THE WHY

      Intentional living is the art of making our own choices before others’ choices make us.

      —RICHIE NORTON

      My first start-up, Paintapic, was born in a closet filled with thousands of thimble-size pots of paint. The service allowed you to turn your photos into a custom paint-by-number kit, complete with a canvas, paints, and brushes. At the time, I also had a demanding full-time day job, so Paintapic was built entirely on nights and weekends.

      Leadership had changed at my nine-to-five, and the new direction had pulled the plug on the creative projects that allowed me to enjoy my job. Over time, this new vision became so limiting that I no longer felt I was adding real value to the company. My potential impact on Paintapic, however, was limited only by the amount of time I was willing to invest. So I Old Yellered my social life for Paintapic’s sake and got to work.

      My cofounder had convinced his employer to rent us an unused storage closet . . . as our office. That dark room with its one small frosted window devoured our nights and weekends for nearly two years. Thousands of decisions were made in that cramped Cyclopean skull of a room. We poured ourselves into every single detail—down to the number of bristles on our brushes.

      Finally, the moment we had been waiting for arrived: launch day. Orders went out. Money came in. We were in the black. We were doing pretty well right out of the gate without any outside investment. That’s rare for a start-up. We were by all accounts a (humble) success.

      As soon as our site launched, I placed an order through our site. I remember how excited I was to receive my kit in the mail. Here it was, real and working! But by the time I had walked up the single flight of stairs to my flat, I was already preoccupied with something else. To this day, that kit remains unopened somewhere, a goofy portrait of a pug (our unofficial mascot) forever waiting to be painted.

      My indifference quickly stained every aspect of running the company. Deep confusion and frustration set in. On paper, I had accomplished everything I was told would make me happy. I sacrificed a lot getting to this point, but now that I was here, it just didn’t seem to matter. I wasn’t alone. My partner seemed to share these feelings. The process of creating the company, the pleasure we got out of building, had blinded us to a simple truth: We were just not paint-by-number guys. Though the product added value to the lives of our customers, it added little to ours. We weren’t passionate about the product—we’d just fallen in love with the entrepreneurial challenge.

      How often do we find ourselves in this position? You’ve worked incredibly hard on something, only to discover that it leaves you feeling empty. You compensate by working even harder. You reason that maybe if you put in more hours, you’ll finally be able to appreciate the fruits of your labor. Why does this happen?

      What is your true motivation for lifting that weight, being on that diet, working so late? Are you trying to lose ten pounds for health reasons, or are you in a toxic relationship that’s stripping you of your confidence? Maybe you don’t realize that you’re killing yourself at work just to put off having a hard conversation with your spouse. If that’s the case, no matter how much time you clock at the office, it won’t offer lasting relief, because you’re climbing the wrong mountain. We need to understand what’s actually driving our motivation before we ascend.

      Our motivations are heavily informed by the media. Our social feeds are populated by endless images of wealth, travel, power, relaxation, beauty, pleasure, and Hollywood love. This virtual runoff perpetually seeps into our consciousness, polluting our sense of reality and self-worth every time we go online. We compare our lives to these largely artificial constructs and structure our plans accordingly, hoping to eventually afford a golden ticket to these misleading fantasies. Conveniently tucked out of sight are the months of planning, the “talent” lined up in audition studios toting their head shots, the production crews, the double-parked trucks filled with camera gear, the long spells of unemployment, the weeks of rain that stopped shooting, the food poisoning on location, the empty sets after they leave. Distracted by the never-ending stream of aspirational media, we forfeit our opportunity to define what is meaningful on our own terms.

      Bronnie Ware, an Australian nurse and author who spent several years working in palliative care with patients in the last weeks of their lives, recorded her patients’ top five regrets. The number one regret was that people wished they had stayed true to themselves.

      When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.⁶

      Choices come in all flavors: the good, the bad, the big, the small, the happy, and the hard choices to name but a few. We can make these choices carelessly, or we can make them with intention. But what does that mean? What does it mean to live an intentional life? The philosopher David Bentley Hart defines intentionality as “the fundamental power of the mind to direct itself toward something . . . a specific object, purpose, or end.”⁷ The term hails from medieval scholastic philosophy, so I’d like to adapt and update it a bit for our purposes: Intentionality is the power of the mind to direct itself toward that which it finds meaningful and take action toward that end.

      If intentionality means acting according to your beliefs, then the opposite would be operating on autopilot. In other words, do you know why you’re doing what you’re doing?

      We can’t be true to ourselves if we don’t know what we want, and more importantly why, so that’s where we must begin. It’s a process that requires the steady cultivation of our self-awareness. This may seem very woo-woo, but it can be as simple as paying attention to what resonates with us, what sparks our interest—and, just as importantly, what does not. As we begin to identify the things we’re drawn to, we can start properly defining our dreams, based on what we actually believe in.

      When