Image via Pexels

27 Life Lessons I Learned By 27

Diego Contreras
12 min readDec 3, 2018


One of my favorite musicians and one of my favorite athletes, Kendrick Lamar and Stephen Curry, both seemed to hit their stride at 27. It makes sense that an athlete’s body moves toward its prime in the late 20s, and as little as I know about the music industry, it does seem like musicians are at their peak before they settle all their angst and issues.

But 27 is young. Lyndon Johnson said, “You know, life begins at forty…” And indeed, he didn’t become Minority Leader in the Senate until age 44, even though he was the youngest ever to do so. And one of Johnson’s political mentors, Sam Rayburn, didn’t reach his career ambition of becoming Speaker of the U.S. House of Representatives until 58. He then went on to hold the longest tenure as Speaker.

Maybe there’s an age or period of years where we see our lives shape into what they will become. Maybe there’s an age where we realize our great hopes and ambitions. But it’s also possible that those hopes and ambitions never happen. It’s possible that what we have now is as good as it ever gets. We might fail on our own self-created quests that we’re embarking on. And that’s OK. Life isn’t a destination of ambition and realizing our wants. As Nietzsche and the Stoics would say, we should love our fate, which or or may not include or wants. Our fate is ours and only ours. And we don’t exactly get to choose it.

The Stoics would also advise to hope for nothing, because the people who expect nothing can’t be disappointed. As the Roman statesman Cicero said in On Old Age, but translated by Philip Freeman in How to Grow Old: Ancient Wisdom for the Second Half of Life, “If you don’t long for something, you don’t miss it. That’s why I say the absence of desire is quite pleasant.”

Cicero’s treatise on old age is written as a fictional conversation between Cato the Elder and his two younger friends Scipio and Laelius. Cicero provides great perspective. He advises that a proper old age begins in youth through practices of moderation, wisdom, and clear thinking. If we start with those habits early, they’ll sustain us as we grow older. He shares that miserable young people never become happier as they grow older. And that, “We truly can’t praise the love and pursuit of wisdom enough, since it allows a person to enjoy every stage of life free from worry.”

Here’s a glimpse of some of Cicero’s wisdom that he writes through the voice of Cato the Elder:

  • “I think, my young friends, that you are admiring me for something that isn’t so difficult. Those who lack within themselves the means for living a blessed and happy life will find any age painful. But for those who seek good things within themselves, nothing imposed on them by nature will seem troublesome. Growing older is a prime example of this. Everyone hopes to reach old age, but when it comes, most of us complain about it. People can be so foolish and inconsistent.”
  • “My dear Scipio and Laelius, old age has its own appropriate defenses, namely, the study and practice of wise and decent living. If you cultivate these in every period of your life, then when you grow old they will yield a rich harvest. Not only will they produce wondrous fruit even at the very end of life — a key point in our discussion — but you will be satisfied to know that you have lived your life well and have many happy memories of these good deeds.”
  • “Ennius was seventy at the time and suffered what men suppose are the two greatest burdens of life — poverty and old age. But he bore them so well you might think he enjoyed them.”
  • “It’s not by strength or speed or swiftness of body that great deeds are done, but by wisdom, character, and sober judgement. These qualities are not lacking in old age but in fact grow richer as time passes.”
  • “Let each use properly whatever strengths he has and strive to use them well. If he does this, he will never find himself lacking.”
  • “And as much as we should care for our bodies, we should pay even more attention to our minds and spirits. For they, like lamps and oil, will grow dim with time if not replenished.”
  • “For a man who has been engaged in studies and activities his whole life does not notice old age creeping up on him. Instead, he gradually and effortlessly slips into his final years, not overcome suddenly but extinguished over a long period.”

Now, it is true that some men are like Lyndon Johnson, and to guarantee that their ambitions and hopes are met, they bend the earth to their will. They cheat, manipulate, and maneuver to no end. “If you do everything, you’ll win,” he said, a sentiment that should be used as a positive, but in some instances he took it to its most dramatic negative.

But there are other men like Cato the Younger who take an uncompromising stand on their principles. Then there are men like Air Force fighter pilot and military strategist John Boyd who realize that a young person comes to a fork in the road where they have to choose to be someone or do something. And Boyd cared about the doing more than the being. Boyd would tell others that people are more important than budgets and hardware, and that doing good work, the honest and noble work that we all know some in bureaucracies aren’t happy with isn’t always easy. “So you got your reward; you got kicked in the teeth. That means you were doing good work. Getting kicked in the teeth is the reward for good work.”

We’re all dealt with biological, environmental, and situational life cards that we have to make sense of and use as best we can. I like to think that similar to the Taoist Yin and Yang, we can move toward the lighter or the darker sides of our impulses. Regardless of what we choose, we have to choose. In our youth we aren’t as aware of ourselves and don’t always realize what we’re choosing, but with adulthood and maturity, we realize we can’t escape our choices.

Those choices have consequences. They reverberate across our friend groups, workplaces, families, communities, and the generations we leave behind. I believe that one of the reasons we don’t have such high regard for older age is because we fear death, but as Jordan Peterson points out in an interview, humans fear much more than death. We fear betrayal, malevolence, and I believe we fear our reflection — looking in the mirror and realizing we aren’t where we should be. Or even more devastating, we aren’t who we should be. These are consequences we can only get close to reconciling as we age if we take responsibility for ourselves and our actions.

But, of course, that pesky fear of dying doesn’t go away easily. In How to Grow Old Cicero reminds us that no one can live peacefully if they’re afraid of dying:

“Now it is true that the process of dying itself may involve some unpleasant sensations, but these are fleeting, especially for the old. Then, after death, either the experience is pleasant or there is nothing at all. We should keep this in mind from our youth so that we do not fear death, since without this belief there can be no peace of mind. We know that we cannot escape deathin fact, it may come for us this very day. Therefore, since death threatens us at every hour, how can anyone who is afraid of it have a steadfast soul?”

And Cicero has even more practical thoughts on the matter. “Why should I be afraid then, since after death I will be either not unhappy or happy?” Then he also reminds us that the wisest among us seem to go the easiest. His great reminder for those who are in old age and much closer to death is also well said. “I follow nature as the best guide and obey her like a god. Since she has carefully planned the other parts of the drama of life, it’s unlikely that she would be a bad playwright and neglect the final act.” Followed by, “An actor does not need to remain on stage throughout a play. It is enough he appears in the appropriate acts.”

Regardless of the age we’re at, or how comforting we find the words of Cicero or any other philosopher, growing old is scary. Death is scary. Betrayal and malevolence and a zillion other things that can happen during our lifetime are scary. Life is a constant existential threat. But we’re strong enough to face it. People have done it before us and people will do it after us.

So, with that, may your journey be with as little turbulence as possible. These are 27 things I learned leading up to my 27th year of life. I hope some of them can be as useful for you as they were for me.

1. Don’t assume anything.

Even if you think you’re great at understanding people, everything you’ve determined is an assumption. Never assume your assumptions are right. You have no idea what’s going on in other people’s heads, not even when they say things.

The best way to determine what people are up to is by watching their actions, because often, the words don’t align with what they’re actually doing.

2. Be patient.

Like Sam Rayburn waiting his years and years be Speaker of the House, some developments of life take more time than we’d ever want to wait for. But great ones before us have waited, and great ones after us will, too. So we better do the same.

Besides, why are we in such a hurry? We’ll only look like fools if we leap into a situation we aren’t prepared for. Remember Epictetus’ words, “It is true, however, that no bull reaches maturity in an instant, nor do men become heroes overnight. We must endure a winter training, and can’t be dashing into situations for which we aren’t yet prepared.”

3. If you do everything, you’ll win.

This is the saying that Lyndon Johnson at times used for bad. But by itself without ill-intentions, it’s a positive.

Every detail. Every effort. Every project. No stone unturned. Like Kobe Bryant said when he retired, he was able to look himself in the mirror and be satisfied with where his cards fell because he gave it everything he had.

4. Say no.

Learn to stand up for yourself and say no and actually mean it.

5. Stand your ground and by what you believe.

Like Cato the Younger, if you believe it, own it.

Be willing to learn and grow and change, but if some conviction is true to who you are, don’t waver or falter.

6. Be careful believing the stories you tell yourself about yourself.

They may not be true. They may inflate your ego. And they may hold you back.

7. Always be yourself.

Like NF says, “Always be yourself, not the person that you pretend to be.”

8. Get stronger. Build character. Cultivate inner strength.

Build what the Stoics had, the inner citadel. When times are tough, we may only have ourselves to rely on.

9. Face your fears.

How? Head on.

10. Let people speak and have different opinions.

Don’t be threatened by people’s opinions. Don’t try to convince them to live like you or feel the need to combat every idea they have. Use the Jordan Peterson saying, “Assume that the person you are listening to might know something you don’t.”

And if their opinion makes you especially uncomfortable, remember that Nietzsche philosophized with a hammer. We should welcome any objection or new perspective so that we can chisel our truth to get it to be as true as possible.

11. Learn to be a leader, even if you don’t have a career as a leader.

Learn leadership skills. Learn how to speak. Learn how to present. Learn how to be wrong. Learn humility.

We all have an influence on those around us. So it’s best to learn to lead. And if you one day become a leader, the best leaders also have to follow.

12. Be decisive.

Anna Wintour is the editor of Vogue. Some people think she’s stern and snappy. It’s not that. She’s decisive.

She doesn’t sit around and second guess herself. She makes a decision and sticks to it. This isn’t one of my best traits, but I’m trying to be like Anna.

13. Once you quit or start something, after awhile you stop thinking much about it.

I quit drinking awhile back and people still ask me many questions. I think about it as little as I think about the last time I ate squid. It’s just faded as part of my life and it’s insignificant.

If you want to make a big lifestyle change or implement a new habit, realize that before you know it you won’t think about it. It’ll be ingrained as part of who you are. You’ll be automatic.

14. The most fun way to learn history is by reading biographies.

I can’t remember who said this, but it’s true.

Also, biographies are one of the best ways to learn how to live.

15. Don’t be too proud for an opportunity. I’ve seen people I know miss out for this reason.

Don’t ever be too good for anything. Some of the smartest people I know work blue collar jobs and make great money. They aren’t too good for anything.

16. No one is wholly good or wholly bad.

People are complicated. We’re cocktails of positive and negative traits and many of them come out because of life circumstances, settings we’re in, mood changes, or even our appetite at the time.

Like we shouldn’t assume what people are thinking, don’t place them in boxes either. One aspect of a person doesn’t determine their whole identity.

17. If you want to improve your running, train for time instead of distance.

Easy peasy.

18. If you want to improve your speed, double your distance.

Easy peasy part II.

19. You can probably drink coffee later in the day than people say.

Try it out.

20. Don’t be annoyed by everything.

How does that minor inconvenience compare against the magnitude of eternity?

21. Be gracious and patient.

It’s tough. But by God can you imagine the patience required to raise kids? Better start trying now. And it’s just the kind thing to do. We can all apply this in our interactions with others.

22. How you do anything is how you’ll do everything.

So aim to be your best, even at the small things.

Ryan Holiday has a great blog post about this.

23. Encourage other people.

It’s a wonder how much people light up when you encourage them or tell them something genuine and true about them without having any ulterior motive.

We all need encouragement from time to time, and it’s a gift we can give each other every day. Here’s what Jordan Peterson says about encouragement in society.

24. Praise the effort.

Effort is always good, even if it doesn’t compare to the effort another person can give.

Don’t hold yourself or others to Herculean standards or expect them to perform as well as professionals. Praise that there’s any effort at all. Some people can’t even give that.

25. Self-help is as useful as it isn’t.

You won’t try one diet or read one book or go to one seminar and have some singular sweeping eureka moment. Life progresses much more slowly than that, and humans grow from natural experiences that we can’t replicate in books or seminars.

Plus, most of these books are trying to take advantage of your naivety so you’ll consume the brand, personality, or product, and they have shallow understandings of the world. Read the ancient thinkers instead, or the good psychologists. Philosophy is the original and timeless self-help.

26. Time goes by normal.

My grandma is almost 83 and in the last stage of her life. When I asked if her life went by fast she said, “well, normal.” I found it comical at first but then the wisdom hit me.

Life doesn’t really go all that slow or all that fast. It’s at just about the right speed. The speed fate decides for us.

27. Be grateful.

I went to a small private school in Amarillo, Texas. My high school graduating class was close to 30 kids, and each class above or below me was similar in size. We all knew each other pretty well.

I’ve had a few classmates pass away in the few years since high school graduation. One passed away recently and would be having a birthday in a few days. Another shared my birthday, so he won’t be here to have his.

Life is tough. It’s dangerous. And it’s serious. But it’s a gift, and a gift that we’d be fools to not take full advantage of. We don’t know how our days are numbered, and we don’t know how our lives affect those around us. So be grateful we get to do it, despite the difficulty, and despite our suffering.



Diego Contreras

I'm a communications and content writer. Follow me on Twitter @thediegonetwork.