A Brief Guide to Being Bad at Email

A Brief Guide to Being Bad at Email post image

I thought about email a lot over the past few weeks. Every morning, I watched messages trickle in and pile up. My replies were sporadic. I scanned the incoming to-dos with a mounting sense of unease.

I re-visited Getting Things Done and read the newest posts on inbox zeroing. I considered the implications of being bad at email. I read random books that have nothing to do with email since I had some spare time.

I wondered about email’s nature. Like how the usefulness of replying to any one email is inversely proportional to the amount of time it’s been in your inbox.

If an email could sit in your inbox for 4 months, and still be worth replying to, it must be special.  It’s a shame then that replying with such a delay is not considered a great compliment.

And about all those piling messages— I did nothing. Trying to get on top of my inbox felt as fruitless as watching Lakers highlights on Youtube.

So I watched Lakers highlights on Youtube.

Screen Shot 2014-11-25 at 5.09.25 PM

watchin’ Kobe doin’ work instead of doin’ work

Peak email.

It happens to most of us. Once or twice a year there is so much to do, so much people are asking of us, that the only thing to do is to re-consider your process.

And for all the GTDing, canning replies, inbox zeroing, time batching, and you name it I’ve tried on my end, I missed something totally obvious. What about sharing with people how to communicate with you effectively?

It was my friend Jodi who planted the idea in my brain. She updated her contact page to let people know what types of emails she’d like to receive, and her inbox improved.

I was tardy on a similar approach before— for years I was baffled by the uneven quality of many TMBA applications. It was very late in the game until I realized it might make sense to explain what I was looking for.

(Which makes me think briefly about my entrepreneurial mistakes: it’s common for me to suspect I’ll learn from them, but it might be a better bet to plan on repeating them and plan accordingly).

Putting energy into your contact form is a great idea even if you don’t have a ton of email volume (this isn’t strictly a volume issue, it’s also a quality issue)– perhaps you could do more to encourage people to reach out to you? Or guide their inquiry so there is less friction in getting to the sale?

So with a little inspiration from Jodi I’m going to create a TMBA contact page. I figure just like any process I can toss it up and evolve it as I see the results. If you have one that’s working I’d love to see it. I’ve posted my first draft below (would love your feedback), and once I double check everything with the team I’ll post it to TMBA as a permanent page.


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  • Step 2: Email. If you prefer to email me your question, please only do so if you don’t mind me answering the question in either a TMBA post or a podcast episode. I will only use your first name unless you specify otherwise (I’m happy to mention your URL if you specify). I love answering business questions and often use them for inspiration for posts and shows, but I honestly can’t get to most of them.

Other inquires?

I love hearing from readers about the following topics:

  • Any and all content suggestions: cool books, podcasts, and blogs. Stuff about philosophy or the general direction of location independent entrepreneurship.
  • “Just saying hi” emails are great. I love it when readers share where they are traveling, what their entrepreneurmobile looks like, encouraging notes, or their photos listening to our podcast.
  • Pointing out typos, errors, or ideas on how we can improve TMBA.
  • Anything regarding the NBA.

If you want to pitch us stuff, keep in mind the following:

  • We are fascinated by lifestyle business strategies, trends, and stories. We aren’t looking for “hits,” traffic, affiliate partners, or cash. I say this because many business people naturally frame things like this, it’s just not what motivates us to do TMBA content.
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If you’ve read all that and want to say hi, you can reach me at Dan at Tropical MBA dot com.

If you have any feedback for me, or thoughts on email processing, I’d love to hear them!




Published on 11.25.14
  • Ben B

    One of the best contact pages I’ve seen is Tim Ferriss’. He explains what, why, and the best ways, and reasons to contact him. http://fourhourworkweek.com/contact/

  • Wow, just by reading that I can get an idea of the magnitude and diversity of your current e-mail deluge!

    Great page and I think it will help you out a lot. You could make the headers expandable thingies, like Benny has done here: http://www.fluentin3months.com/contact-me/

    For anyone looking for a bit simpler implementation, I’ve split my contact page in two: http://espressoenglish.net/contact – each of those goes to a separate folder in my inbox, and customer questions get priority. Not only has it helped in terms of my own organization, but I actually get fewer emails now, and higher-quality ones overall.

  • Thanks for the shout-out but it was actually Mark Manson who gave me this idea, at DCBKK, natch :)

  • thanks for the push in the right direction!!!

  • thanks Shayna I was actually just looking at yours the other day I really like this approach!!!

  • thanks for sharing that Ben, I like how he seems to get it done with less words (and the jokes are good too).

    I feel a little verbose but also I want to continue to receive emails from readers, this guy is basically like “I’M OUT!” :D

  • Contact page added to footer!

  • Dan,

    I always found Neil Patel’s “contact”-page intriguing:


    Re: email. Since my business is now running on Slack, I’ve technically set myself up to be able to check emails once a week – everything important, including support (which I don’t answer myself usually) – goes straight to Slack.

    So why do I keep checking email at least 3x/day? Habits, I guess. I should re-evaluate.

  • wow super fascinating thanks for the link, i really like the inforgraphic style, all in all not that dissuading actually, I’d be very curious about that set up with slack, sounds cool

  • I should write a post about the Slack setup. Basically everything important to my business (Trello comments, Git commits, Support tickets, messages from my developers) goes into Slack. Most of the stuff going to my inbox is “not important” and/or “not urgent”.

  • I see, doesn’t look like our customer service software integrates yet. Would love to see the post.

  • Which tool are you using? I’m using SupportBee and they’ve got a ‘webhook’ feature where I can send a notification to Slack, even tho there isn’t an official integration.

  • ah interesting, we just started using freshdesk

  • Looks like you could set it up with Zapier:


    There might be some other interesting ways to use Zapier in your business, such as

    “PayPal subscription cancelled -> Deactivate Ning user + send followup email”.

    If you’re not familiar with Zapier, check out our latest podcast episode: http://wpcast.fm/zapier

  • thanks so much David I really appreciate that!!!

  • Great tips and a just-in-time kick in the butt for me. My wife’s and my expat site has finally gotten just enough visibility that our email has suddenly pumped way up. Much of it being those types of requests for guest posts, “special opportunities”, Panda-annoying SEOs, none of which we want. Plus more of the sincere comments and questions from readers, sure, but like you to benefit others we’d rather see that happen and our reply be in our online forum community and in post comments. Then there’s the relatively few who demand detailed specific answers and advice, for free. We now in fact have a way to work with them, for an affordable rate, but certainly not for free.

    Thus we definitely were in need of some inspiration for email practice /contact form verbiage updates. Thanks!

  • thanks Mark! so far so good for me, another ‘minimum viable benefit’ of this is that it liberates you to take faster action on requests rather than considering everything as a one off. I’ve found myself feeling free to respond ‘no’ to stuff because i’ve been clear about what we are looking for.

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