Never Skip Twice. What Happens When Tomorrow Becomes Next Month?

As you've probably (hopefully!) realized, I didn’t write this newsletter for well over a month, having previously been consistently publishing on a weekly basis for a year and a half — and I’m not proud of it. I’ve always acclaimed the importance of taking a pause when so required, that we shouldn’t be too hard on ourselves when life gets in the way, and that sometimes taking a break is a necessity. But lately, I’ve been questioning whether that’s always true. There’s a fine line between giving yourself grace and quietly letting yourself drift away from the very habits and commitments that once mattered to you. 

And, yes, over the past month, I crossed that very line without even noticing I so had.

It started so simply. I skipped one week, because, well, life happened. It felt harmless, temporary, justified even. But then one week turned into two, two turned into three, and suddenly I realized that I had stopped showing up entirely. I kept telling myself I was just waiting—waiting for the right topic, for that elusive inspiration to strike, for a better mood, for the perfect words to arrive. But the truth is, I was waiting for perfection. Somewhere in my mind, I believed that my next newsletter had to be “better” than the last, more insightful, more meaningful. And in that quiet pursuit of perfection, I ended up doing nothing at all.

I’ve realized something uncomfortable: waiting for motivation and waiting for perfection leads to exactly the same result—zero action. And when it comes to habits, zero action isn’t neutral; it’s destructive. It doesn’t just pause your progress—it erodes the very momentum you’ve previously worked so hard to build. Publishing a messy, imperfect newsletter—one that maybe only a handful of people would even read—would have been infinitely better than publishing nothing at all, because at least I would have kept the chain intact. 

This insight, of course, isn't  just applicable to writing. It’s true for any habit we work hard to create. Think about the effort it takes to start something new—exercising regularly, eating healthier, journaling, meditating, waking up earlier. It takes energy, focus and determination to push past resistance and create momentum. It takes days, weeks, sometimes even months of consistently showing up to build trust with yourself. But then one day, you let yourself off the hook. You forgive yourself for skipping. You say, “I’ll get back to it tomorrow.” And maybe you do. But if you don’t, if tomorrow becomes “next week” and next week turns into “next month,” the habit quietly slips through your fingers. Not because you weren’t capable of maintaining it, but because you underestimated how fragile progress really is.

And yet, life rarely is that simple. Sometimes you really do need to pause. Sometimes, you’re exhausted, burned out, overwhelmed, or dealing with something far bigger than your regular routine. So how do we know when to push through and when to step back? That’s the question I’ve been sitting with—and I’ve come to believe that the answer isn’t about never missing a day. It’s about how quickly you return.

There’s a rule many habit coaches talk about: “Never miss twice.” Missing once is human. Missing two days in a row? That’s when the loosening begins. The longer the gap, the heavier the resistance, and the more your mind begins to rewrite the story of who you are. Skipping one day doesn’t make you someone who “can’t stick to habits.” But skipping over and over slowly convinces you that you can’t. And that shift is really what kills progress.

So, as you can tell, I’ve been reflecting on this a lot. Maybe the real work isn’t about being perfect or forcing ourselves to show up every single day no matter what. Maybe it’s about noticing the difference between intentional rest and unconscious drifting—and choosing to return to the things that matter before the gap gets too wide. Because showing up imperfectly is still showing up. And sometimes, taking one small, messy step forward is the very thing that rebuilds momentum when you’ve lost it.

For me, writing this newsletter is that step. I’m showing up without waiting for the “perfect” idea or the “right” words. I’m choosing action over perfection because I don’t want to lose the habit that connects me to you—and to myself.

And if I do choose to skip a day, I’ve made myself a promise: I will never skip twice in a row. That’s the rule I’m committing to—and maybe it’s one you should try, too.