Sources of Inspiration

A while back, I got a reader question that was extremely short and sweet.  It was, in essence, asking me about success that I’ve enjoyed.  Given that this is a subjective concern and that I wince at the prospect of self promotion (I’ve learned this is probably a matter of being an introvert), I’d rather deflect this and talk about things that have inspired me over the last number of years.  This post is about those sources of inspiration.

First, though, the reader question.

How did you get to where you are?

To answer that properly would require a good bit of introspection of the form, “where, exactly, do I think that I am.”  I’m not really prepared for that, not because I don’t like introspection, but because I’m pretty content with my life in these terms at the moment.  My life suits me well, but I wouldn’t presume to suggest that it suits others well.  This presents me with the challenge of answering the question, but without the typical, self-help template of “here’s what I did as a blueprint, and you can do it too!”

I think what would go better than that is to talk about some serious sources of inspiration over the last several years.  That way, rather than focusing on what particular things I’ve done, I can focus instead on what I’ve been trying to do and why.  This, I feel, will leave you in a better position to evaluate whether you want to understand “where” I am and whether you also want to be there.

In terms of format, I’m going to talk about four books that have helped me formulate and refine my more recent approach to life.  Using a good bit of wisdom from these books, I’ve gone from working as a software engineer to being an independent technologist.  My work is asynchronous, entirely remote (with some travel), and generally varied in nature.  This makes for a fun mix and it lets me live a pretty low key, mobile life.  All of this is no accident.

So, without further ado, here are the books that have contributed significantly to inspiring my choices.  I’ll describe them briefly, and then the impact they had upon my life.  Keep in mind that these are not in chronological order of my reading of them, but rather in the order I think makes sense to introduce them if you’re looking to pursue a similar path to mine.

Being Productive Where You Are

The first book, pictured above, is “Getting Things Done” (fondly called “GTD”).  David Allen wrote this originally about 15 years ago and has, I believe, released a few editions since.  In a nutshell, the book presents a system for, well, getting things done — improving personal productivity.  This read reinforced to me that a lot of my practices were good ideas, and it helped me be a bit more deliberate about some of them.  I did also get some good new ideas out of it.

I’d summarize the highest value take-aways from this as follows.

• Make sure you have a means of capturing everything you think of that comes into your head in the form of “I need to do X.”
• Make sure you have a way to revisit, filter, and manage this list of all of your “I need to do X.”
• Become efficient at decomposing tasks and framing projects in terms of “next discrete action.”

Why is this so important to me?  Simply put, I currently juggle a lot of separate tasks and projects and have done so for years.  Without a ruthlessly efficient system of tracking work, I wouldn’t be able to do many of the things I can.

If this sounds only like a way to guarantee a lot of work, it’s not — it’s also peace of mind.  You know that feeling of, “I’m pretty sure there’s something I should be doing and I can’t think of it, and it’s driving me crazy?”  I don’t.  I’m serious — it’s been years since I’ve had that feeling.  This isn’t to say I always get everything that I want done.  But I don’t ever have that nagging feeling — in spite of the large amount of stuff on my plate, I sleep well at night, free from this sort of stress.

Shipping Something for Yourself

Gaining efficiency using the techniques from GTD will let you carve out more free time to do any number of things.  I would suggest to anyone that they make at least some of those things entrepreneurial.  This doesn’t have to by major in the slightest.  I have, in the past, suggested that people get the experience of shipping something for themselves, even if it only earns them a dollar.  Having at least some tiny corner of the commercial universe all to yourself is powerful.

The Lean Startup, which I actually read twice, is about entrepreneurship and about building your own empire in a sense (though there is also information for so-called “intrapreneurs” that apply these concepts as wage employees within larger companies).  But, in a more core sense, it’s really about applying the scientific method to business as a means of coping with an environment of extreme uncertainty (like that of a startup).

What I took away from this was the idea that you need to just ship stuff and figure out, on the fly, how to adapt.  I was intrigued by the reading here because it helped me realize that there are many paths to a start-up.  As a programmer, it’s easy to think that startups are the thing where you put together business plans and prototypes, and then have grand unveilings to secure massive angel investment capital.  And sure, that happens, but it need not go that way.

A better way, particularly for me, is to build the smallest, cheapest thing that will prove or disprove whether you have a path to profitability (the iconic “MVP”).  You take the learning you get from that exercise, in whatever form it comes, and let it guide your next actions.  Make observations, form a hypotheses, test the hypotheses, use the results to repeat.  That’s how to get involved in the hustle.

Realizing that Extroversion isn’t the “Right” Answer

Becoming efficient and aware of ways to make money outside of the standard 9-5 job contributed heavily to my current situation, allowing me at first to moonlight and then to define new ways of earning a living.  But, in parallel to that, I was figuring out a bit about my own work preferences.  I was also grappling with how wrong, apparently, I was in what I preferred.  In a world that is increasingly open plan office spaces, daily touchpoints, highly collaborative, and generally seeming to be fueled by Red Bull, I was dismayed to find myself preferring long stretches of quiet and solitude for getting serious work done.  I knew that the right thing to do was to force myself to work in and adapt to these situations, but it was always tiring, and I’d wind up staying at the office long after everyone else left so that I could have a few effective hours to do my work.

Then I read Quiet, and, for the first time, entertained the idea that my introversion was not some sort of inherent personality defect.  In the book, Susan Cain talks about the so-called “Extrovert Ideal” and about how since the early 1900s and the era of the salesman, extroversion somehow became “the right answer” and introversion a personality defect.  I also took to heart her suggestion that this makes no intrinsic sense whatsoever.

This was important to me because it shifted my mindset.  As my work was increasingly remote, autonomous and independent, I had been feeling guilty and slightly ashamed, almost as if I were indulging laziness rather than a preference for an environment where I worked most effectively.  This book helped me kick my introvert guilt once and for all and take pride in having a work arrangement where I work hard and do a lot of quiet contemplating and producing.  Sitting in meetings all day and non-stop collaboration is not a character building exercise that I should always strive for — it’s a source of inefficiency, when the interactions are not targeted and tactical.

Taking Pride in the Non-Traditional

One might say that the three previous sections all culminated for me in The 4 Hour Work Week, and there might be a certain irony to that.  Whereas the other books are sober treatments that one might expect in books cataloging and suggesting improvements for the work condition, Tim Ferriss’ work was… not quite that.  It was certainly loaded with information and instructional, but it was also flashy, showy, and pretty salesman-y (or, at least, I’ll call it “pitch heavy.”)

But if you set that aside, it’s also revolutionary in the sense that it’s a guide for how to hack your life to be exactly what you want (he calls this “lifestyle design.”)  This book has the kind of information that you’d find in GTD, where he stresses becoming more efficient.  But he suggests you do that so that you can persuade bosses to let you work at home or so that you can automate a lot of the work that you do.  Similarly, there might be overlap with the Lean Startup, but only inasmuch as boot-strapping and cheaply learning about building a product will facilitate a life of options.  And Quiet?  Well, I doubt Tim Ferriss is an introvert (though I have no idea, in earnest), but I definitely know that he would support minimizing meetings and working remotely.

The 4 Hour Work Week brought me to a whole new level of non-apology for my life.  I had already managed to veer away 9-5 wage employment, but, as with the hermit-like style of work, I felt as though I were somehow cheating or taking shortcuts.  After all, is it really fair that I often work from a hammock during the summer when others have to attend compliance training meetings and wear khakis?

But there it is, right there, on his cover — a person in a hammock.  I was pleased to find kind of a whole community of “lifestyle design” types out there deliberately doing things that I had stumbled upon.  I went from viewing this as questionable to becoming increasingly convinced that this is the future of knowledge work.

And So, Here I Am

My life has followed an interesting series of twists and turns, and I obviously can’t simply credit a handful of books for all of those or for my current position.  But I do think these books were both extremely formative for my thinking and also representative of it in retrospect.  I also highly recommend all of them, of course.

My path is an unusual one, which might mean it’s not for you.  I travel a lot and go for long, highly non-collaborative stretches where I’m writing, building prototypes, or doing intense analysis.  Sometimes that means I miss camaraderie and collaboration.  Sometimes I miss the steady paycheck and dependability of wage work.  And I’ll probably never work my way up to be an important figure in a major corporation, nor will I ever probably build a startup empire.  But, that’s all okay with me.  It leaves me with the freedom on a random weekday to decide it’s nice out, close my laptop, and go kayaking for a while without giving a heads up about anything to anyone.