Management

Solving problems outside your comfort zone

Merlin — Wed, 10 Oct 2007 15:04:28 -0400

I sometimes think that one factor in success as a business or as a human being has a lot to do with what kind of problems you’re comfortable solving – and how you get better at addressing the stuff that falls outside that comfort zone.

History is littered with revolutionaries who couldn’t run the country they’d overthrown, Generals who’ve insisted on re-ﬁghting the last war, talented programmers who were promoted to becoming ineffective (and very unhappy) managers, and, of course, there’s the countless companies that just couldn’t make the leap when technology or cultural change rendered their comfy old business model moot.

Seems like there’s a thread here that’s worth thinking about.

How do you get better at knowing when you’re trying to solve the wrong problem?

It’s something I’ve been thinking about a lot lately as I take what had been mostly a hobby and try to “Go Pro” with it. For me, that’s meant a lot of stumbles around moving from being a one-man show into what may eventually become a small company (who knows?). I’m ﬁnding it really challenging to stop solving the problems I’m comfortable solving, and to ask for and accept help with the stuff I suck at or that doesn’t represent the best use of my time.

I think this applies to almost everybody, from the time they’re born, right? You ﬁgure out a few things, you do some informal experiments with reality, and then you try to suss out the patterns that won’t get you hit by a car or carted off to jail. But the old patterns almost always stop doing the trick at some point or in some unexpected context. For example, that bawling and tantrum-throwing that got you a hug in kindergarten may not endear you to your company’s board.

The best advice I’ve gleaned so far is to try and stay cognizant of diminishing returns. Just because I know how to do basic sysadmin work doesn’t mean I’m the best person to work on it. And conversely, just because I loathe the idea of becoming a “manager” doesn’t mean I can afford to put off learning the skills forever.

The Question to You

What’s your trick? How’d you learn to start ﬁxing more interesting and unfamiliar problems? Can you think of any particular businesses or people who have (so far) aced the test?

”Solving problems outside your comfort zone” was written by Merlin Mann for 43Folders.com and was originally posted on October 10, 2007. Except as noted, it's ©2009 Merlin Mann and licensed for reuse under CC BY-NC-ND 3.0. "Why a footer?"

Enlightened outsourcing Part 2: The practice

norbauer — Mon, 08 Oct 2007 12:11:03 -0400

Ryan Norbauer returns with the hotly-anticipated conclusion to his series on the psychology and practice of outsourcing your life. If you haven’t read it yet, be sure to start with part 1.
—Merlin.

Now that I’ve primed your pump for an outsourcing extravaganza, it’s time to turn our eyes towards the quotidian. Once you’re ready to hire help, there are two main challenges to face. Firstly, you have to identify portions of your daily work that can be outsourced, and then you have to ﬁnd the right person to do that work for you.

Identifying work someone else can do

Finding ways to outsource your work requires a surprising amount of vigilance and creativity. You have to spend a few days watching yourself work and repeatedly asking: if this task isn’t something I can eliminate entirely, could someone else possibly do it? Don’t worry: after a while, the heuristic becomes a reﬂex. But you have to start out by scrutinizing everything you do and seriously thinking about asking for help with all of it.

Unfortunately, you’ll ﬁnd that some of the most tedious and annoying parts of our lives actually do demand our personal presence: stuff like sitting on the phone with credit card companies (which often refuse to speak to an agent over the phone,) standing in line at the DMV to get some piece of bureaucratic ephemera, and, alas, even going to the gym. Some other tasks, particularly of the one-off variety, require more time to outsource than to do ourselves, merely because of the overhead of explanation and coordination.

The kind of multi-step projects that comprise most of our working lives often seem as if they would fall into this latter category. It’s easy to tell yourself that it would take too long to ﬁgure out how to explain a project to someone else than to do it on your own. After all, you’re the only person who has the grand picture, understands the purpose of the work, and is familiar with the details. But with a bit of pluck and a capacity for seeing projects for what they truly are (collections of discrete actions,) you’ll be astonished at how much you can rid yourself of. I have often found that what at ﬁrst seemed daunting to explain to someone else actually just required a few moments thinking about how the problem needed to be approached—which is a process I was going to have to go through anyway if I were ever going to complete the task in the ﬁrst place.

Ethan Schoonover recently wrote a fabulous piece here at 43folders about the value of formulating your GTD next-action lists as if they were written for someone else to do. If one of your projects isn’t moving forward, as the theory goes, you probably haven’t sufﬁciently clariﬁed precisely what physical, visible actions need to be done in order to complete it. When approached with an eye toward outsourcing, it becomes clear how important and powerful this strategy can be. Not only have you ﬁgured out precisely how the thing needs to be done, you’ve already packaged it up to outsource to someone else with no (or little) additional work.

Admittedly, some sets of instructions take longer to prepare than others. Spending ten minutes to write an email can seem like a lot of work to ask a person to do a thirty-minute task, but there are a couple things to bear in mind here. Firstly, you’ve tripled the amount of work you can do even if just those numbers are correct. But also consider that, especially if most of your daily tasks could be classiﬁed as “thought work,” there are tremendous psychological costs to burying yourself in each additional task in your workday. For one, if you’re banging through your email all at once each morning and assigning outsourcing tasks, you’re working only in one context and you can do them all in one batch. But if you did all those tasks yourself at the appropriate moments throughout the day, you’d have to deal with the overhead of the associated context-switching and the burdens of additional stress that the responsibility for each task incurs. I have found that the drain on my productivity inﬂicted by being responsible for lots of “little” tasks far exceeds the actual time it takes to perform them. I have therefore taken to doubling the amount of time a task will take to complete when estimating whether it’s worth my time writing it up for someone else to do. Ten minutes compared to an hour-long task suddenly sounds more reasonable, and it’s probably closer to the true cost of doing a thirty-minute task myself.

It’s important to remember that you don’t necessarily have to outsource whole projects. To cite an interesting example, we do occasional podcasts at my company. The editing process is enormously tedious and used to take me many hours to turn a two-hour interview into just 30-40 minutes of talk and music. Sure, I’m slow and a total amateur when it comes to audio editing, but that’s really my point. There was clearly someone better suited to doing this work than me.

Since I have embraced outsourcing, I now send the raw audio to my man Ashish at Tech-Synergy, who promptly sends me back a ﬂawless time-indexed transcript in text form. I then mark up that transcript by hand in red ink, which takes about 10 minutes, and scan it rapidly to PDF using my trusty Fujitsu ScanSnap (Amazon: PC|Mac). I send the edits along with the raw audio to a ﬁrm in Argentina who edit it all together as a seamless podcast according to my marks. The whole process costs us less than $75 and saves me many painful hours of work. We’re just getting ready to post the ﬁrst podcast produced under this new arrangement, and I have to say that the process has been so effortless that it has greatly reduced my psychological resistance to going out and recording new interviews.

The reason for breaking the project up in this piecemeal fashion is that I wasn’t able to ﬁnd a ﬁrm at an affordable rate that was comfortable making editing decisions for me about what to cut and what to leave in the interview audio. It still seems a little batty to me to have a single podcast be worked on by various people from Bangalore to Buenos Aires in small little chunks, but the ﬁrms are happy to have the work; they cost very little; the whole thing greatly bolsters my ability to generate creative product; and I can be sure I’m only spending time on the one tiny little piece of the whole work-ﬂow that actually requires my personal judgment and intervention. Hard to argue with all that.

The combinatorial potential of next-action outsourcing is obvious once we approach it as a sort of grammar for assembling the larger language of projects. But we must also examine a bit of that language’s vocabulary. What follows is an enumeration of things for which I have found outsourcing to be the most useful.

A virtual assistant
Design
Fulﬁllment
Audio/video editing
Scanning
Transcription
Artiﬁcial artiﬁcial intelligence
Software development
Domestic work

A virtual assistant

It took a lot of experimentation to ﬁnd a good one, but I now rely heavily on my virtual assistant. She checks and responds to all support emails for my companies, forwarding the ones to me that I must personally handle; she scans and tabulates expense receipts; she helps me draft blog posts; she scours the internet for interesting links to post on our company blog; she handles refunds and complaints; she researches things for me; she even made us a MySpace page. VAs are also great as “attention gatekeepers,” who can screen through things like your voicemail, email, or even RSS feeds to bring important things to your attention, based on criteria you specify, without your having to be distracted by all the chaff.

Design

I enjoy doing web design myself, but sometimes having an outside person come in to add an extra layer of polish or to handle the odd arcane CSS problem can be quite valuable. The Internet is replete with freelance designers with wildly varying aesthetics and fees. Most designers can layer a lovely front-end onto your existing website without your ever having to change the back-end implementation. If you’re the sort of person who, like me, can blow an entire day vacillating between various minute changes in page layout, you might ﬁnd it worth hiring someone who has the experience to be more decisive.

Fulﬁllment

If your business sells physical goods (like my t-shirt shop) or regularly sends out printed matter, then fulﬁllment houses like Shipwire and Sprocket Express will save you a tremendous amount of time and hassle. If the cost of those services seems steep, keep your eyes on Fulﬁllment by Amazon. I can’t recommend it yet due to the immature state of its API and wonky web interface, but FBA promises to become one of the best (and by far cheapest) options out there as they evolve through their beta and ﬁx their funkyness.

Audio/video editing

Like most tasks that involve a human being going through digital media and performing some operation on it, audio and video editing are perfect for outsourcing. However, remember my podcasting example. If you’re fussy about style and nuance, you’ll want to ﬁnd a way to give speciﬁc instructions on the sorts of edits you want to have done. Unless you’re hiring a very esteemed consultant or ﬁrm, leaving subjective decisions about editing up to outsourced help is a bit of a gamble.

Scanning

Document scanning can be one of the most irksome ofﬁce chores. Although the aforelinked Fujitsu ScanSnap does a laudable job, sometimes you need a real human to babysit the scanning of each item in a huge pile of irregularly shaped or specialized documents. For example, I had an old set of bound color catalogs that I wanted in digital form. Because the pages were bound together (and I didn’t want to unbind them because they were somewhat valuable,) digitizing them meant painstakingly placing them page after page on a ﬂatbed scanner. I bid out this task on Elance and was able to ﬁnd someone to do it quite professionally and cheaply. The great thing about this is that I now have searchable PDFs of these old catalogs, which I consult fairly frequently. I can now sell, give away, or recycle the originals. By converting paper documents to searchable PDFs in this way over the past few months, I have reduced the size of my physical reference ﬁling system by 75% (!), and signiﬁcantly boosted the efﬁciency with which I use those ﬁles.

As a part of this outsourcing-enabled move away from paper, I have also used ScanCafe. You send them your photos and negatives, which they ship on to India to be scanned and hand color-corrected, cropped, etc. Rather than spending hours organizing and labeling the backlog in my physical photo library, I sent all my negatives to ScanCafe, stored the resulting digital versions on S3 along with all the newer images I’ve taken with my digital camera, and I threw away the paper originals. They charge $0.19 an image.

Transcription

As mentioned, transcription is a great way to transmit instructions on how to edit A/V media. It’s also great for quickly digesting TV or radio interviews you don’t have time to watch or listen to. (Humans can read much faster than we can listen to the spoken word.)

Having random phone calls come through at all hours of the day greatly saps and impuriﬁes my concentration. To get around this, I have found another great use for outsourced transcription: voicemail. I hardly answer my phone anymore. Instead, I purchased a SimulScribe account but never associated it with an actual phone number (just select “other” as your provider when signing up). I now give that phone number out to most of my contacts (especially sales people,) so when they call, it goes straight through to my recorded message, transcribes the message they leave, and then e-mails me the text. This set-up forces callers to get the point, and allows me to reply at a time that doesn’t disrupt my work-ﬂow.

Artiﬁcial artiﬁcial intelligence

Amazon’s Mechanical Turk service is pure genius. It commodiﬁes and automates the outsourcing of very small intellectual tasks. Here’s how they describe it:

For businesses and entrepreneurs who want tasks completed, the Amazon Mechanical Turk web service solves the problem of getting work done in a cost-effective manner by people who have the skill to do the work. The service provides access to a vast network of human intelligence with the efﬁciencies and cost-effectiveness of computers. Oftentimes, the cost of establishing a network of skilled people to do the work outweighs the value of completing it. By turning the ﬁxed costs into variable costs that scale with business needs, the Amazon Mechanical Turk web service eliminates this barrier and allows work to be completed that before was not economical.

At our online dating site, we use Mechanical Turk to outsource what used to be one of the most maddeningly annoying and boring tasks of my day: approving photos. We don’t want people to upload inappropriate photos into their proﬁles, so uploads have to be manually inspected by a human. (There is no easy way to train a computer to identify an “inappropriate” photo.) Whereas I used to look over every uploaded photograph personally, our site now automatically uploads a task to Mechanical Turk asking whether each new photo meets our approval criteria. Each photo gets checked by a live human being, and costs us only a few cents per approval. I don’t have to spend any time thinking about this chore anymore, and as a bonus, our photo approval latency has gone from several hours to only a couple minutes on average.

Other tasks to which Mechanical Turk is well suited: tagging images, searching images for certain features, transcription, translation, checking for duplicate data (album covers, listings, images, etc.)

Software development

One of the downsides of Mechanical Turk is that it requires a bit of programming if you’re going to integrate it seriously into your business. So you may wish to hire a software developer to help you create a custom application to make use of the service.

I use software consulting heavily in my various businesses because much of my business is itself software. However, you don’t have to run a web company to use the assistance of a good team of developers. An example might be hiring a developer to create a task to do batch work that you normally do manually on your computer—work like resizing groups of photos and then converting them to black-and-white, or uploading certain ﬁles on your hard drive to a back-up service every day. If, for example, you regularly have to turn a big pile of data into some other format manually, or enter data from one piece of software to another, a custom software script could greatly speed up your daily productivity. Obviously, you don’t want to spend the time to learn a programming language just to speed up one of your daily tasks, but if you could hire a developer cheaply to create a script that would do the repetitive data work for you in a fraction of the time each day, it could certainly be worth it. Try posting a task on Elance, asking for your dream piece of software. You might be surprised by how affordable the bids are. Software development is one of the most competitive areas among offshore outsourcing services, so you can usually get a great deal. Quality naturally varies greatly.

Domestic work

This is where we stumble into the uncomfortable Jeeves-and-Wooster realm of outsourcing, but I ﬁnd that domestic work, because it requires skills that almost anyone can acquire, has the highest price-to-payoff ratio for outsourcing. Geo-arbitrage notwithstanding, it’s hard to ﬁnd a skilled Ruby developer (and thus you must pay for the privilege,) but it’s not so hard to ﬁnd someone who knows how to make dinner or sweep the ﬂoor.

There is something luxurious (and, yes, a little weird) in having your household needs seen to by someone else. You feel spoiled and silly for hiring someone to do work that you could so easily do yourself. But outsourcing is about freeing your time and psyche for your most important work, if you can afford to do so.

In my case, I decided to outsource meal preparation, which I used to spend about 5-8 hours on each week. My solution came from an idea in Tim Ferriss’s blog. I posted an ad on Craigslist asking for a local cook who would be willing to prepare food in bulk for our household of three on a weekly basis. I got about 15 impressive responses to my ad and ended up settling on a fellow who was willing to make four or ﬁve dishes for us in large quantity (more than enough for the three of us to have great food for each meal of the week.) He charges us $120-140 per week, which is less than I sometimes used to spend on groceries when I did the cooking myself, and delivery is included! To be fair, I ask that he prepares vegetarian food, which often costs less to make than meat, but I’m sure the cost of meat dishes would be in the same order of magnitude. This works out on average to cost us about $2.00-3.50 per meal per person (depending on how many times we eat each day,) or about $45 per person per week. Under this splendid arrangement, I’ve freed up several hours each week; we’re hardly spending any more money than we used to on food; and we’re helping a local cook make some extra money.

It never hurts to post a task just to see how cheaply you can get it done. Grouping tasks into one bulk job and sharing the service with your neighbors helps. When you look into it, what may seem like the sole province of the wealthy can prove far more accessible than you’d think.

Identifying someone else to do the work

Take a quick look at the number and variety of providers on Elance, OffshoreExperts, and Guru, or make a post on Craigslist and you’ll quickly see that when you’re ready to set up an outsourcing relationship, ﬁnding people willing to do the work isn’t going to be a problem. What you will also ﬁnd, however, is that discerning among them is.

The great thing about most forms of outsourcing is that the barrier to entry is usually rather low. To take one typical project I posted on Elance (scanning those catalogs I mentioned,) I got bids ranging from $50 to $695. If I decided to go with one of the cheaper providers, the money at risk was pretty minimal. And if I found that I liked their work, I could hire them for bigger tasks in future. To save on international shipping, I decided to hire a stay-at-home mom in the Chicago area to do the scanning for me at $100, which was on the low end of the US bids. It took her a bit longer than promised to complete them, but I ultimately decided to use her for further work later on because she was friendly and had no trouble understanding complicated tasks. I’ve done this many times. Sometimes, I’ve gotten awful work, and I just leave it at the initial task. Other times I’ve met providers whom I’ve loved, and I still work with them today.

Feedback on sites like Elance is sometimes helpful, but I ﬁnd that only the satisﬁed customers leave feedback. People who are unsatisﬁed tend not to leave unambiguously negative feedback for fear of a retaliatory strike (rather like eBay.) Sometimes you have to read between the lines.

There are, however, other clues to whether a provider is worth trying out. Beware providers who over-promise in hyperbolic terms. If the bid is worded to make it sound like the provider has been waiting his whole life to do this one task for you, I would look elsewhere. I get these breezy copy-and-paste bids all the time, and close inspection usually reveals that this marketing copy (usually in awkward, broken English) was written by someone who didn’t even spend a second looking at the task I posted. There are a few providers on Elance who will more or less bid on everything, low-balling their fee to win and only then will they spend time to ﬁgure out how to do the task.

There remains the touchy issue of nationality. To be sure, there are plenty of cheap offshore providers available to do “business process outsourcing” of the sort I’ve been discussing in this article. Having worked with outsourcing companies across the globe, I have developed a few rules of thumb about when to go offshore and when to ﬁnd a domestic contractor.

I’ve long been a fervent proponent of Free Trade and global competition for services. (If you have any hesitations, politically or otherwise, about the issue, I recommend this illuminating article from Foreign Affairs.) So my decision-making when it comes to outsourcing is always about value; jingoism doesn’t factor into it. I hope the same will hold true for you.

There is an unfortunate sentiment among many folks in the US that with the cost savings of offshoring comes a decrease in quality. Sometimes it’s true—as I have recently learned in the case of t-shirt manufacture, American-made items are much better quality than their Chinese counterparts—but often it’s not true, particularly in the case of knowledge work. As with ﬁrms within the US, there is a wide diversity in quality among companies abroad. But when Americans encounter bad foreign companies they are too eager to blame it on the company’s country rather than on natural variations in quality among all ﬁrms in that country, which is what they would likely attribute bad work to if they were dealing with a sub-par American ﬁrm. Don’t extrapolate an ill judgment against a whole country based on one or two bad experiences.

I have hired many software consultancies, for example, in the past two years, both domestic and abroad. Interestingly, all of the American ﬁrms I hired were both expensive and inattentive. I ﬁnally decided to give an Indian team of Ruby on Rails consultants a try, and they were so efﬁcient, smart, friendly, and attentive by comparison that I actually ended up going into business with them. This has been my experience with several foreign outsourcing providers. They are oftentimes more motivated and available than domestic contractors, and very much worth their (relatively palatable) fees.

I’ve had some bad offshoring experiences too. One company of Chinese illustrators on Elance was so inept at English that they couldn’t understand the simply-worded instructions for the project they enthusiastically bid on, so we had to switch to something more straightforward. However, after I simpliﬁed the task, I ended up with a sensational end-result for a trivial sum of money. Other providers have sounded great in their bids but proved to be utterly incapable of communicating or delivering even a shadow of what they promised.

If you’re going to go abroad, it’s worth using an offshoring ﬁrm with some physical basis in the US if possible. I used one Asian ﬁrm with a local representative here in Boston who was a native English speaker. This made the whole process go much more smoothly than, for example, those Chinese illustrators who couldn’t understand what I was asking them to do. If you’re of a litigious bent, you’ll also appreciate having a local legal entity with which to sign a domestic contract.

Another potential down-side to foreign ﬁrms concerns cultural sensitivity. I tried three different assistants at the Indian VA ﬁrm GetFriday, but was never able to ﬁnd one who understood American culture and language well enough for me to feel comfortable letting him represent my company. They somehow always managed to make their emails read like ﬂorid Nigerian spam. GetFriday charges about $10 an hour now ($15 without a monthly contract). Since switching from GetFriday, I hired my delightful remote assistant in Texas, whom I found on Elance, at $15 an hour. Not only is she perfectly versed in English and American culture (so that she can actually do things like help me draft blog articles), but she happens to have a higher level college degree than I do. I am much happier with a slightly more expensive remote assistant in the US, because there is so much more I can ask her to do.

GetFriday was great for rote tasks that didn’t require too much independent thinking or cultural awareness. Some good examples: sitting on the phone to Costco to ask if they carry a certain type of rice, removing ads from the PDF of a scanned magazine, calling every Starbucks in Boston to see which one is open latest, and simple research (“when is the best time of the year to go whale-watching off the coast of New England?”) I could never have expected them, however, convincingly to pull off creating a MySpace page for my company, or to draft blog articles.

If most of your work involves spreadsheets and other brainless enterprisey bullshit (I mean that lovingly,) then go with a cheap offshore VA. If, on the other hand, you’re something like a writer, a creative, or a researcher, you’re going to want an assistant in the US (or, to save a little cash, you can usually get a bargain by working with someone in a remote part of Canada or the Antipodes.)

A different aspect of cultural awareness is design. I would be very reticent about hiring a web designer in India, for example, because their national design aesthetic seems to be stuck in the stock-arty world of 1995. If you’re looking for offshore design, go to countries that have low costs of living but close ties to European culture: Argentina, Brazil, or the Czech Republic, for example. If you don’t mind paying the big bucks, Brooklyn and Portland are gathering places for our country’s best hipster designers. The best place place to ﬁnd illustrators in any country is IllustrationMundo.

Above all else, pay attention to the provider’s ability to communicate. Since your instructions must be transmitted largely through an indirect written medium, the ability to understand your contractor and have him understand you is of the utmost importance. Without good communication, you’ll just waste your money and time. If it takes you twice as long to explain yourself to your provider (or worse, it takes two tries to get anything right) you might as well use one who is charging twice as much. If you get a weird feeling in the initial e-mail back-and-forth, a sense that the provider doesn’t quite get what you’re talking about, run the other direction and ﬁnd somebody else. If you can’t understand each other, no matter what the contractor’s fee, I guarantee you’re not getting any bargain.

Homework

Good outsourcing requires earnest experimentation. Now that I’ve given you a thoroughgoing tour of the periodic table of providers, it’s time to do some of your own outsourcing alchemy. Do let us know in the comments what blows up in your face, and what turns to gold.

”Enlightened outsourcing Part 2: The practice” was written by Ryan Norbauer for 43Folders.com and was originally posted on October 08, 2007. Except as noted, it's ©2009 Merlin Mann and licensed for reuse under CC BY-NC-ND 3.0. "Why a footer?"

Enlightened outsourcing, Part 1: The psychology

norbauer — Tue, 25 Sep 2007 11:00:02 -0400

Yesterday, Ethan talked about delegating to yourself. Today, Ryan Norbauer discusses what it takes to delegate well to others. Part one of a two-part series.
Update 2007-10-08: Part 2 of this series is now available. »

I’m Ryan, and you can usually ﬁnd me in the midst of my workday by following the trail of naked yaks. I fear that I’m drawn to arcane tasks not in spite of the fact that they are tangential to my ultimate goals, but precisely because they give me an excuse to avoid them. I don’t need to grapple with the big anxiety-evoking issues of how to make a new one of my companies make more money, for example, if I can instead focus on creating an elaborate triply-redundant, auto-rotating archival ﬁling system for our Apache server logs (which we never look at.)

However, I recently encountered a weirdly tantalizing idea in Tim Ferriss’s The 4-Hour Workweek, which would ultimately disrupt my addiction to the extraneous. The book advocates farming out the more mundane tasks of your existence to outside ﬁrms and consultants, which Ferriss calls “outsourcing your life.” Probably because it would give me an excuse not to do something else more pressing, I decided to give this a go a few months ago. While I did learn quite a lot about outsourcing in the process, my experiments led me to a far grander epiphany about the way I approach life and work generally and helped me form a new set of habits that have utterly rocked my workaday world. I’m about to introduce you to the theory and practice of what I believe to be the forgotten Prime Minister of All Productivity Hacks: asking for help.

In a matter of a few months, I’ve gone from being an obsessively micro-managing perfectionist entrepreneur who reserved even the most miniscule tasks for himself, to someone who gets assistance on an almost daily basis from no fewer than fourteen outside sources, from New Delhi to New York. And a wonderful thing has happened. I ﬁnd myself robbed of all those enticing excuses to avoid doing what I ought to do, and I’m actually spending time on things that matter instead. I can honestly report that nothing I’ve ever tried, including GTD, has so radically transformed my ability to bring the big plans I have for my little universe actually to bear upon reality.

Oh, and as a nice ancillary point, it costs surprisingly little money.

Outsourcing and resistance

Outsourcing has become something of a fad in the past few months, thanks to Mr. Ferris. I think this is in part because many people hadn’t realized that they could do just what American and British corporations have been doing for years: hire workers in the developing world at rates that would make any domestic contractor laugh. I was already well aware of this fact, however, and indeed my interest is not solely in the possibility of hiring folks in Bangalore to make spreadsheets for me at three dollars and hour. For my purposes here outsourcing will instead encompass all forms of outside help, whether it be hiring a Brooklyn designer at $100 an hour, a New Delhi developer at $50, or a Pakistani personal assistant at $5.

The 4-Hour Workweek
by Timothy Ferriss

To me, the far more interesting aspect of my recent embrace of outsourcing is why it took me reading Tim’s book to get to the point where I was willing to start looking for people to help me get stuff done. If I could multiply my productivity by several orders of magnitude merely by hiring help from time to time (which seems obvious,) why did it take me so long to even consider doing it?

The reason, I think, is that that the biggest barriers to truly taking advantage of outsourcing are not cost or logistics (the details of which I’ll address in Part II of this article,) but psychology. Making good use of outsourced help requires being able truly to open yourself to the possibility of asking for help, getting over your delusions of importance, surmounting any weird hang-ups you might have about entitlement or your worthiness to get assistance, and having the creativity necessary to identify the ways in which you can open your workﬂow up to external aid. Before you get on the phone to GetFriday, these are issues worth confronting.

Opening yourself to help

One of the reasons I’ve always recoiled at the notion of getting help from other people has to do with my simple desire not to be an ass. I’ve always been the sort of egalitarian-minded fellow who has trouble letting someone carry his bags at a hotel, not because I mind paying the tip but because who do I think I am. I was raised among earnest hard-working Appalachians whose prime directive was not to put other people to any trouble. The thought of hiring someone to cook every meal for me—which I incidentally do now at the cost of $45 a week—would have been unthinkable in the world in which I grew up, whether one could afford it or not.

When I ﬁrst began experimenting with outsourcing, I had to confront this previously unexamined reﬂex. I had real trouble asking my ﬁrst assistant, Suresh, to do several tasks merely because I hated to put him to the trouble of doing something tedious that I could do myself. I was literally embarrassed to ask him to do a lot of what I had originally hired him to do.

The irrationality of this is manifest. Suresh was literally hired to do boring work and was actively asking me to give him more. I wasn’t doing him any favors by depriving him of billable hours. And the whole point of hiring an assistant is to get some of the tedious, time-consuming stuff out of one’s face and onto the desk of someone who is more suited to doing it.

I’ve watched enough people scream at blameless airport ticketing agents and well-meaning waitresses to know that making one’s expectations known isn’t a problem for a lot of people. But if you share this problem with me, even just a little, you can’t expect any real beneﬁts from outsourcing until you realize that it’s totally irrational and try to overcome it. You’re not a character in an E.M. Forster novel: getting a little help in life doesn’t turn you into an elitist tea-sipping toff. Nobody’s going to be working for you out of a sense of deference or duty. It’s capitalism. The people whom you’re going to hire are your equals (no matter where they live or how much you’re paying them,) and so long as you treat them that way, there’s no reason to cringe at fully taking advantage of the labor which they are willingly proffering.

Once I recognized and worked to get over this daft hang-up, I was ready to start optimizing.

Delusions of importance

Ferriss makes quite a rational argument for the utility of outsourcing, and I think this is what actually pushed me over the edge of trying out an assistant in the ﬁrst place. One of the themes of his book is the Pareto principle (or the “80/20” law). This is a concept with dubious empirical support, but as a sort of thought-game it’s nonetheless useful. The idea is that a common pattern emerges among economic distributions whereby 20% of causes lead to 80% of consequences. In terms of personal productivity, it was easy for me to extend the metaphor.

Before I began outsourcing, a normal day would go something like this:

Wake up. Check and reply to stress-inducing customer support emails. (1 hour)
Check and reply to business development emails. (2-3 hours)
Programming: new feature development and bug ﬁxes (2 hours)
Make lunch. Do a bit of cleaning. (1 hour)
Chase some random pointless, unﬁnishable project, like cutting apart my back issues of Martha Stewart Living, removing the ads, and ﬁling the pages thematically. (2 hours)
An ad hoc mix of programming, more email checking, and taking phone calls. (2 hours)
Start making dinner (1-2 hours)
BONUS Zoning out while wishing I were spending more time promoting my companies and clarifying our business objectives (1 hour in sporadic 5-second sporadic increments all through the day)

A few things stand out about this. Firstly, there is no time when I’m actually not working in some form or another. I’m constantly busy. Yet, if you asked me which task was the one that gave me those 80% of gains whenever I spent time on it, it’s that nebulous last one, which gets almost none of my “busy time.” Whenever I have spent time evaluating and tweaking our business models or working on publicity, the gains far outweigh any incremental improvement in a product feature could give us, or any handful of super-friendly and helpful support emails. But I was so accustomed to the behavioral inertia of the busy-work like programming and answering support emails, that I never quite got around to focusing on that far more important “bonus” task.

I’ve often found GTD to be an enabler in this regard. It allows us to keep on top of our mountain of next actions very efﬁciently, but rarely does it encourage us to stop doing 80% of them.

So, when I set about ﬁnding spots in my daily workﬂow where outsourcing might be able to help, I realized that the 80% of my work that led to minimal incremental beneﬁts could either be entirely abandoned or easily outsourced. My main company gets basically the same 10 support requests over and over again; responding is a pretty brainless job. And I’m not the only guy in the world who can code Ruby well. However, I am the only guy in the world who can do interviews with the press about the company I started, or plan our strategy for the next year.

This all took me admitting a harsh fact to myself. For most of our day-to-day operations, my company could get on just ﬁne without me. I’m simply not that important.

And I suspect that neither are you, no matter what your business or your role in it. Very few businesses have such special internal processes that there isn’t some outside ﬁrm experienced in and willing to do that work, oftentimes more cost-effectively. Are you clinging to some of those straight-forward widget-cranking tasks merely to be able feel useful—so you can point to some concrete bit of “work” at the end of the day, rather than those bigger issues that are so often impossible to quantify? I certainly was.

What is the part of your work (whether personal or professional) that only you can do? And what if you could somehow force yourself to do only that work? In my case, doing precisely this with the help of outsourcing has radically improved my effectiveness. I’ve essentially cut out steps 1-7 of my daily routine above, so I’m freed to focus exclusively on what was previously just a bonus—even though it was actually my most important work.

Try to be as smart as a pigeon

“It allows me to identify ratholes from the outset of a project and assign them to someone else…”

In the 1970s two behavioral researchers, Howie Rachlin and Len Green, studied self-control in pigeons. They found that, when given a choice between a small reward delivered immediately and a larger reward delivered after a 4-second delay, the pigeons invariably chose the smaller immediate reward. In other words pigeons, like people, can be impulsive. In the same way, we often sabotage ourselves by impulsively choosing small immediate rewards over larger more temporally distant ones—like I did when I went out to Starbucks earlier this evening rather than working on this article. Although in the grand scheme of things, I’d rather rather have this article done than have drunk a cup of mint tea, in the moment of my choice the tea just seemed more compelling.

Pigeons, however, are not as dumb as they look—or, for that matter, as dumb as we humans often are. In the second part of the aforementioned study, the pigeons were offered basically three options:

Small reward now
Large reward after a delay, with the option to “defect” to the small any time
Large reward after a delay, with no option for the pigeon to change its mind during the delay.

Interestingly, the pigeons tended to choose option 3. They knew starting out that they wanted the bigger reward, and that they would be tempted to sabotage that goal by defecting to the smaller reward during the delay. So instead they decided at the outset to commit themselves to the larger reward, by robbing themselves of the impulsive option later on.

That’s exactly what outsourcing has become to me. It allows me to identify ratholes from the outset of a project and assign them to someone else (if I’m not willing to let go of them entirely,) so I won’t have the opportunity to defect from the important work towards those yak-shaving tasks later on. I no longer have the excuse of checking our support inbox a hundred times a day when I don’t want to confront the bigger issues that have to be confronted for things truly to progress.

David Allen, when deﬁning productivity “tricks” puts it this way: “the smart part of us sets up things for us to do that the not-so-smart part of us responds to almost automatically.” And philosopher John Perry suggests something very similar in his structured procrastination, which involves taking on ever more grandiose projects so that you’ll work on the projects you’re actually supposed to do as a way of avoiding those bigger projects. I’ve merely taken this one step further (or ﬂipped it on its head, depending on how you look at it.) By outsourcing the means of avoidance, I’ve committed myself to working on the grandiose.

Now, of course, you have to be honest with yourself. You can’t just ﬁll up your life with a whole host of new tangential tasks to replace the ones you’ve farmed out. The good outsourcer learns to develop a healthy reﬂex of either immediately deﬂecting any time-consuming side task to outside help or abandoning it on the spot. It’s taken me a while, but this is becoming second nature to me now. And I try always to bear the 80/20 concept in mind before tucking into any task that might take more than a few moments. If it’s not in the 20%, I simply refuse to do it myself. And, much to my surprise, nothing ill has come of it.

Once you’ve properly embraced an outsourcing world-view in the ways I suggest, you’ll begin to see a universe of possibilities opening that might never have occurred to you previously. And, like GTD, you’ll ﬁnd it giving you a radical new calculus for the sort of commitments you’re willing to take on. You’ll begin to see tasks falling into two natural categories: those which can be delegated, and those which you must do yourself. And you’ll ﬁnd yourself taking the latter far more seriously.

Check back soon for Part 2 of Ryan’s outsourcing series, coming soon to 43 Folders.

”Enlightened outsourcing, Part 1: The psychology” was written by Ryan Norbauer for 43Folders.com and was originally posted on September 25, 2007. Except as noted, it's ©2009 Merlin Mann and licensed for reuse under CC BY-NC-ND 3.0. "Why a footer?"