The peak of my writing career, in terms of productivity, likely occurred in the summer of 2012. I don’t remember the reasoning, but I wrote four different 20-25 page PDF guides in a single week.1 For you college kids out there, that’s like four different 5000-word term papers all in the same week. About a month later, I wrote my (now-retired) long-term travel course (about 200 pages) in three weeks flat. I was a machine.

Looking back, I’m kind of in awe, not just of the sheer hours or output, but rather my ability to just unabashedly lay out my thoughts without any second guessing of the validity or utility of those thoughts.

In hindsight, I’m less impressed by my own work ethic and more impressed by my audacity to assume that I could somehow be an expert on all of these topics at once, in such a short period of time.

The philosopher Bertrand Russell has a quote that I like that goes something like, “The problem in the world is that the people who know a lot are so full of doubt, and the people who know little are so certain of themselves.”

One thing I’ve experienced over the years is that the more I come to learn about human psychology, personal development and culture, the more I experience the pangs of, “Who am I to say this?”

I wouldn’t be able to write those guides in a week today for the simple reason that most of what initially came out in those drafts, I would stop myself and say, “Is this really that useful?” or “Am I sure about this?” or “Do I actually know what I’m talking about?” And the answer, had I asked these questions then, would have often been “no.” But I didn’t care. I soldiered through anyway.

Those guides were eventually removed from the site (because they were bad) or were heavily revised and re-written into what they are today. So they’re up to snuff now.

But I still look back with a strange kind of envy for the creative advantages my ignorance/arrogance gave me back then – it made me so certain of myself that I was able to just write freely, under the assumption that any idea in my head must be somehow unique or useful, when most of them were neither.

As my career has gone on, it’s become increasingly more difficult to produce content. One reason is what I previously described: each year, my standard for the quality of my own work moves higher, thus making it that much harder to produce work that meets my own criteria.

Another reason is that a lot of my writing over the years, particularly in the realm of self-development has been motivated mostly by how fucked up I myself have been.

I’ve always asserted that I don’t write what I write because I think I’m some guru with all the answers, but rather because these are things I’ve struggled with myself, and writing out my process in coping with my issues has been a way to help myself first, and help others second.

In a sense, my writing has been my own little public form of therapy for many years now.

The problem is though, the more I write, the more problems I resolve for myself, the happier and more mature I become, the less shit I have to write about!

It’s like when you first start going to a therapist, an hour doesn’t feel like enough time to dig into all of your hurt and problems. So you go back, again and again. I remember when I started therapy, I went three times the first week.

Then, years later, you show up and you realize you have little or nothing to say anymore. Everything is resolved and so there’s little else to talk about.

I feel like I may be reaching this point with my writing about personal development. I’ve resolved a lot of these issues in myself and I’m in a very happy and confident place in my life. Therefore, I sometimes strain to write about these topics in new or interesting ways. Either that, or I begin to feel as though I’m repeating myself.

Then, of course, there’s simply getting older and the increasing lack of novelty.

Blogging used to be a novel experience. Getting reader comments and emails used to be novel. Posting on social media and waiting anxiously to see if people liked it or not used to consume a lot of mental and emotional energy.

But like anything, after 10+ years, this job becomes routine and often repetitive. Every week when I sit down to write, I confront the same old struggles and mental hurdles I’ve been facing for a decade now. And whereas that struggle used to feel dramatic and epic in scale, now it just feels familiar and sometimes tiresome.

This is not a complaint, by the way. I suppose it’s simply an observation: everything – absolutely everything – if done for long enough, becomes a bit of a grind. And like anybody who is about 10 years into their career, the challenges shift away from confronting the newness to learning to abide by the oldness.

Or to put it in a slightly ironic way, what seemed so special and romantic about this writing 10 years ago, turned out to be exactly what most people in their 30s start to feel about their career – routine, repetitiveness, and sometimes boredom.

It makes me think that maybe more human experiences are universal than we suspect. And much of the time and energy we put into being special unique little snowflakes and doing such unique and interesting things doesn’t result in much difference. And most of the effort is simply for the sake of ourselves and our own need to feel special.

Which comes back to my own ignorance 10 years ago. I was so dead-set on avoiding the
dreaded 9-to-5 life. I wanted to make a career out of something that would avoid such repetitiveness. Yet, here I am, doing the same thing day after day, week after week, for almost 10 years straight. The irony makes me smile. Once again, I discover, I am not so special after all.

As for the future, I’m taking it upon myself this year to find new ways to challenge myself in my writing. I find myself gravitating more towards narrative, and even dabbling a bit in fiction. That challenge for myself is of the utmost importance in the creative process. Because without the challenge, I lose interest. And if the author ever loses interest in the writing, then the reader certainly will as well.


  1. The topics were: Happiness, Courage, Wealth, and Dating. Much of the material has been adapted into the four PDFs I send out to subscribers today.