Tag Archives: Prioritizing & Scheduling

8 Steps to Email Sanity: How to Work on Company Strategy When You’re Drowning in Email

drowning-in-emailBeing a second stage entrepreneur presents some “interesting” challenges. Among them, how in the heck are you supposed to be able to spend time “working on the business” instead of “in the business” when you are always drowning in email?! Chances are, you can’t get ahead on email even if you stay up half the night, because you’re still getting replies and new emails even as the night wears on. Sound familiar?

Step 1: Take a deep breath.

Step 2: Consider declaring email bankruptcy if you have a truly INSANE amount of unread email (e.g. thousands). The general idea: delete all your email, and the stuff you REALLY have to respond to will resurface. Check out these examples from Gawker Media for more info on how email bankruptcy can work.

Step 3: Stop responding so often. Try limiting email to once or twice a day. I know, I know – this sounds blasphemous. If you’re so behind on email, how could you possibly spend less time doing it?! Trust me on this one – a funny thing happens when people learn you’re not going to respond to your email all the time. They start handling things on their own and finding other options. It’s not that anyone is being lazy or anything of the sort! What I am saying is that you have all adjusted to a status quo that’s not good for you – or ultimately, your company. Check out these samples from Tim Ferris’s blog for a couple of email auto-responders you can copy and implement now to explain your healthy new habit.

[Note: If it’s too painful to stop responding right away, try this baby step. Respond, but schedule the email to be sent later if it’s not truly urgent. You’ll start to help others (and yourself ;-) adjust to a longer response time. See our previous post on how to implement email scheduling with Boomerang for more info.]

Step 4: Start unsubscribing from everything humanly possible. Yes, you could organize everything into folders instead, to read later “when you have time”… (I tried that first, so feel free if you must.) However, email is ultimately a lousy way to satiate your curiosity about anything. Subscribe via social media to things you don’t want to lose (easier to tune in or tune out as you have time and interest), and forget about the rest. The time you save will open opportunities to learn and try new things in the real world. You might discover something new that you like, such as triathlons, and open a whole new chapter of your life! (Speaking from personal experience!) Another way of looking at it:

Get on a strict low-information diet and focus on output instead of input; your wallet and weekends [and your family] will thank you for it. – Tim Ferris

Step 5: Automate your inbox. While it may be a bit un-nerving at first to have things filed for you (lest you miss something important!) the magic of it will quickly become apparent.

  • Sanebox: Free trial; from approximately $2-$20 per month. Works with Gmail, Yahoo! AOL, iCloud, Microsoft Outlook and more.
  • Otherinbox: Free. Works with Gmail, Yahoo! AOL and iCloud.

If I were starting from scratch today, I’d try Sanebox first, even though it’s not free. Their mission is specifically to solve your email challenge, where Otherinbox was recently acquired by a company more interested in improving deliverability than fixing your inbox angst. I also figure if people with inordinate amounts of email such as Robert Scoble are liking Sandbox, then it’s a pretty good sign it’ll work for darn near anyone else.

However, if full automation is too big of a leap and you’re already using Gmail, you have a handful of other streamlining options to try:

  • Smartlabels (under Settings, Labs)
  • Priority Inbox (under Settings, Inbox)
  • Stars (under Settings, General) and Multiple Inboxes (under Settings, Labs)
  • Filters (under Settings, Filters)

Step 6. Take another deep breath. If you’ve done even half of what’s outlined above, you should be starting to get your head above water. Create even more space to breathe with these last two, more strategic tips…

Step 7: Rethink meetings. When you set up the right meeting rhythms and actually get things done during meetings, email magically decreases.

Step 8: Rethink delegation. Delegating so you’re in the middle of fewer conversations also helps to alleviate inbox madness, though admittedly delegation is also a challenge in second stage when everyone is over-busy and tight capital doesn’t necessarily allow you to hire someone to fix it. However, you might be surprised if you ask around who’s willing to help you out. I’ve seen more than one business owner that could have been pushed over by a feather when employees volunteered to take stuff off their list, even when they were already busy. Your employees WANT you to be able to lead! So try asking for help. :-)

Here’s hoping these strategies help you gain control of your inbox – and your business!

What are your favorite hacks for inbox management?

Entrepreneurship and The Hardworking Curse


How can hardworking and curse be in the same sentence, you ask? I bet if you’re an entrepreneur grappling with second stage issues, you’re familiar with this phenomena already. Chances are you got to where you are in part, by being hardworking. And that’s a good thing. You’ve been picking up the slack, noticing what needs to be fixed, spotting the opportunities for growth, all-the-while getting up earlier and staying up later to take care of it all. You’re getting better at squeezing more in to your calendar. You skip lunch when duty calls.

And at some point, you run out of hours in a day. Or energy. Or both. And that’s not such a good thing.

Hence, the Hardworking Curse.

The only way to fix it is to do less. To change your mindset from hardworking to something new. I personally found the idea of working smarter, not harder pretty laughable when in this quandary so I understand if you’re equally doubtful a shift is possible. During that time I read “The 4-Hour Workweek” with such disdain, I completely missed all the neat techniques for learning author Timothy Ferriss shared. But I wouldn’t have remembered his tricks anyway – my decreasing ability to retain the volume of stuff I was reading and exposed to in meetings was getting frustrating. Sound familiar?

I’ll also bet you’re hardworking because you’re driven, and it’s hard to imagine achieving what you want by shifting gears. Don’t fret – I’m not talking about work-life balance kind of stuff – that’s a bunch of bunk for another article. I’m talking about simple, practical stuff you can start doing today.

It’s all about choosing a new lens.

Start asking yourself: What are the 3 most important things I can get done today?

Yes, I know there are somewhere between 20 and 100+ things on your list that must get done today. I get that three sounds ridiculously luxurious and ludicrous all at the same time. Stick with me for another couple of minutes, and I’ll explain.

Yes, you probably will still have to do the vast majority of the stuff on your list today. This won’t be an overnight makeover. (Sorry.) The point here is to get your head up above water long enough to identify three things that will help you reach your long term business goals, and make sure those get done, even if something that’s been nagging you could get done in five minutes has to fall off your plate for the day.

If you don’t have time to figure out three things, or fit them into your already overcrowded day, that’s ok. I get that you’re already strapped. Start with one. The point is to start thinking about things differently. And once you do, I’ll bet the natural rewards of your new focus will do the rest.

What are your three things today?


Additional Resources:

  • If it’s hard to figure out the three things, having a framework to figure it out will help. I recommend using any of the one page plan templates out there which I’ve written about here: Using an Operating System for Your Business
  • If you’re like the idea of choosing three things and want to learn more, there’s a whole school of though about prioritizing work called Kanban for you to explore. I personally think the best guy to learn from is Jim Benson.
  • If you want a dashboard for your three things, you can go the Kanban route with AgileZen (what I’m using) or a similar tool which visualizes your priorities for the day/week/month/quarter called Teamly.

Agile Zen – A Helpful Tool For Getting Things Done


Every second stage entrepreneur I’ve met faces the challenge of prioritizing an incredible volume of things to do. With continued growth, the list won’t get shorter – until you achieve clarity (via an Operating System) and observe a few simple truths such as:

“You Can Do Anything, But Not Everything.”

This mantra by David Allen, Author of “Getting Things Done”, is a great one for entrepreneurs who are always aspiring to make an impact. Yes, we entrepreneurs can do anything! Just not everything.

As with other second stage secrets, successful second-stagers follow similar methodologies for managing the tasks at hand. David’s Getting Things Done (GTD) approach is very popular, though I personally found it cumbersome to implement with such a high volume of “stuff” to manage both personally and professionally.

The greatest hack I’ve found shifts the focus from prioritizing/scheduling/organizing/listing tasks to priorities with one very simple premise:

What are the 3 highest priority things I can do today?

In a gross over-simplification, this concept comes from Agile methodology and a tool called Kanban which visualizes and shares work in progress. When you hear about the Toyota way, Kanban was one of the tools used in their incredible transformation. You can easily begin implementing the system without any deeper knowledge than human-beings are only capable of working on so many things at one time, with the consensus being that number is about 3.

In roughly 15 minutes you can get started using this concept by signing up for a free account at http://www.agilezen.com. You’ll quickly create virtual “cards” for what needs to be done, and pull the three priorities you’re working on now into your work-in-progress.

“Wait!”, you say. “I’m working on more than 3 things!” Not really. It’s simply not possible to be ACTIVELY working on many things at the same time. We cheat ourselves (and others) when we think otherwise.

If you want to research more about how this all works before getting started, I highly recommend Jim Benson’s Personal Kanban 101 as a more formal introduction.

If you’re a just-do-it kind of person, use AgileZen.com, complete one priority and move another into your work-in-progress. And then do it again. Work to prioritize what is most strategic. Magic will follow. :-)

Books for further reading:

  • Personal Kanban: Mapping Work | Navigating Life
  • Getting Things Done: The Art of Stress-Free Productivity