Two years of junior high track and cross country were enough for me to put running for exercise on a ten-year hiatus. For me, running is painful, boring, lonely, inconvenient, and a long list of other negative adjectives. However, alongside this list, another list has steadily grown over the years: the reasons I need to improve my lifestyle. Here’s a snapshot:

1. Fitness level is a better predictor of life expectancy than weight is. I understand this to mean that “skinny” does not equal “healthy.” If you want to be healthy, you have to exercise.

2. People who enjoy exercise are more likely to sustain it over long periods of time. I admit that I typically hate many forms of exercise, specifically running.

3. Unhealthy-ness is out of control.The added sugar in a single can of soda might be more than most people would have consumed in an entire year, just a few hundred years ago.” This pertains more to healthy eating than to exercise, but it’s certainly damning evidence against my current lifestyle.

The list went on and on until I caved—I had to start exercising regularly. Over the summer, my wife had been running most days so I decided to do it too. She even signed up for a half marathon, and with a little peer pressure I signed up for that, too. But I made one promise to myself: I had to find a way to enjoy running. Since I had run in the past, I knew that unless I made drastic changes to my approach, I would be submitting myself to a summer of torture. Here’s what I did to make running bearable (even enjoyable), to the point that ultimately ran a full marathon (with my wife!) at the end of the summer.

Waking Up is Hard to Do

The very best time for me to run, based on my work schedule, time with family, and other commitments, is in the morning. If I leave early, no one else is awake at my house so I’m not interrupting family time. It’s also ideal to get it done early so I can’t talk myself out of it later in the day when I’m tired. But if there’s something I hate as much as running, it’s waking up early.

A single app has nearly solved my early morning problem all by itself—it’s called Sleep Cycle. Sleep Cycle monitors your sleeping patterns at night (you place your phone next to you with the app on). The app knows when you’re during the deep REM phase of sleep and when you’re in lighter phases of sleep. You select a timeframe for when you’d like to wake up, and the app sets off the alarm during a light phase of sleep so you’re not violently pulled out of deep sleep.

Using the Sleep Cycle app to wake up early made it significantly easier for me to run in the morning, and it’s a key part of my exercising routine.

Help Yourself by Helping Others

Like many people, I’m always on the lookout for interesting social causes and organizations that I can contribute to (either with time or money). And, like many people, I’ve found it difficult to manage my time so that I can consistently participate in these important causes. One of my favorite apps, Charity Miles, changed the way I think about this.

Charity Miles donates money to a charity for each mile you bike, run, or walk using the app. All of the money comes from large corporate partners, but since it’s based on the mileage that you log, you can literally make a difference by exercising. The contributions aren’t huge (25 cents for walking/running, 10 cents for riding), but consistent use over a long period of time adds up. Just over the summer, I ran 400 miles, which equals $100 that I contributed to good causes without any additional effort.

With Charity Miles, my morning exercises had an extra sense of purpose, and I’m very loyally committed to the app. Any time I walk or run, I pull out the app. I’m not suggesting that the app alone will turn you into an ultra-marathoner; but I do think that every ounce of motivation helps and the Charity Miles app gives real altruistic meaning to exercise.

The App That Made Running Enjoyable

I’ve heard that “real runners” are very focused on running the whole time that they’re running. I suppose that means they’re scoping out the terrain, monitoring pace and heart rate, and using positive psychology strategies. But I don’t fit that definition of a “real runner,” because for me, all of those thoughts would result in pain and boredom. (I’m referring to “healthy” physical pain that comes from normal exercise, not pain related to accidents/injury.) The number one app that saved me from these problems and made running enjoyable was my podcast app. I use the default Apple podcasts app, though I’ve lately been testing out the Overcast podcast app as well.

Listening to my favorite podcasts made a big difference for multiple reasons. First, it keeps me entertained while I’m running. Instead of thinking about pain (which is my primary focus while running without distractions) I focus on the dialogue and story lines of the podcasts. Secondly, podcasts give me more motivation to run, since I won’t have time to listen to the podcasts otherwise. A key aspect of this strategy is having podcasts that I thoroughly enjoy and look forward to—my favorites are: This American Life, The B.S. Report, Freakonomics, The James Altucher Show, and The Dan Patrick Show.

After I got some earbuds that don’t fall out while I run, and a steady stream of fantastic podcasts, running completely changed. I began to enjoy the time to learn and relax, and I always felt alive and productive when I finished running.

Learn to Love Your Good Habits

I’ve written before that the key to sustaining habits is to do things you find enjoyable. While you may never run a marathon and you may not like the apps or ideas I suggested above, the most important point is this: experiment with different strategies that will make your healthy habits enjoyable. If it really is a healthy habit, like exercising, eating healthy, or sleeping well, among other things, your body wants to enjoy it. Keep experimenting and you’ll find the right combination of things that work for you, and in the process you’ll create an enjoyable, sustainable habit.

Max Ogles

Hi, I'm Max Ogles. I'm a behavior designer, entrepreneur, and writer focused on psychology, technology, and business. Read My Full Bio