Every night, millions of people around the world have to grapple with the same difficult decision. Maybe you’re one of them. It’s getting late and your spouse asks whether or not you’re coming to bed. If you say yes, you retire at a reasonable hour and end up with a decent night’s sleep. If you say no, you get sucked into your late-night time-sink of choice–work, internet, Craig Ferguson–whatever. When you look at it this way, that simple question becomes a decision point–a fork in your existence. Down one path, you wake up rested. Down the other, you’re groggy at work the next morning.

For Travis Bogard, VP of Product Management and Strategy at Jawbone, these types of small choices represent some of the greatest potential for wearable computers. Over at Jawbone, they know the import of these choices: According to the company’s vast troves of data, people who sleep with a partner get to bed 35 minutes earlier on average than those who sleep alone. So what happens when you don’t have somebody beckoning you to bed? That, Bogard says, is where your wearable comes in: “We want to be able to create that decision point for someone.”

That’s the point where an activity monitor becomes an activity modifier.

What Wearables Are Missing

This is the territory Jawbone’s exploring with the Up24, its latest fitness bracelet, released last week. The Up24’s greatest addition in terms of the hardware is wireless syncing via Bluetooth, something that competitors like the Nike FuelBand have offered from the start. In that sense, you could say Jawbone’s playing catch-up.

But Jawbone’s additions to the bracelet’s companion app are more forward-thinking. These include notifications intended to spur activity in the moment, deployed at just the right time thanks to the band’s constant connection with your phone. In other words, the new Up was built around a very important idea: Adding wireless to a wearable isn’t just good for letting us see what we’ve done. It’s also crucial for building wearables that can tell us what we should be doing.

It’s an idea we’ve touched on before: Activity tracking is one thing; activity tweaking is something else entirely. That’s why real-life personal trainers are so great. They help you set goals that are relevant to your life, and they help push you to achieve them. They’re personal. This is the piece that most fitness wearables have missed thus far.

Notifications in the Moment

The new Up app, bolstered by its ability to constantly slurp up data from your wristband, takes some bold strides into this territory. At the heart of it are several new types of notifications, sorting out into two broad categories. The first are the notifications you get when things happen. Some of these come courtesy of a new feature called Streaks and Milestones. With it, your phone gives you a little congratulations the moment you establish a three-day streak either of high activity or good sleep.

It’s not necessarily a feature that’s impossible without instantaneous wireless sync, but it’s certainly enhanced by the immediacy. It’s the difference between your friends cheering you on at the end of a marathon and your buddy saying “good job on that thing” when you meet him for beers later in the week. “There’s a dopamine response that happens when you get one of those in the moment,” Bogard says, “Actually being able to connect that dopamine response to the behavior is very powerful to the feedback cycle.”

More interesting are the notifications the app doles out when something’s about to happen. These come in a few varieties. First, if you’re zeroing in on your step goal and it’s near the end of the day, Up might send you a notification encouraging you to make a push for the goal.

Of course, constantly getting pinged about your progress by a chipper smartphone app is no one’s idea of useful, so Jawbone tries to be judicious about its use, reserving them for when you’re actually just on the cusp of meeting your goal. “We’re very smart about when we send these,” Bogard says. “We’re not going to come along and say, ‘Hey! You have 8,000 steps left to do!’”

The other preemptive notifications come through a feature called Today I Will, which lets you opt into day-to-day goals for healthier living. Say in the morning you commit to getting eight hours of sleep. The app will look at your wake-up times, calculate when you need to hit the hay, and send you a notification, say, an hour before that, letting you know it’s time to start winding down. This is the virtual equivalent of a beckoning spouse–a decision point born not out of a domestic routine but data, algorithms, and wireless connectivity.

Of course, giving people notifications is one thing–getting people to heed them is another. So Jawbone’s continually tweaking its messaging for optimal engagement. In-house, the software team calls it “initiative moment parsing,” and the weapons at their disposal are formidable.

For one thing, there’s the data: 500 billion steps and 35 million nights of sleep, all of which can be shaken and sorted for behavioral patterns. The company’s data scientists are also considering deploying different motivational nuggets to different users–essentially A/B testing to find what gets people moving.

Still, the most important thing is catching people at precisely the right time. The challenge, says Jeremiah Robison, is “capturing people in the moment of intent–at that point where they’re deciding to work more or go to sleep, or going to lunch and looking for a place to eat, or deciding whether to walk or drive to work in the morning.”

The Internet of Me

None of this is necessarily what springs to mind when you hear that a gadget can sync wirelessly. What that usually mean is a simple data dump—the ability to look at the contents from one device on another at moment’s notice. What Jawbone’s working towards, however, is something more fluid and far more powerful. They like to call it “the internet of me.”

The idea is that, in the near future, we’ll have a personal network of devices that are constantly exchanging information about where we are and what we’re doing. The new Up app hints at what this looks like in the realm of fitness and personal health: monitoring your activity, comparing it against your own data and that of thousands of other, anonymized individuals, crunching it and piping back to you in helpful, actionable nuggets, just at the right moment, and all in real-time. That’s the point where an activity monitor becomes an activity modifier.

When you look at how that personal cloud of devices could expand, things get even more exciting. Earlier this year, Jawbone teamed up with IFTTT to let the Up bracelet become a component in the service’s “recipes.” Imagine, instead of getting a notification when you were supposed to go to bed, if your house knew to dim the lights in the room you were in—or to gradually turn them on when your wearable sensed you were sleeping the lightest in the morning. Here, those decision points are dressed up as more subtle cues that guide you to better living.

In every case, these things rely on gadgets that are capable of understanding context and analyzing our actions in the moment. Wireless connectivity is just one foundational element of that. So far, wearables have been about seeing what you’ve already done. Things will become much more exciting when they get a better sense of what you’re actually doing.