I sat with her as the tears flowed.

“Thank you, Sarah. Thank you,” she said.—Sniffle, sniffle.
“I appreciate you for all the good things you do for me.” –Heave, heave.
“I love you and I’m so grateful for you.” (Insert howling cry.)

Sarah, mother of three, lifelong coach and encourager of others, was appreciating herself for the very first time in her life. And it was excruciating.

It might seem insane that something as simple as self encouragement could provoke such an intense reaction. But when you go through life subconsciously telling yourself that you’re no good or that you’re never enough, as so many of us do, expressing gratitude to yourself is the most uncomfortable, unnatural-feeling thing in the world.—Sarah later told me that she was mentally cussing me out when I was teaching her how to encourage herself.

As uncomfortable as it may be to learn, though, this skill of self-encouragement is absolutely the most critical part of any change you want to make—whether in your personal life or career. Without it, you lack the self-esteem and confidence to consistently put in enough work to make good things happen for yourself.

We only go above and beyond for our true friends

Imagine one of your third or fourth level friends who are just bordering on acquaintance. Their birthday comes around. Are you going out of your way to make their day and get them something nice?


A month later this friend who has never supported you in any way wants you to help them move all the way across town, which involves at least eight hours of manual labor. Riiiight.

Now replace this person who’s barely a friend with your best friend in the world. Do your answers change?

Of course they do.

You’ll break your back for people who make you feel good, for people who are valuable to you, and for people who support you. That’s just how we are—we don’t like wasting our time on people we don’t love and who don’t love us.

And unfortunately, this rule also applies to our own selves.

If we don’t love ourselves and prove that we’re our own most tireless supporters, that we’re our own best friends, we simply will not put in the work required to fulfill our desires. Because when you shit on yourself by default, and when you never take the time to praise the good things you do, you will have absolutely no motivation to continue doing things that are good for you. You’ll always abandon yourself.

So before you learn any advanced self-improvement techniques, and before you embark on any major change, you must learn and master the most basic habit of self-encouragement first.

How to start being your own best friend

It’s pretty dang simple: When you do good things, you acknowledge and praise your efforts—just like you would anybody else who does something good for you.

“Thank you so much for making that good decision today!” — “Ah, you kicked so much ass on that last project—thank you so much for putting in the effort for me!” — “Thank you so much for taking care of my body…it feels so good to be fit and I love it! Thank you!”

The only problem is that self-encouragement is typically thought of as an intangible goal.

“Okay…yeah, I’ll uh…just be encouraging myself today. Greeeeat,” you might think. But when you set several miniature goals for self-encouragement every day on a daily planning page, the intangible suddenly becomes concrete. Every time you flip open your daily planner and see ten checkboxes staring at you, you’ll know it’s time to encourage yourself for something. This is easy to do when you’re also planning out every other goal in your day—that way when you check off a goal, you automatically check off a box for self-encouragement and appreciate your efforts.

“Good f%@#$n job, mate!”

It might seem silly at first, talking to yourself in your head or out loud. But when you make self-encouragement a habit, you realize how much you actually depend on it. Each of those little acknowledgments of your effort is a confidence booster; and when you’re pumping yourself up all day and acting like your own best friend, you suddenly unlock a new level of energy and will that you never knew you had.

This transition is like going to work for an uplifting and inspiring boss who rewards you for good things after you slaved away for a boss who whipped you every time you did something wrong.—At the new job you’ll work harder, you’ll work better, and you’ll enjoy your work a thousand times more. You need that constant encouragement to persist long enough to see the incredible results that have always evaded you in your health, your career, your finances and your fitness.

Making self-encouragement a full time, automatic habit.

Since the woman mentioned at the beginning of this article Sarah was my coaching client, I was able to give her a brief call or text three times per day for that first critical week and hold her accountable through daily email checkins. But even if I wasn’t helping her in person, Sarah had her daily planner habit, which included 10 self encouragement checkboxes, she had her brag sheet, she had her nightly journaling habit, and she had the practice of logging three good decisions in her ‘Good Decisions’ note tab.

These awesome habits will help you master self encouragement this month:

1-Daily planner.

All you need is a 6×8 blank-paged sketchbook, preferably hardback. Write out your top 3-5 goals—learning, exercise, work) on the left hand side, with checkboxes next to each.

Then in the middle of the page, write ‘Encourage Yourself’—with 10 checkboxes split into two rows. It’ll look like this:

Challenge yourself to enthusiastically* check off each one of those boxes for thirty days straight. Your life will never be the same.

If you run out of things to praise yourself for, then you can simply fall back on a set of affirmations or a mantra, or you can read your bragsheet—step 2.

*Enthusiastically, as in—“Way to freakin go!!!! I’m so frickin’ proud of you—thank you so much!!!! You sexy beast!!! (It’s okay to get a little crazy with it!)

2-Create a brag sheet, then read it to yourself each morning.

You’ve done loads and loads of praiseworthy things in this life that have sadly gone unapplauded by you. Now is the time to reflect on and recall those instances, to write them down on a ‘brag sheet’, and to pump yourself up about them every morning this month. (This practice was popularized by Dr. Ivan Joseph, TEDx presenter.)

The planned self-encouragement will train your mind to automatically look for things to praise yourself for all throughout the day, 1) by training your mind’s eye to actually look for things to encourage yourself for, and 2) by associating self encouragement with the confidence, inspired feelings that come pouring in when you read your brag sheet.

Do it every day for a month.

3-Journal about your good decisions every night

Most people do dozens of praiseworthy things each day that get shoved under the rug when you go to sleep. This is a tragedy, because each of those good decisions is an opportunity to recognize yourself, to appreciate yourself, and to be your own best friend. That’s why you’ve gotta journal for at least 5-10 minutes nightly.

All you have to do is reflect on your good decisions and encourage yourself just like you would do when you encourage yourself in the day. Here’s an example of my own journal:

I made a really good decision by refusing to check email and texts this morning (even when I had a really good excuse, and even though I was super tired and had almost no will power). Instead of distracting myself, I sat down at my writing desk, pulled up an idea I’d written down from last night, and went HAM for 90 minutes to write an incredible article!!! I’m so proud of you Danny!!! Good frickin’ job!”

Since life isn’t just sunshine and rainbows, you’ll also want to reflect on where you could’ve done better or what held you back. But instead of dwelling on that and feeling low, you’ll just write down what you’ll do better and encourage yourself to hit that goal tomorrow. Here’s another example of my own journal:

So I kicked ass pretty much all day. But there was about an hour after lunch where I just zoned out and compulsively checked email and texts and surfed the internet, which didn’t make me feel good. But I did that because I was tired and needed to rest. So tomorrow I’m going to limit myself to two email checks at 2:00 and 7:00pm, and I’m going to read and relax for an hour after lunch. Thanks Danny!!!”

Whatever you do, just give this habit a solid month.


You need to encourage yourself all day every day. You need to encourage yourself alldayeveryday. You need to encourage yourself all–day–every–day!!! If you’re convinced, don’t delay this habit another day. Get accountability through my transformational coaching program. 

And if you don’t know exactly how to do the self-encouragement thing…watch this video!!!

Originally published at millennialsuccess.io


  • Daniel Dowling

    Performance Coach, Writer for Greatist, Fitbit.com, Mindbodygreen, and FastCompany.

    Dan Dowling, here. I was the poster child for lost millennials - couldn’t keep a job…addicted to relationships…constantly checking social media and email. But when I got hungry enough for success as a writer, I gave up my distracted lifestyle and adopted one daily goal that changed my life forever: Do. Your. Best. Today, five years later, I’m a productivity coach who’s published on the world’s biggest sites (including Entrepreneur, Fast Company and Mindbodygreen), and I’m transforming lives through the best-effort, zero-distraction lifestyle that worked so well for me. Come and and learn how to always give your best at Millennial Success!