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Step III:

A is for Automation

SCOTTY: She’s all yours, sir. All systems automated and ready. A chimpanzee and two trainees could run her!

CAPTAIN KIRK: Thank you, Mr. Scott. I’ll try not to take that personally.


8.Outsourcing Life


A man is rich in proportion to the number of things he can afford to let alone.


If I told you this story, you wouldn’t believe me, so I’ll let AJ tell it. It will set the stage for even more incredible things to come, all of which you will do yourself.

My Outsourced Life

A true account by AJ Jacobs, editor-at-large at Esquire magazine (ellipses represent passage of time between entries)

IT BEGAN a month ago. I was midway through The World Is Flat, the bestseller by Tom Friedman. I like Friedman, despite his puzzling decision to wear a mustache. His book is all about how outsourcing to India and China is not just for tech support and carmakers but is poised to transform every industry in America, from law to banking to accounting.

I don’t have a corporation; I don’t even have an up-to-date business card. I’m a writer and editor working from home, usually in my boxer shorts or, if I’m feeling formal, my penguin-themed pajama bottoms. Then again, I think, why should Fortune 500 firms have all the fun? Why can’t I join in on the biggest business trend of the new century? Why can’t I outsource my low-end tasks? Why can’t I outsource my life?

The next day I e-mail Brickwork, one of the companies Friedman mentions in his book. Brickwork—based in Bangalore, India—offers “remote executive assistants,” mostly to financial firms and healthcare companies that want data processed. I explain that I’d like to hire someone to help with Esquire-related tasks—doing research, formatting memos, like that. The company’s CEO, Vivek Kulkarni, responds, “It would be a great pleasure to be talking to a person of your stature.” Already I’m liking this. I’ve never had stature before. In America, I barely command respect from a Bennigan’s maître d’, so it’s nice to know that in India I have stature.

A couple of days later, I get an e-mail from my new “remote executive assistant.”

Dear Jacobs,

My name is Honey K. Balani. I would be assisting you in your editorial and personal job…. I would try to adapt myself as per your requirements that would lead to desired satisfaction.

Desired satisfaction. This is great. Back when I worked at an office, I had assistants, but there was never any talk of desired satisfaction. In fact, if anyone ever used the phrase “desired satisfaction,” we’d all end up in a solemn meeting with HR.

I GO OUT to dinner with my friend Misha, who grew up in India, founded a software firm, and subsequently became nauseatingly rich. I tell him about Operation Outsource. “You should call Your Man in India,” he says. Misha explains that this is a company for Indian businessmen who have moved overseas but who still have parents back in New Delhi or Mumbai. YMII is their overseas concierge service—it buys movie tickets and cell phones and other sundries for abandoned moms.

Perfect. This could kick my outsourcing up to a new level. I can have a nice, clean division of labor: Honey will take care of my business affairs, and YMII can attend to my personal life—pay my bills, make vacation reservations, buy stuff online. Happily, YMII likes the idea, and just like that the support team at Jacobs Inc. has doubled.

HONEY HAS completed her first project for me: research on the person Esquire has chosen as the Sexiest Woman Alive. I’ve been assigned to write a profile of this woman, and I really don’t want to have to slog through all the heavy-breathing fan websites about her. When I open Honey’s file, I have this reaction: America is f cked. There are charts. There are section headers. There is a well-organized breakdown of her pets, measurements, and favorite foods (e.g., swordfish). If all Bangalorians are like Honey, I pity Americans about to graduate college. They’re up against a hungry, polite, Excel-proficient Indian army.

IN FACT, in the next few days, I outsource a whole mess of online errands to Asha (from the personal service YMII): paying my bills, getting stuff from drugstore.com, finding my son a Tickle Me Elmo. (Actually, the store was out of Tickle Me Elmos, so Asha bought a Chicken Dance Elmo—good decision.) I had her call Cingular to ask about my cell-phone plan. I’m just guessing, but I bet her call was routed from Bangalore to New Jersey and then back to a Cingular employee in Bangalore, which makes me happy for some reason.

IT’S THE fourth morning of my new, farmed-out life, and when I flip on my computer, my e-mail inbox is already filled with updates from my overseas aides. It’s a strange feeling having people work for you while you sleep. Strange, but great. I’m not wasting time while I drool on my pillow; things are getting done.

HONEY IS my protector. Consider this: For some reason, the Colorado Tourism Board e-mails me all the time. (Most recently, they informed me about a festival in Colorado Springs featuring the world’s most famous harlequin.) I request that Honey gently ask them to stop with the press releases. Here’s what she sent: Dear All,

Jacobs often receives mails from Colorado news, too often. They are definitely interesting topics. However, these topics are not suitable for “Esquire.”

Further, we do understand that you have taken a lot of initiatives working on these articles and sending it to us. We understand. Unfortunately, these articles and mails are too time consuming to be read.

Currently, these mails are not serving right purpose for both of us. Thus, we request to stop sending these mails.

We do not mean to demean your research work by this.

We hope you understand too.

Thanking you,

Honey K B

That is the best rejection notice in journalism history. It’s exceedingly polite, but there’s a little undercurrent of indignation. Honey seems almost outraged that Colorado would waste the valuable time of Jacobs.

I DECIDE to test the next logical relationship: my marriage. These arguments with my wife are killing me—partly because Julie is a much better debater than I am. Maybe Asha can do better: Hello Asha,

My wife got annoyed at me because I forgot to get cash at the automatic bank machine … I wonder if you could tell her that I love her, but gently remind her that she too forgets things—she has lost her wallet twice in the last month. And she forgot to buy nail clippers for Jasper.


I can’t tell you what a thrill I got from sending that note. It’s pretty hard to get much more passive-aggressive than bickering with your wife via an e-mail from a subcontinent halfway around the world.

The next morning, Asha CC’d me on the e-mail she sent to Julie.


Do understand your anger that I forgot to pick up the cash at the automatic machine. I have been forgetful and I am sorry about that.

But I guess that doesn’t change the fact that I love you so much….



P. S. This is Asha mailing on behalf of Mr. Jacobs.

As if that weren’t enough, she also sent Julie an e-card. I click on it: two teddy bears embracing, with the words, “Anytime you need a hug, I’ve got one for you…. I’m sorry.” Damn! My outsourcers are too friggin’ nice! They kept the apology part but took out my little jabs. They are trying to save me from myself. They are superegoing my id. I feel castrated.

Julie, on the other hand, seems quite pleased: “That’s nice, sweetie. I forgive you.”

DESPITE THREE weeks with my support team, I’m still stressed. Perhaps it’s the fault of Chicken Dance Elmo, whom my son loves to the point of dry humping, but who is driving me slowly insane. Whatever the reason, I figure it’s time to conquer another frontier: outsourcing my inner life.

First, I try to delegate my therapy. My plan is to give Asha a list of my neuroses and a childhood anecdote or two, have her talk to my shrink for 50 minutes, then relay the advice. Smart, right? My shrink refused. Ethics or something. Fine. Instead, I have Asha send me a meticulously researched memo on stress relief. It had a nice Indian flavor to it, with a couple of yogic postures and some visualization.

This was okay, but it didn’t seem quite enough. I decided I needed to outsource my worry. For the last few weeks I’ve been tearing my hair out because a business deal is taking far too long to close. I asked Honey if she would be interested in tearing her hair out in my stead. Just for a few minutes a day. She thought it was a wonderful idea. “I will worry about this every day,” she wrote. “Do not worry.” The outsourcing of my neuroses was one of the most successful experiments of the month. Every time I started to ruminate, I’d remind myself that Honey was already on the case, and I’d relax. No joke—this alone was worth it.

At a Glance: Where You Will Be

The future is here. It’s just not widely distributed yet.

—WILLIAM GIBSON, author of Neuromancer; coined term “cyberspace” in 1984

Here is a sneak preview of full automation.

I woke up this morning, and given that it’s Monday, I checked my e-mail for one hour after an exquisite Buenos Aires breakfast.

Sowmya from India had found a long-lost high school classmate of mine, and Anakool from YMII had put together Excel research reports for retiree happiness and the average annual hours worked in different fields. Interviews for this week had been set by a third Indian virtual assistant, who had also found contact information for the best Kendo schools in Japan and the top salsa teachers in Cuba. In the next e-mail folder, I was pleased to see that my fulfillment account manager in Tennessee, Beth, had resolved nearly two dozen problems in the last week—keeping our largest clients in China and South Africa smiling—and had also coordinated California sales tax filing with my accountants in Michigan. The taxes had been paid via my credit card on file, and a quick glance at my bank accounts confirmed that Shane and the rest of the team at my credit card processor were depositing more cash than last month. All was right in the world of automation.

It was a beautiful sunny day, and I closed my laptop with a smile. For an all-you-can-eat buffet breakfast with coffee and orange juice, I paid $4 U.S. The Indian outsourcers cost between $4–10 U.S. per hour. My domestic outsourcers are paid on performance or when product ships. This creates a curious business phenomenon: Negative cash flow is impossible.

Fun things happen when you earn dollars, live on pesos, and compensate in rupees, but that’s just the beginning.

But I’m an Employee! How Does This Help Me?

Nobody can give you freedom. Nobody can give you equality or justice or anything. If you’re a man, you take it.

—MALCOLM X, Malcolm X Speaks

Getting a remote personal assistant is a huge departure point and marks the moment that you learn how to give orders and be commander instead of the commanded. It is small-scale training wheels for the most critical of NR skills: remote management and communication.

It is time to learn how to be the boss. It isn’t time-consuming. It’s low-cost and it’s low-risk. Whether or not you “need” someone at this point is immaterial. It is an exercise.

It is also a litmus test for entrepreneurship: Can you manage (direct and chastise) other people? Given the proper instruction and practice, I believe so. Most entrepreneurs fail because they jump into the deep end of the pool without learning to swim first. Using a virtual assistant (VA) as a simple exercise with no downside, the basics of management are covered in a 2–4-week test costing between $100–400. This is an investment, not an expense, and the ROI is astounding. It will be repaid in a maximum of 10–14 days, after which it is pure timesaving profit.

Becoming a member of the NR is not just about working smarter. It’s about building a system to replace yourself.

This is the first exercise.

Even if you have no intention of becoming an entrepreneur, this is the ultimate continuation of our 80/20 and elimination process: Preparing someone to replace you (even if it never happens) will produce an ultrarefined set of rules that will cut remaining fat and redundancy from your schedule. Lingering unimportant tasks will disappear as soon as someone else is being paid to do them.

But what about the cost?

This is a hurdle that is hard for most. If I can do it better than an assistant, why should I pay them at all? Because the goal is to free your time to focus on bigger and better things.

This chapter is a low-cost exercise to get you past this lifestyle limiter. It is absolutely necessary that you realize that you can always do something more cheaply yourself. This doesn’t mean you want to spend your time doing it. If you spend your time, worth $20–25 per hour, doing something that someone else will do for $10 per hour, it’s simply a poor use of resources. It is important to take baby steps toward paying others to do work for you. Few do it, which is another reason so few people have their ideal lifestyles.

Even if the cost is occasionally more per hour than you currently earn, the trade is often worth it. Let’s assume you make $50,000 and thus $25 per hour (working from 9–5, Monday through Friday, for 50 weeks per year). If you pay a top-notch assistant $30 per hour and he or she saves you one full 8-hour shift per week, your cost (subtracting what you’re being paid) is $40 to free an extra day. Would you pay $40 per week to work Monday to Thursday? I would, and I do. Keep in mind that this is a worst-case cost scenario.

But what if your boss freaks out?

It’s largely a non-issue, and prevention is better than cure. There is no ethical or legal reason for the boss to know if you choose non-sensitive tasks. The first option is to assign personal items. Time is time, and if you’re spending time on chores and errands that could be spent better elsewhere, a VA will improve life and the management learning curve is similar. Second, you can delegate business tasks that don’t include financial information or identify your company.

Ready to build an army of assistants? Let’s first look at the dark side of delegation. A review is in order to prevent abuses of power and wasteful behavior.

Delegation Dangers: Before Getting Started

The first rule of any technology used in a business is that automation applied to an efficient operation will magnify the efficiency. The second is that automation applied to an inefficient operation will magnify the inefficiency.


Have you ever been given illogical assignments, handed unimportant work, or commanded to do something in the most inefficient fashion possible? Not fun and not productive.

Now it’s your turn to show that you know better. Delegation is to be used as a further step in reduction, not as an excuse to create more movement and add the unimportant. Remember—unless something is well-defined and important, no one should do it.

Eliminate before you delegate.

Never automate something that can be eliminated, and never delegate something that can be automated or streamlined. Otherwise, you waste someone else’s time instead of your own, which now wastes your hard-earned cash. How’s that for incentive to be effective and efficient? Now you’re playing with your own dough. It’s something I want you to get comfortable with, and this baby step is small stakes.

Did I mention to eliminate before you delegate?

For example, it is popular among executives to have assistants read e-mail. In some cases this is valuable. In my case, I use spam filters, autoresponders with FAQs, and automatic forwarding to outsourcers to limit my e-mail obligation to 10–20 e-mail responses per week. It takes me 30 minutes per week because I used systems—elimination and automation—to make it so.

Nor do I use an assistant to set meetings and conference calls because I have eliminated meetings. If I need to set the odd 20-minute call for a given month, I’ll send one two-sentence e-mail and be done with it.

Principle number one is to refine rules and processes before adding people. Using people to leverage a refined process multiplies production; using people as a solution to a poor process multiplies problems.

The Menu: A World of Possibilities

I am not interested in picking up crumbs of compassion thrown from the table of someone who considers himself my master. I want the full menu of rights.

—BISHOP DESMOND TUTU, South African cleric and activist

The next question then becomes, “What should you delegate?” It’s a good question, but I don’t want to answer it. I want to watch Family Guy.

The truth be told, it is a hell of a lot of work writing about not working. Ritika of Brickwork and Venky of YMII are more than capable of writing this section, so I’ll just mention two guidelines and leave the mental hernia of detail work to them.

Golden Rule #1: Each delegated task must be both time-consuming and well-defined. If you’re running around like a chicken with its head cut off and assign your VA to do that for you, it doesn’t improve the order of the universe.

Golden Rule #2: On a lighter note, have some fun with it. Have someone in Bangalore or Shanghai send e-mails to friends as your personal concierge to set lunch dates or similar basics. Harass your boss with odd phone calls in strong accents from unknown numbers. Being effective doesn’t mean being serious all the time. It’s fun being in control for a change. Get a bit of repression off your chest so it doesn’t turn into a complex later.

Getting Personal and Going Howard Hughes

Howard Hughes, the ultrarich filmmaker and eccentric from The Aviator, was notorious for assigning odd tasks to his assistants. Here are a few from Donald Bartlett’s Howard Hughes: His Life and Madness you might want to consider.

  1. After his first plane crash, Hughes confided in a friend that he believed his recovery was due to his consumption of orange juice and its healing properties. He believed that exposure to the air diluted the juice’s potency, so he demanded that fresh oranges be sliced and juiced in front of him.

  2. When Hughes was partaking of the nightlife in Las Vegas, his aides were charged with approaching any girls he took a liking to. If a girl was invited to join the Hughes table and agreed, an aide would pull out a waiver and agreement for her to sign.

  3. Hughes had a barber on call 24/7 but had his hair and nails trimmed about once a year.

  4. In his hotel-bound years, Hughes was rumored to have instructed assistants to place a single cheeseburger in a specific tree outside his penthouse room at a 4:00 P.M. each day, whether he was there or not.

Such a world of possibilities! Just as the Model-T brought transportation to the masses, virtual assistants bring eccentric billionaire behavior within reach of each man, woman, and child. Now, that’s progress.

Without further ado, let me pass the mic. Note that YMII performs both personal and business tasks, whereas Brickwork focuses solely on business projects. Let’s start with the important but dull stuff and move quickly from the sublime to the ridiculous. To give a true taste of what to expect, I have not corrected non-native-sounding English.

Venky: Don’t limit yourself. Just ask us if something is possible. We’ve arranged parties, organized caterers, researched summer courses, cleaned up accounting books, created 3D drafts based on blueprints. Just ask us. We could find the closest kid-friendly restaurant to your house for your son’s birthday, finding out costs and organizing the birthday party. This frees up your time to work or hang out with your son.

What can we not do? We can’t do anything that would require our physical presence. But you would be surprised as to how small a set of tasks that is in this day and age.

Here are the most common tasks we handle:

scheduling interviews and meetings web-research following up on appointments, errands, and tasks online purchases creation of legal documents website maintenance (web design, publishing, uploading files) that doesn’t require a professional designer monitoring, editing, and publishing comments for online discussions posting job vacancies on the web document creation proofreading and editing documents for spelling and formatting online research for updating blogs updating the database for Customer Relationship Management Software managing recruitment processes updating invoices and receiving payments voicemail transcription Ritika at Brickwork added the following:

market research financial research business plans industry analysis market assessment reports preparing presentations reports and newsletters legal research analytics website development search engine optimization maintaining and updating databases credit scoring managing procurement processes Venky: We have a forgetful client who has us call him all the time with various reminders. One of our clients on a custom plan has us wake him up every morning. We’ve done the legwork and found people who fell out of contact after Katrina. Found jobs for clients! My favorite so far: One of our clients has a pair of trousers that he really likes that aren’t in production anymore. He’s sending them to Bangalore (from London) to have created exact replicas at a tiny fraction of the price.

Here are a few other YMII custom requests:

Reminding an overzealous client to pay his current parking fines, as well as not speed and collect parking fines.

Apologizing and sending flowers and cards to spouses of clients.

Charting a diet plan, reminding client on it regularly, ordering groceries based on the specific diet plan.

Getting a job for a person who lost his job due to outsourcing a year back. We did the job search, did the cover letters, did the resume tuning, and got the client a job in 30 days.

Fixing a broken windowpane of a house in Geneva, Switzerland.

Collecting homework information from teacher’s voicemail and e-mailing it to the client (parents of the kid).

Research on how to tie a shoelace meant for a kid (client’s son).

Find a parking slot for your car in some other city even before you make the trip.

Ordered garbage bins for home.

Get an authenticated weather forecast and weather report for a particular time in a particular place on a particular day, five years ago. This was to be used as supportive evidence for a lawsuit.

Talking to parents in our client’s stead.

Here’s another real example of personal outsourcing from reader David Cross, who got a personal chef at home for less than $5 per meal. Just thinking of the possibilities is enough to make you start drooling. He explains: I wanted to find someone to prepare food I love. I trained as a chef but I am often so busy and as I am the only one in the house who really cooks, I often don’t have time to prepare the food that makes me feel the healthiest so I wrote the attached ad and dropped it on Craigslist.

This was a very tight focus—ultraspecific—I had just two applicants in two months—one who was a 2/10 match but the guy we just OK’d was a Hare Krishna follower for many years, lived in India, and his sample menu proved he knew what he’s doing so we just started him.

The food is absolutely awesome. The hourly rate is extremely reasonable, he’s a five-minute detour when either of us are in town to collect food and I now have delicious Indian food for less than $5 a meal and it’s as good as anything I’ve ever eaten anywhere.

I’m going to progress to other cuisines now… Thai, Italian, Chinese, etc., and it means when I do have time to cook I’ll enjoy doing it that much more as I am not the only one cooking!

Indian/Asian Vegetarian Cook Needed

Date: 2007–06–07, 12:25PM PDT


We are a local, international family who love Indian and Asian vegetarian food. We are looking for a cook experienced in this wonderful cuisine to prepare delicious, fresh, healthy, authentic Indian/Asian vegetarian meals for us.

If you’ve cooked a curry once or twice or need to follow recipes, this position is probably not for you, but if you know Indian vegetarian cooking in depth and can prepare delicious, healthy, fresh, authentic Indian vegetarian food then we’d like to hear from you. This could be an ideal opportunity if you are Indian, Pakistani, Punjabi, etc., and are looking for a great way to apply your experience and love of Indian vegetarian food, cooking and culture. Knowledge of Ayurved and how this relates to food and diet is a plus though not essential.

Please reply with details of your experience and some dishes you could prepare. If we like what you have to offer, we’ll arrange for you to cook a sample meal or two which we will pay you for and then we’ll see what works out for us all.

This is a part-time position. You will be self-employed and responsible for your own taxes, etc. We’ll pay you an hourly rate we will agree with you plus grocery bills for the food you prepare. You can prepare food in your own place and we can arrange to collect it from you, possibly for us to freeze for later eating. We will work with you to come up with menus and schedules that work out for you and us.

Thank you for your interest.

Basic Choices: New Delhi or New York?

There are tens of thousands of VAs—how on earth do you find the right one? The resources at the end of this chapter will show you where to look, but it is overwhelming and confusing unless you have a few criteria determined in advance.

It often helps to begin with the question “Where on Earth?”

Remote or Local?

“Made in the USA” doesn’t have the ring it used to. The pros of jumping time zones and visiting third-world currency are twofold: People work while you sleep, and the per-hour expense is less. Time savings and cost savings. Ritika explains the former with an example.

One can give the remote personal assistant in India their assignment when they are leaving work at the end of the day in New York City, and they will have the presentation ready the next morning. Because of the time difference with India, assistants can work on it while they are asleep and have it back in their morning. When they wake up, they will find the completed summary in their inbox. These assistants can also help them keep pace with what they want to read, for example.

Indian and Chinese VAs, as well as most from other developing countries, will run $4–15 per hour, the lower end being limited to simple tasks and the higher end including the equivalent of Harvard or Stanford M.B.A.s and Ph.D.s. Need a business plan to raise funding? Brickwork can provide it for between $2,500–5,000 instead of $15,000–20,000. Foreign assistance isn’t just for the small time. I know from firsthand discussions that executives from big five accounting and management consulting firms routinely charge clients six figures for research reports that are then farmed to India for low four figures.

In the U.S. or Canada, the per-hour range is often $25–100. Seems like an obvious choice, right? Bangalore 100%? It’s not. The important metric is cost per completed task, not cost per hour.

The biggest challenge with overseas help will be the language barrier, which often quadruples back-and-forth discussion and the ultimate cost. The first time I hired an Indian VA, I made the fundamental mistake of not setting an hour cap for three simple tasks. I checked in later that week and found he had spent 23 hours chasing his tail. He had scheduled one tentative interview for the following week, set at the wrong time! Mind boggling. 23 hours? It ended up costing me, at $10 per hour, $230. The same tasks, assigned later that week to a native English speaker in Canada, were completed in two hours at $25 per hour. $50 for more than four times the results. That said, I later requested another Indian VA from the same firm who was able to duplicate the native speaker results.

How do you know which to choose? That’s the beautiful part: You don’t. It’s a matter of testing a few assistants to both sharpen your communication skills and determine who is worth hiring and who is worth firing. Being a results-based boss isn’t as simple as it looks.

There are a number of lessons to be learned here.

First, per-hour cost is not the ultimate determinant of cost. Look at per-task cost. If you need to spend time restating the task and otherwise managing the VA, determine the time required of you and add this (using your per-hour rate from earlier chapters) to the end sticker price of the task. It can be surprising. As cool as it is to say that you have people working for you in three countries, it’s uncool to spend time babysitting people who are supposed to make your life easier.

Second, the proof is in the pudding. It is impossible to predict how well you will work with a given VA without a trial. Luckily, there are things you can do to improve your odds, and one of them is using a VA firm instead of a solo operator.

Solo vs. Support Team

Let’s suppose you find the perfect VA. He or she is performing all of your noncritical tasks and you’ve decided to take a much-deserved vacation to Thailand. It’s nice to know someone besides you will be manning the wheel and putting out fires for a change. Finally, some relief! Two hours before your flight from Bangkok to Phuket, you receive an e-mail: Your VA is out of commission and will be in the hospital for the next week. Not good. Vacation FUBAR.

I don’t like being dependent on one person, and I don’t recommend it in the least. In the world of high technology, this type of dependency would be referred to as a “single point of failure”—one fragile item upon which all else depends. In the world of IT,15 the term “redundancy” is used as a selling point for systems that continue to function if there is a malfunction or mechanical failure in any given part. In the context of VAs, redundancy entails having fallback support.

I recommend that you hire a VA firm or VAs with backup teams instead of sole operators. Examples abound, of course, of people who have had a single assistant for decades without incident, but I suggest that this is the exception rather than the rule. Better safe than sorry. Besides simple disaster avoidance, a group structure provides a pool of talent that allows you to assign multiple tasks without bothering to find a new person with the qualifications. Brickwork and YMII both exemplify this type of structure and provide a single point of contact, a personal account manager, who then farms out your tasks to the most-capable people in the group and across different shifts. Need graphic design? Covered. Need database management? Covered. I don’t like calling and coordinating multiple people. I want one-stop shopping and am willing to pay 10% more to have it. I encourage you to be similarly pound-wise and penny-foolish.

Team preference doesn’t mean that bigger is better, just that multiple people are better than one person. The best VA I have used to date is an Indian with five backup assistants under him. Three can be more than sufficient, but two is toeing the line.

The #1 Fear: “Sweetheart, Did You Buy

a Porsche in China?”

I’m sure you might have your fears. AJ certainly did:

My outsourcers now know an alarming amount about me—not just my schedule but my cholesterol, my infertility problems, my Social Security number, my passwords (including the one that is a particularly adolescent curse word). Sometimes I worry that I can’t piss off my outsourcers or I’ll end up with a $12,000 charge on my MasterCard bill from the Louis Vuitton in Anantapur.

The good news is that misuse of financial and confidential information is rare. In all of the interviews I conducted for this section, I could find only one case of information abuse, and I had to search long and hard. It involved an overworked U.S.-based VA who hired freelance help at the last moment.

Commit to memory the following—never use the new hire. Prohibit small-operation VAs from subcontracting work to untested freelancers without your written permission. The more established and higher-end firms, Brickwork in the below example, have security measures that border on excessive and make it simple to pinpoint abusers in the case of a breach: Employees undergo background checks and sign NDAs (nondisclosure agreements) in accordance with the company policy of maintaining confidentiality of client information Electronic access card for entry and exit

Credit card information keyed only by select supervisors

Removal of paper from the offices is prohibited

VLAN-based access restrictions between different teams; this ensures that there is no unauthorized access of information between people of different teams in the organization Regular reporting on printer logs

Floppy drives and USB ports disabled

BS779 certification for accomplished international security standards

128-bit encryption technology for all data exchange

Secure VPN connection

I bet there is a fair chance that sensitive data is 100 times safer with Brickwork than on your own computer.

Still, information theft is best thought of as inevitable in a digital world, and precautions should be taken with damage control in mind. There are two rules that I use to minimize damage and allow for fast repair.

  1. Never use debit cards for online transactions or with remote assistants. Reversing unauthorized credit card charges, particularly with American Express, is painless and near instantaneous. Recovering funds withdrawn from your checking account via unauthorized debit card use takes dozens of hours in paperwork alone and can take months to receive, if approved at all.

  2. If your VA will be accessing websites on your behalf, create a new unique login and password to be used on those sites. Most of us reuse both logins and passwords on multiple sites, and taking this precaution limits possible damage. Instruct them to use these unique logins to create accounts on new sites if needed. Note that this is particularly important when using assistants who have access to live commercial websites (developers, programmers, etc.).

If information or identity theft hasn’t hit you, it will. Use these guidelines and you’ll realize when it happens that, just like most nightmares, it’s not that big a deal and is reversible.

The Complicated Art of Simplicity:

Common Complaints

My assistant is an idiot! It took him 23 hours to book an interview! This was the first complaint I had, for sure. 23 hours! I was heated up for a shouting match. My original e-mail to this first assistant seemed clear enough.

Dear Abdul,

Here are the first tasks, due at the end of next Tuesday. Please call or e-mail with any questions:

  1. Go to this article http://www.msnbc.msn.com/id/12666060/site/newsweek/, get the phone/e-mail/website contacts for Carol Milligan and Marc and Julie Szekely. Also find the same info for Rob Long here http://www.msnbc.msn.com/id/12652789/site/newsweek/.

  2. Schedule 30-minute interviews for Carol, Marc/Julie, and Rob. Use www.myevents.com (username: notreal, password: donttryit) to book them in my calendar for next week any time between 9–9 ET.

  3. Find the name, e-mail, and phone (phone is least important) of workers in the U.S. who have negotiated remote work agreements (telecommuting) despite resistant bosses. Those who have traveled outside the U.S. are ideal. Other keywords could include “teleworking” and “telecommuting.” The important factor is that they negotiated with difficult bosses. Please send me links to their profiles or write a paragraph describing why they fit the profile above.

Look forward to seeing what you can do. Please e-mail if you don’t understand or have questions.



The truth is—I was at fault. This is not a good debut demand, and I made fatal mistakes even before composing it. If you are an effective person but unaccustomed to issuing commands, assume that most problems at the outset are your fault. It is tempting to immediately point the finger at someone else and huff and puff, but most beginner bosses repeat the same mistakes I made.

  1. I accepted the first person the firm provided and made no special requests at the outset.

Request someone who has “excellent” English and indicate that phone calls will be required (even if not). Be fast to request a replacement if there are repeated communication issues.

  1. I gave imprecise directions.

I asked him to schedule interviews but didn’t indicate that it was for an article. He assumed, based on work with previous clients, that I wanted to hire someone and he misspent time compiling spreadsheets and combing online job sites for additional information I didn’t need.

Sentences should have one possible interpretation and be suitable for a 2nd-grade reading level. This goes for native speakers as well and will make requests clearer. Ten-dollar words disguise imprecision.

Note that I asked him to respond if he didn’t understand or had questions. This is the wrong approach. Ask foreign VAs to rephrase tasks to confirm understanding before getting started.

  1. I gave him a license to waste time.

This brings us again to damage control. Request a status update after a few hours of work on a task to ensure that the task is both understood and achievable. Some tasks are, after initial attempts, impossible.

  1. I set the deadline a week in advance.

Use Parkinson’s Law and assign tasks that are to be completed within no more than 72 hours. I have had the best luck with 48 and 24 hours. This is another compelling reason to use a small group (three or more) rather than a single individual who can become overtaxed with last-minute requests from multiple clients. Using short deadlines does not mean avoiding larger tasks (e.g., business plan), but rather breaking them into smaller milestones that can be completed in shorter time frames (outline, competitive research summaries, chapters, etc.).

  1. I gave him too many tasks and didn’t set an order of importance.

I advise sending one task at a time whenever possible and no more than two. If you want to cause your computer to hang or crash, open 20 windows and applications at the same time. If you want to do the same to your assistant, assign him or her a dozen tasks without prioritizing them. Recall our mantra: Eliminate before you delegate.

WHAT DOES A good VA task e-mail look like? The following example was recently sent to an Indian VA whose results have been nothing short of spectacular:

Dear Sowmya,

Thank you. I would like to start with the following task.

TASK: I need to find the names and e-mails of editors of men’s magazines in the US (for example: maxim, stuff, GQ, esquire, blender, etc.) who also have written books. An example of such a person would be AJ Jacobs who is Editor-at-Large of Esquire (www.ajjacobs.com). I already have his information and need more like him.

Can you do this? If not, please advise. Please reply and confirm what you will plan to do to complete this task.

DEADLINE: Since I’m in a rush, get started after your next e-mail and stop at 3 hours and tell me what results you have. Please begin this task now if possible. The deadline for these 3 hours and reported results is end-of-day ET Monday.

Thank you for your fastest reply,


Short, sweet, and to the point. Clear writing, and therefore clear commands, come from clear thinking. Think simple.

IN THE NEXT several chapters, the communication skills you develop with our virtual assistant experiment will be applied to a much larger and obscenely profitable playing field: automation. The extent to which you will outsource next makes delegation look like finger painting.

In the world of automation, not all business models are created equal. How do you assemble a business and coordinate all its parts without lifting a finger? How do you automate cash deposits in your bank account while avoiding the most common problems? It begins with understanding the options, the art of dodging information flow, and what we will call “muses.” The next chapter is a blueprint for the first step: a product.

Go with the Flow

Here is a flowchart of 4HWW from reader Jed Wood, who has used it for faster decision making, more output with less input, and more time with his wife and children.

  1. Get an assistant—even if you don’t need one.

Develop the comfort of commanding and not being commanded. Begin with a one-time test project or small repetitive task (daily preferred). I advise using domestic help for language-intensive tasks and using foreign assistants in the early stages to improve the general clarity of your communication. Pick one from each group and get started.

The following sites, split up geographically, are useful resources.

U.S. and Canada ($20/hour+)

http://www.iavoa.com (International Association of Virtual Office Assistants). Global directory that includes the U.S.

http://www.cvac.ca (Canadian Virtual Assistant Connection)

http://www.canadianva.net/files/va-locator.html (Canada)


North America and International ($4/hour+)

www.elance.com (Search “virtual assistants,” “personal assistants,” and “executive assistants.”) The client feedback reviews on Elance enabled me to find my best VA to date, who costs $4/hour. Similar marketplaces with positive reviews include www.guru.com and www.rentacoder.com.


www.tryasksunday.com ($20–60 per month for 24/7 concierge, free one-week trial). AskSunday is one of the sophisticated new kids on the personal outsourcing block. Their site was nominated the #2 website of the year in 2007 by Time magazine. Just dial a 212 (NYC) area code and get routed to well-spoken assistants in India and the Philippines. I use this service 80% of the time, as most tasks take less than 10 minues to complete. For longer projects, there are teams available for $12/hour.

www.b2kcorp.com ($15/hour+) From Fortune 10 oil companies and Fortune 500 clients to Big 5 accounting firms and U.S. congressmen, Brickwork can handle it all. This is reflected in the costs of this pure suit-and-tie operation—business only. No flowers for auntie.

www.taskseveryday.com ($6.98/hour for a dedicated virtual assistant) Based in Mumbai, available via phone and e-mail from the U.S., UK, and Australia. Must choose between 20 or 40 hours per week and pre-purchase hours.

www.yourmaninindia.com ($6.25/hour+) YMII handles both business and personal tasks and can work with you in real time (there are people on duty 24/7) and complete work while you sleep. English capability and effectiveness vary tremendously across VAs, so interview yours before getting started or assigning important tasks. Important: Following the publication of the first edition of this book, there have been some complaints of lower quality and up to four-week wait lists to become a client.

  1. Start small but think big.

Tina Forsyth, an online business manager (higher-level VA) who helps six-figure-income clients achieve seven figures with business model redesigns, makes the following recommendations.

Look at your to-do list—what has been sitting on it the longest?

Each time you are interrupted or change tasks, ask, “Could a VA do this?”

Examine pain points—what causes you the most frustration and boredom?

Here are a few common time-consumers in small businesses with online presences.

Submitting articles to drive traffic to site and build mailing lists

Participating in or moderating discussion forums and message boards

Managing affiliate programs

Creating content for and publishing newsletters and blog postings

Background research components of new marketing initiatives or analysis of current marketing results

Don’t expect miracles from a single VA, but don’t expect too little, either. Let go of the controls a bit. Don’t assign crap tasks that end up consuming rather than saving time. It makes little sense to spend 10–15 minutes sending an e-mail to India to get a price quote on a plane ticket when you could do the same online in 10 minutes and avoid all the subsequent back-and-forth.

Push outside your comfort zone—that is the entire point of the exercise.

It is always possible to reclaim a task for yourself if the VA proves incapable, so test the limits of their capabilities. Remember Brickwork’s suggestion: Don’t limit yourself.

  1. Identify your top five time-consuming non-work tasks and five personal tasks you could assign for sheer fun.

  2. Keep in sync: scheduling and calendars.

If you decide to have an assistant schedule appointments and add things to your calendar, it will be important to ensure what you both see is updated. There are several options: BusySync (www.busysync.com) I have two Gmail accounts: one private account for me and one for my assistant, where general e-mail is sent. I use BusySync to synchronize her Google Calendar with iCal (Mac calendar) on my laptop. I have also used SpanningSync (www.spanningsync.com) successfully for the same purpose.

WebEx Office (www.weboffice.com) Share your calendar online while masking personal appointments. Can be synchronized with Outlook, and also offers document sharing and other assistant- or team-friendly features. I suggest you compare this to synchronizing your Outlook with an assistant’s Google Calendar.


Use the Criticism Sandwich (2 Days and Weekly)

Chances are good that someone—be it a co-worker, boss, customer, or significant other—does something irritating or at a subpar level. Rather than avoid the topic out of fear of confrontation, let’s chocolate-coat it and ask them to fix it. Once per day for two days, and then each Thursday (M-W is too tense and Friday is too relaxed) for the next three weeks, resolve to use what I call the Criticism Sandwich with someone. It’s called the Criticism Sandwich because you first praise the person for something, then deliver the criticism, and then close with topic-shifting praise to exit the sensitive topic. Here’s an example with a superior or boss, with keywords and phrases in italics.

You: Hi, Mara. Do you have a second?

Mara: Sure. What’s up?

You: First, I wanted to thank you for helping me with the Meelie Worm account [or whatever]. I really appreciate you showing me how to handle that. You’re really good at fixing the technical issues.

Mara: No problem.

You: Here’s the thing.16 There is a lot of work coming down on everyone, and I’m feeling17 a bit overwhelmed. Normally, priorities are really clear to me18 but I’ve been having trouble recently figuring out which tasks are highest on the list. Could you help me by pointing out the most important items when a handful need to be done? I’m sure it’s just me,19 but I’d really appreciate it, and I think it would help.

Mara: Uhh … I’ll see what I can do.

You: That means a lot to me. Thanks. Before I forget,20 last week’s presentation was excellent.

Mara: Did you think so? Blah, blah, blah …



You’ve suggested people check e-mail only a few times a day. Here’s a twist: I reply to e-mails when it’s convenient, but I time it to arrive when it’s also convenient for me. In Outlook you can delay e-mail delivery to any time of day. For example, when I return e-mails at 3 p.m., I don’t want my staff instantly zinging me responses or clarifying questions. (This also prevents e-mail chats.) So I hit send, but it’s delayed to arrive later in the evening or at 8 A.M. when my employees arrive the next day. This is how e-mail was meant to be! It’s mail, not a chat service.


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