Episode 208 – Writing short books with Hassan Osman

‘I’d love to write a book, but I have a full-time job and a family, I just don’t have time.’

If that sounds like you, you need to hear this. Hassan Osman has a demanding full-time job at Cisco and a young family, but he’s written eight (EIGHT!!) books so far, including four ‘short books for busy managers’ and, of course, one called Write Your Book on the Side. He also hosts the Writer on the Side podcast, helping others to do the same.

If you have excuses, be prepared to shed them now. And pick up some super-practical tips and hacks from this master of productivity.


The Couch Manager: https://www.thecouchmanager.com/

Writer on the Side podcast: https://www.writerontheside.com/

Hassan on Twitter: https://twitter.com/HassanO

Alison on Twitter: https://twitter.com/bookstothesky

The Extraordinary Business Book Club on Facebook: https://www.facebook.com/groups/1447064765612358/

This Book Means Business – the mentorship programme: https://alisonjones.lpages.co/this-book-means-business-mentorship/

The 10-day Business Book Proposal Challenge sign-up link: https://alisonjones.leadpages.co/proposal-challenge/

Alison Jones:                 I’m here today with Hassan Osman, who is a director at Cisco Systems, although important to point out, all views are his own, where he leads global virtual teams on delivering large and complex programmes. He also writes short books for busy managers, and he’s the author of several Amazon bestsellers including Influencing Virtual teams, Don’t Reply All, and Effective Delegation of Authority. I do not know how he finds the time for us. We’re going to go into this. He also hosts the Writer On The Side Podcast that helps other full-time employees write and publish their nonfiction books. It’s brilliant to have you here today, Hassan.

Hassan Osman:             Alison, thank you so much for having me on. I’m really excited about this.

Alison Jones:                 It’s so cool. You write, you podcast, you work, it’s all the kind of magical things that we talk about in this podcast. How the hell do you do all this with a day job? Before we go into the how, let’s talk about the why. What was it that made you start writing?

Hassan Osman:             Oh, gosh. Wow. This is a tough one because honestly it’s a combination of multiple things, but I can tell you what keeps me writing, and I think to your listeners, it’s important to share this because there’s no feeling like it, and that is when you write something and someone somewhere in the world… I mean, I live in the U.S., I’m based out of Boston, so I always choose Australia or China or India. Someone picks up the book on Amazon, reads it, and then sends a personal note just to kind of thank you for improving their life, whether it’s just 0.1%, there’s just no feeling like that. Just that high and gratification of knowing that something you wrote actually helped someone is I think what keeps me going, and really that’s the crux of it.

Alison Jones:                 And is that what got you started though, because I can imagine that’s the sort of thing that when it happens you’re like, “Oh, this is so cool,” but something must have motivated you. It’s not like you didn’t have enough in your life. I know you’ve got a family as well. People, if you have excuses, be prepared to shed them now. But you started writing, so what was the thing that drove you at that kind of first point?

Hassan Osman:             It’s sharing my knowledge. Alison, I think there’s a hungry audience out there. I’m a voracious reader of business books and I’m always hungry to learn more. And so when you think there is something that you can provide out there which is a gap in the market or a different perspective based on your own unique experience, the drive for just sharing that with the world is really what got me started. I really wanted to write something that I wanted to read. Like you said in the intro, short books for busy managers because those are the ones I enjoy, and I saw that particularly in the virtual team space, there wasn’t so much at the time, this was back in 2014, that I enjoyed reading. So I took my experience, my background, my work with Cisco Systems and Ernst and Young, and I said, “Well, why don’t I write a short book that helps other managers influence their teams remotely?”

Alison Jones:                 And that’s that wonderful Toni Morrison quote, isn’t it? “If the book you want to read doesn’t exist yet, then you must write it.”

Hassan Osman:             Absolutely, scratching your own itch.

Alison Jones:                 That’s right. That was a really good place to start. Do you think, what does writing do for you? I mean, clearly you don’t need to do it. You have the full-time job, but what dimension does that bring into your life, do you think?

Hassan Osman:             Yes. You know, it’s so interesting you ask that question, Alison, because a lot of people want to ask a question but are shy to ask it, and that is: do you do it for the money? Let me start with why I don’t do it, and I don’t do it for the money, if you know anything about writing, and I’m very open-

Alison Jones:                 That never even occurred to me to ask that.

Hassan Osman:             I know. Especially you’ve got insider knowledge and you’ve got this great podcast, so you know a lot about this, but for someone who’s never written a book, they get to hear about those international bestsellers and people making millions and millions of dollars, and that is really an anomaly, right? I’m very open about the money I make. I mean, it’s more around the $200 to $300 a month maybe from the business books, so it’s not like you can quit your job anytime soon if you have a stable job out there. So let me kind of start with that, that it’s not about the money. Now, that’s a good thing. Obviously that’s one sort of driver that is not bad, right? I mean, everyone would like to get a little bit of additional income on the side, but I think what it means to me personally and why I do it is because I really think that the exercise of writing on its own helps me think better.

                                    There’s sort of this magic where when you crystallise your thoughts down on paper or in ink or online, obviously you’re going to be criticised for it, and so it sort of helps force you to become a little bit more concise and crisp with your thoughts. And it just, to Richard Feynman’s sort of point of view that if you want to learn something, teach it. And I think through writing there is no better way than to actually teach a subject and think about it that way.

Alison Jones:                 And of course when you’re writing, I mean, let’s take Virtual Teams because that’s a great example. I mean that was something that you were engaged in, you wanted to learn about, you wrote the book, you discovered much more about it that presumably feeds straight back into your professional life as well.

Hassan Osman:             Absolutely. And I think the fact that you writes in a space that is related to your job has a tonne of benefits. I mean, you’ll establish yourself as a thought leader and an expert in your space. It opens up a lot of opportunities for you in terms of keynote speeches and webinars and what have you. And so there’s this amplification effect off writing. And I always say writing a book is like having a business card on steroids. I mean it’s just what better way to kind of showcase your expertise in a specific field than to have written a book and that sort of intellectual thought capital out there that is associated with your name.

Alison Jones:                 Yes. Well absolutely. It’s interesting now that you are a corporate employee, I talk to a lot of people who are business owners who want to position themselves as thought leaders who are kind of running businesses based on their expertise. And there, that whole kind of business card on steroids makes so much sense because you’re hustling, you’re your own brand. Is it a challenge? I mean I know it’s really important to have that kind of ‘all views my own’ thing because you are representing another company as well. Is that a challenge? That kind of conflict between what you can say in your own right and the obligation you have to a company?

Hassan Osman:             Yes. Excellent question and I get that a lot as well from some of my listeners. So let me start by saying every company is different, right? Before you start writing a book, you definitely want to check with your own HR policies, with your manager, and make sure that you check the box on a lot of this before you publish anything. I’ll give you a small anecdote. Before Cisco, I used to work for another international company and I had published a book and didn’t tell anyone about it. And when the time came for me to publish, there was a huge red flag from legal counsel within the company. Not because I did something on the side on my own, but because there was some sort of conflict within the book topic that I had to vet through with the company lawyers first. Because I mentioned a few customers in the book that are related to my other company.

                                    So there was a little bit of a hitch there that we had to kind of clear out, and the lesson learned was that before I publish going forward, I was going to vet this through my company. So it really depends, there’s also a lot of nondisclosure agreements. Depends on the topic that you’re going to be writing about. If it’s more on the, maybe fiction side or even nonfiction, but not directly related to your job. I think for the most part you should be okay. But I would do the due diligence and make sure I check the boxes on all of that, internally with your company first before publishing anything.

Alison Jones:                 Yes, wise words. Absolutely. And then just in terms of the how, having cleared out the why now, I feel comfortable we’ve established the why, how? How on earth do you find time to write multiple books, with family life, podcast, and a full time job?

Hassan Osman:             So I tried to optimise my work as much as possible. But if I were to just choose or hyper focus on the writing aspect of the book, I would say that one, I write short books. I mean that alone helps tremendously, right? Because it shaves off a lot of time that you have to spend writing 400 or 500 pages. So that’s sort of a little hack that you know is a win for you as a writer and a win for your readers. Because a lot of readers these days don’t have the time to read 700-page manuals. Right.

Alison Jones:                 Who does? When you say short though, be specific. Roughly how short?

Hassan Osman:             Sure. So 10,000 to 12,000 words a book. And I say words and not pages because you know with the screen sizes these days.

Alison Jones:                 Oh sure, you don’t know what pages, yes.

Hassan Osman:             Yes but that translates around 60 to 70 pages of standard sized book. Because I do publish my books in print as well. And that’s fairly short.

Alison Jones:                 Oh okay, I thought they were just e-books.

Hassan Osman:             They are all print on demand too, through Amazon’s KDP platform or Kindle Direct Publishing.

Alison Jones:                 Sure.

Hassan Osman:             So it’s very easy to kind of, if you have the Kindle book to also have it available in print. And believe it or not, a lot of people actually still buy print books and they prefer them in some cases over Kindle books.

Alison Jones:                 Oh no, I do believe that. I think the print market has been incredibly resilient. It certainly… I was a pioneer of digital publishing. It certainly surprised me just how well print books have held their value.

Hassan Osman:             Right.

Alison Jones:                 I think actually, in a world that’s increasingly where you’re doing everything on screen, there’s sort of a relief actually in coming off screen and just allowing yourself to be lost into a book.

Hassan Osman:             Agreed. Agree. Then I think a lot of people are still used to that because of that specific reason. So to answer your question, another little hack I use is, and I learned this, I can’t remember from who, but it stuck with me ever since. And that is to separate your writing modes from your editing modes. I think back in the day I used to write an edit and it’s used to take me like seven hours to finish two sentences. And when I said, “All right, if I sort of just focused on, excuse my language, vomit your thoughts on screen with whatever, regardless of grammar or spelling or whatever, just kind of put your thoughts on there. And then the next day come back and sort of edit and rephrase and move things down and crystallise those words as well.” I think those some techniques were really helpful in the way in which I kind of approached it.

Alison Jones:                 Yes, I love that. And it’s so true, isn’t it? You’re right, you can go on and on and on and end up with the best two sentences in the history of the world, but it’s not really going to help is it? It’s not a book, and there’s a real… You’re constantly putting the brakes on. If you’re trying to go back and edit as you’re writing, then you’re constantly getting yourself out of flow. You’re stopping a creative process. Whereas if you just allow yourself to… I have no problem with word vomit. If you allow yourself to vomit onto the page, there’s a kind of energy and momentum and an actual real kind of pleasure and that isn’t it. It’s quite a joyful creative state to be in.

Hassan Osman:             Definitely.

Alison Jones:                 Doesn’t always go like that.

Hassan Osman:             Oh, of course. Yes. Like once in a blue moon, you’re sort of in that mental, what did they call it? The flow phase.

Alison Jones:                 The flow. Yes.

Hassan Osman:             Yes. I mean there’s no-

Alison Jones:                 Mihaly Csikszentmihalyi…

Hassan Osman:             Yep, yep.

Alison Jones:                 Yes. And so, and that editing piece, how do you go back and do that then? So you sort of put the whole thing down. Do you plan the structure up front? Or do you just say, this is roughly what I’m going to do and I got to just write it?

Hassan Osman:             Oh, I always plan. Yes. I mean, I’m a project manager by trade, so I plan everything way ahead of time. But yes, I write an outline, literally keep it very simple. Introduction, main body conclusion. And then in the, sort of main body of the topic that I want to write about. I have the sort of high level chapters laid out and what I’m going to be writing about within those chapters.

                                    And then I really shift between editing and researching. Because a lot of times I kind of stop, something triggers a thought about, hey I probably need to write that little bit more about that. So I hop onto Google, Wikipedia. I kind of do a little bit more research. Even sometimes believe it or not, going to the library and picking up a few books, just the traditional way, and sifting through the table of contents and some paragraphs there that I think are valuable and kind of stitch them together. So you know a lot of layout of the book and the structure is done at the beginning of writing. And then it’s really sort of filling in the gaps. The editing, I mean there’s the content editing, which is way more important to me than the sort of grammar or flow or writing style. Because I get some help with that. I mean, I hire editors to help me out. But the structure to me is the most important is how… Really thinking about the customer or reader experience and how are they sort of getting value from the book.

Alison Jones:                 And, and that really struck me actually reading your book about writing a book. The focus, that relentless focus on write a useful book. Please don’t write a book that isn’t useful and it’s got to be useful for your reader. So for goodness sake, focus on them.

Hassan Osman:             Absolutely. I mean, that’s rule number one to me is write a really, really useful book. Because a lot of times we’re hyper focused on what we want as authors and it’s just a natural psychological thing that you’re thinking about, you and me and my experience as opposed to the person reading the book. And when you really focus on that being a North star and that’s your customer and your reader is the focal point of why am I reading this? Why am I getting value out of this? Why should I spend the time and money on a book? If I can get that information elsewhere. So I’m really looking at it from that experience is important.

Alison Jones:                 Yes. And I mean obviously you’re a voracious reader. Clearly people are reading your books. I’m interested where do you think the book sits now in the whole kind of world of learning when it comes to business? Because we have so many options, don’t we? There’s YouTube, there’s the stuff that our company provides. There’s online courses. What’s the place for the book now? Why is it holding its own so well?

Hassan Osman:             I love that question and I don’t know if I’m educated enough on the sort of state of the union of the book, but I can give you anecdotes from me personally. I sell more books today than I did when I published some of them four years ago. And so maybe that’s a little bit of an indicator. I mean like the book about virtual teams. If I just look at the statistics on how much they sell today versus how much I sold four or five years ago or six years ago now. I sell more today than I did then. Even though there is a lot more information within those five, six years online about virtual teams YouTube, what have you, so on and so forth. So I really think book reading is still part of the arsenal of education.

                                    People learn in different ways and I really think sometimes it’s not even a zero sum game. People would watch a YouTube video about a specific topic. They would read an online article or blog about it as well, and then they’d buy two or three books as well to kind of supplement their knowledge about it too. So I really don’t think that they’re mutually exclusive, and there’s just this way in which we were primed when we were young to read and learn in that way, which is very different than watching a video.

Alison Jones:                 Yes. And actually, if you take that idea that books are holding their own as part of this much broader landscape of ways that we can access content, that leads us nicely to the podcast. I’m quite proud of that link. So tell me a little bit about how the podcast works alongside the books and why it’s important to you.

Hassan Osman:             Yes, so I run a podcast called Writer on the Sides. And then the number one reason why I started that is because of the number of questions I got about how do you write a book while working a full time job. And I think the statistic is somewhere north of like 80% of professionals want to write a book at one point in their life. And the number one reason why they don’t is because they don’t have the time for it. And they don’t know how to market it. They don’t know how to get started, what to write about, so on and so forth. And so I love this medium. I think also the fact that I am a consumer of podcasts. You can multitask while driving, while going to the gym…

Alison Jones:                 That’s right.

Hassan Osman:             …while walking. Yes, exactly. So I thought a lot of those, my target audience is already busy. Family, work life. They just don’t have the time to maybe sit down and watch a course or even read books sometimes. But they do have the time to consume through a podcast. And so it was really just my way of giving back to the community. I mean, I really started it. I don’t have any sponsors, I don’t sell anything on it. It’s just sort of sharing my own experience and interviewing other guests who’ve published books in the past and just sharing that sort of, those tactics and strategies to help people write their first book.

Alison Jones:                 And again, we’ve done this the opposite way around this time. So that was your starting motivation. What keeps you going? What is it about podcasting that, that you love?

Hassan Osman:             Oh yes. Oh my God. You’re asking amazing questions today, Alison. So what keeps me going? I think it’s similar to the books, feedback. It’s people writing to subscribing, just saying, “Oh my God, I love this.” Sharing it too. Just seeing that you’re adding some sort of value. I think that the Dali Lama at one point said, “Share your knowledge. That’s the only way to achieve immortality.” Not that immortality drives me, but it’s just the idea that life is short and to kind of keep a piece of you in this world after you’re gone I think is a good motivator.

Alison Jones:                 That’s a great perspective. I hadn’t ever thought of it in that sort of spiritual dimension almost.

Hassan Osman:             Yes. Even though I don’t want to sound morbid, but I think that’s a good way to kind of think about it sometimes.

Alison Jones:                 Yes. Wonderful. Now we’ve had so many tips from you already, particularly about how you manage your time and how you get on with the books, but I always ask my guests if they had one top tip for people who are listening who are probably actually screaming at their listening device right now saying, “It’s really hard writing a book. How do you making it sound so easy? Stop it right now.” What would you say to them?

Hassan Osman:             Yes, so my advice would be to force a block of time. And what I mean by that is there’s absolutely no way you can write your book if you don’t set aside some sort of time for it. There are no secret magic pills about writing. It’s really about just sitting down and creating habit around it. And my recommendation, and I’ve done this with all my books, is to dedicate 30 minutes a day, five days a week to write your book. And I say 30 minutes because I think anyone can find 30 minutes a day. Even if you’re overworked and you’re a full time parent, you can just wake up a little bit early or go to bed a little bit late or have a shortened lunch, right? I mean, you can even split the 30 minutes a day by writing 15 minutes a day, 15 minutes in the morning and 15 minutes at night.

                                    And I say five days a week because I’m pragmatic, right. Doing that instead of seven means that you can take the weekends off, right and follow through on your own obligations. But start today, I mean it’s sort of like taking that first step out of the thousand step journey, or a thousand mile journey. It might take you six months, it might take you a year, a year and a half. But you’re going to look back and say that you glad you took that first step. So really there is no again, secret formula other than just to kind of force yourself into this habit and start writing today.

Alison Jones:                 Yes. I mean I’m laughing because it’s kind of so obvious that actually that there’s, the other answer is there. You just do it by doing it. But you’re right, I think breaking it down. When you were trying to establish that habit, were there any hacks that you devised for yourself to just hold yourself, make yourself accountable? Or lock it into a sort of period of time where you had space for it.

Hassan Osman:             Yes.

Alison Jones:                 I was interested, I’m reading Tiny Habits at the moment. So I’m very much on kind of behaviour design at the moment. That’s where my head is.

Hassan Osman:             Oh, I need to ask you about that later on because I have it on my to read list. But yes, I do have a quick hack for you. And that is to find your quiet zone. So a quiet zone is basically a physical or mental space that you use when you’re writing. And this is a zone that should be distraction-free, right? So find a spot where you can silence your phone, switch off the TV, shut down Facebook, Instagram, and then ask your family members not to interrupt.

                                    For me, what works is that, because I work from home, I write my books in the same home office that I work from. So it makes it harder to kind of shift my mode from working to writing. So when I do write on the weekends or weeknights, I trick my brain by modifying my environment. And what I do is I turn my space a space into a quiet zone by turning off all the lights in my room. Closing the shades so that the only light source comes from my computer monitor. And then I use earplugs and put on some really faint classical music in the background so that I drown out any ambient noise. And this helps me sort of focus only writing and nothing else for 30 minutes. Right? So I’m really in the zone and kind of sometimes tried to force that flow status. When it hits me.

Alison Jones:                 That’s really smart and I bet now because you’ve been using that so long, as soon as you put those earplugs in, turn that music on, turn the lights off, you know, you’re kind of primed to start writing and it’s much quicker.

Hassan Osman:             Exactly. I want to share one other thing, Alison, with your audience here. Another hack or another great time saver is to jot down notes anywhere, anytime. So whenever in whatever they pop into your head, you’ll have some bursts of ideas about your book. And you want to capture them as soon as possible before you forget them. And so you don’t even need to use any fancy tools. Literally the like the notepad application or your iPhone or anything like that. I usually have like the high level outline of my book already saved and I just sort of look through it and whenever I have a new idea I just pop in a couple of words to help me to mind myself when I’m on my desktop again in writing mode, then kind of pull up those notes. So that really helps as well with the writing.

Alison Jones:                 Oh yes. Because you think you’ll remember. You don’t.

Hassan Osman:             Exactly.

Alison Jones:                 Yes. All my best ideas come to me when I’m out on a run and I’m so used now to just sort of stopping, pulling out the phone and just dictating it to myself and emailing it to myself. That’s my little…

Hassan Osman:             Yes. Yes. There’s a lot of voice apps. One is called Otter, O-T-T-E-R, that I learned from my friend David Perell. You’ve can find it an auto.ai and it sort of transcribes it for you too. So if you’re running and you don’t want to… You can’t type while you’re running and you want to just speak into it. It saves it for you and transcribes it and it’s free.

Alison Jones:                 Cool.

Hassan Osman:             Yes.

Alison Jones:                 Yes. Oh the tips are good. And I heard your David Perell podcast the other day, actually. Man, that man can write, can’t he?

Hassan Osman:             Oh my God, he’s amazing.

Alison Jones:                 Yes, he’s fabulous. Brilliant. All right. And also I always ask people for a business book recommendation, so clearly people should go and check out your books. Obviously they are short, they are useful, are very well written. But what are the business book would you want to point people towards, that’s particularly helped you?

Hassan Osman:             Yes, that’s a great question too. I mean it’s, I’m a voracious reader so it’s very hard for me to pick one. But there is one during the last year that I read twice and it’s called Building a Story Brand.

Alison Jones:                 Oh, I love this.

Hassan Osman:             It’s an amazing book, isn’t it? On your message and how to sort of package what you do in a crisp way. And I think it helps writers and it helps business people and it helps you as a personal brand. So couldn’t recommend that enough.

Alison Jones:                 Yes. Donald Miller, and actually going beyond that, even the book itself is superb, but the whole way that he’s built that book into his business and built his business around it, is an absolute masterclass for anybody who’s writing a book that they want to build a business around.

Hassan Osman:             Exactly. I mean he knows what he’s doing, right. I mean he’s got those workshops too-

Alison Jones:                 Smart guy.

Hassan Osman:             I absolutely love the way he positioned it and it’s so valuable too. It’s not like some of those books where you feel like there are upsells where you know, you’re not getting all the value unless you pay the two, $3,000. this has everything in it. And the workshops that he sells basically just are complements to that as opposed to a completely separate thing.

Alison Jones:                 Yes, that’s a really good point actually because so many people have that kind of ‘sell the sizzle, not the sausage’ mentality. Which is just… you’re cheating your readers and he has absolutely, gone and put everything out there. His best stuff is in the book. And it’s a real, yes, it’s a real great example of how when you do that people rate your worth so much more highly.

Hassan Osman:             Precisely. And I love him for that and that’s why I read the book twice, because it’s so meaty and dense and there’s so much to take from it.

Alison Jones:                 Yes, absolutely. Cracking recommendation. Thank you. Now Hassan, if people want to find out more about you more about the books. I was going to say more about Cisco, but maybe, maybe not. I don’t know. Where should they go?

Hassan Osman:             Sure. So there are two places you can go if you’re interested in the short business books for busy managers. I blog on my personal blog, thecouchmanager.com where you can find links to all the books and you can find the links to some of the articles I publish about working remotely and managing. But if you’re interested more in writing a book yourself and the tips that that can help you act, publish your first nonfiction book. You can find me on writerontheside.com or you can just use your podcast app that you’re listening to now, and just plop in Writer on the Side, and it should show up as one of the first top two searches. So I’m definitely happy to share my knowledge there.

Alison Jones:                 Excellent. I’ll put those links up on the show notes. Actually what we didn’t touch on is that you don’t just do business books. You also do travelling with children books too, don’t you? I just don’t know where to end.

Hassan Osman:             Yes, because I travel with my kids every year. And there are parents who don’t have a lot of time to plan. So I wrote short books, one of them is called Rome in a Weekend With Two Kids, London in Weekend With Two Kids, and Paris in a Weekend with two kids. To help busy parents who have no time to plan.

Alison Jones:                 Love that. One day your kids are going to wake up to this, they’re going to grow up and they go, “Wait a minute, where’s our share? Where’s our royalty split here, dad?”

Hassan Osman:             It’s in the will. It’s in the will.

Alison Jones:                 Hassan, it was so great to talk to you today. Thank you for being so generous with your expertise, but also with all those cracking tips that you shared with us. I really appreciate it.

Hassan Osman:             Thank you so much for having me. I really enjoyed this.

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