You might as well ask because the worst they can say is “no.”

I’m not necessarily advocating that as general advice, but it is advice that I hear a lot. It came up yesterday in a conversation about asking a local grocery story to care a certain type of peppers.

Might as well ask, right? The worst that can happen is that they don’t carry the new peppers and everything is exactly as it is right now, which is not bad, just not as great as it would be if the store carried these amazing peppers.

Email is a perfect medium for this kind of advice, since email opens the door for anyone to ask anything.

I could ask Barack Obama to come on my podcast, but I probably won’t hear back or if I do, I’ll get a no. I could ask a Google high-up if they could bring back Google Reader, but I probably won’t heard back or if I do, I’ll get a no. But if I get a yes, wouldn’t that be amazing?

There are more realistic scenarios. I could ask someone in my field to help me with a problem I’m having. I could ask someone with more influence than me to help spread the word about my product. I could ask the bike shop for a discount. I could ask them if they want to go out with me. I could ask to have pizza for dinner.

Those seem more like tossups whether I’m going to get the answer I want, but hey, might as well try, right?

One way to characterize all this is how Andrea Donderi did:

This is a classic case of Ask Culture meets Guess Culture. In some families, you grow up with the expectation that it’s OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.

In Guess Culture, you avoid putting a request into words unless you’re pretty sure the answer will be yes.

That “might as well ask” idea is Ask Culture. The opposite being someone who rarely asks for things (among other characterizations) which is Guess Culture. It feels right to me, similar to the distinction between introversion and extroversion. (I heard about all this from Rachel).

Me, I’m guess culture, apparently. I don’t often ask for anything, or if I do, it’s a result of heavy calculation on my part. Like I really need to ask because there is a lot of pressure on me to do so, or I feel like I’ve built up enough points that asking is just cashing in on those points.

Is that a weakness though? Shouldn’t I just ask more because who cares if they say no?

My brain won’t let me. I think it’s because when I’m the target of Ask Culture, it bugs the hell out of me. Take the classic (pre-pandemic) email: let’s just get together for a coffee and I’ll pick your brain. That’s Ask Culture. They might as well just ask, since the worst that happens is that I’ll just say no. But that’s not the worst that can happen. Chances are, now I think you’re obnoxious, needy, and selfish, and I don’t want to have anything to do with you. There were actual consequences, because you needed something and not only did you not get it right now, you’ll likely not ever get it from me, because it’s a burnt bridge. That culture might work for you sometimes, or might have worked great in your family dynamic, but I feel doesn’t translate particularly well to the business world.

I don’t mean don’t ask anything, I just mean be more empathetic in your asking and be aware of what the consequences might be.

My Working Day Isn’t Your Working Day… But I Know That, Don’t I?

There is something to like there. A reminder to people about the response expectations of this email.

It also scares me a little bit. Isn’t this the implied social contract of emails? Hasn’t it always been, but especially now-days with many different more immediate communication methods where the social contract is less defined?

I also wonder who the message is for. If they are talking to a stranger, it seems unnecessary. Strangers don’t owe you anything and everyone on both sides of this email knew that. Are the a friend? Weirdly formal for a friend. Are the a co-worker? That seems the most likely, but shouldn’t expectations about communication be such an important work concept that it shouldn’t be the responsibility of an email signature to take that up?

Depressing Moment

When I open my mail email account for Team CSS-Tricks and every single email is someone reaching out to put spam on our site.

The email itself isn’t really spam. It’s a real person (although I doubt it’s a real person named “Lisa Turnbull”) using templates to try to get site owners to update blog posts with their “resources”. It’s spam. If you do it, it will hurt your site and help theirs. I think what they are doing should put them in jail. And yet the world rewards them instead. They make money. What few takers they get on this are enough to keep this spammy world growing.

It’s just a depressing movement, and I mention it here because email is a real enabler of this and I wouldn’t blame anyone for being down on email if this is their main experience with it.

My Own Digital “Decline Letter”

Thanks to Rick Saenz for pointing me to Edmund Wilson’s “Decline Letter”. The earliest reference I can find to it is Tim Ferris’ blog, but Edmund Wilson was born in 1895, so I imagine this has been bouncing around for a while, as evidenced by the extreme artifacting of this image.

This is a bit of an answer to The Fail Zone, where instead of giving no response to an email, you respond with something like this so that at least people know where you stand.

I made my own:

You can see it in full here, or see the code / fork the project here.

I’m probably not going to actually use it for anything, but it was fun to create.


You know what nobody does over email? Send a message saying “hi” and then wait for you to respond before saying what they need to say. I feel like even if your best friend or boss did that over email, I’d just delete it.

But it’s such a common thing over messaging apps like Slack, that there are half-parody websites about the problem.

Just ask the question.

Indeed, please do.

It’s funny how the culture of communication is so different across different types of communication. Part of me thinks it’s age. Like compared to email, Slack is a baby, so the culture there needs time to evolve. But I’m not sure that’s really it.

What I think it is, is that the “hi” messages are shorthand for a much more elaborate message:

Hi. I’m pinging you to see if you respond in a somewhat realtime fashion. I have something to ask you, but it doesn’t matter or isn’t useful if we can’t do a bit of back-and-forth in realtime. If you respond fairly quickly, then I’ll respond with my question so we can kick off this little session how I envision it.

Perhaps chat clients like Slack need a new cultural way to ask for that. Here’s an idea: the 🏹 bow and arrow emoji. Like if I shoot an arrow at your attention, I’m asking to see if you’ve got a sec to do a realtime chat session. And maybe they expire after like 10 minutes?

The Fail Zone

Here’s an email moment where I feel like an asshole. This is something I want to improve. Here’s here’s a really specific example (but I’m thinking broader, generally).

I get an email today from a real, regular, normal person. I don’t know them whatsoever. They aren’t overtly rude, but they want something from me. They want technical help on a website thing. They offer few details, but offer to pay for the help.

The problem is… I don’t do this kind of work. I don’t want to. I have a busy life working on all sorts of different things and nowhere do I suggest that I’m hirable for freelance web work. If I did, I don’t think I’d be the kinda freelancer that’s willing to just get pulled into random situations. One step further, if I was, my quote on work like that would be a number that I could just tell they didn’t want to see.

And because I don’t know this person, I’m also not comfortable suggesting them to anybody I know that does do freelance work.

So I have nothing really to offer. And you know what I did? I just deleted the email. I’m not overcome with guilt about it, but it is a bit of an asshole move.

Really? Not even a “sorry, I don’t do that kind of work” response? I’m afraid not, readers, just gonzo. I sort of dread the potential followup “C’monnnnn I reallllly need help” which will double how bad I feel and pull me deeper into something I can’t help on.

For lack of a better term, this email is in the fail zone for me. I don’t have a system, so the email gets handled in a way I’m not proud of. It’s not just freelance requests, it’s anything where I just don’t know what to do, it can’t just sit in my inbox, so I shoo it away rather than being helpful and building that long term karma that email can be great at.

What kind of response should I have given? My stance on what I can offer isn’t going to change, but I like honestly and could/should have more helpful. I should write something generic that explains how I don’t do freelance and how I don’t do referrals for strangers. I bet I could write something in there there has generically helpful advice. Then save that in a place that’s easy to re-use. That way, I’m being honest, as helpful as I can, and I’m not just punting on email entirely.

Spam Intermediary

One big advantage of having your email go through Gmail is the spam filtering. I don’t know of anything that’s going to do a better job than that, especially for the zero-effort and zero-cost.

I just used Gmail for a complete “intermediary”, by recommendation from a tool-creator, so I thought I’d write it up.

  1. Feedbin is a great RSS reader.
  2. It has a feature where it gives you an email address and anything that gets emailed to it becomes an entry in your feeds. The intention is email newsletters. I’ve used it for years.
  3. Somehow this (secret) email address was leaked, and I started getting spam in my RSS reader (boooo). I can blacklist them from Feedbin, but they were hitting me from random email addresses.
  4. I could reset my email in Feedbin, but that wipes out all my subscriptions.
  5. I did it anyway, because I was way too sick of the spam. But this time, rather than sign up for newsletters directly with it, I use a brand new Gmail address that auto-forwards to my Feedbin email.
  6. Now I can sign up for newsletters with like and know that it’ll be forwarded properly, but also that it’s spam-filtered, plus if it leaks again, I can block that particular +-specific email (unique feature of Gmail).

Even if you don’t actually use Gmail directly, passing email through it can be mighty useful.


Within a few days of each other, I got these email notifications of acquaintances praising different email clients.

Here’s Julie loving Edison (not sure if it’s Edison Mail or OnMail or what).

(Edison is so wild in that they are like: we read your email and sell the data, but, like, anonymously, and they spell it out in a way that somehow makes it seem like that’s OK. But of course, one tiny screwup and 🤮).

And then Luky, on liking Spark:

I’m just guessing here, as I haven’t spoken with either of them, that they like the email client switch because they felt a productivity boost. Like they have a better handle on email and it’s feeling less cumbersome in some way.

That always makes me think: is it really the email client? Or is it that switching clients just awoke a little spark in your email handling habits that has you taking care of business for a while, feeling good about that, and thanking the client instead of yourself.

I wonder about that because it happens to me. Any little switch-up in my normal email routine (new client or otherwise) can give me little bursts of productivity that leave me feeling good.

Does inbox cleanliness have anything to do with actual email productivity?

I’m tempted to say: yes, of course, absolutely.

But I’m not entirely sure.

My wife is a good example. I wouldn’t call her inbox a mess, but from the glimpses I get of it, there are an awful lot of unread emails in there. I don’t get the sense that she spends all that much time on inbox cleanliness. Yet, if I email her, I tend to get a response in like 3 minutes. She’s fast, and I’d call that a trait of email productivity.

I’d like to correct my own thinking on this, and not make sure peddle an idea that you have to have a super clean inbox in order to be good at email. I think I’ll be able to unearth more about this once I get into doing more interviews. If you have thoughts though, I’d love to hear them.

Is it possible to highly productive with email but have a messy inbox?

Email Design Accessibility: Why It Is Important to Improve It

Nataly Birch on Designmodo:

Not only do pandemic and legal enforcement bring this issue to the forefront. There are some other reasons why email design accessibility matters.

• Any kind of disability, even a temporary one, makes it hard to interact with email. Therefore, you won’t get a proper response on your strategy and campaign, to say nothing about driving traffic to the landing page.

• Almost 1.3 billion people worldwide live with some form of impairment. It is a colossal share of the market that you overlook.

• Inaccessibility in email design may lead to a disappointed, frustrated, or angry customer. For example, if you do not provide your images with ALTs, people whose email readers ditch all kinds of visuals by default won’t see your smart pictures, backgrounds, and accompanying material. Therefore, you will lose the click, the sale, and damage or ruin your relationships with the contact.

Email accessibility matters on all levels. It is increasingly vital for your business to thrive, to say nothing about its unintended benefits. Therefore, it should be taken into account each time you create a digital newsletter.

I think this idea has seemed into the global developer consciousness, but just to be clear: accessibility isn’t just about building digital things that work for blind people using screen readers, although that’s important. There are infinite variations of disabilities, temporary and permanent.

On this site that is vaguely about collecting ideas around email productivity, I’m curious both about email construction accessibility and how that effects people’s ability to deal with your one email effectively, but also about disabilities and how they effect people’s ability to be productive with email as a whole. I know almost nothing about this.