#NationalFreelancersDay special – six books that helped me go freelance in 2021

Maybe I’d like to say that deciding to go freelance this year was a spontaneous decision – maybe I’d like to have a “eureka” story to tell at parties. But things are rarely scripted this neatly. Today is National Freelancers Day – my day, as of 3 weeks ago. I want to share six books with you. They helped me make the switch to freelance living this year. Who knows what they will do for you?

0. How to use this list

With a pinch of salt, preferably.

These books won’t give you all you need to become a successful freelancer. They talk of mindsets and values, ideas and ideals – rarely getting into the nitty-gritty of what makes your freelance day “click”. There are plenty of these guides out there, and plenty more wonderful people around you who, I’m sure, would love to help with that.

The list is written in chronological order – starting from the books I read first. This means that many of them may not have aged too well.

And, of course, the list isn’t complete. Is it reasonable to expect another list next year, detailing all the books which made Vic go back to a 9-5 job? Sure, it’s possible 🙂 For now, here are the six books which made me feel better about the freelancing decision.

1. Jay Conrad Levinson, “Guerrilla Marketing”

My edition was a quirky Polish translation which I bought when I was still a student. That must have been close to twenty years ago. This book is still on my shelf.

The term “guerrilla marketing” has evolved in the meantime – and it’s since often been “borrowed” by big corporations to add a flashy label to some perfectly run-of-the-mill marketing activities. Obviously, the world has changed, too – the “brand new world” of digital marketing, which my edition was only beginning to excitedly depict, has since solidified into a predictable, safe landscape.

But I keep coming back to this book, and there’s a good reason: it’s chock-full of attitude. The passage of time and the inadequacies of translation have done nothing to blunt the book’s caffeinated, contagious optimism.

Every page of this book bombards you with ideas and examples. Every section shows you that you don’t need the big guys’ marketing budgets to make an impact – and that your nimbleness is an asset. This hasn’t changed, and the book still gives me the (precisely targeted) kick up the asset when I need it.

2. Tim Ferriss, “The 4-Hour Workweek”

When this book came out in 2007, Facebook was three years old; “The Office” (US version) was barely two; the iPhone had just been launched the same year; and yours truly was two years into an ELT teaching/translating career. “Simpler times” doesn’t begin to describe it.

This means that parts of this book didn’t age well. For this, I am grateful. It’s fair to say that 4HWW was trying hard to sell a vision of white, male Western privilege which depended – and still depends – on cruel maths: 1 dollar buys you a vastly different life in less fortunate countries. It’s an eclectic mix of sales techniques, communication strategies, time management, iffy science and watered-down philosophy. Calling it a “system” is overkill after 14 years – if, indeed, it ever was a system at all. But it still deserves a place on my list.

Ferriss’ book helped me develop a habit of negotiating, testing, and (re)designing the way I wanted to live my life. It helped me realise what is negotiable, what is important – and what is possible. Crucially, even when I first read it back then, it already helped me understand my privilege a bit better – and use it a bit more sensibly.

3. Seth Godin, “The Dip”

I wrote about this book elsewhere already, so I won’t repeat myself too much; I’m keen to get to non-white-dudes on this list soon. “A little book that teaches you when to quit (and when to stick)” – this was exactly what it did for me.

When I first read it, I was mid-way through the ELT teaching adventure (although I didn’t know it yet). I was wondering whether making the move from CELTA to DELTA was worth it. Was this how I wanted to invest my time and money?

“The Dip” helped me make the decision – by showing me that the pricey eight-week boot camp of DELTA was there for a reason, and could become my Dip, with rewards waiting on the other side if I decided to stick. This bit of it came true – and so did the quitting portion of the book. It’s taking some time to make the sticking and the quitting truly my own, but I think I’m getting there now.

4. bell hooks, “Teaching to Transgress”

It’s difficult to describe exactly what this book did to me. This was my introduction to bell hooks, and – by proxy – to Paulo Freire. These two writers were to bring me back to the type of reading and writing which I’d almost forgotten existed: urgent, brave, questioning writing. This time, it was about learning, and teaching, and education, and language, and love.

I read bell hooks when I was already working in educational publishing. Her chapter on “Language” was haunting and ruthless. I kept coming back to it. I kept comparing her point of view with one company policy after another – with the strategy meetings; the publishing plans; the editorial decisions.

There are many ways to teach, learn, use languages. There are many ideas for what language could do – if we allowed it. The vision in bell hooks’ chapter remains one of the more daring, uncompromising lists of demands for what language should do. There’s no easy way to say it: working in-house, I felt like nothing I did could ever come close to helping it become a reality. Maybe I’ve gone freelance to rid myself of that particular excuse?

5. Nathalie Olah, “Steal As Much As You Can”

“Where are all the new punk bands?”

I used to ask this question a lot in the days that followed 2016. Where’s all the rage? Where’s the resistance, the middle-finger attitude to the parade of bad news? It took me a long time to figure out where to look for these.

Nathalie Olah’s book is a discussion of “How to win the culture wars in an age of austerity”. The examples she cites, and the elements of historical background she presents, are definitely UK-centric. But the attitude applies in many other places, too – and it did so even before the pandemic.

There are many good things this book can help you do, and much of is is not as incendiary as the title would have you believe. For me, the best part of the book was the chapter titled “The Problem with Impostor Syndrome” – when I was reading it, I was already at a stage when I was managing other people. This book helped me understand the mis-match between what publishing tells you it wants for you, and what it actually wants to do with you. Further teachings, courtesy of Covid and Niamh Mulvey, were to follow.

The new punk bands/books/movements exist. The rage is still there. It was good to find it, and “Steal As Much As You Can” was a fittingly-named stage on my way there. I realise that I’m not the intended recipient for much of this book any more – the above is what I got from it, and it’s my list, so that’s what goes on here!

6. Katy Milkman, “How to Change”

Let’s end on a positive note!

I’m still making my way through this book, but I already know it deserves to be on this list. Katy Milkman’s work spans behavioural economics and psychology, and her research career saw her work on projects with Angela Duckworth, Google CEOs, and many other household names when it comes to productivity.

For all that, though, “How to Change” is still the book you quietly wish it would be: helpful, warm, and actionable. It takes you through the science of behaviour change, but never loses sight of the human in the middle. All the research is only worth something if you actually get to benefit from it – with Milkman’s book, you actually have a chance to do it again.

This isn’t a book which “changed my life”, in that I’m still me – chaotic, lazy, motivated by weird things like coffee and bikes. “How to Change” isn’t about a revolution. It’s about finding the way to let your context, your background, and your personal history work with you, not against you.

Happy Freelancers Day, everyone!

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(Disclaimer: three good things happen if you buy a book through the links in this post. You support independent bookshops through Bookshop.org, you DON’T support Amazon, and I may get a cut through the affiliate link – at no extra cost to you.)

(Photo by Shridhar Gupta on Unsplash)