Anniversary post: what I've learned in two years of blogging full time

How time flies. It's been an entire year since I wrote my first anniversary post, about your economy, which means I must be due for another post commemorating my second year of working for myself — and working for you!

If my first anniversary post was a retrospective on how I came to be where I am, then I want to use this post to reflect on everything I've learned in the two years since I left graduate school and started blogging full time.

Lesson: the world is hungry for quality content, because there is almost no visible supply

I started this website because, after a year or so of reading FlyerTalk and visiting the most popular travel hacking blogs, I realized that it was almost impossible to find answers to the simple question: "how does it really work?"

The people who knew were too busy promoting their credit card affiliate links, and the people who didn't know weren't curious enough to ask the right questions. But I was curious, so I started investigating and writing about how loyalty programs work in practice.

For example, how do refunds from US Bank Flexperks redemptions work? There's only one place on the web to find out.

And of course, once you spend any time at all sincerely investigating how loyalty and rewards programs work in practice, you invariably stumble over unadvertised opportunities to save money or get outsized value from them.

If you have something good and true to say, and it's not being said elsewhere, you're likely to be able to find an audience of people eager to listen.

Lesson: changing minds is impossible

My goal in my travel hacking practice is simple: to travel whenever and wherever I want, and no more.

To that end, I advocate that readers honestly assess their travel goals and plan out the cheapest possible way to achieve them, using all the techniques I write about here and in the newsletters I periodically send out to blog subscribers.

In two years of full-time blogging and, before that, 16 months of blogging as a side gig while I was in graduate school, I do not believe I have convinced a single person of the merits of my approach, and no longer believe that changing minds is a realistic or even desirable goal.

People who come to my blog intent on experiencing every A380 first class seat will leave with the same goal in mind. Likewise readers who come interested in earning cash back to supplement their income will leave with, hopefully, a useful trick or two for doing so.

Being able to engage readers is an honor, even when you never change a single mind.

Lesson: you can encourage people to think harder and better

While you may never change anyone's opinion, that doesn't mean you can't encourage them to examine their settled opinions more critically.

When people angrily disagree with me, I'm happy to see them angrily disagree with me by subjecting their assumptions to the same analytical scrutiny I apply to my own views.

When I compare that to affiliate bloggers who make a practice of assigning garbage "values" to different point currencies based on which way the credit card payout wind is blowing, I'm satisfied that even readers who don't agree with a single word I write are at least doing the hard work of developing a rewards strategy that works for their actual lifestyle — not some affiliate blogger's.

Challenge people to be their best selves, not your best self.

Lesson: my readers are the best

It's no secret that the internet, like middle school, is full of trolls anxious to tear down anyone who shows a glimmer of creativity or outside-the-box thinking.

As long as I've been writing this blog I appear to have been blissfully exempt from that rule. My readers furiously disagree with me all the time, and very occasionally call each other names, but in over 3 years of blogging I've never felt the urge, let alone the need, to delete or censor any comments here.

I don't know why I'm not subject to constant internet harassment, but I like it.

Lesson: every deal dies eventually

If a travel hacker went to sleep in January, 2012, and woke up today, there's scarcely an element of the landscape they'd recognize. Vanilla Reload Network reload cards off-limits at CVS. OneVanilla prepaid debit cards useless at Walmart. Bluebird and Serve shut down for many or most (they would have slept through Target Prepaid REDcards, of course). Formerly cooperative 7-Eleven store locations refusing credit cards for prepaid debit cards. ISIS!

The lesson some people take from this experience is to not depend excessively on any one deal, but I don't think that's quite right. Leaning heavily on each of those deals as long as it lasted was a fantastically lucrative choice, which I wouldn't dream of second-guessing.

It's a mistake is to believe that any given deal will last forever — it won't.

Lesson: there will always be more deals

Looking at a list of the deals that have died in the last 4 years, you might despair that manufacturing spend must, today, be completely impossible!

I don't think it's interesting or necessary to compare the atmosphere today with that of any previous era.

But I will say that every serious travel hacker I know is manufacturing more, not less, spend today than they were even in the era of unlimited CVS Vanilla Reload Networks cards. They may be doing so at greater (or lesser) expense and greater (or lesser) convenience, but there is no obstacle for a serious US-based travel hacker to manufacture as much spend as they need to meet their travel goals.

Travel hacking is a game that rewards long-term, reciprocal relationships — one more reason you're unlikely to get good advice from affiliate bloggers.


I've come a long way since I started blogging, and even further since I started blogging full time.

I have a lot more respect for deals that give access to a steady stream of moderately-priced points, rather than big, cheap windfalls.

I've become more realistic about the few rewards currencies that give me consistent access to the flights and hotel properties I need, rather than accumulating large speculative balances across programs.

And, as this post suggests, I've become a lot humbler about my role in this travel hacking ecosystem: on my best days, I can help people arrive at the right conclusion for their situation, but on no day will I convince anyone that my approach is the right one for them.

That's a little bit sad (since I'm right!) but it's also a little bit of a relief: we're all stumbling our way forward together, and at the end of the day there are no bonus points for being right first or penalties for being right last.