Should You Automate Your Emails? My Surprising Answer

WELP, spent the last week in Barcelona eating ham, drinking wine, and avoiding Catalan prison with my friend Matthew, who is the smartest person I have ever met when it comes to selling.

One of our main topics of conversation (besides whether or not razor clams are, objectively, “good”)?

Systems.

Which used to be such an annoying concept. I remember in the year 2009, a friend of mine introduced me to author Sam Carpenter, of WORK THE SYSTEM, a book all about—you guessed it!—systems. Specifically, business systems. And I remember thinking: yes, right—but also, how impersonal!

Predictable, for me, meant unimaginative. It meant generic. It meant cold. It meant mechanizing things that I hoped would be human.

So back then, I didn’t champion the idea as much as I should have; it felt like the antithesis of creativity. It was kinda like telling me that engineering was my new career, rather than writing. And, um, hello: if I wanted to be an engineer, I wouldn’t be out here blogging my face off.

I wanted my writing to be the star: not some formulaic equation.

But then the years went by and I learned that, holy shit, you can’t actually run a business on good intentions. You can’t actually run a business unless the business itself has legs. Good luck trying to push that lump of good intentions up a mountain! Your business needs to be able to operate—gasp—without you.

Which is a novel thought. A thought I didn’t like, at first, because clearly I am an egomaniac and everything is about me. (Especially if soft pretzels are involved. THEY. ARE. ALL. MINE.)

But if you ever want to have a life; if you ever want to be able to take a vacation; if you ever want to have a weekend; if you ever want to have a bad day; if you ever want to have a bad YEAR—you need a business that works without you, too.

You need a business that can stand on its own, when tasked.

But, you also need a business that can earn on its own. It’s not just about your involvement; it’s about how effective you are at letting the business be a business. Do you limit the business because of your need to be involved in every aspect, all the time? Do you become a bottleneck? Are you preventing the business from prospering? Are you cockblocking your own business’s potential because of your ego?

So, I started thinking about systems more and more—especially when I found myself wanting to expand. I wanted to launch and experiment and grow and play with new ideas! I wanted to contribute in all-new ways! BUT, I wasn’t willing to do it at the cost of originality.

For a very long time, I had demonized even something as simple as an automated welcome email sequences as being wholly generic and painfully obvious; they seemed like such a faux way of “connecting,” when the alternative to me had always been: “commit to showing the fuck up and you won’t need to fake your connections.”

But then I thought: maybe there’s a way to scale my efforts without sacrificing my integrity. What would that look like? What would it look like to create something that was 100% of service? What would it look like if what I made were actually useful…and not just pretending to care?

Enter: the Meat & Hair daily email newsletter experiment.

My hypothesis was this:

Nobody wants to feel like a damn generic subscriber. Nobody wants your “welcome sequence.” And, nobody wants to be “a lead.”

So, why are we treating people like leads?

Why not really give them something, instead?

Welcome sequences are THE standard, go-to “lead warm-up system” that online business owners have in their businesses, and yet, most welcome sequences are painfully obvious attempts at “getting you primed to sell you something,” and they always sound completely forced, stiff, transactional. Precisely why I never liked them to begin with: if your emails don’t do the job of genuinely connecting, then what’s the point? You literally sound like every other a-hole on the internet. You literally sound like Brian, Ryan, Travis, and Chris wrote your email sequence using their “Top Performing Email Template That’s Sold Millions!!!!!!!!!!

I can’t.

So, for a long time I shied away from anything that even remotely had the faintest whiff of “automated,” because automated meant fake. But then I also realized that if anyone was going to change that?

It might be me.

As someone who believes, with all of her (weirdly monstrous) quads, that our real job in this world is to solve the problems we wish were solved, I decided that it would be a good use of my time to try to solve this particular problem.

So, I started the daily newsletter.

I wrote my ass off, spending 1-2 hours every morning, starting at 5am every day, writing that morning’s newsletter, spending countless of other hours sourcing examples, and showing up each and every day to give my best and my brightest attention to the project. My end goal: convince you that writing with personality > writing without it. That’s the argument of the entire project, and every single day, I strove to make that argument. I showed up. I did not falter. I did not want to falter. That’s one of the biggest benefits of choosing your contributions in this world: when you choose based on passion, you spend your time in passion.

My goal with this was to create something genuinely helpful; something that would be so damn good, people would want to read it every single day.

So instead of asking, “What should I put in my welcome sequence?” I asked a new question: “What would someone want to open every day?” And I meant EVERY. DAY. Because if it’s that good that you want to open it every day, it’s good—period.

And. It. Was. Awesome.

I love how rewarding it feels to have created something meaningful.

I love the emails I get, telling me that it’s been helpful.

But most of all?

I love the decision I made next.

Maybe you saw my announcement the other day, or maybe you didn’t, but the announcement was: “We’ve completed Season 1! We’ll be back after the New Year with Season 2!”

Did you catch that?

Do you know why I did that?

Because now that I spent 3 months making something with integrity, passion, and public usefulness, it’s time to add systems back in. It became time to take what I have made—with all my creativity and love and obsession—and turn it into an operational business; one that has its own legs. (And isn’t just borrowing mine.)

So: I created a system.

I took what I had made.

And I made sure that every single new person will now be able to access that thing I made.

So, right now, anytime anyone opts in for the first time? They start at the top of the series. They receive each and every email, from the beginning, in the exact order that I want them to. There’s never a day off. There’s never a human failure. There’s never a lapse in creativity. They have this really dedicated daily experience that runs for 3 months long, every day, Monday through Friday, without fail. Without me failing. Without “the electricity went out, shit!” failure. Without “spilled coffee on my laptop again, fuck!” failure. Without the failure that sometimes comes with creativity and humanity and life.

I’ve even gone so far as to optimize those emails and see which ones were causing the most unsubscribes and adjusting the content within. I’ve even gone so far as to set reminders for the content that needs to be updated; the things I’d like to change.

This is because originality is important, but so is balance.

And that’s the lesson I’ve learned: you CAN use systems, so long as you’re committed to making DAMN FUCKING GOOD ones. Ones that make a person’s life better.

Right now, I’m pretty proud of the systems I’ve employed—because they’re systematizing something original. And that’s been the difference for me. I’m not systematizing something cheap and throw-away; a self-important “welcome sequence” that nobody cares about. I’m systematizing good work I believe in; work I’ve put my heart into.

And that, turns out, is the real key to selling: believing in your product. Because when you believe in what you’ve made, you’ll want to tell other people about it. THAT’S the litmus test: Do you want to tell other people what you’ve made? Because being embarrassed of what you’re spending your time on every day is a sign you shouldn’t be spending your time on it.

On the other hand, if you find yourself excited and proud to tell a stranger who you are and what you’re working on, this is an excellent sign. And that, for me, is also an invitation to then turn something into a bonafide business that can walk on its own: if it’s beautiful and useful, then it’s a disservice not to spread it wider.

And for that, we do need the help of technology.

Turns out, systems are not unimaginative, generic, cold, mechanical.

They’re a part of the creative process, too.

They’re one more way that you can take your ideas and share them far and wide.

They’re one more way for us to do the work we care about.

They’re one more way to solve the problems you wished were solved.

They’re one more tool in the artist’s apron.

And they’re one more way for you to bring more humanity to the table…when it’s done well. When you care about humanity. And when you care about making things for humans, not leads.

Because nobody wants your email. But they might like your ideas.