Skip to content

26 Lessons from 26 Years

18 min

Birthdays make me feel all types of ways

Melancholy is the primary one. The British philosopher Alain De Botton defines it as “not rage or bitterness; it is a noble species of sadness that arises when we are properly open to the idea that suffering and disappointment are at the heart of the human experience.” I feel this way because I’m grateful for my present self’s life, and it would be invigorating to relive again

Age is a beautiful benchmark in my timeline of how to make sense of life.  With time to reflect on this birthday, I’ve noticed a wonky fear creep into my narrative. Each year since turning 21 years old, I fear that I am decaying. An image passing the peak of my life pops up. I can’t immediately snap myself out of this haze, though I can channel my melancholy and nostalgia from my 26th year to reflect on my past and use it as a vehicle for wisdom.

Taken after a morning surf session at Diamond Head on O’ahu, Hawaii.

I organized my 26 lessons into four themes: my relationships with myself and others, emotional intelligence, decision making, and my life in Hawaii.

These lessons serve as a crystallization to realize what I pay attention to and what’s important in my life. I am trying to redefine what success means for me in order to recalibrate. I want to lead a life that I enjoy that brings me fulfillment now, rather than waiting for someday in the future.

Relationships with myself and others

1. Be unapologetic.

Permission from anyone but myself is unnecessary.

2. Listen to my body.

My body is smart and it’s a disservice to be ignorant towards it. It’s up to me to notice all the data that my senses and biology notice. With cliffs on all sides of me, while hiking a treacherous mountain, my mind must be silenced to trust the biology I was born into.

3. No one can take away my truth.

How I feel and see the world is personal to me. I am an expert in my experiences. I’m strenuously working to improve myself, so I want to own who I am confident. There’s a time to be humble and there’s a time to state facts. If I know how to race a sailboat, then why would I shy away from sharing my knowledge or experiences?

4. Stand up for myself.

Nobody else will. There isn’t any Clark Kent swooping in right other’s wrongs. I’ve never done so many consulting calls or compensation negotiations in my whole life as I did this past year as a freelancer. I learned to advocate for myself when I felt under-appreciated. I knew I’d regret holding my tongue. I didn’t want to leave that gnarly pit of resentment in myself or towards my clients. I want win-win relationships. I forgave myself for being walked over in previous roles and not knowing that I need to speak up for myself. Thank you to my mentor, Aunt Lindy, for helping teach me this.

5. Express myself because I feel like it.

It can feel impulsive. Do it anyway. You’ll regret not attempting to be heard. There are times to listen and there are times to be heard.

6. Look inward.

Nobody is forcing me to be on the hamster wheel, so shed those expectations. That dialogue in my head is formed from the expectations of society and the people around me. My ego unconsciously adopts it as my own truth. These expectations don’t serve me and I need to be skeptical of what externally shapes my worldview and goals.

7. Welcome out my inner child.

The ceiling for joy can never be reached. Just because our age increases with time, doesn’t mean we need to be grumpy boring adults. We can learn from children and channel our past selves. It allows us to improve creative muscles. My inner child cheers me on to shield me against embarrassment and judgment. I don’t need to be polite all the time. Life surely is a heck of a lot more fun.

8. Eat a banana a day because you want to.

All of my past roommates know this about me and my guilty pleasure with eating bananas every day. They appreciate who I am and don’t expect me to change. I have a new opinion on whether humans rely too much on caffeine and whether the news actually helps humanity. I receive love for who I truly am rather than the version I project or aspire to be. Once I figure something out I realize how many other things I don’t know. These are my lovely quirks.

9. Discover the relationships that are long-lasting.

I’ve lost touch with a handful of group chats, have to reach out in new ways and at strange hours, and make an extra effort to nurture and continue some relationships. It can be overwhelming and isolating at times. But I have also found who really had my back, and those are the people I strive to keep close. And I’ve also opened my world to many new and beautiful souls on the journey as well.

10. Invest in myself.

Buying a course on how to create courses for $2500 last summer was not within the learning budget I set for myself. I made up my mind and decided that purchase was an investment in my learning. On an income statement, I would see that as an expense. When I define it as that, it snowballs into guilt, and that never serves me. The relationship I develop with myself is most important. Trusting my decisions to have a return in the future is the best I can do.

11. Attention is fleeting so cherish it.

It doesn’t serve you to be worrying about the future to jade the present. When times are set to meet friends or focus on writing or focus on fitness, stand by them. Trust yourself to be fully present with where you are in the moment. For Pete’s sake, shut off your technology for a phoneless 48 hours to be present, if that is what it comes to. A reset can always help.

12. Find what you love and do it often.

I absolutely LOVE writing cards. It’s not only a great exercise at practicing writing to a specific audience, but it also exudes gratitude. As I wrote in my annual review, I batch-wrote cards to loved ones every few weeks. It grounds me with proof for my future self that I am caring and thoughtful. When I don’t know who to write a card to, I remind myself to write one to myself to be a part of my self-love practice.

Emotional Intelligence

13. Loneliness is a choice.

While living in a hostel for two months, I was always surrounded by so many new people to connect with. I am an extrovert, but I quickly felt drained and needed space and time alone. It has taken me a while to redefine my choice to be alone and not feel pity for myself for being lonely. It affords me to show up as my best version during other interactions when I choose not to be alone. And if bouts of loneliness ever arise, I notice them and can make a choice about reaching out to a friend if needed.

14. Shake off the guilt.

It is my choice to feel something after I observe the sensation coming on. Judgments from others are most likely projections of their own regrets or insecurities. If someone calls me selfish for going after my dreams to find my truth and live a happier life, then so be it. I don’t need to carry that shame on my shoulders.

15. Every emotion I feel is beautiful.

They are each a part of my experience as a human. They each are worthy of being seen and felt. After being observed, I can stray away from their judgment of them and make a choice about whether a pattern is surfacing.

16. Give my intuition the mic.

I need to lean into that well of faith and trust my conscious mind. Counter to this my gut knows me better than my mind ever will, so they need to partner. When I do this, I can make decisions much more quickly rather than overthinking them.

17. Choose courage over fearlessness.

My fears will never go away. They will only appear in different forms over time. The aspiration to be fearless will never be satisfied. I choose to notice the fear and act on the scary thing in spite of embarrassment, rejection, or self-doubt. I choose courage.

18. Have gratitude for curiosity.

It is the most glorious embodiment of humility that exists. It is what sparks joy and love for thoughts every day.

Decision making

19. Unleash crazy ideas.

Ideas are mere abstract thoughts in our minds. They can be unleashed into the world through journaling. It acts as the welcome mat for ideas to meet the physical world. The place where the abstract becomes real. Practice often.

20. Bias for action rather than overthinking.

If you want to do something eventually what is actually holding you back?? I had an arbitrary goal of wanting to get scuba certified before I was 30. Why not sooner? What was actually holding me back? I no longer wanted to anticipate the idea, but to see it through.  As James Clear has written, “The pain of inaction stings longer than the pain of incorrect action.”

21. Self-awareness is necessary to notice happiness.

When a colleague asked me how I was doing after a month living in Hawaii, I wasn’t exactly sure how to respond. While tempted to be vanilla and say “good”, instead, I shared how I’ve been waking up smiling every day. I couldn’t wait to open my eyes every morning and spend time with the students. She said in return, “so you are happy?!” Emphatically YES. I am happy. This was the first time I can recall ever telling someone I was happy in return to a question about my well-being. That was a huge win for me.

22. Nothing is a sunk cost.

The mistakes and dead ends are worth it. I earned the lessons and the scars. Even though my role as a community and operations manager for an education startup was temporary, it was worth it in forming the bridge to a better life living in Hawaii. Everything I’ve done in my past has led me to where I am today and to discover my worth. I pat my past self on the back– she’s been pretty badass. Sure the road was winding, but if it wasn’t, then it wouldn’t be MY life. It wouldn’t be as interesting as I find it to be.

Life in Hawaii

23. Risk rejection over having regrets.

The ceiling is unimaginable. Life feels more full when I take a risk rather than bottling up ideas. I followed up with Barbara Oakley, one of my heroes, countless times after creating this video for her. I don’t regret doing this. I would’ve rather had this rejection of no response rather than the regret of not sending it in the first place.

24. Sit in comfort over life’s discomfort.

Recognize that life is perpetually transient. Once I’ve realized the impermanence of life, where I sleep at night, the people in my life, it pressures me to have urgency and cultivate presence in my daily life otherwise it will pass me by. The speed of life changes drastically differently in a city vs. a village or an island vs. a continent. But no matter where I choose to live, I will never have control over the majority of my life. Comparison is the thief of joy so choose to find joy in missing out on how you’re choosing not to live.

25. See home in a new light.

It used to be the physical place where I grew up. It feels familiar yet foreign for how detached I am from Michigan. I’ve since redefined home as a dynamic feeling of security, safety and openness to express myself freely. When I feel this way, I want to take notes and share them with whoever is around, and let them know they have made me feel at home in this lonely world.

26. My definition of ambition can be different from the definitions of others.

I have a steadfast attitude toward exploring my path and knowing what brings me joy. That does not mean that others will view me as successful even if I view my life as a success. I used to think “island life and ambition can never be synchronous”. That is a previous self-limiting belief that I’ve challenged and shifted.

Many of these are reminders to myself to continue to live out each day in the present. It is undeniable: life is turbulent. I am pleased to have made a few bits of meaning out of what has happened in this last year of my life.

These 26 lessons are reminders I constantly need to refresh myself on. My future self thanks me for these 26 lessons. In retrospect of my life, they are like new muscles I am relearning each day.

This piece wasn’t written alone. Thank you to my writing friends Dan McGlinn and Brendan Stec and to the Foster community for supporting me in editing this: Caryn Tan, Jesse Evers, and Jason Nguyen

Birthdays make me feel all types of ways

Melancholy is the primary one. The British philosopher Alain De Botton defines it as “not rage or bitterness; it is a noble species of sadness that arises when we are properly open to the idea that suffering and disappointment are at the heart of the human experience.” I feel this way because I’m grateful for my present self’s life, and it would be invigorating to relive again

Age is a beautiful benchmark in my timeline of how to make sense of life.  With time to reflect on this birthday, I’ve noticed a wonky fear creep into my narrative. Each year since turning 21 years old, I fear that I am decaying. An image passing the peak of my life pops up. I can’t immediately snap myself out of this haze, though I can channel my melancholy and nostalgia from my 26th year to reflect on my past and use it as a vehicle for wisdom.


Taken after a morning surf session at Diamond Head on O’ahu, Hawaii.

I organized my 26 lessons into four themes: my relationships with myself and others, emotional intelligence, decision making, and my life in Hawaii. 

These lessons serve as a crystallization to realize what I pay attention to and what’s important in my life. I am trying to redefine what success means for me in order to recalibrate. I want to lead a life that I enjoy that brings me fulfillment now, rather than waiting for someday in the future. 

Relationships with myself and others

1. Be unapologetic.

Permission from anyone but myself is unnecessary.

2. Listen to my body.

My body is smart and it’s a disservice to be ignorant towards it. It’s up to me to notice all the data that my senses and biology notice. With cliffs on all sides of me, while hiking a treacherous mountain, my mind must be silenced to trust the biology I was born into.

3. No one can take away my truth.

How I feel and see the world is personal to me. I am an expert in my experiences. I’m strenuously working to improve myself, so I want to own who I am confident. There’s a time to be humble and there’s a time to state facts. If I know how to race a sailboat, then why would I shy away from sharing my knowledge or experiences?

4. Stand up for myself. 

Nobody else will. There isn’t any Clark Kent swooping in right other’s wrongs. I’ve never done so many consulting calls or compensation negotiations in my whole life as I did this past year as a freelancer. I learned to advocate for myself when I felt under-appreciated. I knew I’d regret holding my tongue. I didn’t want to leave that gnarly pit of resentment in myself or towards my clients. I want win-win relationships. I forgave myself for being walked over in previous roles and not knowing that I need to speak up for myself. Thank you to my mentor, Aunt Lindy, for helping teach me this.

5. Express myself because I feel like it. 

It can feel impulsive. Do it anyway. You’ll regret not attempting to be heard. There are times to listen and there are times to be heard.

6. Look inward. 

Nobody is forcing me to be on the hamster wheel, so shed those expectations. That dialogue in my head is formed from the expectations of society and the people around me. My ego unconsciously adopts it as my own truth. These expectations don’t serve me and I need to be skeptical of what externally shapes my worldview and goals.

7. Welcome out my inner child. 

The ceiling for joy can never be reached. Just because our age increases with time, doesn’t mean we need to be grumpy boring adults. We can learn from children and channel our past selves. It allows us to improve creative muscles. My inner child cheers me on to shield me against embarrassment and judgment. I don’t need to be polite all the time. Life surely is a heck of a lot more fun.

8. Eat a banana a day because you want to. 

All of my past roommates know this about me and my guilty pleasure with eating bananas every day. They appreciate who I am and don’t expect me to change. I have a new opinion on whether humans rely too much on caffeine and whether the news actually helps humanity. I receive love for who I truly am rather than the version I project or aspire to be. Once I figure something out I realize how many other things I don’t know. These are my lovely quirks.

9. Discover the relationships that are long-lasting. 

I’ve lost touch with a handful of group chats, have to reach out in new ways and at strange hours, and make an extra effort to nurture and continue some relationships. It can be overwhelming and isolating at times. But I have also found who really had my back, and those are the people I strive to keep close. And I’ve also opened my world to many new and beautiful souls on the journey as well.

10. Invest in myself. 

Buying a course on how to create courses for $2500 last summer was not within the learning budget I set for myself. I made up my mind and decided that purchase was an investment in my learning. On an income statement, I would see that as an expense. When I define it as that, it snowballs into guilt, and that never serves me. The relationship I develop with myself is most important. Trusting my decisions to have a return in the future is the best I can do. 

11. Attention is fleeting so cherish it. 

 It doesn’t serve you to be worrying about the future to jade the present. When times are set to meet friends or focus on writing or focus on fitness, stand by them. Trust yourself to be fully present with where you are in the moment. For Pete’s sake, shut off your technology for a phoneless 48 hours to be present, if that is what it comes to. A reset can always help. 

12. Find what you love and do it often. 

I absolutely LOVE writing cards. It’s not only a great exercise at practicing writing to a specific audience, but it also exudes gratitude. As I wrote in my annual review, I batch-wrote cards to loved ones every few weeks. It grounds me with proof for my future self that I am caring and thoughtful. When I don’t know who to write a card to, I remind myself to write one to myself to be a part of my self-love practice.

Emotional Intelligence

13. Loneliness is a choice. 

While living in a hostel for two months, I was always surrounded by so many new people to connect with. I am an extrovert, but I quickly felt drained and needed space and time alone. It has taken me a while to redefine my choice to be alone and not feel pity for myself for being lonely. It affords me to show up as my best version during other interactions when I choose not to be alone. And if bouts of loneliness ever arise, I notice them and can make a choice about reaching out to a friend if needed.

14. Shake off the guilt. 

It is my choice to feel something after I observe the sensation coming on. Judgments from others are most likely projections of their own regrets or insecurities. If someone calls me selfish for going after my dreams to find my truth and live a happier life, then so be it. I don’t need to carry that shame on my shoulders.

15. Every emotion I feel is beautiful.  

They are each a part of my experience as a human. They each are worthy of being seen and felt. After being observed, I can stray away from their judgment of them and make a choice about whether a pattern is surfacing.

16. Give my intuition the mic. 

I need to lean into that well of faith and trust my conscious mind. Counter to this my gut knows me better than my mind ever will, so they need to partner. When I do this, I can make decisions much more quickly rather than overthinking them. 

17. Choose courage over fearlessness. 

My fears will never go away. They will only appear in different forms over time. The aspiration to be fearless will never be satisfied. I choose to notice the fear and act on the scary thing in spite of embarrassment, rejection, or self-doubt. I choose courage. 

18. Have gratitude for curiosity.

It is the most glorious embodiment of humility that exists. It is what sparks joy and love for thoughts every day. 

Decision making 

19. Unleash crazy ideas.

Ideas are mere abstract thoughts in our minds. They can be unleashed into the world through journaling. It acts as the welcome mat for ideas to meet the physical world. The place where the abstract becomes real. Practice often. 

20. Bias for action rather than overthinking. 

If you want to do something eventually what is actually holding you back?? I had an arbitrary goal of wanting to get scuba certified before I was 30. Why not sooner? What was actually holding me back? I no longer wanted to anticipate the idea, but to see it through.  As James Clear has written, “The pain of inaction stings longer than the pain of incorrect action.”

21. Self-awareness is necessary to notice happiness. 

When a colleague asked me how I was doing after a month living in Hawaii, I wasn’t exactly sure how to respond. While tempted to be vanilla and say “good”, instead, I shared how I’ve been waking up smiling every day. I couldn’t wait to open my eyes every morning and spend time with the students. She said in return, “so you are happy?!” Emphatically YES. I am happy. This was the first time I can recall ever telling someone I was happy in return to a question about my well-being. That was a huge win for me. 

22. Nothing is a sunk cost. 

The mistakes and dead ends are worth it. I earned the lessons and the scars. Even though my role as a community and operations manager for an education startup was temporary, it was worth it in forming the bridge to a better life living in Hawaii. Everything I’ve done in my past has led me to where I am today and to discover my worth. I pat my past self on the back– she’s been pretty badass. Sure the road was winding, but if it wasn’t, then it wouldn’t be MY life. It wouldn’t be as interesting as I find it to be.

Life in Hawaii

23. Risk rejection over having regrets. 

The ceiling is unimaginable. Life feels more full when I take a risk rather than bottling up ideas. I followed up with Barbara Oakley, one of my heroes, countless times after creating this video for her. I don’t regret doing this. I would’ve rather had this rejection of no response rather than the regret of not sending it in the first place. 

24. Sit in comfort over life’s discomfort. 

Recognize that life is perpetually transient. Once I’ve realized the impermanence of life, where I sleep at night, the people in my life, it pressures me to have urgency and cultivate presence in my daily life otherwise it will pass me by. The speed of life changes drastically differently in a city vs. a village or an island vs. a continent. But no matter where I choose to live, I will never have control over the majority of my life. Comparison is the thief of joy so choose to find joy in missing out on how you’re choosing not to live. 

25. See home in a new light. 

It used to be the physical place where I grew up. It feels familiar yet foreign for how detached I am from Michigan. I’ve since redefined home as a dynamic feeling of security, safety and openness to express myself freely. When I feel this way, I want to take notes and share them with whoever is around, and let them know they have made me feel at home in this lonely world.

26. My definition of ambition can be different from the definitions of others. 

I have a steadfast attitude toward exploring my path and knowing what brings me joy. That does not mean that others will view me as successful even if I view my life as a success. I used to think “island life and ambition can never be synchronous”. That is a previous self-limiting belief that I’ve challenged and shifted.

Many of these are reminders to myself to continue to live out each day in the present. It is undeniable: life is turbulent. I am pleased to have made a few bits of meaning out of what has happened in this last year of my life. 

These 26 lessons are reminders I constantly need to refresh myself on. My future self thanks me for these 26 lessons. In retrospect of my life, they are like new muscles I am relearning each day.

This piece wasn’t written alone. Thank you to my writing friends Dan McGlinn and Brendan Stec and to the Foster community for supporting me in editing this: Caryn Tan, Jesse Evers, and Jason Nguyen

Next

Subscribe to receive the latest posts in your inbox.