The Dreaded Middle
Jul 25, 2025
Whenever you’re doing something, be it writing a novel, running sprints or running a shift in a restaurant, in my experience, the start and the finish are rarely the problem.
It’s something I call The Dreaded Middle, and it makes time seemingly stand still, slowing you down to the point where you call it quits.
The Dreaded Middle is universal.
- If you’re a writer, it’s Act II of your next book.
- If you’re a sprinter, it’s between twenty and forty meters of the 100-meter dash.
- If you’re a powerlifter, it’s coming out of the hole on the squat.
- If you sell life insurance, it’s filling out the application before underwriting.
- If you’re an entrepreneur, it’s when you’re unsure if you need your first Big Hire.
- If you’re running a shift at Taco Bell, it’s between 2 and 5 PM when cars are few enough to make you bored but not frequent enough to make time go by faster.
And since The Dreaded Middle is always the hardest part to get through, it’s where self-sabotage reigns supreme. In most cases, it looks like:
- Not controlling your emotions.
- Looking for immediate gratification, pivoting your pursuit that results in a meaningless win.
- Becoming resentful and developing a general malaise for life itself, (it sounds dramatic but it’s true).
I guess that’s why there are so few good books written; so few world-class sprinters and powerlifters; why there hasn’t been another Ben Feldman since Ben Feldman; why more than eighty-percent of businesses fail within the first five years; why so few people make a career in fast-food, and so on.
I know this to be true, because no one self-sabotages more than me. That’s why I consider myself the leading expert on the subject. Not because I have risen above it and no longer commit perhaps the most treasonous act one can. Because I do it all the time. Consider it continuing education. But I’m aware of it when it happens, and I’m quick to stop it; which is more than most can say. Most don’t even know they’re doing it, and so they keep on keeping on and wonder why they’re stuck.
Speaking of being aware when it happens, I was at the track on Monday getting a workout in. Speed-changes were on the menu. Specifically, easy-hard-easy, which is basically:
- Accelerate from 0-20 yards
- Sprint full speed from 20-40 yards
- Decelerate from 40-60 yards
I set the timing gates for the hard section, (from 20-40 yards) clocking a 2.07, which is a little less than twenty miles per hour.
“Come on,” I said, shaking my head when I saw my time. “No way.”
The week prior I did hard-easy-hard, clocking a 1.95, (faster than twenty-one miles per hour) but the timing gates were at the finish (from 40-60 yards) where I was at top-speed instead of the middle of the sprint where I was still in late acceleration.
That’s when the concept of The Dreaded Middle came to me.
It made perfect sense. Of course I wouldn’t be as fast in the middle of the sprint than the end; I wasn’t at full-speed yet. Said another, more liberating way: I was still gaining speed.
When you look at whatever you’re working on through that lens, it doesn’t make The Dreaded Middle any easier to get through, but it makes you realize it’s where the biggest payoff awaits.
- If Act II is gaining speed, the better the climax your story will have.
- If you’re still gaining speed in late acceleration, then your top-speed will be that faster.
- If you’re gaining speed out of the hole on the squat, you’ll PR at every meet.
- The faster you fill out an application and get it to underwriting, your book of business—and commissions—starts gaining speed.
- The faster you replicate yourself, your business starts gaining speed and scaling.
- If you’re keeping busy, i.e. gaining speed, during your slow time, the faster you’ll be once the dinner rush hits.
So, how does one not only get through, but gain speed in The Dreaded Middle?
- You have to realize you’re in it, which as mentioned before is more than half the battle. Most don’t know, which is why most people self-sabotage.
- It has to be measured. What gets measured gets improved. I ran a 2.07 on Monday. I have a much better chance at improvement now that I have an objective way to show improvement. Find a way to objectively measure whatever The Dreaded Middle is for you, and you’ll find a way to improve it.
- Repeat steps one and two over and over again. It takes me twenty drafts to write a book; hundreds of sprints to get faster; countless hours working with employees before a store runs itself.
Now that you know about The Dreaded Middle the question is: what are you going to do about it? Because neither the start, nor the finish, of whatever you’re working on is the problem.
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