What Is “The Life of Riley?”

A Phrase that Has Become My Personal Philosophy

Michael Riley
Ascent Publication
Published in
4 min readFeb 16, 2017

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If you follow me on social media or have been reading my weekly emails, you’ve probably realized that I tend to associate myself with the phrase “The Life of Riley.”

Maybe you’re wondering what the heck it means. And maybe you’ve never even thought twice about it. Whatever camp you’re in doesn’t matter. Today’s the day I enlighten you :)

Unsurprisingly, I first heard the phrase from my dad, the one responsible for giving me the Riley name. It was something his family would use from time to time, so naturally he brought it into ours. Whenever he would use it, it was in contexts when life was treating you or the person he was talking about well. I thought it was a cool expression but never considered using it for myself or looking up its actual meaning.

In 2010, I joined Twitter as a sophomore in college and had to choose a username. Since all the handles that reflected combinations of my first and last name were taken, I ended up going with @LifeofRiley29, a blend of a phrase I was somewhat familiar with as well as my birthday number (born on June 29th). On the one hand, I thought my Twitter handle was clever since any tweets that would come from me would technically reflect what’s going on in my life at that very moment.

However, what really sealed the deal for me in choosing that username was when I finally Googled “the life of riley” to learn its meaning. Dictionary.com defines it as the following:

A CAREFREE, COMFORTABLE, AND THOROUGHLY ENJOYABLE WAY OF LIVING.

Once I read the definition, I immediately knew it was something I wanted to associate myself with. Whenever people would ask me about what the “Life of Riley” part of my username meant, I restated the above definition and delivered it with a smile.

Now that I’ve had over 6 years on the internet associating my brand with that phrase, I thought it would be a good time to further break down its key elements and what they mean to me.

1) CAREFREE

Def. without anxiety or worry.

All right. I know it’s impossible to live a life where you’re not concerned about anything. That doesn’t mean it’s something I don’t strive for every day. Sure, I worry about the same things you do: happiness, career growth, money, purpose, etc. However, these are things I think about occasionally (vs. every day) and don’t let them control my life. I have such an optimistic attitude and outlook that I know those things will fall into place for me. That translates into living the kind of life where I try not to sweat the small stuff. I just focus on the bigger picture and trust that the smaller things will take care of themselves. You can do that, too.

2) COMFORTABLE

Def. contented; at ease; more than adequate or sufficient.

Being comfortable means being able to honestly say, “Life is good.” You’re able to appreciate the present and are grateful for everything you have. A level of balance exists across your relationships, health, wealth, and mind. You’re doing exactly the kind of work you want to be doing day in and day out.

There are different levels of comfort for everyone, and no one is more right than the other. It all depends on your personal preference. I’m looking to find a happy medium between a base level of comfort and maximum comfort. On the one hand, I want to be able to say that all the facets of comfort I mentioned above are “great,” not just “good.” At the same time, I don’t want to become too obsessed with pursuing maximum comfort as there will always be a desire for more. I’m afraid I’ll get too caught up in that chase and never be able to take a step back and truly appreciate what I’ve accomplished and enjoy everything life has to offer.

3) THOROUGHLY ENJOYABLE

Def. giving or capable of giving complete / perfect / utter joy or pleasure.

This final aspect of “The Life of Riley” is all about having fun and getting the most out of everything you do. It’s about making the ordinary extraordinary. You don’t take life too seriously; you laugh often. Every experience is an opportunity to create a new memory. The way you carry yourself is infectious; people are attracted to your energy. You know how to live.

Life is too short to waste any time not enjoying it. We’re all going to have our down moments from time to time, but we can’t wallow in them. We must learn to see the positivity in everything and move on. I’m definitely enjoying my life so far but always know there’s more I can squeeze out of it. Every day is a new adventure just waiting to be enjoyed by those who intentionally seek it. Let’s have fun today, together.

Now that I’ve explained to you what “The Life of Riley” means, I hope you have a better sense of what I and all my content stands for. I’m definitely not the first Riley to associate myself with the phrase, but I strive to be the best. My hope is to inspire you to adapt this philosophy to your life and make it your own. We all need some sort of set of guiding principles to live by, and this is a great place to start.

What characteristics make up “The Life of [INSERT YOUR LAST NAME]?”

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Michael Riley
Ascent Publication

Writer of "The Life of Riley" blog (thelifeofriley.co) | Account Manager at Julius