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Habits: 4 Ways to Build and Upgrade Them Effectively

Chad Grills
Feb 14, 2017 · 10 min read
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Photo, Unsplash

Intuitively, you know that your habits are the only things standing between you and everything you want in life.

“All our life, so far as it has definite form, is but a mass of habits — practical, emotional, and intellectual — systematically organized for our weal or woe, and bearing us irresistibly toward our destiny, whatever the latter may be.” –William James

But in practice, doing the work necessary to upgrade your habits isn’t easy. In fact, it might be one of the most difficult battles you’ll ever fight. The stakes couldn’t be higher: you know a better quality of life is available to you and those you care about if you upgrade your habits. If you don’t upgrade your habits, eventually you’ll have to face enormous regrets.

The Power of Habit is one of the most important primers and science backed starting points for upgrading your habits. The book contains vital reminders:

“Once you know a habit exists, you have the responsibility to change it . . . others have done so . . . That, in some ways, is the point of this book. Perhaps a sleep-walking murderer can plausibly argue that he wasn’t aware of his habit, and so he doesn’t bear responsibility for his crime, but almost all of the other patterns that exist in most people’s lives — how we eat and sleep and talk to our kids, how we unthinkingly spend our time, attention and money — those are habits that we know exist. And once you understand that habits can change, you have the freedom and the responsibility to remake them. Once you understand that habits can be rebuilt, the power of habit becomes easier to grasp and the only option left is to get to work.” ― Charles Duhigg, The Power of Habit: Why We Do What We Do in Life and Business

Duhigg boils it down brilliantly:

“The Golden Rule of Habit Change: You can’t extinguish a bad habit, you can only change it.”

I’ve found four things are game changers to help effectively build and upgrade habits. They are: Systems, Mindset, Identification, and Implementation. We’ll run through each of them here, plus a few brief tips and ideas to help apply and immediately implement them.

1. Systems: Set up the exact systems you need for incentives and accountability… then ensure you can’t escape.

This year I didn’t just set new year’s resolutions. I set up systems with accountability and incentives to ensure I know exactly what I need to daily, weekly, monthly, and even quarterly. I got started by simply keeping a better record of what I did throughout the day. After each month, my wife and I go over our records. Because we write them down, it makes it easy to go over them at the end of each month and quarter. We then talk about how those tasks are helping us reach larger quarterly goals. Either we’re on track, or we’re not. With this system, I know I have to record what I’m doing because I’m going to be discussing it with someone else who is doing the same thing… When you know that your Monday through Friday tasks aren’t going to be forgotten, you start making different choices. When you know that someone is going to hold you accountable… you become much more likely to upgrade your habits to ones that better serve you.

If you want to setup this system for accountability today, stop planning. Pick up your phone right now and text a friend, spouse, or even acquaintance with the challenge, “I want to (workout more). Let’s track our workouts M-F, and keep each other accountable.” It’s that easy to get started, but most people won’t. It’s that easy to talk about, but actually following through and being serious about it is where the rubber meets the road. Ideally, you want to setup a system of accountability where both parties can’t escape, and where you win a few victories together. You’ve got to work hard to make this system of accountability fun so it’s easy to follow through.

I can guarantee that every person reading this knows at least a few people who would love to help them be more accountable.

2. Mindset: Upgrade your mindset and linguistic skills so you can align incentives, and negotiate scenarios that help create more value for everyone involved.

“The limits of my language mean the limits of my world.” –Ludwig Wittgenstein

Once you have systems set up for accountability, the next battle is to develop a mindset necessary to foster habit building and upgrades.

The best way to do this?


Why? If you can’t say what you intend to do, change, or become, you’ll have a hard time turning it into a reality. You must wage a constant battle to upgrade your language so you can better articulate your vision, actions, and plans.

Like clockwork, when I read and spend time in the presence of someone who is wise… I leave their words feeling refreshed and brimming with a mindset that is conducive to creating good works. The practice of reading gives us new language and new words which expand our definitions of what is possible. When you can better articulate what you want, you exponentially increase the likelihood that you’ll be able to create it.

Take the idea of upgrading your habits. I found that it wasn’t until I read The Power of Habit, that I became armed with the language and concepts to make upgrading my habits easier.

Reading TPOH led me to Spark: The Revolutionary New Science of Exercise and the Brain.

After I read Spark, I realized that my brain would work better if I did more cardio to cause my body and brain to release more Brain Derived Neurotrophic Factor. So I upgraded my workout to include more cardio. After this upgrade, my mind and physiology were feeling great, which led me to read Travels.

There, I became obsessed with direct experience, which put me in a very receptive state when I came across the next book I read.

That book was written by Mike McDerment called Breaking the Time Barrier.

Full Disclosure: FreshBooks is The Mission’s sponsor for the month of February!

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If you’d like a free copy of Breaking the Time Barrier, just subscribe to the FreshBooks newsletter!

Yes, I’m a user and fan of their accounting software, but it wasn’t until a week ago that I discovered the co-founder of FreshBooks, Mike McDerment, wrote Breaking the Time Barrier.

Mike is someone who has the direct experience of growing a business to 1.6M subscribers. When I discovered that someone who posses direct experience that I admire writes a book… I read it!

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“People constantly ask me ‘How can I get a 4-hour workweek with a service business?’ This story is the short answer.” — Tim Ferriss

You can get a free copy of Breaking The Time Barrier when you subscribe to the FreshBooks blog (which contains awesome resources for any freelancer or small business owner).

One of the most valuable insights from the book is already helping me build better habits:

“Selling hours actually creates a conflict of interest.” –Mike McDerment

I’m currently interviewing our first hires, and talking to several potential clients and sponsors.

Now, I’m primed to avoid the bad habit — selling hours of time. Instead, I’m laser focused on creating value and making sure that the focus is on aligning incentives and long term interests.

After you have the systems in place, upgrading your mindset through reading is a powerful catalyst to help identify the exact habits you need to upgrade.

3. Identify: How to accurately identify your three biggest limiting habits.

One thing that stops people from upgrading their habits is a mistaken belief that they can only change one thing at a time. I’ve stopped listening to the “science” behind why you should only change one thing at a time and started observing what works best for me.

I’ve found it’s much easier to upgrade 2–4 habits at a time than it is to focus on 1 thing at a time.

“Habits come in pairs, triplets, and quadruplets. Any habit which weakens one’s will power invites a flock of its relatives to move in and take possession of the mind.” — Napoleon Hill

The challenge is to identify the ~3 habits that are weakening your willpower. The best way to identify your 3 most limiting habits is by keeping a record.

“However, I demonstrated a great value to keeping a diary, and have kept one even since. I reread Franklin’s Autobiography, and noted that he kept a record of himself, as I did, for exactly the same reasons. This most practical and observant of men had decided that careful record-keeping was the only way to find out what he was really doing.” –Michael Crichton, Travels

What might keeping a record of what you do help you discover?

“After a few weeks, I looked back over my notes with astonishment. Every day, I was so critical! One nasty comment after another, about something or somebody. I didn’t regard myself as particularly critical, but evidently I was. I began to observe my state more carefully during each day. It did indeed seem that I was frequently judgmental and snappish, even when I didn’t mean to be. So I decided to watch for that behavior and modify it. It was surprisingly difficult to do.” –Michael Crichton, Travels

If you record what you do long enough, and reflect on it objectively enough, you’ll be forced to view the habits you need to upgrade. Once you have a good guess about what your 3 most limiting habits are, ask the person who knows you best for their perspective. For me, I ask my wife, who is quick to identify my sub-optimal habits :)

I weigh her feedback, and am usually left with the exact habits I need to upgrade. For instance, my 3 most limiting habits I’m currently upgrading: I’ve become too negative, I’ve been skipping my workouts, my diet is unhealthy and I’m eating too much sugar. So to simplify, I need to upgrade my habits involving: my mindset, fitness, and diet.

Now that I’ve identified the 3 habits I need to upgrade… here comes the most difficult part… implementation.

4. Implementation: An example of the actual process of upgrading bad habits.

“But to change an old habit, you must address an old craving. You have to keep the same cues and rewards as before, and feed the craving by inserting a new routine.” Charles Duhigg, The Power of Habit

My morning routine had become something like this: I’d wake up, take the dog out, come back, start drinking coffee, start working, and work through the time where I would normally workout.

Time to upgrade.

Now, before I go to sleep at night, I put three things on the counter. A lemon, the juicer, and the latest book I’m reading. Then, I head to bed in my workout clothes.

I wake up and walk directly to the lemon. I juice it, make lemon water, and drink it. I’ve found that this single upgrade of healthy hydration makes it easier to do everything else throughout the day. This single change to my diet makes upgrading my habits around fitness and mindset easier.

About this time, our puppy Toasty is stumbling around and ready to go outside to the bathroom. I’ve slept in my workout clothes, so I put on my running shoes and take Toasty out. The second we’re outside, I’m moving. When he’s done his business, we start jogging. It’s not a big workout, it’s not even 2 miles, but that early morning movement sets the stage for a much more active day. I’ve found that even if I jog just a single mile, I have much more energy throughout the day. Usually I’ll have headphones in and am listening to a book, podcast, or a message conducive to building and maintaining the mindset I need to win the day.

Back at home, I feed Toasty, and either keep listening to the audiobook, or pick up the book I’ve left out on the counter.

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Meet Toasty… he has trouble staying still for pictures!

By simply introducing these three small habit upgrades in the mornings, I’ve found it makes everything else easier throughout the day. My diet is improved. My blood has already been flowing. My mindset is nurtured with positive ideas. I find myself less reliant on caffeine, less interested in sugar, social media, etc…

The systems, mindset, identification, and implementation you need to upgrade your habits are available to you right now.

It’s simple to read about, but it takes courage to make the first step of setting up the systems you need. If you do that, you’ll find that building and maintaining a healthy mindset becomes easier. Once your mindset is right, you’ll be more receptive to admitting, recording, and identifying the exact habits you need to upgrade. As you begin implementing your habit upgrades, you’ll find that everything becomes easier.

Whether we want them to or not… habits rule everyone around us. Cheers to upgrading them!

Looking for some amazing book recommendations? Check out my latest book obsessions:

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Chad Grills

Written by

CEO, , a network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

Chad Grills

Written by

CEO, , a network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

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