Over the past two months, I have written a fair amount on Medium about the ins and outs of running a small business, the unique challenges of being a niche media company, and some more general truths about personal finance (which is, as you might have guessed, what my niche media company talks about). I feel like I’ve covered a lot of ground and have been more introspective than I ever usually am about what it means to be both a CEO and — I hope — an ethical and compassionate woman. But that introspection would not be complete unless…

I remember the first time I was with friends and thought, holy shit, they are really rich.

Around the sixth grade, I moved from a humble suburb of Charlotte, North Carolina, to an affluent, WASPy sailing town on the Chesapeake Bay. The median on nearly everything around me rose with a whiplash-inducing immediacy: the clothes kids wore to school, the cars their parents dropped them off in, the houses they ran into for their afternoon snacks (and the overflowing, all-brand-name-stocked pantries those snacks were housed in).

My relatively humble home life, with its sale shopping and coupon clipping, suddenly felt…

Since starting The Financial Diet nearly three years ago, I’ve probably read, edited, or personally written hundreds of articles on budget travel. It’s no surprise that this is a popular topic — who doesn’t want to broaden their horizons and see new things without having to bleed money the way so much travel demands?

There are a million variations out there on the same ideas (point strategies, airfare hacking, knowing the right seasons and times, etc), but there is rarely a true exploration of what it really means to travel well and thoughtfully while sticking to a pared-down budget.

We…

There is very little about digital media in 2017 that isn’t at least a little bit ugly. It’s a tough business financially, with race-to-the-bottom practices that lead us all to write dumber copy, use sketchier advertising models, and cast ever-wider nets to reach an audience that is as fickle as it is vague. As clicks and eyeballs are devalued, the strategies become more desperate, and the rolling layoffs seem never-ending.

The landscape is bleak in many ways, and even in running something niche and sustainable—the Financial Diet, a digital media company that talks personal finance for young women — we…

I never intended (or really wanted) to have my own business. I was always open to the idea of freelancing, as someone whose father has been a freelance illustrator as long as I’ve been alive, but working for yourself is very different from having a small business (even with just a few people). The nuances and complications of having to manage, administrate, and organize a growing team are entirely separate from the (already daunting) challenges of working solo, and I still believe, even after doing this for more than two years, that I’m not particularly well-suited to the job. I…

I’ve worked on the internet for about six years now, which in most industries is a very short time, but in digital media terms, that’s long enough to witness tectonic shifts.

I’ve seen the golden age of social media distribution, where sharing a well-packaged article on Facebook meant an almost instant viral lift. I’ve seen the shift from programmatic to custom content as clicks and eyeballs are devalued by the day.

I’ve seen the video-as-panacea-to-all-problems and the ensuing retreat from video, which led to mass layoffs, editorial restructuring, and abandoning deeply held convictions à la “millennials don’t like reading.”

I’ve…

In August 2014, I was working as creative director of branded content at a large millennial-focused website that I had been a part of for more than three years. It was the kind of place where I could write anything—I had spent my first two years as a staff writer, which often meant writing four original pieces of my choosing for the site per day. But that freedom often left me feeling like I couldn’t write anything. …