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Aug. 25, 2020, 10 a.m.
Writer William Gallagher On How OmniFocus Streamlines His Workflow

William Gallagher is the deputy chair of the Writers’ Guild of Great Britain. From his Youtube channel, 58keys to writing Doctor Who radio dramas and feature articles for AppleInsider - William shares his experiences appropriating OMNI's software to get it all done.

Show Notes:

Having authored over 19 non-fiction books, William's passion for writing a well-turned phrase utilizing the best software is self-evident. This conversation ranges from information organization to utilizing OMNI's apps in unorthodox ways.

You can find William on the web at

Some other people, places, and things mentioned:

  • Dr. Who Radio Dramas
  • The Beiderbecke Affair (BFI TV Classics)
  • Apple Insider
  • The BBC
  • OmniPlan
  • OmniFocus
  • OmniGraffle
  • OmniOutliner
  • Transcript:

    Andrew J. Mason: All right. William, I think we're good to get going. Did you have any other questions before we get started?

    William Gallagher: I would love to know someday what a graffle is.

    Andrew J. Mason: You're listening to the Omni Show. Get to know the people and stories behind the Omni Group's award-winning productivity apps for Mac and iOS. My name's Andrew J. Mason and today we're talking to William Gallagher about how he uses Omni Software to get things done.

    Andrew J. Mason: Hello, everybody. Welcome back to the Omni Show. Today's guest is William Gallagher. He's the deputy chair of the Writer's Guild and he presents 58keys, it's a YouTube series for writers using Apple Gear. He also writes Dr. Who radio dramas and feature articles for AppleInsider, and he's the author of 19 nonfiction books, including the British Film Institute's BFI TV Classics, all right I might need some help with this, The Beiderbecke Affair?

    William Gallagher: Oh, very good, very good. Beiderbecke, yes. Very impressive.

    Andrew J. Mason: Good. Oh my gosh, I should have asked you that before starting. His first collection of short stories is due to be published in 2021 and he once had afternoon tea on a Russian nuclear submarine and regrets calling the place a dive.

    Andrew J. Mason: Michael, thank you so much for joining us today for the Omni Show.

    William Gallagher: Thank you, and well done for delivering the dive joke with a straight face, it was very good.

    Andrew J. Mason: Much appreciated. And actually respect in your direction because that was a mouthful in your introduction of a diverse spectrum of projects that you seem to handle here. We've got Dr. Who, we've got AppleInsider, 19 nonfiction books. I think there might be a clue as to why we might have asked you on the show. Before we get started in earnest, I really do have to ask you a question that I had asked Ken last episode. It's an icebreaker that I will deem, what would your MacOS code name be? They had announced Big Sur MacOS 11 and Ken's answer was that he didn't necessarily know his MacOS code name but he did share that the Mac mini in their office was codenamed Spinal Tap, so I thought that was appropriate. The same question I'm going to pose to you, MacOS comes out, they come to you, they say, "William, you are allowed to code name this OS anything that you like. What's it going to be?"

    William Gallagher: Well, this is going to sound dreadful but what can you do? The first thing that popped into my head as you were asking me that question was, "Why not?" MacOS William Gallagher. Can you imagine all of these serious articles about bugs in MacOS William Gallagher and William Gallagher 1.1 and all of this? No. No.

    Andrew J. Mason: No, I love it actually because anytime that their operating system crashes they can say, "William Gallagher crashed last night."

    William Gallagher: Yes. Yeah, okay. I started off egotistical, now I'm destroying everybody's Macs. I like it. All right, yes, MacOS William Gallagher. Thank you very much.

    Andrew J. Mason: Excellent. Okay, I love that. All seriousness though, let's head back to that wide array of projects you have going on. That's a lot. Do you have a short form answer for when somebody comes up to you and says, "William, how do you get it all done?"

    William Gallagher: I don't, actually. This is going to sound so terrible but yes I do and it is OmniFocus, I'm not kidding. The people on AppleInsider every now and again if I start to say something they'll go, "Is it OmniFocus again ..." or something, sort of that key transformative. I've been freelance since about '94 or so, major changes throughout it and since using OmniFocus it's made a dramatic difference to how I cope with everything, so God bless OmniFocus.

    Andrew J. Mason: Beautiful. Yeah, no I completely understand. You mentioned how OmniFocus actually helped you through a pretty difficult time and I'd love for you to talk through that because it was a really interesting story. You mentioned that things got more complex, but yet you were the most free you felt like you've ever been.

    William Gallagher: Oh, this would be ... I've done quite a lot for the BBC over the years but there was one patch, maybe 10 years, maybe a little bit more, where even though I was freelance, everywhere I was freelancing for was different parts of the BBC, so BBC news online, BBC Ceefax, and then Radio Times, which is like the UK equivalent of TV Guide, it's a magazine and a website. I basically ended up doing the equivalent of eight days' work a week across the different parts of Radio Times and BBC. That was great and unfortunately it was so great and I loved it so much that I did the bad thing freelancers should never do, I forgot to look for any other work. When the BBC had one of its periodic canceling of all freelancers, I got caught with that and I practically overnight went from having about one client and three editors to having none of them and having to build up all the people I used to write for get new businesses.

    William Gallagher: Within about a month, two months I worked out I now had 15 editors across a dozen companies or something like that. Some of it huge projects, some of it very, very bitty. So much juggling and not just of the work that I was used to juggling, but a lot of the apparatus around it of getting the work, pitching it, invoicing, checking it was delivered. I remember three months or so into that my wife, Angela, commented that I seemed lighter than I had in years and that was actually the first time I said to somebody that it's because of OmniFocus. I'm so glad I had started using it. Less than six months before all that BBC work ended I tried out OmniFocus and I hadn't realized actually how steeped in it I'd become so quickly.

    William Gallagher: But it was ... I am life support dependent on OmniFocus now. It's not like you're paying me for this, you couldn't pay me. I remember ... Sorry, that just popped straight into my head, but I remember saying to somebody once, "I love OmniFocus so much that I would buy it again." And then some years ago there was a new version of it and I did buy it again straightaway.

    Andrew J. Mason: That's so interesting, but you've been doing this for a long time. Do you remember how you came across the Omni Group or OmniFocus?

    William Gallagher: I actually think ... It wouldn't have been for AppleInsider because it was quite a long time ago now. AppleInsider has been around for a long time, but I've been involved with them for a few years. I probably was reviewing it for somewhere. I'm very keen on getting stuff done, so I had a to-do app. I remember being very frustrated with it, just some things it wouldn't do, and I looked at some of the more heavyweight ones. No, I must have reviewed it because I actually remember writing the line about OmniFocus that ... Oh, what's the phrase? It was something like, "First it destroys your mind, then it owns your soul ..." or something.

    William Gallagher: OmniFocus is a lot easier to use now than it ever was, but all that time ago there was quite a steep learning curve, I thought. I remember at first, really quickly actually, thinking, "This is too much, I can't handle this. I don't understand it, it's too powerful for me." But I couldn't go back to the one I had before because it was too good in that bit. And then over time ... I do still review things, I do still try other ones, so I'm aware of how OmniFocus fits with the rest of it, but it's so far ahead of the rest.

    Andrew J. Mason: I have to compliment you, it owns your soul is a very ... Gosh, that's a good turn of phrase right there. I want to talk a little bit about OmniOutliner because you say you hate outlines but you love OmniOutliner?

    William Gallagher: Well, I'm a professional writer, I have to write outline sometimes. The book you mentioned, The Beiderbecke Affair, and I cannot tell you how impressed I am that you ... The show itself makes jokes about people not being able to do that, but you got it. To get that with the British Film Institute I had to give them effectively an outline, like a chapter breakdown. And actually later we radically abandoned it when I found some new material, but I couldn't have got the job without that. The Doctor Who things you do, you start off with ... You throw them one line so that they can come back with, "No, we've already got one set in a desert," or something. And if they like that, you go to just a paragraph and then after that it starts becoming a bit more and more and you end up outlining a two-hour story, and I use OmniOutliner for that as well.

    William Gallagher: When I have to ... I understand outlining, just in my heart I would rather sit down and write and fully accept that I'm going to write rubbish. Not only would I, if I wrote a hundred thousand words, I not only would be willing to throw away 90,000 as rubbish, I have done and I think that's a bargain. I got 10,000 good words just for the cost of the 90,000 rubbish ones.

    William Gallagher: But I was interviewing a producer for Radio Times once and for some reason we got onto this topic and he said to me, "Yes, it's all very nice writing something and if it's bad throwing it away, but I can't have a blank screen on BBC One on Tuesday night, I've got to have something there, which means I've got to make sure it happens. I can't risk my wonderful flight of fancy going wrong." And an outline was the best way he had of making sure something was there, and I completely get it.

    William Gallagher: I'm doing a project now where I am trying an outline just because it's really a complicated drama, but really despite all of this I use OmniOutliner every day. I was on it three or four times today because I do a lot of events, a lot of workshops, even now under the current situation I'm doing this. I do a six-hour Zoom workshop for one client and that needs a lot of planning, so shaping and things. I think OmniOutliner might even be misnamed, it's Omni Ideas Organizer Refire or something. It helps me sort out anything complicated and it also helps me see when I missed something. For that six-hour workshop I know when lunch has to be and I know the topics that are heavy and the ones that are light and I can move the heavy ones to ... Don't give them something heavy right after lunch and things. Now I know I do need something after lunch, what can go there? And that's how I build up an outline.

    Andrew J. Mason: Oh, I see. For somebody with not as much experience in OmniOutliner, I really do appreciate that because I just have this need to brain dump all of this information out, and it's not always a task-related thing, it's something that I do in a sequence but I don't necessarily have a great way for that to go, so I may give OmniOutliner a go on that.

    William Gallagher: Well, I have one complaint of OmniOutliner, which is that sometimes ... This is mostly with nonfiction pieces of some AppleInsider articles but some pieces up to maybe four or five thousand words when it's more complicated than a little news story but not a book kind of thing. I will be going through thinking, "Well obviously I've got to mention that," and I'll write down what it is, then I'll think, "Well actually, how am I going to explain that?" So I'll write a little explanation and then I find I hit return and I write the next paragraph and the next and the next, and so many times I've found I've written the entire article in OmniOutliner and I've then got to get it out.

    Andrew J. Mason: I got it, so a great way to export the data in a way that makes sense in a reading format, so maybe a feature request there, I'm not sure. Speaking of feature requests and all the different software, you're the first person I've run across that uses pretty much every single piece of software throughout your day-to-day, and so let's move over to OmniPlan. OmniPlan, I love this nontraditional thinking, but you say among other high-level planning projects, you've used OmniPlan primarily to get out of doing projects?

    William Gallagher: Yeah, I did say ... Just in case the people I did this with are listening, it wasn't you it was another project, okay? I have done my bit. I wrote a script for something and the project had fallen apart because all the people involved, including me, were very busy on different things. But every now and again when one of them would lose their BBC contract or whatever it was they would suddenly revive interest in this and they would try to drive it forward. We got to a point where I was so busy. I couldn't go on with it but the other two could. I really like them, they're my friends, it was an interesting project.

    William Gallagher: For some reason it fell to me to almost produce it, only very basically, like the admin side rather than the full show. But I did them a Gantt chart in OmniPlan and I sent them this with all of the things they had to do, all of the dependencies, this can't happen until that's done. But I rigged it so that everything I had to do came after everything they had to do because I was pretty sure they wouldn't do it, and that's true. I looked brilliant, presented this wonderful-looking chart and I've been very generous with their time limits and things, but I never saw them again, it was really quite handy, so yeah. I didn't get to do all the Monte Carlo simulation stuff that I don't understand in OmniPlan, but the basic stuff was very, very useful to me that day.

    Andrew J. Mason: For all intents and purposes, I'd have to say that was an effective use of your time.

    William Gallagher: Yes, it was. Yeah. I'm not sure they'll put this on the box or whatever, how to get out of planning your projects, but it worked for me.

    Andrew J. Mason: Any more conventional uses for OmniPlan?

    William Gallagher: I should say I have also used it ... I knew how to use it because I've used it for serious ... The 19 books, or five of them that were actually predominantly written by me but shared amongst other writers, other producers and things. Actually they were technical books and four out of the five were best sellers on Amazon. None of us can ever work out what did we do wrong with the fifth? But they were all planned in OmniPlan, so a serious piece of software but really handy for getting out of things.

    Andrew J. Mason: Well this wasn't anywhere in my script of questions but I do have a personal question in terms of ... You process so much information and it all lands in different spots depending on the application. Do you have a way of deciding this is where it all starts? You've got that seed of an idea and you're ready to grow it or flesh it out into something else. Where does it head next?

    William Gallagher: That's really interesting because it's funny, I've been having this debate recently but with writing tools because I use Drafts, Final Draft, Pages, Word, which one do you go for? There's something unconscious about it. It's a script I know I'm going to be in Final Draft. It's a novel, I know I'm going to be in Scrivener and things. I just seem to reach for the nearest screen and device. I think when you put it the way you just did there, I realize OmniOutliner is probably the start of everything. If it's only going to be a note then it could be in anything at all, but if it's going to have more than a couple of bits to it I will start an OmniOutliner and I'll shape it.

    William Gallagher: I do online courses for writers and things and one of them was amazingly bitty of how to do all these things. OmniOutliner helped me get the sequence and then when I had the sequence I moved the whole thing over into OmniFocus so that then I knew I could just tick as I did each one and know that I was getting to the end of it. That's one of those where you know the start and you know the end. Quite often you only know the beginning so you chuck a few things into OmniFocus and know that as you're going through them, as you're reviewing it, you'll think of what the next thing is. OmniOutliner for everything, OmniFocus to get it done.

    Andrew J. Mason: It's so interesting that you mentioned it being kind of this intuitive process that you sense, I wish I had a template, I don't necessarily have much other of a template other than the fact that if it's actionable or remindable it goes into OmniFocus for me. Other sorts of things where I'm just working with bits of information and fleshing it out, it can go in text edit honestly. That's why I'm excited by this idea of OmniOutliner.

    William Gallagher: Well, it's just funny you should say about templates because I've realized one of the things I have come to really ... As I said, I do lots of workshops but hardly any of them, just a very small percentage are entirely mine, they're usually for another company. In fact, four companies hire me to do, there must be about a dozen different workshops and now I have it because of OmniFocus' ability to read TaskPaper. I've created a shortcut that I set it running and it asks me which company is the workshop for. Then from those. which one of the ones I do for them is it? Where is it, online or an actual place? And the date. And then it goes off and it chucks into OmniFocus. All the tasks have to do with that because most of them are quite complicated with ... 10 days before I have to produce this document, two days after I have to invoice in certain ways and things like that.

    William Gallagher: And also when I'm traveling I carry a lot of equipment so it actually pops in a packing list for me for the night before and things like that. The first time I did it it took ages, but now I get a call, I tell them straightaway whether I can do the date or not. I press one button and I know I can get on with whatever else I'm doing that date, all handled.

    Andrew J. Mason: And you say this is all done in TaskPaper?

    William Gallagher: Yeah. TaskPaper is ... There is a to-do app called TaskPaper, I think, but it's also a format, a way of describing tasks and for writing down in like command line entries, which OmniFocus is able to understand. Within the shortcuts I have a text field that is this list. It'll be things like ... That document I write, it's write document for ... And it will insert the name of the company at the session date minus 10 days or something. OmniFocus interprets that and it slots it into the right project, puts it in the right date on the calendar. Whatever 10 days before that workshop is, OmniFocus works it out and puts it in for me using this format.

    Andrew J. Mason: That's so beautiful and honestly it reminds me of what Ken was talking about last episode where it's just you work so hard to get that first project airtight there's smoke coming out of your ears.

    William Gallagher: Yes.

    Andrew J. Mason: Once it's there you have this templatable process that anybody else can use that there just won't be any holes in it. Do you have any suggestions for somebody that's looking to lean a little bit more in that automation direction?

    William Gallagher: With shortcuts and planning and templates and things like that?

    Andrew J. Mason: Yeah.

    William Gallagher: Because I can tell you ... Because it's the situation we're in now. The one client that I used to travel around the UK for doing things started doing online ones so I went to my shortcuts and I added an online section and I broke the whole shortcut. I looked at this and it was too much effort to go work it all out again and put it into OmniFocus. I spent half a day fixing the shortcut just so I could do it. If I had not had that, if I'd been more unprepared, I could have done it once in OmniFocus and then saved a copy of that project as a template and probably effectively done much the same thing. But I'm not sure how that would work with the kind of relative dates, the 10 days before, the two days after.

    William Gallagher: Most things I do in OmniFocus I slap them straight in because they're usually one or two parts and I trust that when I come to review everything I will add others to it. Longer term plans, actually yes that one with OmniFocus, that shortcut, you'll never guess what I worked it out in. I did it in OmniOutliner first so I could move things around. The document requires certain information, so before I could do the document 10 days before I have to get this information 12 days before and things like that. I worked out the pattern and then ... I'm an Omni anorak.

    Andrew J. Mason: No shame at all about that. I do want to switch gears and talk about ... You have a YouTube channel that you fired up with all things Macintosh and software review and that ecosystem. Talk to us a little bit about 58keys.

    William Gallagher: 58keys. Weirdly enough, it was a project several years ago. I was supposed to come up with a name for something and I didn't, somebody else I was working with did. 58keys just stuck with me as a title. There is a meaning behind it, but keys and writing, I was not seeing stuff on YouTube that I wanted to see. I didn't see any pieces about OmniOutliner for example, and there has been an entire 58keys episode just about that. It's actually ... It might be the most popular episode I've done so far, it was certainly very successful for it. The number of people who've emailed me since saying they've tried OmniOutliner and are now hooked, like I was. It's really gratifying. It's for writers who use ... Writers like me, really, who use all of this Apple gear, how to get much more out of it.

    William Gallagher: I know I'm talking a lot ... Obviously I'm talking a lot about Omni now, but I'm a real software nut, far more than I ever have been hardware. Get me started on Scrivener or Pages versus Word, all of this stuff. There is hardware actually in 58keys because I think ... Even though I want it to be that it's how writers can get more out of your Apple gear, you have to get Apple gear first. I have one talking about the ways you can get refurb Macs and things for cheaper and there are certain things to do with the business of writing.

    William Gallagher: You don't write anything in OmniFocus but it's so vital as a freelance writer that it feels like it's part of the same tool. Actually very soon now there's going to be an OmniFocus episode coming out there and then later how to use OmniPlan to get out of things, that will come too.

    Andrew J. Mason: Yeah. I cannot wait to use that trick, that is amazing. William. I want to let everybody know about where they can find you, I know about And it's just been an honor talking to you. It's such a cool, wide spectrum of stuff that you're involved with and just getting to see all of that through this lens, so cool. Thank you.

    William Gallagher: Thank you. I always felt that even though I write a lot about technology, I'm a drama writer who does this. I feel like I'm right on the cusp between technology and drama. There are so many people I work with as a writer who have no idea I use all this stuff and so many people I write technology about who have no idea I do dramas and things like this. And bringing them together, being able to talk about them both in one go, it's a thrill so thank you very much for asking me.

    Andrew J. Mason: Absolutely. And thank everybody for listening today too, we're so grateful that you spent this time with us. If you'd like to keep up with what the Omni Group is up to you can always head to or find out more about this show at The Omni Show on Twitter.