4 Life-Changing Lessons I Wish I’d Known in my 20’s

The twenty-somethings really tug at me lately.

Imagine what it’s like to be graduating into this mess we find ourselves in? Yes, I mean the pandemic, but I also mean the ever-devolving state of discourse and how ‘truth’ has taken the form of mercury at room temperature, a gelatinous mirror, elusive until it slowly evaporates.

It’s not supposed to be this way, and if I’ve learned anything over the years, it won’t be this way for too long. When viewed through the prism of years instead of months, society always gets better. (If you are at all interested, I delivered a commencement address on this topic called Tacking).

So while we wait for The Year We Came Undone to mercifully draw to a close, I would like to help my younger friends out there make up for lost time by skipping some of the mistakes I made.

1. There is almost nothing you break in your 20’s that you cannot fix in your 30’s

I guarantee you that anyone in their 30’s or older will tell you that their biggest regrets are not the things they did in their 20’s, but the things they didn’t do while they had the chance.

Now is not the time to be risk averse. Now is the time to pursue your passions and learn from your mistakes. Don’t be so precious about where you end up, or so terrified of making a mistake, that you avoid opportunities because they don’t fit into your perfect 10-year plan. You just need to keep moving in the general direction of your ultimate ambition. The longer you live, the more you will come to realize that nothing ever goes in a straight line.

A hospice nurse wrote a fascinating book, The Top Five Regrets of the Dying: A Life Transformed by the Dearly Departed, in which she identified the number one regret shared by the most people: They had lived someone else’s life and let fear impede their dreams. Failure did not even make the list.

So whatever crazy dream is burning inside, keeping you up at night, now is the time to chuck it all and just go for it. Do as much as you can in the next 10-15 years, even if it doesn’t align with your long-term goal. Travel the world (when it’s safe to do so), stand up and fight for what you believe in, pursue a crazy dream, give that relationship a go. Your future self will thank you.

2. The only person judging you is the voice in your head – and it’s a giant waste of time

When I was 32, I was diagnosed with testicular cancer out of left field (Men, be a man and don’t ignore a lump). Just 48 hours later, a surgeon extracted a very large tumor along with a very important piece of my anatomy. For several dark and lonely days, I thought this might be the end of my young life. It was a depressing time for sure but one I savor because it gave me this incredible insight: At the moment when I came face to face with my maker, I was so mad at myself for caring about what other people think. I felt like I had squandered this gift of life and desperately wanted a do-over.

Why do we spend so much time anticipating judgement from people we don’t even respect in the first place, and then conform our behavior to seek their validation? It makes zero sense. And here’s the worst part. In your 40’s, you will discover a harsh reality of life: Everyone is way too preoccupied with their own problems, way too consumed by their fears or enamored with their talents, to even devote more than a nanosecond to judging you. When you learn this lesson firsthand, you will experience the most deflating feeling of them all – regret, the only truly self-inflicted and preventable emotion.

The next time you start chastising yourself, remember one thing: You were born whole. You don’t need anyone else to validate you. You are an unfinished work of art designed never to be completed, and that is what makes you so absolutely perfect.

You go to bed at night and rise in the morning with one job that can never be outsourced to another – not to mom, or dad, or some significant other - and that job is to love yourself.

And if not you, then who?

3.  Opportunity always comes before recognition

Make yourself indispensable at whatever it is you’re doing, and you will always get promoted – but sometimes you have to be patient.

It took me awhile to realize that recognition is a lagging indicator, and new opportunities with greater responsibility are leading indicators of future success. Most often, you will get an opportunity (more work!) when you are excelling, but the recognition – and the compensation – come later. I’m sorry, but these rarely move in lockstep.

You may find yourself becoming frustrated, bitter and impatient. I know I did. Be patient. In most cases, your time will come. Consider if there is still more to learn, still more to improve upon. And then decide for yourself the demarcation line between being patient and being exploited. It starts by dispassionately and objectively knowing your own worth and assessing how long is too long for your work to be recognized.

But when that time does come, and you realize someone’s finger is tipping the scale in their favor, don’t be afraid to get right up and walk away. We all know when someone is never going to appropriately value our work – or our love for that matter – and the world is too big to waste with small people.

4. Be here now

The happiest people on earth live in Bhutan. They do not blissfully ignore their own mortality; they contemplate it five times a day, and in so doing, they remember to savor the time they have left on this earth. Fear of dying loses its grip on the living.

Hold on to the moment with everything you’ve got. The greatest gift we are given in life is the present, and it is the only thing we are promised. Limit the forces and people in your life that fill your mind with dread and take you away from the here and now. When you wake up to the moment, life suddenly seems so abundant instead of so lacking.

Well that’s all I’ve figured out so far. 

Oh, actually one more thing. No matter what any dictionary says, irregardless is not a word. 

Let’s start a discussion in the comments: If you are over 30, what lessons do you wish you had known in your 20’s? And if you’re lucky enough to still be in your 20’s, what do you want to learn from your (slightly older) peers?