27 Years On Earth: 27 Lessons, Triumphs & Regrets [27 Lesson Quotes + Free Journal]

Updated October 2020 | by Livv Mills | This post may contain affiliate links

For those of you who have read my self-discovery story, you know that life has taken me through some ups and downs. But through it all, I made it through the fire, and I am happy to say that I found some lessons amidst the flames.


In a few months, I am approaching my 28th birthday and I made a vow with myself that my 28th birthday wouldn't be like all the others... a repeat of the previously confused and slightly crappy year.


So, I thought for that to happen, I need to form a list of lessons I learned for every year I've lived on earth.


So here it goes!


Be sure to download the free Lessons Learned Journal from the Freebie Library so you can start documenting the things you've learned throughout your life!


Lesson # 1: Find out who you are as early as possible

"You've got to find yourself first. Everything else'll follow." - Charles de Lint

I am a firm believer that to know what you want and where you're going, you must first recognize who you are and where you've been. Take the time to get to know yourself inside and out so you can go out into the world and enjoy life with no regrets.


Lesson #2: Don't let go of your childhood passions

"Passion is energy. Feel the power that comes from focusing on what excites you." - Oprah Winfrey

We all get sucked into the (ever-so-popular phrase) "rat-race of life," and most of us are either too stressed, too busy, or too "grown" to revisit the passions we held in our adolescent years. Take some time to write a list of all the things you used to do in your youth, big or small…just write.


Lesson #3: Adulting is hard AF but don't hold it off for too long

"That horrifying moment when you're looking for an adult, and you realize that you are an adult. So you start looking for an adultier adult." - Unknown

How often do you feel like a total teenager in your mid to late twenties? Raise your hand….*both hands go up* Do yourself a favor and stop trying to figure out how long you can hold off the inevitable. Start preparing as soon as you possibly can. I suggest the following:

  • Start building a nest egg, NOW!

  • Don't buy that brand new car…used is the way to go.

  • And keep your credit all the way together…trust me on this one :)




Lesson #4: Speak your mind all the time (be polite, but remain truthful)

"Don't be afraid to be unique or speak your mind, because that's what makes you different from everyone else." - Dave Thomas

What will people think? What will the people say? What will THEY feel? I've spent too much of my life holding in thoughts and feelings that would have better served me outside of my brain. A word of advice, for the sake of your own mental sanity and wellbeing - screw what those PEOPLE have to say, think, or feel….but just make sure you're not too harsh 😁


Lesson #5: Get rid of the people in your life that no longer serve you

"We strive our whole lives to love people unconditionally, but sometimes we need to get rid of people unconditionally." - Bryant McGill

We hardly think about hoarding people in the same way that we think about hoarding "things." Some things we hold onto because they have sentimental value or provide nostalgic memories or give us comfort. But once those things become a nuisance and they no longer serve us, we do away with them because they have now become uncomfortable to live with. Maybe there are people in our lives who need to be done away with as well…





Lesson #6: Don't be afraid to move on to the next phase in your life, even if it's frightening

"The hardest thing to do is leaving your comfort zone. But you have to let go of the life you're familiar with to take the risk to live the life you dream about." - T. Argio

Take risks and make mistakes, but don't leave anything on the table. I've spent a lot of time waiting for the "right moments" or for things to be "perfect," which, in retrospect, I realize was fear of the unknown keeping me from experiencing life.


Lesson #7: Learn to accept responsibility early on

"We are made wise not by the recollection of our past, but by the responsibility for our future." - George Bernard Shaw

Life and all of its unexpected wonders and burdens are going to come at you no matter what; maybe not all at once, but they'll knock on your door eventually. Let them in, with caution, of course, and just see what they want.


Lesson #8: Don't settle for other peoples definitions of success and happiness

"Define success on your own terms, achieve it by your own rules, and build a life you're proud to live." - Anne Sweeney

Don't let society's definition of success make you feel inadequate, lazy, or undeserving. Much like how time is a human construct, success is a social one. If you continue to chase the fictional standard of success, you will be continuously met with disappointment. Set your own standard, be happy, be successful…in your own way, of course. 😁😁


Lesson #9: Stretching is good for you...ouch

"You know you're getting old when everything hurts. And what doesn't hurt doesn't work." - Hy Gardner

I know I'm not that old, but I can now start to feel all of the 27 years I've been living. Like that time I fell while rollerblading a few years ago…yeah… it's catching up with me.





Lesson #10: Find the life-work balance…(yes, I meant life-work)

"Never get so busy making a living that you forget to make a life." - Dolly Parton

Life is going to pass you by no matter what you do with your time. Make sure you make time for your family, your friends, and your health. You don't want to get to the end of your life, wishing you spent less time at the office.


Lesson #11: Both SELFISH-ness and SELFLESS-ness have a place in your world

"Self-Care is not selfish. You cannot serve from an empty vessel. "- Eleanor Brownn

If you give all of yourself out to the world, what do you have leftover for you when it's all said and done? While giving to people feeds one part of the soul, giving to yourself feeds another.


Lesson #12: You don't know it all…sometimes it takes a lifetime

"The greatest enemy of knowledge is not ignorance, it is the illusion of knowledge." - Stephen Hawking

Have you ever heard the phrase "the more you know, you realize the less you do?" Now that isn't a direct quote, but the intention is there. 😁 In 27 years of life, I feel like I have experienced and learned quite a bit. But the more I venture out, the more I realize that I have so much more to learn. And it's okay not to have all the answers; ignorance can be quite blissful.




Lesson #13: Ask all the questions

"The only way to learn new things is to ask questions and be curious. Find the people who inspire your curiosity because those are the ones you will learn from the most." - James Altucher

Remain curious throughout your life, and you'll never get bored. There are so many wonders to explore, experience, and learn…take advantage of every moment.


Lesson #14: Don't waste your youth

"Youth is not a time of life, it is a state of mind. You are as old as your doubt, your fear, your despair. The way to keep young is to keep your faith young. Keep your self-confidence young. Keep your hope young." - Luella F. Phean

You are as young as you feel!


Lesson #15: Pay your bills on time...for real...ON-TIME

"Money is a terrible master but an excellent servant." - P.T. Barnum

I think the quote says it all.





Lesson #16: Be kind to yourself always

"It's easy to blame your old self for the choices you've made, but it's important to be kind and empathetic to all parts of you, especially the parts of you, you least liked." - Unknown

When I started this journey of self-discovery, I definitely had the wrong intentions. I thought that I needed to breakdown and destroy the parts of myself that I hated. I have now realized that all the mistakes and decisions I made were for a reason.

You must be kind to past versions of yourself; you didn't know what you know now.


Lesson #17: Realize that you create the stress in your life

"When I look back on all these worries, I remember the story of the old man who said on his deathbed that he had had a lot of trouble in his life, most of which had never happened." - Winston Churchill

Whenever I am faced with a huge, whopping pile of trouble, worry, doubt, fear, and stress… it's really helpful for me to remember that "10% of life is what happens to you…the other 90% is how you respond."


Lesson #18: Listen to your gut and trust yourself

"Never apologize for trusting your intuition - your brain can play tricks, your heart can blind, but your gut is always right." - Rachel Wolchin

I can't tell you how many times my gut has saved my butt (PUN INTENDED). Over the years, I've learned that if there is one thing I can almost always count on, it's my intuition.



Lesson #19: Don't be afraid to fail

"Try a thing you haven't done three times. Once, to get over the fear of doing it. Twice, to learn how to do it. And a third time to figure out whether you like it or not." - Virgil Thomson

This is one of my favorite quotes because it presents an interesting and practical way to look at failure. We always think of failure as this force that means "you ain't shit." But, what if we tried all the things we wanted to try and said, "so what if I fail? I'm proud of stepping out of my realm of fear and trying something new." Stop putting so much pressure on yourself and do every damn thing you want to.


Lesson #20: Stop apologizing and start saying thank you!

"Would 'sorry' have made any difference? Does it ever? It's just a word…" - Sarah Ockler

'Sorry' has become one of the most overused words in so many of our vocabularies…I am not excluded from this. I say sorry for the most ridiculous things like:

  • "I forgot to ask for a tortilla on the side; sorry for the inconvenience."

  • *I swipe my card when I'm supposed to insert, and the cashier tells me how to do it correctly* What do I say? "Ohh, sorry!"

- Definition time -


Sorry /'särē,' sôrē/. Adjective

  • feeling distress, especially through sympathy with someone else's misfortune; feeling regret or penitence

What could these situations possibly make me feel distressed or regretful about? Absolutely nothing! I would confuse situations like this, and they would result in me placing unnecessary blame on myself.


But, I realized that these situations don't require an apology. Better yet, the real response should be, "thank you!" "Thank you for taking the time to grab that tortilla for me." "Thank you for helping me use this credit card machine properly." The real lesson here is: there are a shit ton of things for us to be blamed for daily, let's try not to add on anymore.






Lesson #21: Saying sorry when it really matters

"Not admitting a mistake is a bigger mistake." - Robert Half

Unlike the previous lesson, this is definitely the time to apologize. Sometimes we want to be "right" so badly that we could end up causing other people harm in the process. Realize the error in your ways, accept your responsibility for the part you played, and apologize.

Lesson #22: Learn to love yourself, even when you're alone

"You're always with yourself, so you might as well enjoy the company." - Diane Von Furstenberg

Most of us are guilty of treating ourselves worse than our annoying next-door neighbor. We put ourselves down, we second guess ourselves, and we critique ourselves to no end. It's a no-brainier why 40% of people are anxious and depressed. Well, to that, I say no more…recognize your power, your beauty, and your talent. You are the shit!

Lesson #23: Feed your mind with positivity

"The more you feed your mind with positive thoughts, the more you can attract great things into your life." - Roy T. Bennett

With so much negativity in our lives, we need the positive stuff to help us get through the dread, the stress, the heartbreak, and the disappointment. If we don't nourish our minds with the good stuff, it only makes it that much easier for the bad to creep in and ruin your self-confidence, make your doubt yourself, and hold you back.


Lesson #24: You've never lived this life before…give yourself a break

"Sometimes you climb out of bed in the morning and think, I'm not going to make it, but you laugh inside - remembering all the times you've felt that way." - Unknown

There is much of life to be enjoyed and there is much that causes us despair. We don't have all the answers, we haven't all been through the same experiences, and we will definitely make a lot of mistakes. The thing to remember is that…there isn't a blueprint for life. You are doing the best that you can and so is everyone else.


Lesson #25: Look on the bright side…this too shall pass

"If you have a positive attitude and constantly strive to give your best effort, eventually you will overcome your immediate problems and find you are ready for greater challenges." - Pat Riley

Whenever we face trouble in our lives, we always feel like it will last an eternity. But I'm sure you could look back on some negative things that have happened in your life and say, "I got through it." And always remember that this too shall pass.

Lesson #26: Remain grateful and thankful always

"Learn to be thankful for what you already have while you pursue all that you want." - Jim Rohn

How often do we forget to have an appreciation for the little wonders in our lives, the breath in our lungs, the earth maintaining perfect distance from the sun, and of course, the existence of the internet? There are so many things to be grateful for. Over the years, I've learned that expressing gratitude as often as possible is one of the keys to gaining mental clarity.

Lesson #27: Do what you want and what you can now because 27 really sneaks up on you

"If you don't go after what you want, you'll never have it. If you don't ask, the answer is always no. If you don't step forward, you're always in the same place." - Nora Roberts

This is probably one of the most recent lessons I learned. I try not to live a life of regret, although some regrets have slipped through the cracks.


At this point, I can only think of my regrets and mistakes as learning notches on the belt of life.


I realized that I was stuck in the same place for more than 6 years and it took my 27th birthday for me to finally see that I didn't say or do the things that I wanted to and should have.


I am now mentally compelled to go back and mend fences, right some wrongs, and explore the world that I missed out on.

Well, there you have it, folks! 27 Years on Earth and 27 Lessons. When I review these lessons and think about the experiences that resulted in each one…I must laugh because I can now see how far I've come.


I will definitely continue to do this every year. Maybe I'll add a new lesson each year and keep it as a tome to pass down to my children.


Now, I am not going to ask you to comment your *insert age number here* lessons, but maybe you'd like to comment one of the biggest life lessons you learned this past year.


Maybe one of my lessons has inspired you to write your own list.


I'll make it easy for you…


Download the Lessons Learned Journal in the Freebie Library and start documenting the lessons you've learned throughout your life and on your journey to self!

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