We live in a world where day dreams are more common than dream jobs, where money clouds our search for meaning in search for profit. We sacrifice our quest for purpose and in the pursuit of those paychecks, we give up our passion.

The idea of being able to choose your own career path is actually a relatively novel concept. And the idea that your job should be able to fulfill some sort of personal passion, that it should relate to your personal interests is newer still. It really wasn’t all that long ago that nearly all of us would have been subsistence farmers. And it was even more recent that most of us would have thought about our jobs as nothing more than paychecks, as a means to an end.

But society has shifted considerably, especially in the last few decades. For the first time in human history, so many of us are afforded the opportunity not only to explore our personal interests, but also to parlay those interests into possibly viable careers. Then, reality sets in and we realize we still need to make ends meet. So, we pursue the paycheck instead.

I didn’t know about Jay Shetty until a week or two ago when one of his “viral” videos started making waves across the Internet. He was named as part of Forbes 30 Under 30 Class last year and he hosts a daily show on HuffPost Live where he has interviewed such inspirational figures as Deepak Chopra and Russell Simmons. Oh, and apparently he used to be a monk.

You know what it’s like, we spend our whole day trying to get our work on time, but then spend all of our time thinking about work. We wish our out of office could be permanent. We wish that our inbox would always remain empty.

Some of us may be quick to dismiss figures like Jay Shetty. We might say that their heads are in the clouds and their “inspirational wisdom” is not at all grounded in the day-to-day reality of most people. We might say that his videos are filled with “Oprah-isms” that are nice to hear, but not actually practical, like learning to “embrace the situation” or how we should think positive and leverage the “law of attraction.”

I get it.

But sometimes we need these not-so-subtle reminders of what our lives could be. Are you commuting to a job that you don’t actually enjoy, just so you can afford to pay for things that don’t actually bring your joy either? Are you working for the weekend, yearning for the day when you no longer need to work?

For my part, working from home as a self-employed freelance writer affords me a great deal of flexibility, to be sure, but I still find myself stuck between a rock and a hard place. Work responsibilities are always weighing heavily on my mind, even if I am passionate about certain aspects of my work. Like blogging here about inspiration and parenthood.

I know that we’ve all been in that position feeling confused and seriously lacking mission, but then I ask myself – at the end of my life, what will I regret? And the answer is clear. The pain of regret far outweighs the pain of risk. So, next time you’re going through challenges, just remember this: a winner is just a loser who tried one more time.

I suffer from a severe fear of missing out and maybe that’s part of what drew me toward my freelance career in the first place. I want to have the flexibility to pursue so-called “passion projects,” even if they don’t end up particularly profitable.

It was definitely a risk going through the work of writing and publishing a couple of books, but as Jay Shetty reminds us here, the regret of not writing those books would have hurt me even more. I’d always wonder what could have been. What do you really want to do with your life? Are you willing to try one more time?