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.

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:

1. Wake up. Check and reply to stress-inducing customer support emails. (1 hour)
2. Check and reply to business development emails. (2-3 hours)
3. Programming: new feature development and bug fixes (2 hours)
4. Make lunch. Do a bit of cleaning. (1 hour)
5. 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)
6. An ad hoc mix of programming, more email checking, and taking phone calls. (2 hours)
7. Start making dinner (1-2 hours)
8. 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

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:

1. Small reward now
2. Large reward after a delay, with the option to “defect” to the small any time
3. 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.