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Career 2.0: What’s your strategy?

Jared Richardson and Matthew Bass are working on a new book on actively managing your career, and as part of that effort they’ve started a blog on it called Career 2.0. On Monday their entry was “What’s Your Strategy?” where they asked:

  • What’s the single best career move you’ve made?
  • The worst?
  • Do you have a plan today? Have you ever?
  • What career advice do you wish someone had told you X years ago?

Jared asked for feedback in the comments but I wanted to talk about this here, in part so I can look back later and see how things have changed.

What’s the single best career move you’ve made? Hard to say but the top two are probably starting OpenAvenue in 1999 (with Jayson Minard), and to start working on the open source project CruiseControl in 2001.

Starting a company was a great experience, a real adventure. We were able to define our own culture and we were very successful at creating the product we wanted on the schedule we wanted. When the market went south in 2000 we were just a couple weeks away from closing a round of funding that would have seen us through the down turn. Things ended badly for the company when the tech bubble burst but just about everyone involved in OpenAvenue said that they would do it again. For me the biggest takeaway has been a sense of agency, the feeling that I can make things happen, along with the belief that everyone has the ability if they have the belief — which is why I think the book idea is excellent!

I started working on CruiseControl in 2001 as a continuation of our vision from OpenAvenue. We had been making hosted development tools and planned to add a feature “like Tinderbox” for any hosted project, what is now called continuous integration. With the demise of OpenAvenue I decided to create the system for a company rather than the product/platform we’d had in mind, then I found CC. I’ve spent a lot of hours over the last 8 years working on CC and answering questions on the mailing list. Helping people has really been its own reward. But from a career perspective this has also given me a platform for articles, blog entries, talks at conferences around the world, consulting, and even starting my own (with Paul Julius) conference series (CITCON: Continuous Integration and Testing Conference).

The worst? It was a move not made.

Back in 1994 I was the manager of all online services for technical support at Borland. At that time “online services” meant CompuServe, Bix and GEnie, as well as our FTP site and our own dial-up BBS. One of the people working for me was Roger Wegehoft who managed our in-house systems and who researched new technologies we should consider in support. One day Roger came to show me something, NCSA Mosaic and “The World Wide Web”. I was blown away. The potential was obvious! We spent about 3 hours in animated conversation describing the following 5 years of the web, ecommerce and all. Roger mentioned that one of the guys who worked on Mosaic, along with Jim Clark of SGI, had started a company over in Mountian View to create a commercial version… and I’m pretty sure we ended our conversation with the understatement of my lifetime: “someone’s going to make a lot of money off of this”.

We did create a website, repurposing our BBS technical support content, and then we were part of the team that presented to the executive staff that Borland should have a corporate website. And my following 3 years at Borland were interesting and in many ways successful (I was the 3rd person on the JBuilder team). But I’d like to think that the person I am now would have left the conversation and driven immediately over to Mountain View to get a job at Nextscape.

Do you have a plan today? Have you ever? Yes and no. Even though I consult on marketing I’m a consultant with a marketing problem. Since the original incarnation of Agitar wound down in April 2008 I’ve consulted on a wide range of topics with different clients: product management, interaction design, code reviews, unit testing, continuous integration, iPhone application development, QA test automation, marketing and corporate strategy. The range of topics makes it difficult to describe what I do, but part of my joy comes from that range. That’s a dilemma I’ve only partially solved with the niche marketing effort of The CI Guys.

My current plan is to continue what I call philanthropic marketing: I give away valuable stuff and hope that leads people to hire me. A large part of this is through CruiseControl and The CI Guys but it is also in the form of organizing CITCON, the Silicon Valley Agile/BayXP meetup, and the Santa Cruz iPhone Developers meetup.

What career advice do you wish someone had told you X years ago? Slam dunk: Find your passion. Follow it. Sol said it perfectly: Passion is recession proof.

I’m a consultant right now because I have a passion for helping people do their work better. When I’m doing my job well I feel like I’m making the world a better place, that I’m reducing the amount of suffering in the world.

I strongly believe that joy in your work is important to do it well. Maybe I’m wrong and you can rise to the top of your field without passion… but why spend your life doing something that doesn’t turn you on?

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