In conjunction with his appearance on Time’s 100 Most Influential People list, Sen. Rand Paul attended a gala sponsored by the magazine, where he toasted Henry David Thoreau—“just a guy,” Paul explained, who “wanted to live by himself,” but “society wouldn’t leave him alone.”

Obviously, the Kentucky senator, and possible 2016 presidential contender, chose to highlight Thoreau not just because he was an idealistic, contemplative loner. In the broader context of the liberty movement’s desire to see the Republican party reclaim the mantle of individual rights, it makes perfect sense that Paul would cheer Thoreau’s legacy of civil disobedience in the face of slavery and imperialism.

More, one can imagine Paul approvingly quoting Thoreau’s paean to trade and “commerce”—“its enterprise and bravery”:

Commerce is unexpectedly confident and serene, alert, adventurous, and unwearied. It is very natural in its methods withal, far more so than many fantastic enterprises and sentimental experiments, and hence its singular success. I am refreshed and expanded when the freight train rattles past me, and I smell the stores which go dispensing their odors all the way from Long Wharf to Lake Champlain, reminding me of foreign parts, of coral reefs, and Indian oceans, and tropical climes. I feel more like a citizen of the world at the sight of the palm-leaf which will cover so many flaxen New England heads the next summer, the Manilla hemp and cocoanut husks, the old junk, gunny bags, scrap iron, and rusty nails …

Yet the pairing, however brief, of Paul and Thoreau had me stewing this past weekend. I was thinking about the desire to “be left alone.” Laissez-faire. Liberty defined as the absence of restraint. In order to “live deliberately, to front only the essential facts of life,” Thoreau withdrew from the community, from the polis.

Thoreau’s spiritual mission was idiosyncratic; it doesn’t project easily onto the ideological map of the 21st century. But bear with me:

Today, it’s hard to truly go “off-grid,” but there is negative liberty to be found in rural America. The farther away from an urban core you are—provided you’re on private property and not in some government-protected wilderness preserve (like, er, Walden Woods!)—you will be “freer” in the libertarian sense than you would be in, say, downtown Manhattan: freer to exercise your Second Amendment rights, and far, far less likely to have your Fourth and Fifth Amendment rights violated. Within reason, and with respect to the basic rights of others, you are free to do as you please.

The closer you get to an urban core, your negative liberty diminishes. Your elbow room becomes considerably more cramped. You must obey noise ordinances. Building permits become an even bigger hassle to obtain. If you’re like me, you have to pay twenty bucks to a county government just to garage your damn car.

Yet as your pure negative liberty diminishes, practical economic opportunity increases along with the accretion of rules and regulations. Jobs are more plentiful by orders of magnitude. Your right to free speech takes on more meaning, as there are more people around you to either respond favorably or be offended by your words. Your right to property becomes more meaningful, at least in the sense that it becomes more valuable. You cannot fire a gun in downtown Manhattan as freely as you could in the woods, but you may engage in all manner of self-expressive behavior.

If the woods offers negative liberty, the city offers positive freedom.

Republicans and rightists of Rand Paul’s stripe rightly claim they don’t seek to withdraw from community; rather, they seek to limit government so that communities may thrive. Fine. My friendly advice to the liberty movement is this: increasingly, when voters hear the cry “let us alone!”, they don’t think of a solitary Thoreau-like figure; they hear what George Romney heard in “rugged individualism”: “nothing but a political banner to cover up greed.”

If he has any hope of national success in ’16, Rand Paul needs to figure out how to sell country liberty to the city.