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How to Succeed In Something You've Never Done Before: "Ready, Fire, Aim"

You don't have to know where you're going. You just have to start going.

This is a newsletter about how to become more optimistic and resilient, and how to turn moments of change into great opportunity. Ready to seize tomorrow? Subscribe here — and to hear me debunk today's greatest fears about change, check out my podcast*

Ready, Aim, Fire.

That’s the usual order of things. But the usual order does not always apply. When we are forging into the unknown and reaching beyond our limits, there is nothing to aim for. We don’t know what success looks like. We might have no idea what we are ultimately building.

In this case, we must reverse order: Ready, Fire, Aim.

You may have heard the phrase before; it's come to mean a lot of things to a lot of people, and is now one of those things people casually say without defining. But I think it can be really powerful — and want to share three stories that bring it to life, and get you thinking about how it can apply to your own journey.

Story 1: Killing a $30 Million Business

Andy Monfried was once at the forefront of online advertising. His company, Lotame, was a pioneer in the targeted ad space, and this drove a lot of money. It only took two years for Lotame to hit $30 million in revenue. But one day, a client told Andy some bad news: They had built their own ad-targeting system, and no longer needed to pay for his.

Then another client did the same thing.

In a moment like this, most people take one of two paths: They either panic and make a bad decision, or they do nothing and slowly crumble. But Andy did something else. He gave his industry a deep look, determined that he was in irreversible trouble, and then scrapped his entire ad-targeting business. This meant laying off half his staff, all over the course of ten days.

“People thought I was nuts,” he told me when I interviewed him for my podcast. Lotame was still quite profitable. His employees (and many investors) could not understand why he wouldn’t at least keep the ad-targeting business running while he forged a new, more sustainable one.

But Andy had a good reason. He didn’t want to be distracted by a dying cash cow; it would be hard to build a new business while the old one still demanded resources. He instead created an entirely new concept, where publishers paid for help utilizing their data and understanding their audiences.

Same general skill set, new business. But that shift required a major overhaul of the company, which most people would have been too daunted to take on.

I asked Monfried what kind of leader he thinks he is, and he put it plainly: “Ready, fire, aim,” he said.

He believes that if he indulges in the luxury of time, he and his ventures will fall behind. Did he know that this new venture would work? No, he didn’t — but he definitely knew that his old venture would fail. At that point, he defaulted to action: He assessed, acted, and then directed the outcome of his actions.

When we spoke back in 2018, only a few years after his big pivot, Lotame had rebuilt its $30 million business and then some.

Story 2: Imposter syndrome laid bare

Neil Strauss is an accomplished writer who’s written multiple best-selling books (including, I should note, the yucky pickup artist book The Game). But back in his early career, he was just a guy who, like so many people, was struggling with imposter syndrome.

He wrote a letter to his childhood nanny (who he says was like a second mom to him) when his career was starting to pick up. Here’s a bit of what it said:

“I also wrote my first article for--gulp--The New York Times. I'll find out this Sunday whether they ran it or not. I hope they did. I feel really weird about writing for these places, like I'm underqualified or too unprofessional. I'm always really nervous on the phone with my editors. I feel like it's a mistake that they have me writing for them. Either I'll get over this feeling as I write for them more, or my insecurities are correct and they'll can me…”

My friend Paul Kix found Strauss’s letter recently, and shared it in his newsletter about writing. Paul framed this as a “ready, fire, aim” moment, and I really appreciate what he wrote. Here’s Paul:

“It's the ability to gather enough core information—the Ready part—to then stare down the imposter or perfectionist in the mirror and send that pitch to your dream publication, launch that podcast, write that book, well before you think you "should": the Fire part. The Aim part comes last: Scoping out what the terrain looks like in response to your action. Learning from the response to your action, in other words—and then gathering the new sets of core knowledge to act again.”

That’s what Strauss did — and, for better or worse, it worked out for him. Paul sums it up nicely: “You don't have to remove all of your flaws and insecurities in order to succeed.”

But you do have to move forward, even if you don’t exactly know how.

Story 3: How I got to here

I have done a version of this myself. When I launched my first podcast, called Pessimists Archive, I had no idea who it was for or what its purpose was.

I knew only three things: One, I love podcasts and wanted to make one myself. Two, I’d have fun creating something that I enjoyed. And three, maybe something good would come from it.

Years passed. My audience grew. The show attracted notable fans and partners. I became a better podcast host and writer. And then, in 2020, I hired a consultancy called Pen Name to help me grow the show. One of the women on their team, Richelle DeVoe, did a deep dive into my audience and discovered insights about why they listen (and don't listen) to the podcast. The #1 reason the keep coming back: It helps them feel more resilient about the future.

That core insight helped me understand everything I do. It gave my work a particular focus and purpose — and it led to me rebranding the podcast as Build For Tomorrow, and then creating this newsletter, and it became the central insight that I built my book proposal around, which led to the book I have coming out this September.

I could not have understood any of that at the very beginning. It would have been impossible to aim, fire, and hit this target.

Instead, I had to fire first: I had to create something, and learn from the experience that thing created. Then — and only then — could I aim.

If you think through this lens, I bet you’ll realize there are times in your life when you’ve followed this pattern yourself. Was it effective? Did you learn from it? Drop me a line and tell me your story — I’d love to know, and may share it in a future edition of the newsletter.


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Cover credit: Getty Images / Colin Anderson