Lessons Learned After One Year of Writing

12 months gone, over 800 articles written, more than 30 podcasts recorded, and too many new friends to count.

With one lesson for each month, here's some of the most fundamental things I've gotten wrong, observed, and learned over the past year.


November, 2011: Be Humble

Accepting your position as an inexperienced newcomer is of the utmost importance.

Feigning superiority or believing your introduction represents the next tidal shift in technology writing will inevitably result in unpopularity.

Instead, you must ask questions and, more importantly, observe and listen to the wisdom of people with experience.

Emulating the path of successful people is an effort in futility, but, if you seek to simply comprehend the psychology and methodology beneath each successful person’s digital demeanor, you will learn a lot.

From this vantage point, you will make friends, you will endear yourself to the reader, and you will learn to humbly plot a trajectory for your writing.


December, 2011: Ignore the Numbers, Just Write

The decision to write online should not stem from a desire for fame or praise. Rather, a personal weblog should represent the development of a sincere wish to share your thoughts with other like-minded people.

Unfortunately, in the earliest moments of this genesis, few people will take the time to read your writing.

In an industry characterized and shaped by statistics, it’s extraordinarily easy to succumb to the lure of uninspired content and page view-driven nonsense. But, as you will come to realize, such content-spewing publications are of little long-term interest to the discerning reader.

And, in a time during which long-form content is making a welcome return to popularity, it’s the intellectual, patient, and thoughtful writers who stand to make the greatest profit.

So, in those early days, as so few people are visiting your weblog, do not be disheartened and do not succumb to producing soulless content. Leverage those quiet days and weeks to develop your voice.

If you write with conviction, readers will come. That’s as simple as it is.


January, 2012: The Importance of People

Although the life of a writer is frequently resigned to sitting quietly alone, it’s important to remember that there are tens, hundreds, and thousands of others in the same situation.

Engaging with the people of the industry in which you have chosen to reside and work is of pivotal significance in your path toward success.

Visit conferences, reach out to local writers and journalists, and schedule lunches. Garner columns in lifestyle magazines, speak on podcasts, and email other people as frequently as you can bear.

Perhaps you are working for your personal success and yours alone, but I daresay you will not find it without socializing, appreciating, and harmonizing with the people you are competing with, regardless of how friendly the competition may be.

In essence, you must nurture curiosity not only with your subject matter, but also with the people who comprise your community. Without that contextual knowledge, you will not be able to gauge any success you might enjoy.


February, 2012: Ignore the Negativity Around You

Upon reaching some semblance of popular awareness within your community, your opinions, ethics, and motivations will come under microscopic scrutiny. Onlookers will query your intentions, writers will dismiss your conclusions, and anonymous individuals from across the ethereal landscapes of Twitter and App.net will feel entitled to decry your best work.

For some, this gauntlet catalyzes a self-defense mechanism wherein the individual feels righteous to engage, defend, and swipe at those who choose to deride them. For others, negative responses serve to dishearten and undermine the goodness of writing.

For me, the best course of action is much more moderate. Negative responses are certainly upsetting, but they mustn’t be taken to heart. Barring the sole exception of intelligent criticism and thoughtful suggestion, I simply do not engage with those who seek to undermine my work.

At its core, writing is an intensely personal act. Thus, when self-publishing a stream of personal responses to news, media, design, and whatnot, you mustn’t allow your writing to be polluted with the goals, rules, and personalities that others wish to inflict upon you.

So, on the day when you are questioned by a renowned personality online, you mustn’t flinch. Justify your beliefs and conclusions, but do it in a measured, thoughtful, and friendly manner.

Disagreement does not necessarily translate to dismissal and it should not be considered in the same vein as Twitter tirades made under the guise of anonymity.

Stay true to yourself, engage with those deserving of your thoughts, and pay no mind to those who wish to mindlessly hurt you.


March, 2012: Be Yourself, Be Respectful, And Earn Your Place

Despite the fact that writing is an “intensely personal act,” there is a tendency to mimic tried-and-true writing methodologies online. There’s certainly something to be said for the success of John Gruber’s link-list weblog format, but that is not to say that it is the best methodology in self-publishing.

In many respects, link-lists have engendered a mundanity in the broader technology community. Rather than contributing thoughtful commentary, regardless of word count, many have appropriated the format as a means for crude, quick, and pointless posting.

John Gruber and Jim Dalrymple may post as little as one word when commenting on an article, but, due to the critical mass of their respective readerships, these statements carry far more meaning than they would otherwise. Gruber and Dalrymple, in their years of experience, have imparted and infused their personalities into their digital identities. We, as readers, know how each writer feels about a given topic, thus rendering shortened commentary to be truly meaningful. A “yep” from Jim is not an instance of careless contribution, but a well-known and oft-admired feat of respect, wisdom, and knowledge.

For all of this, the lesson learned is that you must earn your own voice and personality online, and the best road to this is not typically uncovered by emulating the success of others. Have and nurture the confidence to operate and write in your own personal fashion.

Introduce recurring articles, question the status quo, and write in a manner befitting your tone, intellect, and desire. Regurgitating articles and offering a sentence of commentary is utterly meaningless without defining your own position and personality as a writer.

Treat your writing, your readers, and your weblog with respect. Embrace the fact that your independent outlet is most certainly not a large-scale news website. There is no need to rush, nor are there any standards you must meet outside of your own.

Be unafraid to unabashedly write and operate as yourself and nothing more.


April, 2012: Be Patient

Observing the success of independent writers like Shawn Blanc, there is an implacable tendency to feel a sense of self-entitlement. Another writer — one who writes much in the same way as you — is able to make a full-time living out of his writing, so why can’t you do the same?

Perhaps there’s merit to this thought process, but it overlooks two fundamental tenets of successful writing online: time and respect.

Shawn did not simply launch a weblog and then monetize it immediately. For Shawn, it took years of writing and slowly increasing his earnings and readership until his site reached a point of monetary sustenance. And, even then, Shawn did not simply smother his weblog in ads. Instead, Shawn sought to find a new route toward monetizing his writing. In doing so, Shawn pioneered an altogether different way to operate as a full-time writer.

In the months since, dozens of other writers have sought to prematurely replicate Shawn’s success. Operating solely upon the sentiment of entitlement for earning for their writing, these individuals have all suffered a comparable lack of success. Their writing may be phenomenal and their weblogs aesthetically endearing, but they did not allow themselves the patience to wait for the right moment.

Attempting to monetize your writing prematurely is an unattractive thing for your readers. For every attempt you make to squeeze more money from each keystroke you’ve dedicated to your weblog, the more it undermines the goodness of the writing itself.

I would wholeheartedly love to produce my weblog on a full-time basis, but I’m unequivocally aware that any attempt to do so would not only be unsuccessful, but it would also alienate my readers.

The solution is, simply, to embrace patience. Write for the sake of writing, not for romantic visions of full-time self-publishing. Oddly enough, when you cross this psychological threshold, you will find so many more doors will open for you.

While I may not operate my weblog full-time, I am now self-employed, successful, happy, and moving in wonderful new directions. I attribute the entirety of my success herein to writing my weblog in a respectful, patient, and educational way.

For every day that you write, you will learn. For every day that you learn, you will find new opportunities for yourself.

Do not project a reward upon your writing, rather, allow the writing to define the reward for you.


May, 2012: The Ratio of Focus to Distraction

Writing is governed by a ratio of focus to distraction. Without the perfect balance of the two, it becomes increasingly difficult to do your best work.

Typically distractions will come in the form of loud rooms, the allure of laziness, and so on. Sometimes, however, far greater matters will necessitate a move away from writing.

For me, the transition from a corporate employee to a so-called “entrepreneur” was fraught with difficulties. The time coincided with innumerable personal challenges, the largest of which was a significant death in my family.

In this time, I came to question the significance of my writing. Articles became infrequent, my voice became negative, and I became angry at the misery engendered by the flagrant consumerism each weblog encourages.

All of my readers, peers, and friends shifted to contextually bereft puppets touting products, republishing rumors, and expressing rage that their expectations were not sufficiently satiated. The world of writing and thoughtfully considering the nature of innovation and human ingenuity devolved into a mired sty of masturbatory nonsense about the next iPhone or the next version of OS X.

Perhaps the message here is that life will sometimes distract and undermine your work. But, in my eyes, the lesson grew to be that you should allow these moments of stark negativity to inform your writing.

At this point of anger, I was able to uncover a psychological narrative I had been subconsciously dancing around for months. I learned that my weblog need not be a place for re-sharing news and app reviews, but it could be an outlet for the sharing and articulation of context. Rather than mindlessly sharing and supporting opinions of my peers, my tangible life re-shaped my presence online.

From this dark point, I learned my most valuable lesson so far. That is, I learned that real life constitutes much of what it is to be a writer focused upon technology. I learned that there is a nuanced, but endlessly important thread between the tangible and digital worlds.

Perhaps it sounds obvious to you, but I cannot express the importance of this comprehension enough.

Regardless of your chosen subject matter, allow your actual disconnected life to inform your digital world. Do not be afraid to leave your smartphone at home and challenge yourself to comprehend what it is that drives you as a writer. From here, you will discover the purpose and narrative for your writing.


June, 2012: Surround Yourself with Like-Minded People

Although I’ve already spoken to the importance of meeting with the people of your given industry, I did not comprehend how this should be done until mid-2012.

In January, as I visited Macworld, I knew few people and I knew little of how to interact with world-renowned writers and developers. I handed out business cards, as it seemed the thing to do, and I pitched myself to developers in the hope that I might add a few new betas to my otherwise-dormant TestFlight account. Barring the grouping of writers I was able to meet and get along with, the process was altogether unfamiliar and jarring. In fact, by the end of the trip, I spent more of my time visiting bars with friends in San Francisco than I did meeting with members of the technology community in which I was sorely hoping to be a part.

Still, I walked away knowing a core group of people far better than I’d known them beforehand. I set myself up for a great deal more publicity and success. But I didn’t quite know them enough and, more importantly, I had forgotten to truly share my own personality.

In June, visiting WWDC, the environment was different. I didn’t hand out business cards unless they were requested, I met anyone and everyone that I possibly could, and I went out every night with different groups of people. Each morning was mired with intense hangovers and my back was sore from sleeping on a sofa for six nights, but I learned so much more.

Sitting outside a restaurant with Pat Dryburgh, I remember him remarking, “Dude, you’re so much cooler now. What happened?” Although he was (mostly) joking, the sentiment summarized precisely what I learned on that second trip to San Francisco.

That is, when you’re in and amongst the people of your industry, you are amidst your psychological home. The people around you share in the same joys and passions that you do, and all are in the same business. Where your actual home may be hostile to entrepreneurial endeavors or tech-centric philosophies, events like WWDC are ripe with people that are fascinated with who you are and what you do.

So, when you find yourself in that environment — as unfamiliar as it may be — do not shy away from your personality. Do not obscure your passions and your flagrant nerdery for the sake of typical sociability. Instead, you must allow your true self to emerge.

Although I’ve ostensibly considered each visit to San Francisco a business trip, I’ve always left the city more rejuvenated and impassioned than I’ve ever left a restful holiday.

Even if its for a fleeting time, surrounding yourself with like-minded people is of the utmost importance to understanding your true identity. In this friendly environment, you can explore who you really are and who you wish to be.

Beyond the obvious catharsis, you will walk away confident, passionate, and fundamentally optimistic. And that’s an invaluable thing.


July, 2012: Be Comfortable with Silence

Publishing your own independent weblog removes you from the rat race for page views and headlines. Thus, in the summer months, the simple advice to remember is that you need not fill the silent void of news with inane content. For each piece of pointless content you share, the fewer people will be there for when the news returns to its quicker pace in the fall months.


August, 2012: Non-Traditional Profit

In mid-August, I joined the chief executive of a large European venture capital firm for breakfast in Knightsbridge, London. Somewhat nervous to meet with such a high-ranking gentleman, I was immediately disarmed when he unabashedly stated, “I hadn’t realized I was having lunch with an Internet celebrity.”

Although I’m certainly not an “Internet celebrity,” the sentiment he had expressed was one I’ve become increasingly familiar with. That is, although my weblog is still in its infancy, the mere fact that I write and engage with a community of intellectuals online is of great significance to businesspeople in various industries.

Whilst I do not earn much from my weblog, my podcast, or the various columns and magazines I contribute to, I have earned an enormous amount of credibility. Considering I am now self-employed and am just past twenty-four years old, any shred of support and credibility is invaluable to my business.

Writing online has satiated a passion for industry commentary, analysis, and creativity which my life was sorely lacking. I write purely for the sake of writing, and it’s a genuine privilege that people choose to read and consider my thoughts. But, more than that, my writing has profited me in a great many indirect fashions — all for which I am endlessly grateful.

Producing a weblog is, at the end of the day, an entrepreneurial endeavor. Whether you like to admit it or not, if you’re independently writing online, you’re in the business of growing your personal brand, identity, and so on. Whilst it may take years before this writing is profitable enough to rely upon as a sole means for income, it immediately begins to open doors and profit you in far more ways than you might’ve otherwise imagined.

I certainly do not mean to encourage people to callously begin commenting on technology news for the sake of personal gain, but I mean to provide a glimpse of the light at the end of the tunnel. I’m very far away from gaining true success with my weblog, but, on the way toward it, I’ve learned and gained far more than I would’ve ever hoped.

Whether it’s the friends, colleagues, and peers I’ve gained, or the business opportunities my writing has served as a foundation for, my year-old website provides a very great deal for me. Perhaps, in an ideal world, I might write full-time. But, for now, I have a very real medium through which I can meet and learn more.

Thus, whenever I see people offering resoundingly negative reflections on the lack of money in online writing, I cannot help but feel somewhat upset. Perhaps there is little money, but that is not the only source of profit you can elicit from writing. Nor should it be the focus of it.

Anything you earn whilst writing — be it money, friends, connections, or otherwise — is a gift that you would not have had otherwise. To embrace an attitude of self-entitlement and demand more is not only excessive, but it is rather embarrassing.

The lesson is that pursuing things you are passionate about and enjoy will inevitably benefit you in an astounding manner. But, if you choose to pre-define the shape of these gains, you will find yourself disappointed and disillusioned.

Enjoy a sense of blind optimism and write for the sake of writing. You will unquestionably be rewarded for doing so.


September, 2012: Mindful Commentary and Sharing

Whilst you must resist the tendency to fill the news void in the summer months, it’s important not to feel responsible to write about every item of news in the busier ones. There will be an enormous quantity of relevant and interesting news to comment upon, but that shouldn’t require you to write about each of them.

Writing independently requires a certain level of responsibility to your readers, wherein it’s ill-advised to link to precisely the same content that they are. John Gruber, for instance, is often the object of rampant and repetitive linking from independent writers. This process offers little in the way of value to the reader.

In the busiest months, writing unique content is perhaps the best route toward sustained relevance. Contemplating the larger meaning of a product announcement is far more interesting than simply posting images of a new iPhone.

Avoid being swept up in the hype around the products of others and remain focused upon producing the best product you can possibly produce yourself.


October, 2012: Avoiding Personality Cults

There is a sad propensity in the technology community toward mindlessly endorsing those who have already found success. Rather than finding the best writing possible, people gravitate towards the bigger names in the hope that they might be swept up in the popularity.

The trend is embarrassingly easy to observe. Marco Arment, for instance, might write an article of cutting analysis and insight. And then, literally moments later, a brief comment will appear beneath a block quote on another website.

The block quote will frequently be taken from the concluding paragraph and the ensuing commentary will be little more than a sentence of vapid agreement.

Beyond the obvious lack of tact and self-control this behavior demonstrates, it has repeatedly led me to unsubscribe from a weblog. I simply do not wish to read self-serving links written in the hope of gleaning a glimpse of glory. It’s unbecoming of a writer, it does no justice to the source content, and it’s embarrassing for all to see.

Moreover, for those who make the argument that you should not re-hash an article if someone else has already written it, that’s absolute nonsense. You should write whatever you wish to write and whatever you believe might be of value to your audience. At no point should the matter of “bigger personalities” come into play.

The number of Twitter followers and page views you have is not some sort of gauge for intelligence or popularity. You could have far fewer page views than another website, but be far more popular with the readers that you do have than the other.

The lesson is simple, you mustn’t write and share content for anything other than a sincere sense of interest. If you’re sharing an article due to the personality cult surrounding a person, decrying a product you’ve never tried, mindlessly nodding your head without reading the text, or feigning intelligence about something you do not comprehend, you should stop immediately.

People value your personality and input online for your thoughts, not for your agreement. Have pride in that.


November, 2012: Gratitude

One year later, the trajectory of my weblog continues to rise. And, for that, I am thankful.

I feel honored to receive emails, Tweets, and links of endorsement, and I feel driven to continue working.

More than anything else, though, I appreciate the support of the people in the community. There are some phenomenal writers, developers, and businesspeople out there, and I highly recommend reaching out to them whenever you have a chance.

Thank you for reading.