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American View: What’s the write thing to do with your downtime?

One of the most impactful compliments I’ve ever received is “you should write a book!” I’d been told that once or twice as a younger man, but it didn’t really hit home until February of 2014.

One of the most impactful compliments I’ve ever received is “you should write a book!” I’d been told that once or twice as a younger man, but it didn’t really hit home until February of 2014. I’d just finished delivering my cybercrime presentation at The European Information Security Summit and was chatting with attendees in the conference centre. Three different CXO types all told me, “You should write a book!” and I took that to heart. 

 

I spent most of my London-to-Dallas flight home pondering what to write about. Should I try fiction? Non-fiction? Should I be serious? Snarky? What could I write that people would pay to read? Somewhere over the Midwest I realised that was the wrong question. I’d signed on to be a columnist for Business Technology – Business Reporter’s sister brand – because I wanted to help people … That is, I wanted to advise readers how to survive and thrive in the inherently awful business world. I wasn’t devoting my weekends to this endeavour to get rich; I was trying to make people’s lives better through my entertaining tales of working life.  

 

From there, moving from “you should” to “I am” it was a simple matter of deciding topics. I already had an armoury full of published columns to draw on. What if I assembled pieces that spoke to a specific topic then added additional commentary to tie all the stories together? Forget staring as a blank sheet of paper until inspiration struck. I already had the motivation and momentum. [feel free to play a supervillain laugh sound file here] 

 

My first topic was IT-sector interviewing. I’d endured so many awful interviews – on both sides of the table! – that savvy interviewing was the topic I’d been asked about more than any other by the friends and colleagues I’d mentored. I reckoned that since everyone was bad at interviewing, it was the most important working life issue to try and improve. I self-published my first book --Why Are You Here?: A Curmudgeon’s Guide to IT Interviewing  -- six months later in August 2014. Over the next three years, I gifted copies of WAYH? To three of my co-workers. All three of those folks went on to secure much better gigs and credited my advice from WAYH? as the deciding factor in their selection. That was all I needed to hear. 

I reckon it was like finding the first gold nugget in the stream. You focus on the positives and forget all the dreary hours of failure.

Encouraged, I took advantage of being laid off (again) to devote my “free” time to write my second book: High Tea Leadership: Leading IT Teams in Non-Tech Organisations. It’s theme is clearly declared in the title: how do you succeed running the IT function in a business that (a) needs you but (b) doesn’t understand what you do? I wrote HTL for two reasons: (a) because I knew a lot of people stuck in that situation, and (b) because I had a narrow window to get this manuscript printed.  

 

To be clear, I didn’t (and still don’t) have a publisher. I’m a scrappy part-time columnist from Texas, not a bestselling author or industry sector celebrity like my idols Geoff White and Jenny Radcliffe. I kept my expectations reasonable: HTL would maybe sell a few physical copies to friends and family. Success for the print version would come during my next make-or-break interview.  

 

Sure enough, in February of 2016, during my last interview for a GRC contractor position, the sceptical VP running the team bluntly demanded to know if I had any meaningful experience in program management. I smiled and laconically replied “Well, I’ve written a book about that” and dropped a print copy of HTL face up on the VP’s desk. From the man’s dumbfounded expression you’d have thought I’d shot him. That stunt tipped the balance and got me the job. The $4k I spent on the print run became $100k in contractor pay and later transitioned into a salaried employee position. Worth every penny. 

 

My third book -- In Bob We Trust: Lessons Learned from Terrible Bosses – has remained my most popular work since it went live in September of 2015. IBWT is an sardonic analysis of twelve different crap supervisor archetypes with the intent of exploring why they acted the way they did and how the reader can survive someone like them. As an aside, I’d been giving all my real subjects the pseudonym “Bob” in my columns to avoid revealing their identities. Sharing the stories and their lessons was the point; naming-and-shaming wasn’t … so, “Bob.” I swear I hadn’t heard of internet film critic Bob Chipman or his “In Bob We Trust video essay series until way later. Sorry, Bob; love your stuff.  

I/m confident there’s no risk of brand confusion, but still … Yikes!

My next two books carried on where IBWT ended. Lost Allusions: Making Sense of Dysfunctional Company Cultures explores how and why poor leaders create bad working environments and vice versa. It went live in April of 2016. Part of its appeal was that every chapter was built around an allusion to a link to a book, film, or other piece of art (hence the title) (which, in turn, was an allusion to Honoré de Balzac’s novel Lost Illusions). 

 

Eight months later, the conclusion to my informal trilogy -- Office Cowboys: Cautionary Tales from the Cubicle Frontier -- came out. Like IBWT, OC is a compendium of awful boss stories, but it focused mainly on bullies and how to survive them. I devote an entire third of the work to a profile of a bully so odious that he earned a unique non-Bob pseudonym: he got the name Mongo, after the character from Mel Brooks’ masterpiece Blazing Saddles

 

After OC posted I shifted my focus to making my five eBooks available in audiobook form. Several of my readers had told me they would rather listen to my books while commuting or working out, so … sure! Between February 2017 and November 2020, my old college and Army buddy Jack Nolan and I made it happen. They’re all available, so if you have unused Audible credits gathering digital dust, why not give one of my books a try? 

 

My last two eBooks were one-offs. While seemingly universal, the truth is that I wrote each book for just one person. In July of 2018, a recruiter buddy at the contracting agency TEKsystems asked to pick my brain about the security awareness career field. He had a role to fill but didn’t know enough about the profession to confidently evaluate his slate of candidates. I met him at our usual pub and gave him a free three-hour class on the subject. The next day, I typed up my advice and published it as Hiring Security Awareness People: A Practical Guide for Leaders and Recruiters. Then I gifted the eBook to my recruiter buddy so he wouldn’t have to work from memory.  

 

My second one-off book took a lot longer to write. One of my best mates was preparing to separate from the military and was rightfully concerned about negative bias towards former squaddies in corporate America. In March of 2019 I published Hiring "Forever War" Veterans: Myths, Misconceptions, Misunderstanding … This extended argument for hiring combat veterans is meant to help all ex-squaddies by persuading supervisors, recruiters, and hiring managers to reconsider the negative stories they’ve heard so that every applicant gets a fair chance. It didn’t start out as a crusade to mitigate discrimination industry-wide; it started as a way to help one mate get hired in the civilian sector.  

Most of the veterans I know would do anything to help a brother- or sister-in-arms. Even calling out the FORTUNE 500 for their smug hypocrisy time and again.

If all this seems like a massive investment of time, funds, and sanity you’re absolutely correct. There’s no possible way to justify this effort on financial grounds. All told, I think I’ve invested $8,5k of my savings in this “hobby.” That’s $4k for HTL’s printing and another $4k for IBWT. The latter got a small print run in 2017, and I still have most of them. Looking back on all my sales through all formats and channels, I’ve made back less than $500 of that investment and that’s okay! Sure, I’d enjoy getting signed by a publishing house so my stuff could get some real exposure (and maybe bring in some revenue). That would be cool … but that’s never been the point. I write these columns and the books that they evolve into exclusively to help people.  

 

Back in 2015 when I was working at Verizon Enterprise, my pal Blake read a few of BR columns and told me one morning that I should write a book. I laughed and showed him that I had … WAYH? and HTL were active. Blake bought both and discussed the stories from them with me over coffee every day for weeks. Not long after, our department was dissolved in an organisational restructuring and 90% of us were laid off, Blake included. Perfectly normal corpo behaviour.  

 

The thing is, Blake was the first of us to score a new gig. I met him at our favourite pub that night to celebrate his success. Blake was ecstatic, as you’d expect, but he was also deeply grateful: the techniques he’d learned by reading WAYH?, Blake said, had won him the gig. As a career coder, he’d always been awkward in interviews. After internalising my advice, he killed it with this new employer.  

So, again: was it all worth it? You’re danged right it was! Blake’s success alone made my massive “hobby” worth every keystroke and typo. I firmly believe that helping others survive this insane existence is a moral imperative. It is for me, anyway. Getting to by snarky while doing it is just a fringe benefit. That’s why I tell folks that they don’t have to buy my books. I don’t mean by that that they should pirate them … Instead, I mean that I’ll gift my eBooks to them. If they like what they read, then all I ask is they consider gifting a copy to someone else. 

That’s why I’m here every Tuesday. Hope to see you here again on the 24th.  

Business Reporter

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