Today we're going to play a game called good email vs. lousy email

Hey, friends.

Today I'm wearing my f*ck-off-pink (not actually called that) lipstick. This is generally a sign that I'm ready to step up my game. Just like when a batter crowds the plate, I am announcing my presence with authority.

In the last couple of weeks, I've been on the receiving end of a bunch of lousy, horrible, awful, no-good, very bad emails. So, for today's #entrylevelboss, I'm going play a game I just made up called "Good Email vs. Lousy Email" to demonstrate exactly what I mean when I say your email game is lame. The gist is always this:

Make it stupid-easy for people to help you.

Too many people are out there thinking it's good enough to "ask for advice" and hope to get a job out of it. Now, that works sometimes. Straight up. It does. In fact, here's a cold email I wrote to a Notre Dame alumnus in San Francisco and it got me hired:

Subject Line: Young, Wide-Eyed Domer in SF

Hi Rick!

I'm Alexa: Notre Dame ('11) and a recent transplant to San Francisco. After finishing my MA in England earlier this year, I've officially set up shop on American soil again and am currently in the process of trolling through the San Francisco start-up world on the lookout for passionate people producing creative work--naturally, you'll understand how I came to stumble upon you and creativeLIVE.

As an English major with a resume stacked in marketing and content creation, I'm very much so interested in trying to find a foot in the door in the creative content space. I'dso love to come and chat with you about the work that's happening at creativeLIVE, if you'd be willing to dole out some advice to a young alumnae.

Thanks so much for taking the time to read through my eager request -- I'll look forward to hearing from you soon.


A little personality and humility will take you far in this life, my child. I successfully capitalized on that whole alumni-bond-thing (and I know he's reading this, so...hey Rick) by reaching out for advice in the right way. Meeting with someone in the industry you want to go into is an awesome way to explore said industry. But don't waste their time by being vague and wishy-washy. Even if you aren't sure the industry for you, you best believe you should pretend like it is when you talk to them. No one can help you if you don't know what you want help with... except for a life coach. You can hire one of those.

Oh, and pro tip: Always offer to come to their office.

But I could have gotten even more specific, right? I didn't even propose a time or date. So, here's an email I wrote when I was trying to start networking in Berlin:

Subject Line: New Community Manager in Berlin!


Hope this email finds you well! I'm Alexa. I've been following EyeEm and the Berlin tech scene for the last few months, as I'm moving to your fabulous city in two weeks!

I'm coming to Berlin from Silicon Valley, where I've been working in content strategy and community management for a Crunchie-nominated, venture-backed online education startup. CreativeLive specializes in photo education, so I have a true soft spot for what EyeEm is doing.

I wanted to reach out to you now, as I'm sure you're incredibly busy, and see if I could buy you lunch/coffee/beer and talk shop about community management, maybe pick your brain on the Berlin startup world. Are you in town the 7-10 of May? Let me know what you think. Cheers!

Have a lovely night,

I repeat: Are you in town the 7-10 of May? Don't make someone look through their calendar and ask you when you're free. You're the one who wants help, remember? So make it stupid-easy for people to help you. (Epilogue: This girl was super rad. She responded, I went to their office, and we talked about photography and California. And then I wound up going out for a BBQ with all of her friends/colleagues, some of whom I still hang out with from time to time.)

Here's the part where I tell you to go watch Episode 5 of #entrylevelboss -- but there have been a few hiccups with uploading today. Fingers crossed it will be ready to rock by tomorrow, and we can all play Good Email vs. Lousy Email together.

Hugs until then,

PS: Is it helpful for you to see my emails IRL like this? If yes: I ask you to please support #entrylevelboss by forwarding this email to a friend with your stamp of approval.

PPS: Are you following me on Instagram? You should, for real. I'm on Day 24 of #the100dayproject and I'm taking requests.