7 Steps to Email Freedom

Email is a massive drain on productivity for Entrepreneurs.  It’s time to fight back!

Below I share how I’ve cracked the code and now enjoy phenomenal email freedom.

I’ve helped other entrepreneurs do the same, including a few famous guys including Andrew Warner, founder of Mixergy.com:

“Tim finally solved my email inbox. I’ve tried everything else – helpdesk software, shutting off email with an autoresponder (people were really pissed), and I considered secret second email inboxes and none of it worked. Until I used Tim’s advice, and now I’m finally free.” – Andrew Warner

Here’s what I told Andrew…

7 Steps to Email Freedom

1. Trust Your Assistant

First, you must trust your Assistant.

You *do* have an Assistant, right?  They’re more affordable than you think.

Trust takes time. Wouldn’t make it the first task I delegated to a new Assistant; in fact, I’d probably wait 6-12 months, *and* do a criminal record check, *and* references, *and* sign a confidentiality agreement.

This is one of the reasons I only hire USA / CAN Executive Assistants – the laws are similar, and the legal systems are too. And I could hunt someone down if I really needed to.

Also, make sure you’re using Google Apps / Gmail. If you aren’t, switch over immediately – you are extremely late to the party. Every day you aren’t on Google Apps, you are missing out on a massive productivity jump. Ditch Outlook, your PC, and 1995… it’s time for Google Apps.

2. Mass Unsubscribe

Run Unroll.me to get rid of 95% of email subscriptions (except from: Ryan Levesque of course!). There’s no sense making your Assistant repeatedly delete unwanted emails. As many outsourcing experts say, “ELIMINATE – Automate – Delegate.” Eliminate as many recurring emails as you can before handing over to Assistant. If you’re worried about privacy, immediately unsubscribe from Unroll.me afterwards.

3. Create Private, “! – Tim Review” Label

In Gmail / Google Apps, create a “! – Tim Review” label. The “!” makes it appear at the top of your list of labels. This is the one label your Assistant can never-ever click on. They could if they wanted to, but they won’t because they’ve promised they won’t click on it, and you trust them. **This is the one leap of faith in my system. But if you trust your Assistant (see above), the leap won’t feel as big.**

4. Filters for Loved Ones ONLY

Personally create filters for your loved ones. And perhaps a lawyer or accountant. Filter their messages directly to your “! – Tim Review” label.

But no one else gets the full-filter treatment, not even your most A+ clients, peers, associates who pay you big bucks or have big influence.

This is because you can actually give *better* service to your A+ clients, associates, friends, if you have the team approach (you + Assistant) to your inbox. Sometimes when $500/hr clients have written me with something simple (e.g. scheduling, getting a file from me), Sarah will intervene to get them an appointment (or whatever) as fast as humanly possible.

5. Hand Over Root Access

Handover root access – username and password – to your most basic email account.

NO SECRET EMAIL ACCOUNTS: it sounds fun and effective in the short-term, but sooner or later word gets out and it all falls apart, and you’re back at square one. Take the leap and give your most root-level, ground-zero, no-other-places-to-hide email account.

NOTE: this was a brutal, painful moment-of-truth for me. Sarah had to pry my email inbox out of my hands. You’d swear I was a crack addict clucthing to the last piece o’ rock in the county. Expect this to be difficult and painful. I hope you are pleasantly surprised, and I want to tell it to you straight, it could be emotional.

Looking back, though, my blinding fear was truly ridiculous and childish. Now I wish I would have made the jump years earlier. You’ll feel the same way.

6. Coach Your Assistant for a Week

Look over your Assistants shoulder for a 4-5 sessions of 45-60 mins each. Coach them on how to file away messages, and how to answer on your behalf.

You’ll be amazed by session 4 or 5 when they’re really starting to pick it up. Within a week, they’re rolling with you.

TAKE NOTE, THIS IS REALLY IMPORTANT: When your Assistant answers, they will answer from your email account, and will always open with:

“Hi Firstname, this is Tim’s Assistant Sarah. I got to your email before Tim did, and I thought you’d appreciate the fastest possible reply, so… (insert whatever the reply is).”

…literally, and legitimately, most recipients will feel tickled to receive such speedy, white-glove service. We’ve received great feedback.

7. Check Only Your “! – Review” Label

From now on, only check your “! – Tim Review” label.

Obivously, if you need to (Assistant is sick, and/or you’re waiting for a really important and urgent email to arrive), you can easily check the main inbox. But your general rule, now, is only to check your personal “! – Review” label.

You’ll see your Assistant will take care of 90%+ of your email, and you’ll suddenly wonder what the hell you used to do all day.


How good is this system? I stress-tested it twice last year. In Jan 2015 I went to Jamaica for 8 days, with no email, phone, or text contact of any kind. (And no Slack, Project Mgmt, etc… so – NO CONTACT.)

Repeated the test in July 2015 when I went to Hawaii for 10 days. Same disconnection from work, and same amazing outcome – total freedom and relaxation!

The combination of this email system, plus my great Assistant Sarah, plus all the other systems and DMGs I have setup with her, and I enjoyed a blissful tropical holiday, no problems at all. Sarah took care of it all.

Tim with Luau Dancers - cropped for Facebook

And best of all?

When I came home, there was no “Welcome Home” avalanche of 500 emails. Just a few, which took me less than an hour to reply to.

Yes, my friends, Email Inbox freedom truly is at hand.

Onwards and Upwards,

Tim :)

P.S. If you’re interested in learning more about getting your own Assistant to help take over your email inbox, visit www.GreatAssistant.com

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2 thoughts on “7 Steps to Email Freedom

  1. I have to disagree re Google apps. Microsoft Exchange has always been and remains a far better solution for a whole host of reasons:

    1. Outlook integrates 1000x better and the UI of Outlook trumps any online UI. Some significant ways are:

    – multiple email addresses, I realize this might seem to go against your system but there are times for many people for many reasons when you need multiple email addresses and being able to switch between them seamlessly and easily is much more important there's no better way to do this than outlook

    – message thread organization particularly as related to attachments, unfortunately, Gmail doesn't handle this well and can make finding old details challenging, combine this with outlook social connector and you get far better functionality

    – folders still Trump tags for filing messages, this one you can argue as being comparable except when you robustly put them through the gauntlet, this shows up largely when you want to eliminate tags or apply an efficient hierarchy, both of which work far better with folders

    – tons of little difficult to quantity shortcuts like the fact that everything can be managed from the keyboard, better handling of signatures, little features for efficiently adding attachments, etc. I've also got strong argument against working out of the browser vs a separate app, which relates a lot to distraction

    2. Far better delegation permissions and privileges – for example you can actually share individual folders within your email easily, you can delegate access to certain parts of your email without giving up administrative control (as an aside I highly recommend LastPass to help manage logins to people on your team)

    3. Distribution lists as alternatives to email addresses

    4. Contacts sharing

    The list goes on. Frankly Exchange is simply a much more robust refined offering that scales better. As a single user with a single email address you likely won't notice it as much but the bigger you grow the more it makes a difference.

  2. Michael Bruce Rosmer – thanks for the robust reply, haha. Maybe Gmail added this feature since the last time you checked it out, but it also allows for both sending and receiving from multiple email addresses.

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