45 Life Lessons: Reflections from 45 Years of Living
As I reflect on my 45 years of life, I am reminded that the lessons I’ve learned are personal observations that have shaped my worldview. While these lessons have been invaluable, I recognize that they may not apply universally. I encourage you to question and consider each lesson in the context of your own life and to take what resonates with you and leave what does not. In this post, I share 45 of my personal observations and the insights I’ve gained from them. I hope these reflections will encourage you to reflect on your experiences and help you navigate your journey with greater self-awareness and intentionality.
This is a lengthy post packed with valuable insights that I’ve gained from my life experiences. If you prefer a PDF version for easier reading or future reference, we’ve got you covered. Click this link and enter your email address to download our free PDF version.
Relationships and Social Connection
Relationships and social connections are key components of a life well lived. They bring us joy, support, and a sense of belonging. It’s essential to learn how to navigate them to experience the fullness of life.
1. Don’t Let Life’s Fleeting Moments Pass You By
After my nephew was born in October of last year, my sister and brother-in-law, and I came home to my parents for four months. My sister said, “This is really special that all of us could be here.” Any parent will tell you that seeing the world through the eyes of a baby is like experiencing the world for the first time.
If an adult called you and said, “Hey, I figured out how to get my feet in my mouth,” you’d think they were insane. But when a baby does it, it’s magical.
Realize there are priceless moments in life that you’ll never be able to recreate and value accordingly.
2. Stop Believing in Fairy Tales
Pop culture teaches us that love is what we hear in music lyrics and see in movie scenes. This reinforces our belief that infatuation and love are one and the same. However, infatuation fades while real love sustains. We need to be realistic about our expectations of love and recognize the difference between the two.
3. Lukewarm Romance Is Worse Than None at All
A lot of people chase potential partners whose interest in them is lukewarm. When someone’s feelings about you are lukewarm, hoping their feelings will change is a fool’s errand. The time you waste on lukewarm romance is time you could have spent connecting with someone who is truly excited about you.
4. Never Overlook the Value of a Message Because of the Messenger
Often our beliefs and opinions about a person can influence the value we place on their input. We should be open to learning from anyone who has a valuable message, regardless of our opinions about them.
5. Never Be a Dick to People Who Serve You Food or Alcohol
We should never be rude to those who serve us food or alcohol. These people have more power than we realize, and being kind to them can result in better service and even free drinks. We should not confuse power with authority and identify power brokers to build relationships with them.
6. What Your Parents Think Is Best for Is Not Always Right for You
When it comes to parenting, it’s important to remember that what your parents think is best for you is not always right for you. Your parents want to make sure you stay safe and make the right decisions, but they can’t always see the bigger picture. They can’t see the experiences you need to have in order to grow and learn. So it’s important to make sure you take the time to explain your decisions to your parents and to give them the opportunity to understand why you’re making them.
7. Don’t Wait to Tell the Most Important People in Your Life How Much They Matter
“We spent all this time imagining we’re going to get ready for our dying. And I think it’s a kind of absurd idea to imagine that at the time of our death, we will have the strength of body, the emotional stability, and the mental clarity to do the work of a lifetime. It’s an absurd gamble. So we should do this work now. And that includes those of us who are not dying. Our aging parents, for example, be with them for now. Tell them you love them now. Waiting is full of expectations. Waiting for the moment of dying. We miss all the moments in between.”
With age, the reality of our mortality becomes more apparent. Friends start losing parents, relatives die of old age, and in the most tragic of cases, people die sooner than expected. It’s important to tell the people you care about how important they are because tomorrow isn’t guaranteed to any of us.
8. Let Your Kids Break Their Bones
“When we overprotect our children, denying them the opportunity to practice their own skills, learn to make wise and foolish choices, experience pain and loss, and generally make an almighty mess, we believe we’re treating them with love-but we may also be limiting their scope to become fully human.” — Tim Harford, Messy.
Let your kids break their bones. Or you might end up with an adult son like me with a pathological need to tie boards to my feed and ride them on water, land, or any other surface I can find. I wouldn’t wish this on any parent other than mine. They’re stuck with me. You’re not.
Caveat: This is easy for me to say since I’m not a parent.
9. The Grass on the Other Side Isn’t Always Greener
“No matter what age you are, it’s likely that your life has taken some unexpected turns. In the film ‘Mr. Destiny,’ James Belushi enters a bar and expresses to Michael Caine that his life is ordinary. Michael Caine then offers him a glimpse into an alternative version of his life, where he is married to the prom queen, the CEO of a successful company, lives in a lavish mansion, and possesses a collection of high-end sports cars. However, in this ‘better’ life, his parents are divorced, and he has lost touch with his best friend. It’s important to remember that when we yearn for a different life, we may also have to give up some of the most valuable aspects of the life we currently have.
Life, Career, and Productivity
Life is full of challenges and opportunities. It’s important to stay focused on our goals while also being open to unexpected detours. Being mindful of our decisions and their potential consequences is key to navigating life and achieving success on our own terms. Here are some lessons that I’ve learned along the way.
10. All Prescriptive Advice is Context Dependent
Prescriptive advice often presents itself as universal and foolproof, but it consistently leaves out the essential variable that alters its effectiveness: the person applying the advice. What works for one person might not work for another, such as diets or productivity hacks. Despite this, we are sold on the dream because it’s good for business. Context alters and determines outcomes in every area of life, and almost nothing is universally true, even when backed by science, as everyone’s body is different. Advice that changes one person’s life can fuck up another person’s life
11. Produce More Than You Consume
Producing more than consuming leads to greater rewards, self-reliance, and power. The distribution of rewards between producers and consumers has been disproportionate for thousands of years and is even more so today. The person who built the factory made more money than the people who worked there, and content creators benefit more than those who consume it.
12. Don’t Follow Your Passion. Pay Attention to What You Find Engaging
The common advice to “follow your passion” is often not practical and can lead to disappointment and frustration. Instead, pay attention to what you find engaging and interesting. Don’t simply follow or suppress your intuition, but try new things and conduct experiments to discover what really excites you. Don’t be afraid to explore new interests and take risks, even if you don’t know where it will lead. Keep an engagement diary to track what activities sustain your attention, challenge you, and make time fly. By discovering what you find engaging, you’ll be on your way to finding your passion and achieving your goals.
13. Unexpected Detours Are Not Dead Ends
Over the last 13 years of my life, I’ve learned that nothing in life follows a linear path. Unexpected detours can happen at any moment. Moving back to my parent’s house as an adult was not part of my plan, but it taught me that time with loved ones is a precious, non-renewable resource. Graduating from business school during a recession led to dead ends that turned out to detour leading to better things. Even now, at age 45, I find myself back at my parents’ house, but I am grateful for the opportunity to spend time with my newborn nephew. I try not to worry about the future too much and instead focus on the present.
14. Never Follow Anyone’s Advice to the Letter
In the education system, teachers teach students to pass tests, but this approach does not work in the real world, where life gives you tests first and lessons second. When taking online courses, it’s crucial to account for hidden variables in causality and consider the messy middle. Learning from experienced creators is not about replicating their results but rather mixing their ingredients for new recipes and applying proven principles in an original context. Acknowledging limitations to capitalize on strengths is also crucial, as prescriptive advice is a framework, not a formula, that needs to be adapted and modified. Following someone else’s advice in the letter is not recommended because everyone has genetic limitations and strengths, and their path to success cannot be copied and pasted.
15. Build a Resume of Experiences Instead of Accolades
As a society, we tend to glorify and recognize accolades and accomplishments. However, when we pass away, the bullet points on our resumes won’t hold as much significance as we once believed. Even with all the achievements, we’ll ultimately reach a point of diminishing returns. It’s more worthwhile to create a resume filled with experiences — such as traveling to new places, sharing meals with loved ones, and engaging with art that ignites your passions. Ultimately, when we depart this world, the only thing we can take with us are the memories we’ve created.
16. Dream As If You’ll Live Forever, Live as If You’ll Die in a Year
The famous quote by James Dean, “Dream as if you’ll live forever, live as if you’ll die today,” sounds inspiring, but it’s not realistic. Dreams don’t come true in a day, and everything takes longer than you think. While it’s true that we’re all on borrowed time, living as if we’ll die today can lead to recklessness instead of intelligent risk-taking. It’s important to modify inspirational quotes with a dose of realism to make them useful. Instead of living as if we’ll die today, we can ask ourselves what we would change if we knew we had only a year left to live. This can lead us to say “yes” to new experiences and creative impulses. By doing so, we can make the most of the time we have left and make our dreams come true.
17. You Can’t Copy and Paste Your Previous Path to Success
Success is not a fixed formula that you can copy and paste to achieve your goals repeatedly. What worked for you in the past may not necessarily guarantee success in the future. Although it can be tempting to stick to a familiar path, it is important to remain open to new ideas and approaches, to experiment and adapt to changing circumstances. Being too attached to the way things have always been done could lead to stagnation and hinder your growth.
18. Explore Before You Commit
David Epstein says: “We will underestimate future change at every time point, even when we’re very old. But at no time is that more true than from about 18 to the late twenties. That’s when you undergo the fastest time of personality change. And so essentially, right at the start of that period, we’re saying someone picks now, which is really asking them to pick for a person they don’t yet know. And certainly, in a world, they can’t yet conceive unless they have a crystal ball that most people don’t. It’s a particularly bad time to make an ironclad long-term plan. Explore your options before committing one, and you’ll avoid ending up in a life and career you hate.
19. You Don’t Need Anybody’s Permission Do Something Creative
Many aspiring creatives fall victim to the belief that they need permission or validation from others to pursue their creative passions. In Seth Godin’s words, they are trapped in the “tyranny of being picked,” waiting for approval from record labels, publishers, or investors. However, as entrepreneur Alexis Ohanian notes, the world is changing, and the future will be built without the need for permission. Don’t wait for someone else to give you the green light to be creative — take ownership of your passion and create something that speaks to you.
20. Ambition Always Has an Opportunity Cost
Personal ambition always comes with a price, and often that price is the sacrifice of personal relationships. It’s a tough decision to make, but one that many ambitious people face on their path to success. Regardless of your moral compass, there will come a time when you have to choose between a career and personal life.
21. Don’t Underestimate the Impact of Small-Focused Projects
Almost every significant creative project I’ve worked on in the past 13 years started small.
Unmistakable Creative started as a weekly series called Interviews with up-and-coming bloggers. I recorded a conversation on Skype and uploaded it to my blog.
Small projects can have a big impact, so don’t underestimate them. Achieving ambitious goals can be challenging and require endurance through difficult times. People often give up because they feel like they can’t handle the pain. However, breaking down daily tasks into manageable chunks and focusing on small projects can help to make progress and achieve long-term success.
22. Consistency Trumps Perfection
In my view, I am an ordinary writer who puts in a lot of effort. Nonetheless, due to my consistent writing habits, I am occasionally able to produce something that is truly worth reading. Maintaining an average level of performance on a regular basis is more likely to lead to extraordinary outcomes than striving for inconsistent bouts of excellence.
23. Different Actions Produce Different Results in Different Contexts
The same ideas that work in one setting may be detrimental in another. Personal advice, such as about diets or money, can have varying effects on different individuals. It is crucial to consider the context of the advice to avoid catastrophic consequences and to modify it accordingly to fit your life.
Personal Growth
Personal growth is an essential part of living a fulfilled life. It’s important to be open to new experiences and to challenge yourself to become the best version of yourself. Here are some lessons I’ve learned on my journey of personal growth.
24. Comfort and Safety Are Paradoxically Dangerous
Comfort and safety are paradoxically dangerous because they both result in path dependence. We do what we’ve done before because it’s what we know. But what we’ve done before may not always be the optimal choice. When we stay stuck in our comfort zones, we miss out on opportunities to learn from what happens, whether we succeed or fail. Staying stuck is a way to stay comfortable, but it also prevents us from taking risks and exploring new opportunities. We need to be willing to step outside of our comfort zone and embrace the discomfort of not knowing if we want to make progress in any area of our life.
25. Whenever You’re Stuck in Your Life, There’s a Hidden Benefit
There can be a hidden benefit in staying stuck even when we want to change something. For example, avoiding intimacy might keep us from getting hurt. However, this secondary benefit can also prevent us from achieving our desired outcome.
26. Decisions That Give You Short-Term Pleasure Can Cause Long-Term Pain
In life, all decisions involve a tradeoff between short-term pleasure and long-term pain. Before making a decision, take a moment to consider the potential consequences. For instance, while it may be tempting to have that extra drink on a Friday night, it could lead to a hangover the next morning. Similarly, buying expensive designer items may bring short-term pleasure but could cause financial difficulties in the long term if you can’t afford them. To avoid making decisions that provide short-term pleasure and cause long-term pain, always think about the consequences and consider the bigger picture.
27. Consider the Immediate and Delayed Consequences of Your Habits
Developing good habits and avoiding bad habits are crucial for a successful and fulfilling life. However, many people fail to recognize the importance of considering the delayed consequences of their actions. Habits with delayed consequences, whether good or bad, can have a significant impact on your future. Therefore, it’s essential to act on behalf of your future self and focus on the long-term potential of your habits. To avoid bad habits with delayed consequences, consider the negative impact of your behavior in the future, even if you don’t feel it immediately. For good habits with delayed consequences, focus on the process instead of the outcome and be patient in waiting for positive results. Remember that habits are the compound interest of self-improvement, and small changes can lead to significant improvements in your life.
28. Never Make a Major Life Decision After a Peak Experience
Peak experiences can lead to delusional optimism and emotional decision-making, which can result in detrimental consequences. Making major life decisions after such experiences overlooks the second-order consequences and can lead to poor outcomes. It is important to value incremental change and take small steps toward progress rather than making hasty decisions.
29. Your Potential Declines in Proportion to Your Defensiveness
Being defensive can limit your potential. Accurate criticism is valuable feedback, and resisting it can hinder success. People whose opinions matter will give you honest feedback, even if it’s not what you want to hear. The feedback that is constructive and accurate, even if it is not sugarcoated, can help improve skills and lead to greater success. For public figures and business owners, focusing on solving customers’ problems is more important than personal issues.
30. Self Awareness Increases in Proportion to Your Ability to Question Your Beliefs
Questioning your beliefs is crucial for increasing self-awareness. Defensiveness can hinder personal growth. Refusing to ask for directions, whether in a car or in life, can lead to wasted time and frustration. It’s important to question the source of information and be open to the possibility of being wrong. Self-awareness declines with ego.
31. Make Hell Yes Decisions
When faced with uncertainty, it’s easy to tolerate it and become indecisive. However, indecisiveness can lead to unnecessary suffering. I experienced this firsthand during my recent break-up. I was dating someone long-distance, and while our conversations were filled with arguments, I still felt uncertain about whether to stay or leave. When I finally asked if my partner was excited about seeing me again, their response was, “I’m not excited, and I’m not excited.” This response made me realize that it’s better to make clear and confident decisions, even if they are difficult. To avoid unnecessary suffering, make hell-yes decisions and avoid straddling or tolerating uncertainty in any situation.
32. Every Decision Has Multiple Consequences
Most people only look at the immediate outcome of the decisions they make. First Order Consequences are the immediate outcome of our decision. The second-order consequences are the multiple future outcomes of our decision. The third Order Consequences are the consequences of the second-order consequences. Account for all the consequences, and you’re more likely to make better decisions.
33. Spend Time in a Developing Country Where You Don’t Speak the Language
Traveling to a developing country where the language is unfamiliar can increase your awareness of the interdependence of our society. Through this experience, you’ll recognize how individual actions affect collective outcomes not only in your home country but also globally. Additionally, you’ll appreciate how fortunate you are to live in a Westernized country.
Happiness and Well Being
The pursuit of happiness is a journey, not a destination. It’s important to recognize that happiness is an emotion that comes and goes and to find joy in the journey. Here are some lessons I’ve learned about happiness and well-being.
34. Unhappiness Is the Result of Trying to Control the Uncontrollable
Attempting to control something we can’t is only a waste of time and energy; it leads to a lot of unnecessary suffering. As Ryan Reynolds said in the movie Van Wilder, “Worrying is like a rocking chair. It gives you something to do but doesn’t really get you anywhere.” We can lose fortunes, lovers, career opportunities, and so much more, but what we create internally is the only thing that can never be taken away from us. The economic sustainability of a consumer society depends on the eternal dissatisfaction of the people who live within it, but the spiritual sustainability of humanity depends on our ability to appreciate what we have without always wanting more.
35. Satisfaction Decreases in Proportion to Expectations
Living without expectations can help us find value in every situation, regardless of the outcome. Expectations are often a recipe for disappointment in many aspects of our lives. We tend to be happier when our expectations align with reality, but that isn’t always the case. By letting go of expectations, we can learn to appreciate every moment, regardless of what happens.
36. Some Part of Your Life Always Sucks
The “perfect life” is an illusion. Life by nature is imperfect. And parts of it always suck. You might think that getting what you want, love, success, wealth, or fame will make your problems go away. But your problems never go away. All that changes is your capacity to handle them. Your abilities to do extraordinary things increase in proportion to your capacity to handle problems.
37. Learn to Be Skeptical and Open-Minded Simultaneously
This might seem someone what contradictory. Our cognitive biases determine how we interpret the knowledge and information we’re exposed to. Because of this, there’s always a risk of not being open-minded enough or skeptical enough. By being able to do both simultaneously, we learn to Be Analytical Instead of Emotional.
38. Learn the Difference Between Performative and Genuine Vulnerability
Performative vulnerability is a bullshit version of who you are. You seek pity instead of serving and sensationalizing the gory details of your life. Nothing good comes from this. Genuine vulnerability comes from a place of service.
39. What You Want to Hear Feels Good. What You Need to Hear Is Better
Hearing what you need to hear is better than what you want to hear. Tough feedback from people whose opinions matter can lead to personal growth and success. Tim Ferriss’s wrestling coach pushed his team to exceed their limits, leading to their future success. Harsh feedback from a mentor and a writing coach improved the author’s work. Critical feedback, though not always pleasant, can be valuable if received from trustworthy sources.
40. The Art of Connecting the Dots: Crafting Your Unique Path
Plot out the high and low points of your life over the past 10 to 15 years, and you’ll be amazed at what it reveals. As you look back, you’ll likely notice that it’s the moments when you’ve dared greatly, fallen down, and gotten back up that has been the most rewarding. You’ll also notice that the moments when you’ve followed the straight and narrow paths rarely intersect with the most interesting destinations. The dots you’re connecting today were likely ones you couldn’t have seen in the past, but by actively engaging with life by writing, exploring, learning, and growing, you craft a unique path for yourself.
41. The Utility of Money and Time Will Change With Age
As you age, there comes the point where you can no longer maximize experiences with your money, known as the peak utility of money. Despite having more money as you get older, the utility of money declines with age due to limitations in physical abilities and opportunities. It’s important to make the most of your youth while you still have the health and energy to do so. Eventually, your time and money will reach peak utility and decline in value. Embrace the sex, drugs, and rock and roll of youth and create memories that will last a lifetime, as nobody wants to party with a 90-year-old. Have some unforgettable nights with friends and enjoy the present moment while you still can.
42. Quit Before You Reach the Point of Diminishing Returns
While the idea of never giving up seems admirable, it can often lead to the sunk cost fallacy, causing individuals to persist on a fruitless path. It’s important to recognize when it’s time to quit and not continue investing time, money, and other resources into something with a low probability of success. Persisting when failure is inevitable results in wasted time and resources, and instead, you should allocate them towards something more likely to succeed.
43. Travel Without Baggage
In the movie Scent of a Woman, Al Pacino’s character tells Chris O’Donnell’s character that he’s carrying the weight of the world on his shoulders. Similarly, carrying negative emotions from the past can weigh us down and prevent us from living fulfilling lives. To travel without baggage, it’s essential to let go of bad experiences, failed relationships, and negative memories that no longer serve us. When you show up for work, life, or art, let go of expectations of how the future should unfold. Avoid bringing unnecessary emotional baggage with you, and you’ll be able to experience life more fully. Remember, you don’t need everything from the past to survive or thrive in the future. Let go of excess emotional baggage and experience life as a participant, not a spectator.
44. Don’t Reach for the Stars; Touch the Ceiling
Setting ambitious goals and resolutions can lead to more dreaming than doing. Rather than reaching for the stars, start by touching the ceiling and then aim a little higher. When you focus on short-term goals, like the week or month ahead, and concentrate on the first six weeks of the year, you are more likely to achieve long-term success.
45. Live a Good Enough Life
Conventional wisdom tells us to relentlessly pursue more and better, but this approach can lead to a life of scarcity rather than abundance. Instead, embrace a good enough life. Appreciate what you have in the present moment, rather than always striving for more. In the pursuit of more, we overlook and undervalue what we already have. A good enough life is not about settling but about finding satisfaction and appreciation for what we already have. Remember that your level of happiness profoundly impacts what you can accomplish. If you’re not happy with where you are and what you have, you’ll self-impose limitations on what’s possible. Embrace a good enough life, and paradoxically, it’s more likely to lead to a good life.
Even though my life hasn’t turned out the way I thought it would, I’m grateful for the past 45 years. It’s been filled with unplanned adventures, unexpected detours, joy, and heartache. But it certainly hasn’t been uninteresting.
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