There’s countless things you probably wish you knew in your 20s. The trouble is you only realize this after you’ve grown up and had a chance to reflect back on these typically chaotic years.
Hindsight is a wonderful thing, right?
But it’s also part of being in your 20s. Fucking up is truly a rite of passage. It’s something that helps us improve, grow, and be better people for the rest of our lives.
We reached out to some of our favourite authors to see what they wish they knew at the start of their 20s. We hope that it can give your prime years a jumpstart, or help you find some direction. More importantly, we hope you realize you’re not only in your struggles to make sense of your 20s.
Sensitivity Is A Strength / Melody Wilding
If I could go back in time, I’d tell myself “one day you’ll realize your sensitivity is your greatest strength.” In my twenties, I wasted so much time and energy beating myself up for thinking and feeling everything so deeply. I looked around and wondered why everyone else was so confident when it seemed like I took everything personally.
I didn’t have the language or framework for it then, but today I’m able to step back and see what a gift having this trait is. It’s what allows me to be intuitive, empathetic, and see nuances or make connections that others miss. Profoundly sensing and feeling the world around me is a superpower, and now I wouldn’t give it up for anything in the world.
I Wish I Knew a Lot of Things / Tim Denning
I wish I knew in my 20s how to be kind to myself. Or, that school taught me how to manage my mind and notice mental illness. When it came to money, I wish I knew how it worked earlier in life and that governments could just print it out of thin air and call it “stimulus.”
I wish I had learned to be kind earlier, and that generosity was something I admired at 26 rather than selfishness. I wish I didn’t buy stupid luxury cars and try to impress people that treated me like garbage.
It turns out, I wish a lot of things.
Saying No Doesn’t Make You ‘Mean’ / Jessica Wildfire
Declaring your boundaries is hard when you’re 24 going on 17. Everyone thinks you’re their teenager to boss around. Everyone wants to dump their grunt work on you and call it “valuable experience.”
They don’t like hearing the word “no” out of someone so small.
Say it however you can. Just say it. Even to your boss. Your time is worth more than their ego.
I Wish I Knew to Experiment / Anthony Moore
Focus on experimenting as much and as intensely as possible.
Most people in their 20’s are running around like chickens without a head – unfocused, random, frantic. At the same time, most people are afraid of failure (especially publicly) and usually operate out of fear and pain-avoidance. But if you can be someone that isn’t afraid of looking stupid, and trying things (and failing) over and over, more than almost anyone else, you’re going to have more success than most people by the time you’re 30.
You Have to Be True to Yourself / Nicole Akers
Self awareness is the key to success in life, not stuff.
Most people around me wanted material possessions in their 20’s and I wasn’t much different. If I had known then what I know now, I’d say two things: 1. Stuff doesn’t matter nearly as much as you think it does. You’ll be much happier with less.
And, 2: You have to be true to yourself, whatever that means for you. In my 20’s I didn’t know who I was, much less who I wanted to be. The desire that’s burning within you will take you on the right path if you listen and do the work. Show up and be willing to try new things. As you explore life, you’ll learn things about yourself you never knew and the discovery will put you on a path that makes sense for where you’re going. When you get where you’re going, it’s going to be awesome and you’ll have some great stories to tell.
Life Isn’t About You / Michael Thompson
I wish I knew in my 20s that life isn’t all about me. This may sound depressing. But our own individual dreams aren’t worth all that much and if that’s your only focus no matter what you achieve it won’t feel whole unless you are proactively doing something to directly influence your immediate community.
Oh, and chase advice, not money. Your success in life is a direct reflection of how curious you are and the people you choose to spend time with.
I Wish I Knew to Be Confident / Fab Giovanetti
As I am about to jump straight in the big 30s, I am actually looking at the past 10 years quite fondly. I wish I knew that it’s okay to change, adapt, and try new things in my 20s. Though I did that a lot, I always felt underlying guilt for doing so, which is a shame. I wish I had felt more confident and proud of trying new things, adapting and evolving instead of deeming those as failures.
In a way, I would not change that as it’s been a big lesson for me. Yet if it can help others who feel the same way, I’d be happy to pass that wisdom.
There’s More Time Than It Seems, Even If Time Flies / Danny Forest
Oh man, I was so afraid of turning 30! I felt like time was going too fast and that by my 30s, I should be a lot more successful. Whatever that even meant… By then, I had owned and sold a property, I had been married for over half of my 20s, I had travelled to 50 countries, started 5 companies, and more. And yet, I still felt like that wasn’t enough. I wanted to learn more. I wanted to have started a truly successful company, like, Virgin or Amazon successful. Unfortunately, I didn’t accept that these things take time.
I’m approaching 34 now and let me tell you, the 30s have absolutely rocked. They’re by far superior to my 20s. Time still flies, but here’s a thing. If it takes 10,000 hours to master a highly competitive skill, that means you can master one skill every 5 years. With life expectancy only going up, starting in your 20s, you can easily master close to 20 skills in your life. And that’s for something that takes a really long time! Imagine how much you can travel! How much you can do while you’re alive! Time is on your side. In my 20s, I wish I knew how much was achievable in a single decade and how much each decade gets better than the one before.
I Wish I Had Been Brave / Shannon Ashley
Be brave. I wish I’d gone after the life I wanted without fear of the people who never really did have my best interests at heart. I wasted my twenties, and largely gave them up for fear. The fear that I’d fail, the fear that my family would hate me, and the fear that I could never really trust myself to know what was right for me. I wish I knew that regardless of the outcome, I would never regret being brave. I don’t regret it – I only regret giving in to fear.
Also? Romantic relationships aren’t as important as we think they are. Like a lot of young people, I thought I needed romance and marriage to lead a full life. I went hunting for those things because that’s what everybody says matters. I lost myself for a long time. Now that I’m approaching 40, I can safely say that’s not the life everyone needs or even wants, but it takes a whole lot of unlearning to figure out where you stand. Coupledom is so ingrained in our culture, that most of us grow up with a serious bias to think that’s the life we want.
Have a Plan, Any Plan / Christopher D. Connors
That the importance of having a plan – even knowing that plans will change – is the best piece of advice I could give someone. I wasn’t playing the long game. I was playing the short game and flying by the seat of my pants. The importance of having a 5-year plan is enormously important, and helps you to understand the things you want in your life – and that they will very likely take time. And that’s OK! As long as you’re going in the right direction, while making tweaks and pivots along the way.
I always knew things I was passionate about, but I didn’t pursue them right away because I didn’t have a plan. I ended up getting my Master’s and starting a prestigious job in consulting – all things I’m proud of. But because I didn’t have a plan, I struggled at times and didn’t succeed in the way I wanted. I’d also say – giving your all and learning what you need to learn to continue getting better each day is so important. It’s why I’ve arrived at doing the emotional intelligence and leadership development work that I do.
That I Could Easily Change My Major and Career / Luke Rowley
I wouldn’t change a lot about my 20’s because I fulfilled a lot of big life goals during them. I lived in a different country for 24 months, got married, had kids, ran a marathon, and more. All of that was worth it and I would do those things over again in a heartbeat. If I hadn’t done them, those are the things I’d be answering this question with! But the one thing I would change is my career. I got a degree in something that I liked okay but wasn’t totally passionate about. You’ve heard “follow your passion” hundreds of times, but 30-40 years is a long time to spend in a career that you’re not excited about!
I would have taken more time to explore my strengths and interests. I would have taken semesters at a time off from school to spend months job shadowing people in the field I was considering. And I definitely would have changed my major had I known what I do now! Thankfully, I’ve discovered that changing careers isn’t too difficult in the digital age!
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