This year I did what I always do, I set a New Year Resolution on January 1. It’s the same one I’ve been setting for the last several years because I always give up on it. This year would be different, I told myself thought I didn’t have any real plan at the time. I always tell myself that.

Just prior to January 1, 2022, on our family trip, inspired with the sense of possibility that that Chicago at Christmastime always gives me, I decided to spend more time writing my blog – A Day On. I missed the game of finding out what I thought about things.

By January 2nd I was sure that even though I had skipped the first day of my resolution, that it wasn’t too late to still get on the horse. But I didn’t. I didn’t think about it much for a week or so.

Then in a conversation with a friend, we both talked about how we should buckle down and produce more work.

I blurted out: “We should bet each other $1000 so that we actually stick with it.” He accepted.

My Blog Changed My Life the Better – That Was The Problem

My blog followed a principle I later heard preached by Tim Ferriss. It was to “scratch my own itch.” I had been swirling around in a holding pattern that I couldn’t break out of when it came to work. I kept finding job after job that left me disappointed and anxious. Would my lifetime be a series of dreading going to various jobs – each depleting me more and more?

A Day On was meant only to be a collection of my thoughts about what I wanted for my life. A kind of vision board. And, it worked. And maybe that’s why I had become complacent about contributing to it.

The blog had “worked” for a test group of one, then I kinda let it slip.

You’re Not Hungry to Achieve Goals When You’re Satisfied

Motivation can be hard to capture and hang onto because I’m satisfied. Most of my needs are met. This is the most bountiful time in which to live.

Every morning it seems more reasonable to stay under the covers than to head out into the cold, difficult world of putting in effort.

How to stay in the game if you have some comfort in your life?


Using Friends to Achieve Personal Goals

On his podcast, Tim Ferriss often preaches an idea to motivate yourself using a bet with a friend.

You can bet an amount of money that you REALLY don’t want to lose. I threw out the number $1000 to my friend, Mitchell, because it’s substantial. It seemed to command some respect from me. And as I write this right now I know that I partially do so because I will be fined if I don’t.

But just doing it isn’t enough. I don’t want to game the system. I want to run my best race. I’m not competing with Mitchell, I’m training myself. He’s my spotter. I don’t want him to be able to be reasoned with when I consider changing the terms a bit. It’s too late, I threw down the gauntlet and now I have to perform… for myself.

People Hate Losing Something More Than They Like Gaining Something

According to Tim Ferriss who cites studies, it’s generally more of a motivation to people to not lose something than it is to potentially gain something.

I’m not that motivated to win – more to just play, but if my friends said they would stop playing with me if I didn’t start winning, I would be motivated to kick effort into a higher gear.

Generally in some kind of transformative goal, the predicted outcome promises to be a pretty big payoff – weight loss, new physique, better job, new skill. But we drop out because we’re not as driven by gaining something (even if it’s the world).

We must trick ourselves into achieving by promising ourselves that we will lose something if we give up. Makes sense.

Climbing Out Of My Own Primordial Soup

Achieving a goal of transformation requires more than the imagination to project ourselves into a better reality. It requires the everyday diligence that runs counter to present reality. We’re stuck in the mud because pulling our feet out of the mud is difficult and not pulling is comfortable.

The only thing more difficult than doing a difficult thing is not getting past it – waking up another day in the mud. We tell ourselves we’re swimming when in fact we know we’re treading water. Get on with it. Place a $1000 alligator behind you.

The mud-free life is cleaner and lighter.  But until you’ve pulled every last part of you out of the sucking soup and into the sun, it’s VERY easy to remain in the mud. The mud-free life leaves you open to choose your direction… and that’s scary as hell.

What goal do you give up on? Tightening up that belly, finding love, starting your own business, getting an education, being honest with a loved one, etc?  

How Much Money Are Your Big Goals Worth?

What amount of money would make you go through the effort every day to pull yourself out of the mud with intention? As if being covered in mud weren’t bad enough, what amount of money being pulled from your grasp would make you put in the extra effort every day toward achieving your set goals?

$1000 seemed worthwhile for me to get my butt out of bed a little early and get to work on the stuff I already love to do, but just need a firm, non-negotiable directive to actually do it.

$500 probably would have been worth it for me to live up to this commitment, but $1000 seems like it leaves no wiggle room at all. I can’t imagine, what would allow me to give up $1000. I likely haven’t even encountered it yet.

So, now, having made this bet,  simply declaring that I would pay someone $1000 if I failed to keep my word, I have discovered accountability. Having recorded the video on this page, and having written this explanation to you… once again, I click the button that says, Publish.