I sipped on my lukewarm hazelnut coffee, blinking my bleary eyes while the light from my monitor seared my corneas.

Glanced at the clock – it was after 11pm. Still two more chapters to go. About 4,500 words. I won’t be sleeping well tonight.

I pushed myself away from the kitchen table, stood up, and paced around the living room for a moment, just to stretch my legs and get my blood moving again before sitting down and digging into another 45 minutes of writing.

It was Wednesday night – the night before Thanksgiving. And I was determined to get all my work done before the holiday.

Ah, the glamorous life of an entrepreneur…

It’s moments like these that make me laugh whenever somebody thinks about entrepreneurship.

Every time – every time – somebody finds out that I work for myself, they say, “Oh, that’s nice!” They give me an impressed face, like I’m living the life.

Vacations whenever I want! My own schedule! No dressing up! No annoying coworkers! And so on.

Some of those things are true. And I wouldn’t trade my work life for any other career.

I don’t have office politics or a long commute or a dress code. I have full control over my schedule for the most part (though that’s not as big of a deal as you might think).

But I’m also not working on the beach with my feet up while lounging in the sun. I can’t just take breaks whenever I feel like it. And I’m held to an accountability standard that a lot of employees don’t have to deal with.

And forget about being paid while I’m sick.

While there are times when being an entrepreneur is absolutely awesome and totally worth it, there are also times where you are running on empty and starting to question your sanity about the whole doggone thing.

This occurs most often during the holidays.

What’s a “paid holiday”?

You know how a lot of people get paid time off? “Hey, get time-and-a-half if you work the holiday, or you’ll get 8 hours of holiday pay on your paycheck”?

Yeah, that doesn’t happen when you work for yourself.

I’ve worked through lots of weekends and even holidays in the past year, so when Thanksgiving came around, I told my wife I wanted to spent it with her and the kids.

That weekend is the kickoff to the Christmas season. There’s lots to do, lots of fun to have, and frankly, I just wanted to spend four whole days with my family.

Most of my work was manageable. I could clear a lot of it out of the way ahead of time. But I had a ghostwriting project with a deadline of the Friday after Thanksgiving.

I had stayed on pace most of the month, churning out chapters so that I could get it done before Thanksgiving. But in the final week, as edits started coming through and changes had to be made to the book, I slowed down to a crawl, and I found myself with 12 chapters left heading into Wednesday.

Here’s what I could have done: worked hard all day, knocked out 7 chapters, then split the remaining five chapters across Thursday and Friday. It would come out to about two hours of work each day – not terrible at all. Could even be done during my kids’ nap times.

Instead, I hunkered down on Wednesday night and finished the final 5 chapters before going to bed.

The problem with all-nighters

I stopped writing that day at about 5:00pm and spent the next 3 hours doing family stuff: dinner, playing with the kids, and bedtime.

Then, I sat down to write. Figuring an hour per chapter, I could wrap up around 1:00am and head to bed, which is late but not brutal.

But that’s not really how it goes when I stay up late.

First, once I hit 11:00pm as described above, my productivity slowed down incredibly. Words were there, but getting them from my brain to my fingers started to become an arduous task.

I wasn’t dozing at my keyboard, which is also a problem with late nights, but my pace just couldn’t keep up.

As a result, I was still writing until about 1:45am, when I finally finished the last chapter and compiled the final chunk of the manuscript, sent it over to the client, passed on an invoice, and closed my laptop for the night.

“But wait!” you say to your computer screen for some reason as you read this even though I can’t hear you, “the title says you were up until 3:45. What gives?”

A funny thing happens when you work for five hours… you brain can’t shut off. Even though my body was exhausted, there was no chance I could fall asleep.

I had to “come down” from the high of writing.

First, I made a snack and watched a little YouTube in the living room. Then, I crawled into bed with a book.

After 2:30am, there was still no sleep coming.

So I returned to the couch for my foolproof sitcom strategy: turn on something amusing and light that I have seen before, curl up with a blanket, and let my body doze off to that.

Of course, I also made the strategic error of choosing the first Thanksgiving episode of Brooklyn Nine-Nine, which was way too funny to fall asleep to. I wound up laughing more than yawning, so it may have just delayed my sleep.

I finally knocked off about 3:45am.

The next morning, I was so out of it that, when my kids came downstairs at 7:00am on the nose and crawled on top of me, I didn’t realize that I wasn’t in bed.

I ran the whole day – two family Thanksgivings – on around 3 1/2 hours of sleep.

And it was awesome.

The gift of no work due

I could have rather easily handled the work if it spilled over into Thursday and Friday. I could have gone to sleep at, say, midnight and had 2-3 chapters left instead, with a solid 7 hours of sleep.

But the key to managing your work-from-home life is drawing boundaries between your work and your family.

If I had let the work spill, I would have always had it in the back of my mind as I decorated the Christmas tree with the kids or ate apple pie while watching Planes, Trains, and Automobiles with my wife.

I would have been, as I describe it, “low-level annoyed”. I wouldn’t have been present with my family completely, and that’s all I wanted over the weekend.

I gave up a little sleep, yes. I was tired, yes. And while people were ramping up for the holidays with fun on Wednesday night, I was working.

But then, for four glorious days, I had zero work. I was completely caught up on my responsibilities, and I felt great.

I went to family Thanksgivings and thoroughly enjoyed myself. I could have a few glasses of wine knowing I didn’t need to keep my energy up for any late-night writing.

I could watch Christmas movies with my family and decorate the house.

I could bake apple pies on Thursday morning while watching the parade with my kids.

I could just, you know, be the dad and husband I am supposed to be all weekend.

Plus, I could cruise into the following week with a clean slate, knowing I wasn’t behind on any deadlines.

And all of that was worth a little lost sleep.