I used to believe that life was a series of checkboxes. Do the work. Hit the goals. Earn the reward. Be happy. That’s what I was taught. Or maybe, that’s what I assumed. So I worked hard. Pushed through sleepless nights, sacrificed weekends, said no to things that didn’t “fit the plan.” I told myself, “Once I get there, it’ll all be worth it.” And...

I was having a chat with a friend of mine who’s an accountant, and we somehow ended up talking about why so many people are always broke—even when they have decent incomes. He’s worked with hundreds of individuals and businesses over the years, so I was curious to hear his take. According to him, there are two main reasons that stand out the most. First, people don’t...