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17 important life lessons I learned at 27

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In my 27th year, I quit my stable job, entered self-employment, started a business, went on 17 trips, read countless self-development books and studied the advice of my mentors front to back and back again. I learned some stuff. I saw some shit. I wouldn’t have progressed to this extent without that knowledge, so I wanted to share the 17 most important life lessons I learned this year because they have truly changed my life. Hopefully, some of these can change yours too. Let’s dive in.

1) Never Stop Learning

And I don’t mean that long division, cells of a leaf, square root of infinity bullshit that we learned in school for no reason. As an entrepreneur, education is the key to success. This was a common theme throughout a lot of the self-development and business books I read this past year.

As soon as you stop learning, you’re behind the competition. Set aside time every week for education. Read blog posts, read a book, throw on a podcast, or set up a Facetime call with someone for the soul purpose of sharing knowledge with one another. We’d like to think we have all the answers, but we don’t. Continue to grow through learning.

2) Human Connection & Relationships > Everything

This is something we all think we’ve known for years. Yet we fail to put this into practice on a daily basis. Do you value and honour the people in your life over your work or material things? Are you making decisions in your life that counter this? AKA working more, taking on more clients, spending more time on your phone than interacting with people?

This is one of the most important life lessons to learn, especially for entrepreneurs or those working from home. I was totally guilty of this. I’d be working all night and as I crawled into bed I’d realize I hadn’t carried a real, distraction free conversation with my boyfriend. I now put my phone away when I’m around family and friends, and think of them when I meditate to bring myself back to what matters before I start my day.

3) Speaking of Meditation…

Meditation is a hot ass topic right now. Everyone is crossing their legs, closing their eyes and namastayin’ it up these days. I didn’t realize that starting a business would hijack my thoughts to the extent that it did. 90% of my day is spent thinking about posts, algorithms, marketing strategy, or whether or not I used the proper form of “their” in that piece of copy. It’s both the angel and the devil on my shoulders, either whispering sweet nothings or screaming paralyzing self-doubt.

I added mediation to my morning routine and it has helped immensely. I started small, and it’s important to know that it doesn’t have to be this daunting spiritual journey. It can be super simple.

Try this: I like to think of 3 things I’m grateful for, 3 things I want my future to look like, and spend a few minutes in stillness trying my best to connect with the universe.

4) Action is the antagonist to overthinking

Hi, I’m Kaylee and I’m an over-thinker. I didn’t know this about myself until this year when I turned my life upside down and quit my job. It sometimes takes a total uprooting of your life for you to see your true self in all its unflattering shades. Simply just taking action and chipping away at a to-do list really helps avoid those thoughts in your head that you don’t need.

Netflix and red wine also help but wouldn’t recommend those if you want to actually progress in your business (that’s for Saturday nights with your girls.)

5) Sometimes the path you were positive was clear is really a shitstorm of obstacle courses set in the amazon

What a lesson this was. I started out the year thinking a travel blog was exactly what I wanted this website to focus on. Then I started writing travel content and realized that at the core of my being, I’m a creative writer. While I love to travel, the where to eat and what to do posts were too restrictive for me. As I get older, I am also finding myself craving time at home, and travel isn’t as big of a priority as it once was.

Realizing this was a real karate kick to the face.

At first I didn’t want to admit it because admitting it would mean telling myself I was wrong, and a downward spiral of self-doubt and “WTF am I doing with my life’s” might swarm in like a bag of bees (bag of bees? Not sure where I was going with that but I kind of like the visual). And oh, spiralled I did. But it was such an important and valuable lesson. I never would have known what I didn’t want unless I actually took the time to see it through.

As we talk about important life lessons, I think one of the biggest is to stop treating things that don’t work out as failures.  The outcomes may not be designed by us, but they lead to bigger and better things we couldn’t have possibly dreamed up for ourselves. They lead us to a place that is in alignment with our true purpose, one we rarely know at the beginning of a journey.

So, instead of wallowing in spinach dip and sourdough bread (okay, I may have done that first), we must simply continue and learn to trust. Everyone has their own obstacle course in the amazon. It won’t be a straight shot out of the rainforest, but the more anacondas you fight, the more vines you swing across, the more sexual tension you have with Tarzan, the sooner that path will start looking more like a calm river and less like a crocodile infested swamp.

6) Don’t let your ego get in the way of your goals, vision and impact

Our ego’s are a real pain in the ass, aren’t they? Ego’s are behind 99% of the fights we have, decisions we make and conversations we have. One of the most important life lessons I’ve learned this year is the need to lock my ego in a tiny dark box in order to get really clear about why I’m reacting a certain way to something.

Is it because someone has said something that I’m insecure about so I immediately go up on the defence? Am I writing a certain blog post because I think I should? Am I not starting that project because I’m afraid of what people might think? Setting your ego aside is uncomfortable as hell but pivotal for both your success, your happiness and your relationships.

7) You can’t control other people but you can control how you react

I learned this one from Mark Manson’s “The Subtle Art of not giving a F*ck.” –  You can be the most self-aware person in the world, and there will be someone that just wants to fuck shit up in your life. We all have debilitating insecurities and the reasons we do what we do. You can’t control someone else, but you can control how you react to it.

Your boss is in a real Meryl Streep Devil Wears Prada Mood for no reason? You could get defensive and snippy back. You could fume at your desk breathing like one of Khalessi’s dragons after being locked up in a dungeon. Or you could go for a quick walk, collect your thoughts, and realize that her actions have nothing to do with you, and move on the best way you can by continuing to do your work.

8) Gauge success by how you’re living your day-to-day, not by achievements

We so often attribute success to milestones. In actuality, living a successful life isn’t about those moments at all. A truly successful life is enjoying all the days that string together to create a life you love. Not all days will be poolside with a margarita in hand, some days will be the total shits. It is also unrealistic to think there is a perfect job out there for you where no bad days exist.

If you look at someone’s career you’d love to model, you betta-BELIEVE they have days they don’t want to work, or tasks they are avoiding. It isn’t about finding perfection. It’s merely about finding something that you enjoy most of the time.

“What is the ultimate quantification of success? For me, it’s not how much time you spend doing what you love. It’s how little time you spend doing what you hate.” – Casey Neistat

9) It’s okay to be sensitive, in fact, it’s an asset

There’s a stigma attached to sensitive. This year I learned that being sensitive is a superpower. It fosters deep and meaningful relationships and promotes empathy and self awareness. I’ve struggled with thinking that my sensitivity is a weakness. Most people mistake it for introversion. It’s not that either.

The definition of “sensitive” is: having or displaying a quick and delicate appreciation of others’ feelings. Who wouldn’t want to possess this quality??

I’ve replayed moments in my head where I wish I’d been snarky back to someone, or when I’ve kicked myself for letting people under my skin. Remember #6? Being sensitive means you not only care deeply, but you’re allowing your ego to be checked at the door.

As you know if you’ve watched Brene Brown’s Ted Talk, vulnerability = human connection, which is what we are all seeking on this earth anyways. Go ahead, embrace your sensitive side.

10) Don’t put your mentors up on a pedestal

You have the ability to achieve everything your mentors have. They all started somewhere. Continue to put in the work and the time, and you will get there. Steve Jobs said this best:

“Life can be much broader, once you discover one simple fact, and that is that everything around you that you call ‘life’ was made up by people that were no smarter than you. And you can influence it, you can build your own things that other people can use. Once you learn that, you’ll never be the same again” – Steve Jobs

11) It ain’t about the money, honey

So many successful people say this. As cliché as “money can’t buy happiness” is – it’s true. When you get that ugly feeling in your gut that you don’t want to do something, but the pay cheque has you doing the pondering emoji, just don’t do it.

12) You need to get uncomfortable if you want to make an impact

Taking risks, having uncomfortable conversations with yourself and others, flipping the norm upside down and asking why things are the way they are. These are all things CEO’s and billionaires do to make a bigger impact, to create magical things, to push through the noise. Momentary discomfort leads to lasting results.

13) Show up as you are in social media & IRL

Social Mediiiiaaaaa. Oh man. These days everyone is focusing on the numbers. How many followers do you have? How many likes did you get on that photo? People are spending so much energy on curating beautiful feeds but most aren’t letting their personalities shine through. Own who you are, all the weird and wonderful, the messy and the magical. People will respond to it, and those that don’t were never your audience anyways.

14) Saying “No” doesn’t mean you’re missing out

#FOMO. It’ll get ya! While saying no can feel like you’re giving something up, it really means you’re making space for another yes that is more in alignment with what you desire. You are saying yes to your wellbeing, your happiness, your energy, deeper connections, laughter, love, and to good health. I plan on saying no a lot more, and not gonna lie, I’m pretttyyyyy prettyyyyyy pretyyyyyyy excited about it.

15) Success is scary

As soon as you’re successful, things change. Are you ready for that? We so often focus on the fear of failure, but what most people don’t realize is that they are just as terrified of success.

When I look at what I want my life to look like, it does scare me a little (okay, maybe a lot). It will mean a great deal of change, but the excitement is propelling me forward and I’m learning to channel the nerves into momentum.

16) People aren’t paying attention to you like you think they are

“And you know what I tell people all the time? If Will Smith isn’t in a movie for 3 years, you’re not walking around saying “Where’s Will Smith?” No one is paying attention to anyone else at all. You think everyone is, but they’re not.

So take as long as you want if you’re talented. You’ll get their attention again if you have a reason to.”

I read this quote from BJ Novak in the book “Tools of Titans” and it resonated with me. We feel the need to hurry up and get there, or feel pressured to move onto the next thing when we have reached a goal. In such a competitive world, taking a step back or taking things slow can sometimes feel like entrepreneurial suicide.

This reminded me that that’s all just in our heads. No one else cares as much as you do. Go at your own pace. Move on only if it feels right. Don’t worry about what anyone else thinks or has to say. Chances are they won’t even notice.

In other words, you do you, boo.

17) When you need realignment in life, think of someone you’ve loved and lost

Whenever I need to check myself, I think of my late grandma. When I find myself not feeling quite right about a project I’m working on, or letting comparison creep in, I think of her. I think of the life she lived and how matter of fact her advice was. There was such a beauty in the simplicity of it. I think of what advice she might give me and I realize how silly I am being for spending time worrying about such trivial things.

If you are feeling out of alignment, or not quite sure what path to take, think of someone whose advice you cherish or someones outlook on life you wish to emulate. Channel that and move forward without thinking too much. It’s one of the best exercises I’ve found to truly live a life that is true to me and no one else’s.

As you can tell, this year was full of a wholleee lotta soul searching, discomfort and incredible highs that led to uncovering some of the most important life lessons. This growth has shown me how powerful human beings can be if we harness our energy for good, stop doubting ourselves, build stronger more meaningful connections, and never stop learning or asking questions. I can’t wait to see what this year has up its sleeve.

The comments +

  1. Elizabeth says:

    #16 is one of the best…they are all great but #16 is so very true!!!

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