How I Became a Full-Time Blogger: Reflections on Ten Years of

Ten years ago I wrote the first entry to this blog. Since then, it’s gone from zero to hundreds of thousands of monthly readers, four books, three courses and over a thousand articles. It’s also been my full-time occupation for the last five of those ten years.

Becoming a full-time blogger was little more than a fantasy when I got started. There were a handful of people who were full-time bloggers, but they were the best of the best. It took having a Top-100 blog in the world to even be making a six-figure salary. Needless to say, it wasn’t exactly a well-worn career path to select.

Today, the opportunities are much bigger. I know many people who blog full-time, and many more that are in a position where they could go full-time with just a little work. Nowadays, having a Top-100 blog almost certainly means you’re a media organization, with dozens of employees. Blogging has become serious business.

In this article, I want to share the history of growing this blog from the random typings of a high-school senior into a successful, full-time income. I want to try to share the behind-the-scenes which might not have been obvious, even if you were subscribed to my blog at the time.

I want to do this because starting a blog and writing have done so much for me, that I want to give back. The world needs more writers, not less. We all benefit from having more viewpoints, ideas and experiences shared instead of left silent. If reading this encourages even one person to give writing a shot, I think the world will be better for it.

An Exception to My Usual Policy

I try not to talk about online business too much on this blog. There’s two reasons for that.

First, like films about filmmaking or novels about writing, there’s an excessive tendency for a medium to become self-absorbed. Second, because in the particular case of online business, people’s online businesses increasingly become about teaching other people to start online businesses. The whole thing starts to look like a Ponzi scheme, and while I don’t fault other authors that do it, it’s a temptation I try to avoid.

The truth is, most bloggers don’t make their money selling blogging tips, and so the industry as a whole (while far from perfect) isn’t the pyramid-scheme it can sometimes look like if you venture too far into the self-referential corners of online businesses telling you how to start online businesses.

The 60-Second Highlight Reel

Here’s the quick view of the evolution of this blog as a business over the last ten years:

  • February 2006 – I write the first blog article. My original motivation for starting was to practice writing skills I would need for a piece of interactive software I was working on. The software was a dud, but the writing kept going.
  • May 2006 – I write a 5-part series about changing habits and send the link to Lifehacker. They publish a link and I get my first ever traffic spike.
  • August 2006 – I earn my first dollar with the website. I set up AdSense ads. At the time it was the most common revenue stream for bloggers. The first month’s earnings reach $40. I’m ecstatic.
  • March 2007 – I write the first article about holistic learning, shortly after I write a short free ebook. The feedback shifts the blog from being more generically self-help to learning skills.
  • June 2007 – Based on my experience writing the free ebook, I write, design and illustrate the first ebook I want to sell, How to Change a Habit. I sell about a dozen copies in the first month.
  • February 2008 – I release Learn More, Study Less. This book is more successful, and thanks to a generous review from Leo Babauta, I’m able to earn over $4000 in one month later that summer. The financial bump wouldn’t last, but it convinced me to migrate away from advertising as the main income source for the blog.
  • Later 2008 – I release another ebook, and I’ve now picked up some freelance writing spots, paying $30/article. For some time I’m writing ten, 900-word articles every week.
  • September 2009 – I release my fourth ebook, wanting to build off the success of Learn More, Study Less. It’s a disaster, making less than $500 the first month. (I still think the book is decent, it just had an unfortunate title and marketing.)
  • Late 2009 – I’ve become somewhat disillusioned with the idea that I can make a full-time living out of blogging. It’s been almost four years. I’ve tried a lot of things, but they haven’t worked. I convince myself that I have another year and a half of university, so I’ll keep at it until I graduate, but I may need to come up with a different business idea if I want to become an entrepreneur.
  • January 2010 – I launch Learning on Steroids. Charging $14/month, I restrict the first session to 100 people. Privately, I tell myself that more than 70 sales would be a success, but I’d keep it going as long as we get at least 30 people. It sells out in 33 minutes.
  • March 2010 – Expanding, I launch a second session of Learning on Steroids and add another few hundred people to the program. I’m now earning enough money to plausibly live off of. Although it would be over a year until I graduated and went full-time, this moment made that possible.
  • Late 2010/2011 – I build a larger course and integrate it with Learning on Steroids. This builds on the previous successes. By the time I graduate from university, I’m earning roughly $45,000/year. The decision to go full-time was an easy one since I told myself I’d do it with less than half of that.
  • September 2011 – I start the MIT Challenge. My income drops during this time, but the residual income is still enough to support me until I finish.
  • October 2012 – I launch Learning on Steroids, now for the fifth time, only a month after finishing the MIT Challenge. It’s my most successful launch ever, bringing in almost 1200 new subscribers. The income from the blog is now over six-figures.
  • March 2013 – Cal Newport has just published his career-advice book. We discuss the idea of doing a course about deliberate practice for career skills. We wanted to do a limited pilot with 100 seats. Because my shopping cart doesn’t have capacity restrictions, I need to turn it off manually to stop sales. They come too fast and after only a few minutes of sales we end up with 212 students. Oops.
  • September 2013 – Following the MIT Challenge, Vat and I start the year without English.
  • October 2014 – Services Ltd. is incorporated.
  • November 2014 – Cal and I do another pilot for our deliberate practice course.
  • June 2015 – I launch Learning on Steroids for the last time. Although it continues to sell, each launch is a bit smaller than the one before, signaling that it’s time to move onto fresh ideas.
  • October 2015 – Cal and I open our deliberate practice course, which we’ve named Top Performer. Sales are over double our original expectation. While the continued success of the program remains to be seen, it solidifies a trend in this business from being a one-man operation to a company with a small team. There are now almost a dozen people working in some capacity with the blog, including two people full-time.

The future of the blog remains to be seen. While I’m very happy with the business success, and what it has enabled me to do, just making more and more money doesn’t inspire me. Instead, I hope that this success will help me tackle on more interesting projects like the MIT Challenge.

Lessons Learned from Ten Years of Blogging

Looking over the history of the blog during the last ten years, I think there are a couple lessons to be learned.

1. Things Can Take a (Really) Long Time to Become Successful

Skimming through the highlight-reel of the blog, the first half of it was far from unambiguously successful. On a strictly financial basis, the first few years of the blog were abject failures. Although I was getting traffic and readers at this time, the idea that it took me four years to break the poverty line, often when I was writing ten articles per week, is a sobering fact.

Yet, right after the moment when I had almost given up was when things turned around. Things haven’t been perfectly smooth since then, but from those inauspicious beginnings, the business has not only become quite profitable, but also fairly stable—continuing to provide a full-time income even when I’ve been engaged in non-revenue related projects like the MIT Challenge and the year without English.

2. You Don’t Need to Be an Expert to Start Writing

I started writing as a seventeen year-old, interested in self-improvement. I had no life experience, no credentials, and no reason for people to listen to what I had to say.

But, I built up experience over time. I pushed into a niche (learning and student success) that fit my life experiences more. I read everything I could about learning, memory and productivity, so that I could be more informed on those topics. Doing challenges like the MIT Challenge and year without English gave me a unique perspective to talk about those subjects.

Whatever expertise I may possess today is entirely because of this blog. This blog didn’t become successful because I was an expert. Rather, it was because I wrote this blog, I was pushed to build my knowledge and do interesting things.

3. The Benefits of Writing are Mostly Non-Financial

I’ve focused on the financial aspect of my blogging journey. I’ve done this because it’s a side of the blog I normally avoid writing about, and because it’s also the subject that interests most people who want to eventually become writers full time. It’s lovely to talk about the great experiences that have come from blogging, but those don’t pay the bills.

However, looking back, money was probably the smallest reward from writing. Writing has made me a better person—forcing me to live up to the standards I espouse on this blog. Writing here has been a kind of affirmation for me, stating my goals and values so that I’m forced to live a little closer to my ideal self. While I sometimes fall short, and I do my best to acknowledge those shortcomings, the net result has been making me into a better version of myself.