas an awful manager will negate most other work pleasures. Good managers get promoted and often their best people rise with them. For what I do now, my diversity of experience is an asset, but my career at Microsoft suffered for it. From an industry/career perspective, continuing to work for Joe Belfiore, Chris Jones or Hadi Partovi would have been a wiser move.
Abandoning my network. When I moved from job to job at Microsoft I basically abandoned most of the friends and contacts I’d made. I liked many of these people and built trust with them, but I was too much of a loner, and in my early 20s just didn’t understand the value of those connections and relationships until they were gone. I worked on the early days of the web, ’94 to ’99, and met tons of people at other companies and start-ups, but didn’t understand what that could have meant for my own learning, growth and connections. I still struggle with it now, as I’m very self-reliant and tend towards introversion, but there is a respect granted to people by simply indicating you remember who they are. I try to reply to every email I get and acknowledge any nod of recognition, as in a way my fan base is my extended network. But it’s a struggle.
Doubts about self promotion. My greatest struggle as an independent is how to sell myself to others while still keeping my sense of integrity and dignity intact. I believe in work and that good work gets spread more easily than the rest. But being a writer is tough – there is a ridiculous amount of competition for people’s attention and book buying dollars. To succeed I have to help it along. I know Walt Whitman sold his books door to door, and even wrote anonymous reviews of his own books. But I’m no Walt Whitman. And I don’t like people who a) are better at sales than at making whatever it is they are selling, b) who promise the impossible to create sales, or c) shamelessly inflame and hype purely to generate attention. My mistake here, given how long I’ve been online, is seeing others who have had more success, with less talent and quality of work, because they have fewer doubts about self-promotion. But I don’t think I want more book sales or web traffic if I have to lose my self-respect to get it. I know these are not mutually exclusive (e.g. subscribing to this blog or finding me on twitter could be easier), but I struggle with finding the line every day.
(Not) giving fans a way to be fans. Related to #3, I know some of you would call yourselves fans of my work. Or at least one of my books. But there’s no fan club, or fan list or any easy way for people to be rewarded for feeling this way. This is oh so dumb. I’d love to do more to reward people who are my supporters, and do more to help them spread the word, but I don’t know quite how to make this happen, in part because of #3. I am truly grateful and try to use this blog (and this reader’s choice thing) as a way to give back. But I suspect there’s more I can do. If you’re a fan, how can I help you to spread word of my work? I’m all ears. (Update: there is a berkun-fan mailing list and a Facebook fan page)
Not publishing my novel. My ambition is to write about everything. I don’t want to be just a management writer, or creativity author dude. I want to be, simply, a great writer. I want to work to be smart, honest and expressive enough to write well about almost anything, and apply the way I think about the world to as many things as possible, The only way to develop into this is to keep writing about different things (which explains the diversity of topics here). I have a novel I’ve kicked around for years, and publishing it, even by myself, even if it sucks, demonstrates I can attack writing challenges wider than what I’ve done before. One of my (now failed) goals for 2010 is to finish it up and get it out there.
Not following in Tufte’s footsteps.My primary goal is to write, and I will speak, teach and consult to make that possible. I’ve toyed with the seminar business for years, and I’ve studied what Edward Tufte and others have done. In Tufte’s case, he does the same basic full day lecture in several cities, for ~$380 per person, and fills 800+ person halls. The numbers here speak for themselves. I’m sure he started small and grew this business, as I would have to do to even attempt anything like his level of success. But managing the logistics, promotion, etc. of this has very little appeal compared to the simplicity of being a for-hire speaker at other people’s events. Once a machine like this is running, the creative costs for me would be low, and the revenue stream would be useful in driving me to take bigger risks as a writer.
Not learning to draw. I’m a visual thinker, at least some of the time.When I work with people on anything, I work at whiteboards and on big sheets of paper. But I can’t actually draw with sufficient aesthetics to warrant posting them here, or including them in books. This is a liability. But it’s one I plan to correct this year, as one of my goals for 2010 is to learn to draw. I’m working from Drawing on the Right side of the brain, and it’s going well so far.
I’m a creative lone wolf. I love the idea of an Algonquin Round Table or the Inklings, a group of creatives who meet regularly and help each other with their work. I don’t have one and never have. There are people I get feedback from now and then, but I’ve failed to build a group, or join one, that I rely on or contribute to. Writers are just weirdos, I think, and I include myself in this. We’re an annoying, arrogant, needy bunch. Most of the groups I come across are people mostly in other professions who dabble in creative pursuits, and those conversations rarely put anyone on equal footing. I’ve rarely had mentors in my life, although I do see the value and wish I knew someone I respected who was interested in playing that role. Or had a group of talent folks with mutual respect, who help each other produce more and better work.

I have some very dramatic and entertaining failures in my professional life, but they were momentary things. It’s these mistakes above that stay with me and, in some cases, are ones I’m still making. I think about them often perhaps because it’s not too late, and if I could sort them out, everyone would win.