diff --git a/bin/now-deploy b/bin/now-deploy
index 019a22a..86aa9f4 100755
--- a/bin/now-deploy
+++ b/bin/now-deploy
@@ -10,6 +10,7 @@ import bytes from 'bytes';
 import chalk from 'chalk';
 import minimist from 'minimist';
 import Now from '../lib';
+import toHumanPath from '../lib/utils/to-human-path';
 import ms from 'ms';
 import { handleError, error } from '../lib/error';
 
@@ -138,7 +139,7 @@ async function sync (token) {
   const start = Date.now();
 
   if (!quiet) {
-    console.log(`> Deploying "${path}"`);
+    console.log(`> Deploying ${chalk.bold(toHumanPath(path))}`);
   }
 
   const now = new Now(apiUrl, token, { debug });
diff --git a/lib/utils/to-human-path.js b/lib/utils/to-human-path.js
new file mode 100644
index 0000000..a8533c9
--- /dev/null
+++ b/lib/utils/to-human-path.js
@@ -0,0 +1,14 @@
+import { resolve } from 'path';
+
+// cleaned-up `$HOME` (i.e.: no trailing slash)
+const HOME = resolve(process.env.HOME);
+
+/**
+ * Attempts to show the given path in
+ * a human-friendly form. For example,
+ * `/Users/rauchg/test.js` becomes `~/test.js`
+ */
+
+export default function toHumanPath (path) {
+  return path.replace(HOME, '~');
+}