The Not-So-Secret Secret Prolific Writers Rely On


Every corporate blogger or content marketer faces the same horrifying challenge: Generate meaningful ideas and turn those into content. Then do the same thing tomorrow, and the next day, and the next day, and so on.

It’s daunting and exhausting, and it’s enough to make people stop caring about quality and just try to make something — anything — that will appease the demands of your boss or your sales team.

In the world of creating on-demand, every writer battles a common enemy:

That damn blinking cursor.

You know the one. It sits there taunting you when you open up your blogging software, causing you to break out into cold sweats because you don’t know what on this sweet earth to write.

Or maybe you’re really feeling it when you wake up. You might open your laptop, coffee in hand, excited to create something awesome. Who knows? It might go “viral” and get you “syndicated” or drive some “leads” so you can get “promoted” and finally make enough “money” to propose to your “girlfriend” who watches too much “Bachelor” and drives you up a "wall"….erm, uh…I digress.

Writing is hard! Doing it every stinking day is even worse (especially if the day is somehow actually stinky. Then I'd suggest new employment.)

So you, my smelly friend, need an idea pipeline.

What’s an idea pipeline, I pretend you ask as I write this? It's an app that syncs between mobile and desktop. That’s all! Trello, Evernote, Google Drive, and more — they all count. (I use Evernote for personal writing and Trello for teams.)

You use this app to save any and all random thoughts, half-baked paragraphs, working headlines, stats you hear and may want to write about, links that inspire creativity, graphics or videos you wish to embed and share, and so forth. EVERY SINGLE THOUGHT that could be worth writing about, you save. If your idea pipeline were your best friend, she’d tell you to just shut the hell up already. But she’s not. She’s your idea pipeline. Which, incidentally, is a writer's best friend. Only she doesn't want you to shut up -- she wants you to write more, and write better. (Cuz quality, like, matters you guys...)

Great idea pipelines contain two parts:

The first and most obvious half is merely a list of random, singular post ideas: data points you find interesting, half-baked headlines, a paragraph or two you bust out when a free moment presents itself, a link you found, etc. These are used to create one post per idea.

The second half is where some creators go from good to great. I call this half “The Well.” You can dip into The Well over and over without running dry. This section contains ideas for templates, series, or tropes that you can launch repeatedly. So it might read something like this:

  • Answer customer questions
  • Weekly link roundup
  • Embed and react to infographics
  • Meatball Mondays
  • Pinterest Week

These are all things you either suspect or know will resonate. (By the way, let me know if you launch Meatball Mondays? I’m Italian, so…I'm contractually obligated to enjoy that.)

Using templates or recurring segments doesn’t come from the marketing world.

A quick look at any major media outlet will reveal their use of The Well. Take my favorite show of all-time, The Bachel—I MEAN SPORTSCENTER! SportsCenter is my favorite show!

So yeah, take SportsCenter: They’ll have plenty of unique, news-based clips and reports, a few deeper dives into the bigger stories of the day, a few original graphics showing interesting trends, and so on. But they’ll also regularly run a 60-second segment featuring the guys from Pardon the Interruption, or bring in a football analyst for Coors Light Cold Hard Facts, or (everyone’s favorite) count down the top 10 plays of the day -- which becomes the "not top 10" bloopers every Friday. (It's like a Well within The Well. Is that content inception? Cue this sound.)

Back to the marketing world: Moz has become famous for their Whiteboard Fridays video series. At HubSpot, the blog editor Corey Eridon had an idea to do “marketing in 100 words” one Saturday morning and, given some positive feedback, turned it into a recurring thing.

The Well helps you fill gaps in between your individual moments of brilliance or your larger projects which aren’t ready to launch.

They also help audiences anticipate recurring themes that feel special, like they’re in the club.

And if all else fails, there’s always Meatball Mondays...

In my next post, I’ll share some visual examples of a few different styles of idea pipelines, including the one we used at HubSpot to manage a blog that publishes four times per day to over 230,000 subscribers (so it's a spicy one! ...and THAT is my final meatball reference, I promise).

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Posted on April 15, 2014 .

A Plea to Friends Suffering in Jobs They Hate: Leave!

Note: This post is re-published from just over a year ago. It got so much positive traction (in that more than just my mom read it and liked it) that I wanted to be sure to bring it over to this new site. Hope you enjoy!

In the last 15 months, I’ve met with about a dozen friends and former colleagues for one reason: They really don’t like their jobs. Most of them are lucky to work at awesome companies with very recognizable brands. Most of them are brilliant. I’m lucky to know them. HOWEVER, most of them never decide to take action to change their situation. Maybe sharing my quick story will help. It’s not groundbreaking, but it’s honest.

Here’s that story…

Just over a year ago [Editor's Note: This was written in 2012], I made a decision that, at the time, was pretty damn hard. I chose to leave Google. (Google! The food! The brand! All of that.)

And, in a way, the hardest part was changing my stupid LinkedIn profile to read “CampusLIVE” - a young company with a young (read: not-so-great-looking) product and, let’s be honest, a pretty lousy name.

Looking back, the “risk” I took was really no risk at all. My mentality heading into the decision was just that, too. I remember thinking to myself, If this startup fails, I’ll at least learn a ton and meet some great contacts to expand my network. Plus, I’ll know definitively that I gave startups a try.

But through all the reasoning with myself, the fact remained that it was still an impossibly hard decision to leave a place like Google. Here’s the punchline though: It should have been easy. There was literally no reason for me to stay at my old job because I’d learned all I could there — at least for the direction in which I wanted to steer my career. (This is a positive, by the way. I learned a ton. I'm thankful that I could learn there, but I also felt the learning slowing down or even stopping. That’s a warning sign.)

Let me be clear by saying that Google was and is incredible. The people, the perks, the brand, and the energy make for the ideal post-college job. But, again, I’d learned what to do to succeed at a high level, and I felt my unhappiness clinging to me everyday. I knew my next move wouldn’t be available to me for some time due to HR policies. Plus, a job function I wanted wouldn’t be open for two years, and even then, it would not be located in Boston where I hoped to live for a few more years.

So, I sucked it up and found something worth moving towards (rather than moving AWAY from something — that’s a hugely important concept). And in the interest of full disclosure, here’s what happened:

  • A few managers raised their eyebrows and cautioned against the decision. They pointed to the learning opportunities at Google vs. at a startup. I agree that for some, Google’s a better environment. For me, I needed to get my hands dirty and move at a faster pace than six- or 12-month increments. 
  • I received a lot of support from friends (a lot more than I anticipated, too). I guess they sense it was the right call by looking at my motivation, my blog output, my attitude, and my happiness level because I didn’t really explain the decision to most of them.
  • I took a pay cut — a rather large one. Did it affect my life? Luckily, not really. (And of course, most of this post doesn't apply if one is struggling to pay rent.) But I was willing to trade off a chunk of salary for a butt-load of happiness, which I believe that’s the technical term...
  • I struggled with changing my online profiles and announcing to the world that I was moving from a company that people everywhere recognized to one that, if I was asked where you worked and what you did, didn’t hold much clout. 
  • And in the end, after 15 months [at the time of this writing in 2012], I can safely say that the things I was hoping to address in my career and in my life were addressed. I’m blessed to have had this opportunity.

Again, this was my own personal experience of my transition from one specific job to a new one. This won’t be the case for everyone, I know. And this is most certainly not me trying to paint a picture of all of Google. But I can tell from my talks with a few friends working across several companies that they’re in similar situations.

So, my advice is this: Be open to and accepting of advice from others, but ultimately, just do whatever feels right in your heart and in your mind. Take that risk while you’re in your twenties, because the only thing that matters now is that you’re learning each and every day. 


Making money is nice, but we're too early in the workforce and want to maximize the rest of our professional lives by learning a ton right now.

I know my friends. I know when they’re unhappy, it’s due in large part because they’re not challenged. Their brains atrophy. They don’t feel creative. They coast after figuring out the "system" of their larger organizations, full of red tape and politics and a bubble that's hard to escape.

At the risk of sounding a little conceited, my friends are very talented people. They’re smart as all hell. (Again, I’m the lucky one to even know them. I’m not saying I’m they’re equal because, for the most part, I’m really not.)

These talented people have passions, energies, ambitions, and drive…none of which seems to be present or used in their current posts.

So, to my friends, my message is simple: please take action. Stop talking and go DO something. You’re young, smart, hungry, and destined to be really successful if you work hard enough.

Will it be easy to get things in motion? No. Will others judge? Probably. Is there risk involved? Not as much as you’d think! Especially not if you’re finding new ways to learn while you’re still young.

If you finally stand up and decide to make a change, I promise you’ll look back in a year and realize something: It was the best damn decision you’ve ever made.

Posted on April 13, 2014 .

How Your Favorite Sites Spin Headlines Into Stories

Media companies and corporate blogs alike love to latch onto one core story and beat it to dea--I mean "give an official POV" on it. (In reality, writing about popular events does absolutely work to drive readership. The more relevant the event is to your business, the better of course.)

Here's a look at how all of this goes down, as well as a quiz to see how good you are at recognizing popular headline styles around the web!

(Note: I say "we" in this referring to HubSpot, as I created this while working there.)

Posted on April 9, 2014 and filed under writing, content marketing.

Interviewing for Google & ESPN, a Dinky Little Blog Emerged

This post is dedicated to any college students who may read this. If you know one who's driven to work in tech, I hope you'll share it with them if you find it at all valuable. (And thanks for reading.)

Some might say blogging is an art form. Others might say it's a science. But most might say it’s verbal vomit and tremendous noise adding to the most noise ever created by humanity. (Fact: According to Google's Eric Schmidt, the same amount of information created from the dawn of mankind up until 2003 is now being replicated every 48 hours. So. Freaking. Insane.)

So if tweets can be dubbed the farts of the internet, then as the bigger medium, blogging is...well, you get the picture.

But that does NOT have to be the case. This post was inspired by my interview process back in 2008 with Google, after which I worked there as a digital media strategist. At the time, I was surprised at how much time my interviewers spent asking me about this dinky sports blog I wrote in college, which I ran for fun without ever breaking 100 readers in a day. But, years in digital marketing later, I totally get it.

A blog is documented, semi-permanent proof that you are both passionate and can execute against that. Anyone hiring, especially those hiring young employees, that googles your name (and they most certainly do) and finds your blog will learn three distinct things quickly:

  1. You’re motivated. Keeping up a blog, even casually, is a very big commitment.
  2. You’re passionate. Writing a blog doesn’t automatically make you an expert per se, but it does show your willingness to pursue a specific topic or skill.
  3. You’re “digitally savvy” or a "digital native." I can’t tell you how many employers check for this, or even use this phrase in the job description. (Just five weeks ago, I took a director job at NextView Ventures which was described, in part, as needing to be a digital native.)

Jay, cut the crap - you’re writing a blog right now. Why should I listen to you? You’re totally biased!

Look, I won’t claim to have decades of professional experience (cuz, like...I don't). Nor will I try to regale you with tales from my career and “the way it used to be.” But I will offer two very quick, very true pieces of evidence to support what I’m saying: Regularly writing a blog can give you a distinct advantage in your career.


First, when I interviewed for an internship with ESPN in 2007, I found myself discussing a generic sports blog with everyone I met ( - it’s still live but has been gathering digital dust for years now). I spent probably 30 minutes across several interviews easily and passionately and confidently discussing something I loved, something which allowed me to highlight my love for working hard, writing, sports, and my personal style and differentiating factors.

The blog more or less opened up a great conversation with each person that met with me that day, as well as a memorable conversation I later had with an ESPN SVP named Chris LaPlaca. This senior decision maker wanted to hear about my blog over everything else on the resume, which by the time I reached him, he just assumed would all be buttoned up.

That stupid little blog led directly to my internship and, I’m convinced, future doors opening.


Second, when I applied to Google online (literally - I sent my resume through their online site without a single reference), one of my eventual colleagues who interviewed me admitted that my blog had jumped out. She didn't know or even care that I got barely 20 views a day if I was lucky.

Google looks for smart, creative, well-rounded people who show a deep interest in many things. (I was SUPER lucky to even be considered among them.) Because the company moves so fast, they need flexible people who can succeed in an ever-changing the role. The blog, my eventual colleague and erstwhile interview said, stood out but because I’d shown a willingness to pour myself into something as a testing ground for my personal passions.


Here's to you pursuing a personal passion, even if (and especially if) you don't know what you want to be when you grow up. Cuz I sure as hell don't. 

Using a simple blog, be it Tumblr or Blogger or Wordpress or Squarespace, I hope you start writing about the industry or skill set you hope to pursue. Do you HAVE TO blog? No, absolutely not. But if you’re thinking about it, then do it. It can be a source of instant conversation with employers and help your true self shine through in plenty of authentic ways.

Interviews are a horse and pony show. References are your hand-selected advocates. But your blog? That’s fully you -- and that's a beautiful thing.

Posted on April 7, 2014 and filed under writing.

Creativity Held Ransom by Daily Routine

I arose today to discover with horror the following note in my brain:

Dear Jay,

We have your precious Creativity. Here are our demands.

1) Answer the emails. That’s right: alllllll the emails.

You’re gonna check email every second you get. We’ve installed a Gmail app on your phone that you’re gonna check nervously between meetings, on your commute, at home when your wife is talking to you, in the bathroom, and generally every moment of gap time you have in your day.

Gap time otherwise spent allowing your mind to wander.

Gap time otherwise spent allowing your deeper thoughts to come out.

Gap time otherwise spent connecting the dots between disparate events and experiences and drawing valuable conclusions and creating remarkable new concepts for content.

Oh, and don’t forget to check email when you’re physically in front of a computer too. Yeah. Do that.

2) Attend the meetings. That’s right: alllllll the meetings.

You’re gonna sit in on lots of meetings. Some of them, you’ll find pointless. Some of them, you’ll find are counterproductive. Some of them, you’ll find enjoyable and start thinking positively about meetings — UNTIL YOU REALIZE IT JUST ADDED A USELESS PROJECT TO YOUR DAY! Mwahahaha!

Go on - attend the meetings. You know you want to. You could be missing something really, really important…

3) Check off your to-do list items. That’s right: alllllll the items.

You’re gonna compile a to-do list full of mundane tasks. Then you’re gonna cross off each task, one by one, until your to-do list is empty. And you’re gonna feel great about each item you cross off, despite none of these tasks moving the needle on your major projects or goals.

That’s right, Jay: you’re gonna feel great about doing mundane work and about generally lacking in creativity all day.

4) Get a coffee before you dig into your next big creative project. That’s right: alllllll the—well, okay, that’s probably not realistic. I mean, we’re kidnappers, not coffee nazis here. But yeah -- get that coffee, sucker! 

You’re gonna finish your to-do list, and you’re gonna face a solid hour or two of creative time. But you’re gonna get up, adjust some items on your desk, and go walk to get a coffee. “But why?” you ask? “I don’t actually NEED a coffee,” you say?

You don’t have a choice.

You will do this because we are holding your Creativity hostage, and when you return, you will realize you have precious little time left in your open window before the next meeting.

Do this, or else!

Email, Meetings, and Distractions
The Daily Routine Gang

PS: It’s already 11pm. Too late. We've killed your Creativity. 

Don’t let your routine kill your Creativity. Take back your day. Say no to things. Be structured. And work on what's most important.

And if all else fails, start by watching this pep talk and get back to being awesome. Good luck!

Posted on April 7, 2014 and filed under creativity.