Let’s go back a few hundred years to Feudal England. Chances are that you’re born into an agricultural family. You’ll likely be working the land of the same farm from the time you’re old enough to wield a pitchfork to the day you die at the ripe old age of 40. And that’s only if you’re extremely lucky. You didn’t have too many vocational decisions to make.

And even as recently as a generation ago (or even to this day in certain parts of the world), the main reason why you chose any given job was that it was something you could do to keep a roof over your head and food on the table. The notion of finding a sense of life fulfillment through your work was reserved only for the elite. But times have changed, mostly for the better, but it has introduced a new set of challenges.

Do what you love… and don’t worry about the money.

How many times have you heard that before? The very possibility of chasing your dreams is a fairly recent development and it has led to a great deal of existential angst and disappointment. To further exacerbate the situation, we now face a near infinite number of possibilities. The challenge of making money doing the “thing that you love” is a problem of privilege, a problem that many others before us weren’t so lucky to have.

And this leads all the way around to the occupational choices I have made along the way. Make no mistake. I feel incredibly lucky that I am able to work from home, run my own business, and earn a comfortable (albeit not especially lucrative) middle class income. I certainly endure my fair share of “adulting” problems, but I am lucky to have them. But as I said in a recent vlog, they’re still problems and they cause me a lot of grief, angst and anxiety.

Truth be told, and this is in no way meant to be boastful, there isn’t too much in my professional life that has to be done right this moment. Or even today. Or this week. I have minimal daily blogging duties. Most assignments I receive usually have a window of at least a couple business days. Many give me as much as a month as my window. This work is on my radar and can usually be kicked a little further down the field. I can always wait until tomorrow.

This lends itself a very similar conundrum on most nights.

After putting my daughter to bed for the night, do I go to sleep myself, because the work can be done tomorrow (and tomorrow and tomorrow)? Or do I force myself to sit in front of the computer, attempt to achieve flow in the third shift, and try my hardest to be productive? It’s a hard decision, because I lose both ways.

If I go to bed, I’m riddled with guilt because of the “lost” opportunity to do more. If I go to the home office, I drain myself even further, I have a harder time falling asleep afterward (due largely to the late night screen time), and I feel like a mindless zombie the next morning, groaning for more coffee. Either decision is “wrong,” depending on what I think I want to value more.

Put another way, the endless opportunity for procrastination (I can sleep early, because I can always work on that project tomorrow) battles against the crushing failure of an unfinished to-do list. I stare down not at what I accomplished, but rather all the things I didn’t do that day. I never finish and it eats me up inside, tearing away at any sense of self worth. But the allure of a good night’s sleep cannot be ignored, beckoning to me to bed like the Sirens in Homer’s Odyssey.

As author Greg McKeown once said, it’s the quiet pain of trying desperately to do everything, perfectly, now. Indeed, I am writing this exact post right here late at night when I should really be going to sleep.

But the very fact that I have this choice to make practically every night and it represents one of the biggest problems in my life is a luxurious privilege denied to many. And all that does is make me feel guilty for complaining about it. Am I alone?