It’s an unwritten law of entrepreneurship that for every project you stick with, there are at least three you’ll quit or never start.
In my case, there’s the car blog, the car Instagram, the inspired quotes Instagram, the animated quotes app, the anti-stress course, and hundreds of deleted article ideas — and those are just some of the least public of my failures. I quit my Substack newsletter after six weeks, quit as editor of Better Marketing, and quit another newsletter to write a book, which I then quit to write another book. I’m now on book #3 and have given up announcing. Quit, quit, quit.
On the plus side, it is only out of this flaming pile of failures that a handful of lasting, rewarding projects were able to emerge. Projects like Four Minute Books or my writing course, which pay the bills and align well with my long-term mission of being a writing-focused writer.
On Shark Tank, one of Kevin O’Leary aka Mr. Wonderful’s most common pieces of advice is to “take that idea behind the barn and shoot it.” He has no qualms about telling people with six figures in sales to drop a product that’s already dead but doesn’t know it yet. But how can you tell? What do you do if you don’t have Mr. Wonderful yelling in your face?
One mistake we make is that we try to evaluate each new idea on its own merits rather than relative to what we’re already doing. Everyone wants 100,000 Twitter followers, but unless you have indication to believe tweeting would be a better use of your time than your current project, you shouldn’t start posting memes on a whim. Similarly, while writing a book is hard and takes forever, it could be the right move at the right stage in your career.
To help you determine what to drop and what to rock, here are three lessons I’ve learned over the years. I try to live by these rules, and they’ve made my life a lot easier.
1. Don’t be afraid to drop what’s not working for something that might.
I canned my newsletter because after going hard at it for six weeks, it amounted to 1% of my annual income while taking 50% of my time. It was obvious it wasn’t working because even a 10x improvement wouldn’t have made a big enough difference. A book, meanwhile, is about the scariest project any writer can tackle. There’s never a guarantee it’ll sell, especially if it’s your first one — but it might.
When your alternative is continuing to spin your wheels, it shouldn’t take much to convince you to try something new. Usually, you can tell by the fact that half your excitement about a new idea comes from the prospect of ditching what feels like a slog to nowhere.
While that’s a good sign you should consider moving on, it is not a sign you should move on to just anything. Don’t trade one mud-crawl for another, or you’ll only keep running in circles.
Try to prove, at least on paper, your new idea’s potential. Why do you feel drawn to it? Is it more likely to generate an immediate, favorable response? Or at least more aligned with your long-term goals? For me, writing a book was the definitive next step on my career ladder. Even if it flopped, I would learn the basics of publishing, which I’d need for future books anyway.
You should also look back at what got you here: Why is your current project going nowhere? Will your new endeavor be less prone to its flaws? If they’re similar, how can you prevent potential pitfalls? My Substack newsletter just didn’t feel like essential reading to anyone. It was a nice-to-have and convenient way for existing fans to support me. That’s neat for a side hustle but won’t sustain a full-time income.
Having a strong gut feeling that you’re on the wrong track is worth a lot. Lean into that feeling. Switch tracks fast and often, but never jump in with two feet before doing your homework.
2. Don’t be afraid to drop what’s working well for something that might work even better.
After one year of blogging, studying SEO finally paid off. I scored some hits, and my traffic went into the thousands — but my blog was still unfocused. It was a random collection of ideas, and my process was neither structured nor easily repeatable.
“What if I do this on a set schedule with a set theme and article structure?” That’s how Four Minute Books was born, and with that site, I managed to hit the same and even better numbers within a few months.
It’s easy to give up something that’s not working. It’s hard to abandon “good” in hopes of “better” — but that too is sometimes necessary. A decent indicator is when you feel you’ve outgrown your current pursuit. You’ve learned the right skills but on the wrong project. Now, you need to apply them to the right one to reap the rewards of what you’ve sown.
Long timelines can make this difficult. I had already invested a year into my blog. Would my new site be in better shape another 12 months down the line? My blog would definitely suffer.
When you’re in doubt, take solace in the feeling of gears clicking into place. Planning your follow-up gig should feel like molding clay quickly and efficiently. “This is the SEO-friendly name I’ll use. This’ll be the structure for each post.” If designing your roadmap doesn’t feel like injecting nitrous into your fuel tank, you’re not ready. But if you can come up with a clear vision fast, that’s a good sign the rubber is about to hit the road.
They say don’t let perfect be the enemy of good, but you also mustn’t let “good” be the enemy of “better.”
3. Don’t be afraid to drop anything for something you KNOW will work.
One cold September morning, I woke up and was ready — ready to make a writing course. I had paid my dues for four years, and that day, in one near-magic instant, a fully fleshed out lesson plan appeared in my notes.
For a few days, everything else on my schedule disappeared. I wrote down talking points, created a sales page, drafted launch emails, and a month later, I pre-sold 100 units for a grand total of $20,000 in a single week. I started recording and released modules monthly. Since then, I haven’t been selling it super actively, but it still made another $30,000 to date.
I know it’s a cliché, but: Sometimes, you just know. An idea takes hold of you, and you can feel it in every fiber: This is it. Everything fits. The stars are aligned.
In some ways, “divine interventions” are the easiest ideas to abandon everything else for. Their inspiration factor is incredibly strong. At the same time, the simple act of stepping aside, of not shooting down your shooting star, can be very difficult. After all, it’s the exact opposite of what you’re supposed to do most of the time!
I’d love to offer some clever rationale here, but these rare moments of genius are the one time when rationality will be wholly out of place. When you know, you know — and then it’s time to throw caution to the wind. Go all in. Fuel the fire. Pen 50 pages in a frenzy, or produce an entire launch funnel out of thin air. Cherish your extraordinary bursts of unlimited creativity.
I’ve only had two such incidents in the last seven years. While the initial fire never lasts, for me, it jumpstarted both projects enough so I would see them through to completion — and that alone is one of the best things any entrepreneur can say.
When you know, you know. Knowledge may be the forbidden fruit, but there’s no point in throwing away a half-eaten apple.
Quit, quit, quit.
In a world where everyone’s trying to do everything, quitting isn’t just good for your health. It’s a superpower.
Only he who quits the wrong stuff can do the right stuff right. When everyone’s tending to seven social media platforms at once, working on a novel for four hours straight makes Norman Normal look like Clark Kent.
Quit, quit, quit. Quit what’s not working for what might. Quit what’s going well for what might do even better. And quit anything, absolutely anything, for what, deep in your heart, you know is going to work.
Focus turns mediocre effort into extraordinary results — and the only way to focus is to quit.