It Happened to Me

RailsConf 2006: Nathaniel Talbott: “Homesteading: A Thriver’s Guide”

(This article also appears in Tucows Farm.)

“Paul Graham might have be the first speaker at this conference to quote the Old Testament,” said Nathaniel Talbott at the start of his presentation titled Homesteading: A Thriver’s Guide, “but he won’t be the last!” He then quipped that unlike Graham, he wasn’t going to contradict the Old Testament, so as not to put his soul in peril.

Like Graham, the talk he gave is applicable to people outside the Rails community or even outside the field of programming.


Consider the case of “Bobby”, a shopkeeper in Boston in 1870. Perhaps it might be more accurate to call him a shop manager, since he really doesn’t own the shop, but merely operates it for the owner. Through his work and experience, he knows the in and outs of running a shop.

Bobby is still a young man. He’s married, with a couple of young children. As a shop manager in Boston, he is limited; he’ll never have the money to own his own land and his own shop — he’ll always be in the employ of someone else.

He’s starting to hear things about the frontier — the great expanses of land out west, where the opportunities for a young, resourceful man like Bobby lie. If he took the train out west, he could own his own land thanks to the Homestead Act.

Sidenote: The Homestead Act

The Homestead Act, more formally called the Homestead Act of 1862, was a law that made large areas of land in the public domain available for claim by private citizens. If you were the head of the household and at least 21 years old, you could claim up to 160 acres of land — equivalent to a square a half-mile on each side — as long as you lived on the land for 5 years, built a home, made improvements and paid a $18 filing fee at the end of the 5-year period. Anyone, from established men with families from eastern cities to single women to freed slaves could be a homesteader. Thanks to the Homestead Act, about 270 million acres — roughly 10% of the area of the United States — was settled and claimed.

For more details about homesteading, see this site.

There is a 21st century equivalent for homesteading: building small, sustainable businesses that we own. Successful examples of such homesteaders are:

  • Firewheel Design: A company that designs icons, web applications and brands.
  • 37Signals: A Chicago-based company that develops simple but clever web applications that help people get their work done. Ruby on Rails was derived from the process of building applications for 37Signals.
  • Pragmatic Bookshelf: When two programming consultants’ business started to dry up as a result of the bubble burst, they started getting into publishing useful books for software developers, which is now a successful business in itself.

Why should you homestead?
One thing to consider is the concept of opportunity cost. Simply put, it’s “the value of the next best thing you could be doing”.

For example, if you decided to stay as an employee of a company, your opportunity cost is the money and benefits that come from being an independent contractor. Another example is the answer to the question “What could I be learning if I wasn’t doing what I was doing right now?”

Sidenote: Opportunity Cost

When I was working at a dot-com in San Francisco, I read an article in SF Weekly that permanently seared one particular type of opportunity cost in my brain.

The article, titled Forgive Me, for I Live in the Marina, was about the Marina neighbourhood, an area reviled by people in the city’s grungier districts (say the Mission or Haight) for being “ground zero for the yuppie materialism that is supposedly L.A.-ifying our city”. In the article, a number of former fratboys and sorority girls, now yuppies, are profiled, and even years later, one stands out in my mind for its use of the term “opportunity cost”:

Jeff Cohn and his friend, who asked that she go by Lindsay, engage in apres-workout cocktails and reflect on the stereotype “Marina Person” — which they admit they fit. They suffer from Peter Pan Syndrome, they joke, because at 31 and 34, respectively, they’re still living in a kind of collegiate Never- Never Land. Jeff and Lindsay describe a world full of gorgeous, fun-loving people who party from Thursday to Saturday at Marina bars, dating each other, fearing, as Cohn puts it, the “opportunity cost” of commitment.

Maybe it’s me, but I always find it a bit unsettling whenever people apply business terminology to relationships.

The opportunity cost that Bobby has to consider is what he’d be missing out on by staying in Boston and continuing to work for someone else and living on someone else’s property. Buying a ticket on the train heading out west is a risk, which he has to weigh.

Life is an exercise in risk management. Each of us has risk, which is tied to the limited amount of time that makes up our future. There’s a relevant bible quote: “So teach us to number our days, that we may multiply our hearts unto wisdom.” We don’t know what’s happening in the future; that’s the risk. Everyone in this room is at risk.


Prepare your outside work, make it fit for yourself in the field, and afterward build your house.

Bobby decides to buy a ticket and stake out some land in the frontier out west. The train goes all the way to the west coast, which leads to the question: where shall he stop along the way? He does research.

That question can be generalized to “Where do I want to be? What do I want to see? What interests me? How can I take my skills and do what I love?”

In the 21st century, the question “What shall I do, as I switch from being a shopkeeper to being a homesteader?” is still applicable. For example, if you’re currently a full-time employee, but want to start your own service-based business, you might say to yourself: “What if I started out by doing consulting? I’d still be taking in money and I’d learn about startups and business processes along the way.”

One of the cool things about land (in our 21st century case) is that it’s limitless. “You have limitless opportunities to turn your dreams into code,” says Talbott. Don’t think that all the space in the software world is taken; there’s plenty of room for everybody.

In the end, Bobby finds a town along the train route where he can set up a shop and stakes out some nearby land by the mountains where he builds his house.


A little sleep, a little slumber, a little folding of the hands to sleep — so shall your poverty come on you like a prowler, and your need like an armed man.

As a homesteader, the work involved keeps Bobby busy — very busy.

Homesteading in the 21st century will keep you busy as well, so time management is of the utmost importance. Time is our most precious resource, because it’s non-renewable.

Nathaniel recommends David Allen’s Getting Things Done, a time management book that’s undergone a bit of a renaissance thanks to new-found attention from the geek world.


Though one may be overpowered by another, two can withstand him. And a threefold cord is not quickly broken.

In the frontier, you’re in trouble if you’re on your own. Bobby needs help from the people around him, as and 21st century homesteaders, so do we.

There are three parts to “community”:

  • Family:
    • Integral, necessary part of running a homestead
    • Even though getting family members involved in your business can cause problems, it doesn’t mean that you shouldn’t do so
    • Getting the kids involved in the family business is a valuable form of homeschooling, even if they go to school outside the house
    • Take care of your family, and they will take care of you
    • Family’s not just blood relations, but also your partners
  • Neighbours:
    • Homesteading is not a zero-sum game. Someone else does not have to lose in order for you to win. Therefore finding and making neighbours is advantageous
    • When expounding on this, someone once told Nathaniel “It sounds like you’re making competitors for yourself,” to which he replied “YEAH! It’s a star, not a minus sign”
    • Sharing is good — in the long run, it helps everyone
    • He cites his company, Terralien, as an example. He calls his business a “platform for doing contract consulting work”. He knows all these cool contractors and consultants and enjoys the process of finding work. So he wondered what would happen if he went about finding work and farmed it out? His partners sign the simplest non-disclosure agreement possible: “Don’t share my clients’ data”
    • The adage “Good fences make good neighbours” is applicable. In the 21st century case, it refers to setting expectations with your neighbours and keeping an open dialogue about them. The number one relationship-breaker is the failure to keep up with expectations.
  • Towns:
    • You need a place where you can stretch out but still have infrastructure, where you can work with people other than your direct neighbours.

Family, neighbours and town all make up community.


Where no oxen are, the trough is clean; but much increase comes by the strength of an ox.

Bobby has to till his land, and ploughing is very difficult without a horse or ox. He needs tools, which are basically multipliers — they multiply what you can do.

In our 21st century version of homesteading, “tools” doesn’t refer to just software development tools, but tools for all aspects of the business. Consider marketing — it’s a tool, since it’s essentially sales automation.

Remember, there are things that you can do that your tools can never do. Do what you do best, and let your tools do what they do best.


For all his days are sorrowful, and his work burdensome; even in the night his heart takes no rest. This also is vanity.

In 1800, Bobby would have at least toned down his activity on Sunday, if he didn’t stop working outright. We too need rest, a change of pace; it actually helps us do more.

Now by rest, what we mean is a change of activity. It doesn’t necessarily mean just vegging out. If you don’t take time out for yourself, you’ll become miserable, and what’s the point of doing something if you’re having a terrible time?

If your response to rest is “But I don’t have time!”, then you’re probably doing something wrong.


A good man leaves an inheritance to his children’s children.

One of the values of Bobby’s actions is that he’s taking raw, untamed wilderness and building wealth. Better still, it’s not just for himself, but for his kids and their kids and his descendants to come.

Wealth-building is not zero-sum, and it’s not just monetary. It can also be time.

Many parents say “I just want to provide kids with the things that I didn’t have,” but in the end, things didn’t define who we were.

It was the non-material gifts from our parents that made us.

Homesteading, whether in 1870 or now, provides you with an opportunity to pass valuable skills onto your children. It doesn’t matter if those skills fill a marginal niche; if they please your customers, they’re valuable and worth passing on.


Nothing is better for a man than that he should eat and drink, and that his soul should enjoy good in his labour.

After 5 years out west, Bobby looks back at what he’s done. He’s no longer working in town, but on his homestead full-time. He enjoys the land he owns, the amazing thing he’s been able to carve out the wilderness.

What do you love?

There’s was a sort of fixation about apparent security, about landing a job at a place that would give you “cradle to grave” employment. Those days are gone, and the best course of action is to find work you love.

There will always aspects of our work that we don’t love, but they allow us to do the work that welove.

Never lose your love for people. There’s all sorts of things you can learn from them.

Never lose your love for learning and improving. It’s a continuous process, and it’s part of rest cycles.

Nathaniel runs into people who are just working at their job without passion, who surrendered to the 9-to-5. Don’t be like that!


Like fish taken in a cruel net, like birds caught in a snare, so the sons of men are snared in an evil time…

One day, it starts to rain and Bobby can see it’s going to be a terrible storm, so he runs about securing things.

“Weather” in our 21st century homesteading metaphor is that which can’t be predicted nor controlled, just as in Bobby’s case. It can be your best friend and your worst enemy.

You have to watch out for assumptions! Of course, you’ll have to make them, but make sure you call those out and ask yourself: “What are the assumptions I’ve been making turn out to be wrong? What’s the worst-case scenario?”

If you have homesteading skills, they’re the most useful no matter what the current circumstances are. Consider how many people affected by the shrinkage of the contracting market, among whom were the Pragmatic Programmers. Thet took what they knew from the consulting business and applied it to the book business.

Homesteading skills will help you during evil times. You’re not dependent on your employer.

Be aware of debt — it’s a killer, especially to homesteaders. It’s also so prevalent in our society. Nathaniel’s goal is to be debt-free.


To everything there is a season, a time for every purpose under heaven: A time to be born, a time to die…

Nathaniel: “This is sort of a morbid way to wrap up the talk.”

After a long life, Bobby is dead. How is Bobby’s tombstone going to be different from the one he would have had, had he stayed in Boston?

All homesteaders cease at some point. One thing to consider is some kind of exit plan: once the usefulness of the company is over, what should be done? Let it peter out? Let it get bought out? You should decide.

Nathaniel went into a slight aside about how some large corporations have no exit plan and can’t even conceive of one; they exist to keep existing long after their usefulness, like zombies, the walking dead.

Knowing that there is an end also brings up important questions:

  • How are you going to measure success?
  • If you knew you were going to die tomorrow, would you still be doing the same things today? If not, why not?
  • How will you make it so that you’re spending your life to the maximum? Enjoying every moment of it?

In order to live life well, we need to keep the end in view. In order to do a project well, we need to keep the end in view, too.

Buy the ticket!

The one thing that Nathaniel wanted us to walk out of the presentation with was to reconsider our current situations. Are we happy doing what we’re doing?

He made an aside about why the lucky stiff — he clearly loves what he’s doing, which is making us laugh and leaving us scratching our heads.

We’re all at risk. That’s normal. We need to measure that risk, find out what right and wrong assumptions we’re making, and consider everything we do.

He exhorted the audience to “turn your dreams into code and make something that the person beside you can use”.

He suggested that we get involved in the modern-day equivalent of barn raisings. Find other like-minded people, prep up bunch of stuff, get some food and like the Amish, “help one of the neighbours raise their barn”. Come together as a community, and next month, build someone else’s barn.

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