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:

  1. 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.
  2. 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.
  3. 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.
  4. (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)
  5. 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.
  6. 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.
  7. 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.
  8. 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.

37 Responses to “My biggest mistakes”

  1. Kai

    Great post, #1 is oh so true!

    Not to be nitpicking, but #4 confused me at first. Wouldn’t it be clearer if the first sentence was: “Not giving fans a way to be fans”?

  2. Ioana Burcea

    You can always create a “fan club”. One simple idea: create a page on this site where you add the names & websites of your fans. You can even have some rules for what it means to be your fan (e.g., wrote a review for one of your books on our personal blog; so if I want to be called your fan, I have to do something in return). You’re a creative fellow, so I’m pretty sure you can come up with ways of creating this virtual fan club.

    BTW, I really like your Confessions, I’ll write a review on it – this life, I promise.

    Good luck with your work!

  3. Daniel Howard

    I bet that many of us share your mistakes, so I probably speak for others when I say that I appreciate this post and relate to it.

    However, I would say that, perhaps in one regard, skipping around Microsoft was a mistake, but in the long view it was perhaps right for you, even if you should have maintained your professional network.

    I remember a few years back my mother asking if I have any regrets, and I said that while I can admit to plenty of failures, I haven’t any regrets, because we all make mistakes, and I have had plenty to learn from.

    Good work with your novel. Maybe for your fans you want an opt-in “newsletter” to which you can broadcast when you get that novel published, or line up some speaking engagements. :)


  4. Steven B. Levy

    Like you, Scott, I jumped around Microsoft for many years, though I did have five-plus-year stints in a couple of groups working for great managers. It seems in retrospect to have been the best of both worlds — lots of depth in a couple of areas plus lots of exposure to other areas, doing new things, and learning. I probably could have wangled an extra promotion or two by playing the career game, but it wouldn’t have been nearly as much fun… and I think Microsoft also gained in the deal.

    Re #8, there are authors groups around, both online and locally. That said, I haven’t found one I fit well with yet either.

    Re #6, you should do this — at least the find-an-agent part. Then she or he will get you booked, and you’ll be terrific. I think #6 is perfect for you.

  5. Geoff Crane

    Some of the points in this article really speak to me. In particular, abandoning your network. I was with Citibank when I moved overseas to the Far East. I had a great career in Asia for ten years; but I abandoned my network in Canada where I’m from. When I finally returned home, there was nobody here who remembered me–my network was now entirely based in Asia. It was a long struggle to regain a comparable position that I was happy with.

  6. Jeff Osier-Mixon

    Hi Scott,

    I have been a technical writer since 1992, and for most of my career I also considered myself to be a lone wolf – many times I was the only writer in a company full of engineers. That has changed dramatically since I found myself responsible for an online community. Being flung headlong into community management has forced me to rethink group dynamics and my role in them. And, frankly, I think I have also become both a better writer and a better (and more honest) self-promoter as a result.

    The most intense lessons so far have been through participation in the Community Leadership Summit ( This unconference was initially put together by people in charge of geek communities, Ubuntu in particular, but managed to draw a lot of participation from a very diverse selection of communities, some of which were not even online. The result is a really interesting cross-cultural gathering under the umbrella of enabling people to get along in groups, online and off. Come and join us the weekend before OSCON in Portland, you’ll be most welcome and I’ll buy you a drink.

  7. Franke

    Re: not learning to draw– glad that you’re seeing it’s a skill that can be acquired, not an intrinsic ability. Drawing well is as much as learning to see, and in that vein, I recommend the book called “Zen of Seeing.” It’s a beautifully drawn book, and the text in it is handwritten, which is somehow incredibly soothing.

  8. Michael Zerman

    I certainly wouldn’t call it a mistake, but your note to self at the end of Myths about not having read earlier in your life that wonderful book, EH Carr’s “What is History?”, was a great reminder to me to find a copy and re-read it.

    The book has recently been re-released by Penguin in their small, cheap, “classics” series, so thanks for the heads up.

    Michael Zerman
    Adelaide, AUSTRALIA

  9. ZacsPrince2Training

    I can totally relate to the ‘creative lone wolf’, writing can be a lonely process (whatever the subject matter) but I’ve found it massively helpful to share my work with others, once i feel its ready of course, but relinquishing control and getting feedback can be both liberating and help you improve your work ten fold.

    1. Scott Berkun

      Zacs: It’s actually not a fear of feedback. I’m not generally sensitive in that way. It’s more that “groups” tend to be more about people’s social needs than driving hard to make the work better. Every writer’s group I’ve been do has one or two people that give good feedback, 4 or 5 who are useful now and then, and a handful of people who don’t add much value or slow things to a crawl. I tend to feel I’d be better off using that hour on my own than spending it with the group.

      The fantasy is to find a smaller tribe of serious writers who are good at critique and like each other enough to be useful. I haven’t found that yet.

  10. Raj

    Why would you call your internal moves within MS a mistake when you also say “For what I do now, my diversity of experience is an asset”. For what you ultimately wanted to become, your career moves seems like the right thing to do.

    1. Scott Berkun

      I didn’t know what I was going to do at the time Raj. And now and then I do wonder what would have happened if I followed the generally good advice I describe. Maybe I’d still have quit, and still have been a writer, but the path and the nature of my work would just be different.

  11. Mélanie Duclos (Meloyul)

    Wow! Thanks for sharing these with us. I feel I connect with a lot of these mistakes myself. Now to read it just makes me realize how important it is to acknowledge them and try to sort them out so I can learn and grow out of it. Another story to be continued… :)

  12. Laura Lorek

    This is a philosophical discussion about choices made or not made. A mistake is when you get someone’s name wrong in the paper like I did with Steve Rubel and I had to run a correction. Or when I wrote quaffed and I meant coiffed. That was a doozy.

  13. Smaranda

    A very touching post. As always, the honesty is much appreciated.

  14. Luciano Evaristo Guerche (Gorše)


    With regard to item #2, what about engaging on social networks (twitter, facebook, etc.) in a try to reconnect to long lost conections as well as making new friends online?

    As for the item #4, why not creating a fan page on facebook? It won’t hurt (ROI) in case it does not succeed at all.

  15. Justin

    Thanks for the post. I definitely think I need to develop my own Mastermind group, or Algonquin Round Table or whatever you want to call it.

    Basically its always a little easier to try it on your own, but I don’t think it works nearly as well as if you have a group helping!

  16. Dick

    Thanks for sharing Scott.

    My list would be different–and difficult to write–but there would be major overlap. #3 especially hits home as I ponder just what my third career will be.

    Count me a fan whether there’s a club or not! It won’t help you spread the word much but there’s you’re a prominent part of my corner of the thinking world Presentation Impact .

  17. Greg Comfort

    Kia ora/thank you Scott for this article. I saw aspects of myself in what you have written, in particular the abandoning of one’s networks. I have recently moved back into an industry I left five years ago (publishing and communications), and although I didn’t completely cut myself off from all previous colleagues, I see now I could have done a better job of keeping in touch with many. Certainly maintaining some sort of contact is better than none, and for me LinkedIn does a good job of this. But there’s no beating personal contact, and I suspect I may find myself in my new role re-meeting people I once worked with.

  18. JFunk

    I remember a brief period for several years where I let comfort and stability be too dominant in my work life. I loved my job, loved the people, loved the work. I’m forever grateful for the opportunity, opportunities and friendships made during that period. But when I look back now, I equate those years someone like when you’re sitting comfortably on your favorite sofa. Warm, at peace, status quo as opposed to staying engaged, curious, wanting more, eager to jump for more opportunity.

    Often people in that sort of situation can let opportunities, wanted or unwanted slip right by without even noticing.

    Great blog btw!!!!

    twitter @branddynamite

  19. Michael McWatters

    My biggest mistake: going for a job with better benefits and pay when I was young, instead of the one that would have been better for my portfolio.

  20. Alice Dagley

    Thanks for sharing your experience. It will really help people to avoid their own mistakes.

    I also think that people should follow their vocation and do the work they like and they are able to do. Designers shouldn



  1. […] My biggest mistakes « Scott Berkun – Great advice from Scott – especially if you're in a large multi-dis consultancy: "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 different 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 all the time 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." […]

  2. […] Berkun, a self-described creative lone wolf, blogged about his biggest [professional] mistakes, one of which is failing to find and engage with like-minded people. “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 talented folks with mutual respect who help each other produce more and better work.” […]

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