My undergrad degree is in Journalism/Philosophy. I'm very Web savvy and good at researching/writing. But in my career now I'm a community reporter. Can a technical writer out there tell me what's different about their career and how this jump can be made?

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Journalists often make good tech writers because they try to write with the user in mind and are less prone to use tech jargon. A good technical writer knows how to research thoroughly, how to interview people to tease out the information needed, and how to put this all together in a document or other materials for users. Wikipedia has a nice description of technical writing, so you can understand the difference with journalism http://en.wikipedia.org/wiki/Technical_writing If you work at a small company, is there any technical writing there you can do now? For instance, you say you are very web savvy -- are your fellow reporters and other staff members? If not, could you write a set of troubleshooting guides or a short tutorial that would help? Also, consider volunteering in order to get practical experience and build up your technical writing portfolio. Lots of nonprofits need help with writing up procedures (they often have procedures, but they aren't documented), annual reports, getting-started guides for new volunteers, film or video scripts, tailored reference documents, tutorials and user guides for clients, etc.