I was not a country kid, but ten years ago Melissa and I bought a little hobby farm in Southeastern Ohio.

The thing about Southeastern Ohio is that it’s hilly—like real hilly.

I had a 1960s Ford 861 Tractor with a brush hog on the back. Theoretically, I was supposed to mow down six acres of hills a few times a year.

It was terrifying.

Any hill that’s scary to sled down is scarier to mow.

Every time I’m on this hill, I feel like it’s going to roll over. The grass is wet, or the front wheels are bouncing all over the clumps and rocks. I’m riddled with anxiety—a white-knuckled mess until the job is over.

Not without good cause. Tractor rollovers are actually the leading cause of fatal injuries on farms in the USA. An old tractor like I had didn’t have the rollover bars or safety equipment, either.

If this tractor rolls, I’m hitting the ground with 2,900 pounds of mid-century steel on top of me.

Big Hill

I asked my father-in-law about it. He’s a country guy, through and through, and he’s always lived in that area. He told me, “Well, you just kind of do it, and if it feels like the tractor is starting to tip, just turn a little bit.”

To me, it always felt like the tractor was about to tip over.

It seemed to me that the only way to really know what it feels like to nearly roll a tractor would be to actually roll a tractor. Then I can subtract one from that.

The only way to really know what it feels like to nearly roll a tractor would be to actually roll a tractor.

Obviously, my personal metric for what it felt like when a tractor was about to roll was way off. Because he could mow that field no problem, without a care in the world.

I did it a little bit, but then my father-in-law “fixed” my tractor for me so good that it never ran again. So eventually I just hired somebody to mow the field for me.

Is your tractor tipping?

The reason I tell this story is that if you’re going to do big things with your life, sometimes you’re going to have to roll the tractor.

If you want to make big progress in an industry, you have to push. You have to bite off more than you can chew. You have to overcommit. Then you have to make it happen anyways.

I can’t tell you how many times someone would hire me to do something and they’d ask, “Can you do this?” And I’d say, “yes.” But what I really meant was that I was very confident I could figure it out.

One time I was working with a friend—I was doing the content for websites and he was doing the back-end programming. We took on this massive project to build a rate quoting system for a trucking company, and then he disappeared (which was not unlike him to do from time to time). So I went ahead and learned PHP, developed the front and back of the website myself by the deadline, and kept all the money. It was a miserable few months, but now I was armed with a whole new skillset that I took with me to future projects.

Most of the time, when you overcommit, you’ll buckle down, push through, and it will be a little bit miserable for a moment, but you’ll get it done. That will level you up and open new doors.

But sometimes, you’ll roll the tractor. Despite your best intentions, you’ll take on too much.

Over time, you’ll learn what it feels like to roll the tractor. You’ll get better at identifying how far you can push yourself without breaking. Pay attention to that, learn from it.

Until that time comes: break on purpose.

Break on Purpose

When you have too many projects, too much stress, too high of expectations—don’t break randomly. You choose where and how to break.

Don’t let everything fall apart. Don’t let your loudest client dictate your priorities. You take a step back and choose on purpose what’s going to get done and what’s not. Then you communicate, apologetically and honestly, to the people that are affected by your shortcoming.

It’s better to choose one project, one client, one timeline that has to break, than it is to give everybody less than they deserve. When that happens, be honest, communicate as early as you can, do what you can, in time, to make it right. But it’s better to break one than break all.

The Sacrifice Bunt

In baseball, a team will sometimes utilize the sacrifice bunt. That’s where the batter bunts, a real short, dumpy hit, and the batter’s pretty much guaranteed that he’ll be tagged out. But it allows another runner to advance on the bases. You take one out on purpose in order to maximize the inning. Usually, the player that bunts and takes the out wasn’t very likely to get a great hit anyway.

When we don’t break on purpose, sometimes we just do a shoddy job on all of our projects. But oftentimes, we break in even worse ways. We break with alcohol, addiction, and unhealthy lifestyles.

Don’t be fooled into thinking that just because your work projects are getting done that you’re not breaking. You may not notice it right away, but you may be breaking in your family, your health, or your faith.

It’s better to win 98% of your games and sacrifice 2%, but be the person that you’re going to be happy with ten years from now.

I’m not advocating for failing your commitments. I’m not advocating for taking on commitments you really know you can’t fulfill. I’ve been on the receiving end of that enough times.

But in order to stretch as far as you can, there will have to be times when you commit in good faith, but the confluence of circumstances just leaves you in over your head.

Sometimes a project takes an unexpected turn. Sometimes a client (or more than one!) drops the ball on their end and makes your life a lot harder. Sometimes you count on somebody to help and they fall short.

Especially if you’re working independently (like as a small business owner, freelancer, or consultant), you have to fill your schedule every day, because that’s how you get paid. Sometimes something will show up and overflow your calendar.

Sometimes you roll the tractor.

If you always roll the tractor, you’ll never get ahead. You’ll develop that reputation pretty fast. Try your hardest to get it done.

When the tractor rolls…

But when you feel the tractor tipping, here’s what you need to do:

  1. Take a step back so that you can look at all of your commitments objectively.
  2. Choose on purpose one commitment to break. Not the loudest client, not necessarily the smallest pay day—because you’ve done step 1 you can look wholistically and see what’s the least important item on your plate—the least likely to move you towards your goals.
  3. Communicate. As early as possible. Be honest. Without re-overcommitting yourself, suggest a new solution. Can you set a new timeline, or change the scope of the project? Can you refer them to someone else and at least be available to bring the new person up to speed?
  4. Reflect. How did you contribute to this outcome? What could you do differently in the future? What red flags could you observe in the future to see this coming even further in advance?

It’s no fun to roll the tractor. You’re going to mess up your tractor. Try really hard not to do it.

But if the tractor’s going to roll, do it on your terms, on purpose, not on anybody else’s.

You’ll be far better served by wowing most of your clients and failing one than you will be by shortchanging all of your projects.

And down the road, you’ll be really happy that you broke by failing one client that you chose on purpose rather than releasing the pressure through an unhealthy lifestyle.

How about you?

Are you super stressed? About to blow? Beginning to bend your lifestyle—even simple indicators like drinking too much coffee, staying up to late, or doomscrolling Instagram?

Start step 1 today. Take a step back, look over your commitments, and choose one thing that has to go, even if it hurts.


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