Don’t Wait Until It’s Too Late

Although I know precious little about the teen magazine Rookie, Tevi Gevinson’s (the founder’s) goodbye letter quickly made its way around the internet late last year. In it, she wrote:

“In one way, this [ending the magazine] is not my decision, because digital media has become an increasingly difficult business, and Rookie in its current form is no longer financially sustainable. And in another way, it is my decision—to not do the things that might make it financially sustainable, like selling it to new owners, taking money from investors, or asking readers for donations or subscriptions.”

Just a few weeks later, a website I do follow echoed Tevi’s sentiments in their own “end-of-blog” announcement. Unlike Rookie, which ended immediately with the letter, this blog will continue publishing new content until August. The author goes on to ask and answer the obvious follow up:

“So what are we doing this year? Quite simply: Everything. We’ll of course keep up with our normal schedule, but we’re also going to focus on projects and trips and posts that have joy as their main goal…We’re going to throw caution and sponsorship and all the rules of what we “should” be doing [out] the window…”

My first thought was—”well, why was she not doing those things before?”


I definitely do not want this to come across as an attack or a dig. I have followed the site for the last year and enjoyed it. I am disappointed it’s going away. But I wonder why it took the end of the website for her to pursue these goals? Why did she have to shut down her blog to throw out the rules?

In one respect, the answer is obvious—taking big risks, especially when something is already working, isn’t easy. “If it ain’t broke, don’t fix it.” The website is/was her job. She has a staff. She has thousands (tens of thousands? millions?) of readers. She has a responsibility to each and every one of those people. Switching it up in pursuit of a new goal, experimenting with new ideas, could turn off fans and cost her financially.

But what would have happened if, two years ago (without an end-date in mind), she had thrown caution and sponsorship and all the rules out the window? What would have changed? Yes, she might have lost some readers or a sponsor. But maybe she would have made up for it with a bigger audience, a new sponsor, more money? Would she have learned something in that process that allowed her to grow her business in a way that aligned with her own values? Would she still be shutting down her website today?

It’s impossible to know the counterfactual. And it’s easy for me to ask these questions, sitting here with zero sponsors, no money on the line, far fewer readers, and no staff to support. But I know from personal experience that just going through the motions, doing what you think you’re supposed to do, is a recipe for disaster.

In a post from a year and a half ago, when I was feeling stuck, I wrote:

“A big reason why writing this blog has been hard in the last couple months is that I’ve felt compelled to stick to what I’ve always been doing. That got me here, so why stop now? I worry that if I experiment, if I do something different, I might lose folks. But that’s the opposite of what I should be doing. It’s unnecessary and harmful stress.”

In response, someone I respect suggested that, instead, I should do what feels like “cake.” It turns out that was the solution. Mentally casting off the self-imposed pressure re-inspired my writing and kept me going.

david's cake text

Not just in blogging, but in life, people wait until it’s too late. On the extreme end, they wait until a family member is dying to tell them all the things they wish they’d said before. On the medium end, people put off the big European vacation until retirement or the career change until it’s too late to make a move. On the low end, they wait until they have more time, or someone’s permission, which they never get, to start a blog or try comedy.

Don’t let an expiration date be the impetus to do thing you’ve been wanting to do. Take the risk today, because it might actually pay off.


Each Monday, I share strategies to help you pursue your passions. Try it. You’ll like it.

Header photo by Landis Brown on Unsplash

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