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Rightsizing Your Email Habits: How to Become More Effective as an Entrepreneur

As an entrepreneur, your most important work is to answer the big, unasked questions—the sort of questions that won't arrive in an email.

Chase Damiano
6 min read
Rightsizing Your Email Habits: How to Become More Effective as an Entrepreneur

It can feel highly productive to mow through your inbox. But what if most of the time you spend on emails is just that: merely the feeling of getting things done?

Is all that time spent really moving the needle on your work?

As an entrepreneur, your most important work is to answer the big, unasked questions—the sort of questions that won’t arrive in an email, and won’t likely be asked by someone else.

While answering emails and communicating with people is imperative, it’s important to remember that simply getting things done is very different than getting the right things done.

So when email is necessary but inefficient, how can you allocate the right amount of your time to it? Your time is your most valuable, non-renewable resource—so rightsizing your inbox management is a task that might seem trivial, but one that can have huge downstream effects on where your time and focus are directed on a daily basis, and therefore also on the ultimate success of your company.

The default habit: email as a to-do list

Throughout the day, how often do you check your email? For me, it used to be all the time: when I was bored, just sitting on the couch, or during time in between meetings—basically in any otherwise empty time-space.

Our phones are part of us now, and the mail icon is always right there. It’s too easy. But constantly checking email forces us into a reactive behavioral pattern: get email, take action. (Even if that action is to boomerang or archive.) Habitual email use creates a perpetual to-do list.

Obviously, we need email because it’s the de facto method to communicate with parties outside of our company. I’m not saying we have to stop emailing entirely. However, a business and internal culture driven primarily by email is highly inefficient. It’s hard to understand what decisions or actions are taken from an email conversation. From an efficiency standpoint, long email conversations are much better suited for meetings or calls.

By living in our inbox this way, perpetually checking and reacting, we unwittingly feed into a vicious cycle. We create a world in which we receive a lot of email, which keeps us stuck in email—which, consequently, means our thinking stays stuck in email too. Pretty much all day, every day. This is not good.

Why? Because the inbox is where other peoples’ tasks live: those of your clients, employees, investors, and the outside world. And your own thinking should not stay stuck in other people’s worlds.

Remember: The probability of getting an “Oh my god, I need to respond to this mail immediately, because this is a real emergency” email is near zero. If something is a true emergency, people should (and will) call.

If you and your colleagues spend a lot of time in email, you’ll naturally get really good—and, yes, even efficient—at email. But getting really good at email is different than getting really good at growing the business.

Email, rightsized

Instead, successful businesses are built with successful ideas. So as an entrepreneur, you need to give your conscious attention the chance to focus more on ideas, not emails.

Ask yourself, “Why am I checking email so much?”

Your answer probably has a lot more to do with the stuff of daily operations, and not the big picture, which is what you should be focusing on as the leader of your company.

How to rightsize your use of email

Rightsizing your use of email as an entrepreneur is about achieving non-attachment to email.

It’s about more than “inbox zero.” Inbox zero helps us prioritize our inbox, and boomerang low-priority emails to the future. (My latest favorite email app has been Superhuman, which has features for this, but native Gmail has these features, too.) To correct this, implementing lean email practices are the first order of business—but only the first.

1. Gather data

First (and it might seem unthinkable, but trust me), allow your inbox to pile up for one week, without answering or opening anything. You’ll get the data you need to gain a fresh perspective on what’s coming to your inbox. This is easiest when you’re conducting a Think Week or otherwise disengaged from the day-to-day operations.

If that sounds out of reach, open up your archive and pull in the emails you’ve received over the last week.

2. Analyze

When you return after a week, have an analytical eye. Study what you see. What types of email are coming to your inbox? Look for:

  • Messages from clients
  • Messages from team members
  • Newsletters, articles, subscriptions
  • Receipts
  • Marketing junk mail from various apps and platforms
  • Updates and notifications from god-knows-what-else!

How many emails did you get from each category? What themes emerge? What are the team members really asking you about? What types of newsletters are you subscribed to?

3. Take action

Next, categorize, label, and take action to reduce the overall “noise” in your world.

  • Bubble-up VIP-level email addresses to surface truly important client emails. Employ filters and labels to make sure they are always marked “important” and come first. They can be from key clients, or from a priority email address, such as a sales lead form that generates an email.
  • Transition teams to more innovative internal communication softwares. Slack for simple communication; Notion, Asana, or Trello for knowledge/project/task management.
  • Unsubscribe from all the crap you’re getting. Be diligent. While it’s easier to archive or delete than it is to unsubscribe, there’s a real mental tax you pay every time you see (unconsciously desired) garbage in your inbox. Take the time to unsubscribe/block/spam and have it gone forever.
  • Filter out receipts, notifications, and other recurring/operational information. Have it stored in a label but skip the inbox, so you keep a record, but it doesn’t break your email flow.

Lastly, only check email in batches at specific times of the day—not when you get notified. Better yet, turn off email notifications, and kill the badges on iPhone. (Trust me, you’ll be glad you did.)

It’s too easy to react to Outlook/Gmail/Superhuman notifications when they appear. But it breaks your train of thought, and that microsecond of mental switching is costly and adds up. And since most of us have deeply ingrained email-checking habits already, we must proactively open these tools on our devices to temper them. You’ll notice you still want to check a lot, but overall, without notifications to prompt you, your checking will become more conscious and intentional.

By doing so, you’re creating a world in which the only emails you receive are those that really must be communicated by email, as well as a world in which you’re able to respond on your terms. It’s both possible and best practice for your business.

Entrepreneur, not emailer

Even more drastic correctives are plausible. For instance, you can uninstall your email client on your phone, or get an executive assistant. When any of these tactics corral your use of email, freeing up your thinking to work on the hard problems that “it’s hard to find time” for, that’s a good thing.

If you want to flex your design muscles, for instance, you must create the time to do so. If you don’t prioritize it, it won’t happen. Yes, it requires discipline, action, and a mindset shift around work. But that’s the only way to live in a world in which we are effective, not merely productive.

When guided by habits and default notification settings, only a small percentage of your working hours will actually move the needle. But if you reclaim your time for deep work—starting with time spent in email—and allow the unimportant to fall away, the needle might just jump.

Helpful Gmail resources

Here are some additional resources I’ve used for Gmail specifically to better manage my inbox and instill more effective email habits:

  • Use Gmail’s Snooze feature to make emails disappear, then arrive again later at a specified time. If you have a dedicated time you want to respond to emails, this helps triage those emails into the future.
  • Use Gmail filters to automatically have emails skip the inbox, apply labels, or assign importance based on predetermined rules that are highly customizable.
  • Set up Multiple Inboxes to visually separate types of emails. Good for to-dos, or sorting “FYIs” from “action required,” or separating out notifications, like from payroll software.
  • Use Inbox Categories to automatically separate emails that look like promotions, social media, updates, forum posts, etc.
  • Learn the Gmail keyboard shortcuts to blaze through emails faster. This has made a huge difference for me personally.

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