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25 Lessons from 25 Years

12 min

Birthdays tend to make me feel all types of ways. It’s usually heaps of excitement, dollops of love, scoops of gratitude, dashes of reflection, sprinklings of joy throughout, and a hint of melancholy. Yet this year feels different than others. Not quite stolen but fast-forwarded. I didn’t have clear expectations of where I’d be today, but I know I am far from whatever was on the agenda. I’m slowly realizing life tends to do that.

These lessons are helping me crystallize ideas and realize what’s important in my life. I am trying to redefine what success means for me in order to navigate my own compass and recalibrate from here. I want to lead a life that I enjoy, and that brings me richness now rather than waiting for someday in the future. This one year changed my life.

The debut of being a hand model.
My debut as a hand model.

I organized my lessons into four themes: I learned five things from losing my job, five things about learning, eight things on reinventing myself, and seven things about relationships 

Job Loss

1.Mood follows action.

Focus on what is in your control.  I think I slept more at the end of April than I ever had in my whole life. I didn’t have a sense of purpose as a large piece of my identity was torn away from me without a job. Later I discovered this is what depression is like where it swallows you whole. I was such a victim after losing my job and canceling my travel plans. I thought the world was against me.

If you’ve got 8 plus hours of sleep, force yourself to get going. Ruts build on themselves but so do actions. You don’t need to feel good to get going. You get going and then you feel good. This is why I started using an accountability tracker to partner with me as a tool to see what I was actually moving the needle on. Your beliefs are implicit in your actions. For example, I believe reflection is a key part of life, so I journal every day whether I feel like it or not. I believe in having trial periods in life to act on and choose to be deliberate about habits. Be intentional and after acting on them, I can better distinguish whether a cold shower is something I really believe in. 

2. Don’t dither on answers that aren’t there. 

In the words of one of my favorite musical artists, Mike Posner, Move On.  I wrote myself a letter at the end of 2019 as if I were writing a friend’s advice. This was something perk performance coach and author Brad Stulberg recommended I do on his community call. This exercise is also called Solomon’s Paradox. I integrated a SWOT analysis of my job at Korn Ferry after being there for six months. I felt like I didn’t have a compass of where I was going like my potential was under-indexed, but it was hard to come to terms with. That 15-minute call with the head of HR on my calendar was one of the bigger blindsides I ever received. I felt like I was the chosen one and I didn’t know why. There weren’t any answers and I hated it. Since I have realized that sometimes there aren’t answers and you just need to focus on what you do know. For me, that was running month-long experiments and trying to figure out more of who I am and what lights me up. 

3. Rewrite your story. 

My loss of a corporate job was a great way to pull the carpet out from under me. It forced me to really ask myself what I wanted to spend my time doing and who I was. I feel empowered to have ownership over my time, the freedom to explore my curiosities, and the choice of who I want to work with. I have found more of my voice. Without there being a ladder in a formal sense at startups, it’s forced me to stay more present at what’s in my control now. It feels like I am being paid to be a rigorous student. This is a dream come true. So, when gaining life experiences, empower yourself through the stories you share to make meaning to others. These will at the end of the day define who you are. If you do not provide additional context while explaining yourself to others, then you are allowing the world to choose who you are. I learned this when I started sharing that I have dyslexia and what it means for me.  

4. Don’t overlook dividends. 

By living at my childhood home for four months, I saved money that I historically spent on groceries, the train, and social events. Despite this, I financially felt like the least productive person in my life without an inflow of cash. A sad sack you might say. My stock portfolio felt otherwise and had a mind of its own that excelled past my expectations. In essence, I was making money while I slept. Because I canceled trips, I reinvested that budget amount into the market instead. This has been a decision I am grateful for and will continue to make moving forward. 

5. Take more risks. 

Missed opportunities become ingrained into your skull. The person you didn’t send the email draft to. The questions you didn’t raise your hand to ask.  The inaction builds up in your memory and creates “shoulda coulda woulda’s” in life that keeps you up late at night. Taking risks helps you find the edge of your comfort zone. Ask yourself: what’s the worst that can happen? Nobody is actually paying that much attention to you. Stop giving a damn of what others think and think about what your future self would want you to do. 


6. Keep a fucket list. 

It’s like a bucket list but better. One of my heroes, Jesse Itzler introduced me to this concept of a Fucket list in his course a couple of years ago. These are all things that you want to experience someday for no point other than that you are curious about them or think they’d bring joy to your life. For me, some of these things are: to live abroad for at least a year to be culturally immersed, to go skydiving, to teach creativity, to become PADI certified, to become fluent in a second language. 

7. Planning instead of plans.

 As Dwight D. Eisenhower said, “Plans are worthless, but planning is everything.” Plans are stagnant, so instead opt for planning. I could have never seen the two job opportunities I landed come my way. I never sent cover letters or felt like I had to be a different version of myself. These were both friends. One I met at the Next Gen Summit and another in a breakout room of an online class who both became clients. The same goes for plans for what you want to learn. You could have a completely regimented schedule with a slew of classes to take and books to read, but if your energy is pulled elsewhere, start planning again. Choose to be fluid rather than stagnant. 

8. Have intentionality with learning. 

This is why I love courses so much. You get thrown into the deep end with the support of so many things you never had an inkling to exist. There is a map presented to you with what you’ve learned, where you need to unlearn, and the shifts in your mindset to get you to the light at the end.

9. If you don’t ask, you won’t receive. 

Sure, being humble is a nice gesture, but if you don’t put yourself out there and get rejected, you’ll never know how far is too far. I got admitted to a couple of online courses in 2020 because I was honest with my finances. In return, I received money off to be able to join in. These opened doors to joining communities of people that I want to be more like by surrounding myself with. Those experiences helped me make me the person I am today, so I am beyond grateful that I spoke up. 

10. Write online and don’t stop.

Over this past year, I discovered the world of online writing. Write of Passage was the game-changer for me. It opened my eyes to the possibilities of online writing. It took me three times of the course to finally feel like I was living out what is taught. Many of my most proud accomplishments stemmed from the tools I learned in this course of starting my newsletter and writing online. I believe in this to my core and I am excited to see what other magic can happen as I continue to write online.


11. Evidence breeds confidence.

If you ever think that you are incompetent, do it a bunch of times to prove to yourself that you are not and then you will believe it. It is through taking action that these fears can be overcome. For altMBA, I stepped up my game to maximize this tool and created a personal challenge to ship an article for 100 days. The closet writer Jen in 2019 could not fathom this as being possible. In my past year of writing my word count has surpassed 100,000 published words online.

12. Trust in yourself to manifest your desires. 

Much of my life today was manifested in my journal last year. I wrote that I missed being surrounded by creative people in the fall of 2019. Every day now I have the opportunity to connect and be inspired. Through this, I’ve found that daily journaling is more than nice-to-have. It is a non-negotiable. It is part of who I am now so I do not feel a need to set a metric for it. I’ve convinced many people on Twitter and friends to start journaling by sharing my Art of Journaling practice more. 

13. Know WHY you are pursuing something. 

When the rationale is clearly in alignment with your essence then you don’t double guess yourself down the road. You can go full-force into it. A helpful question is to ask yourself: Will this matter to you 10 years from now? I know writing already started to pay dividends, so I have chosen to commit and contract myself to write.

14. Set boundaries. 

Don’t underestimate the use of tools to help you get away from your vices. Freedom Software is a lifesaver. Accept the fact that your human biology is addicted to dopamine. Set boundaries. Two weekends ago, I pursued a Think Weekend where I unplugged for 60 hours from screens for solitude by myself to read, write and think. It is always refreshing to realize that life is beautiful and can be lived perfectly well without being connected online or being milliseconds away from a genie who can answer almost any question for you. Sometimes the boundaries feel like I am giving the teenage version of myself a curfew, but without the boundaries, it’s easy to give into loops of behaviors we don’t admire. Try sleeping without your phone in a different room and buy a good ol’ alarm clock. 

15. Be the scientist and run experiments.

René Descartes was one of the first modern philosophers who wrote about the scientific method back in 1637. We can all benefit from still using this lens on life where a test of an alleged truth has clarity by seeing if it is true or false. You don’t really know if something will work for you so give it a go. Seek to gain clarity through action, not thought. Ask yourself: what is the smallest action I can experiment with to see if I like this? An example for me was last November I tried meditating every day and couldn’t maintain it. I opt to get my thinking time now on my morning flânerie strolls to clear my head. 

16. Do things that make you feel young again. 

Just because you’re not getting any younger doesn’t mean you can’t bring out your inner child. I left the warmth of a jacuzzi on Christmas Eve to run around the house in the snow in a bathing suit. Why? Just for the heck of it. Ask yourself what different lives would look like today if you pursued those aspirations you once had. I looked up to Amelia Earhart, Anne Frank, and Vincent Van Gogh in elementary school. I am now still aspiring to be more like them in their adventure, storytelling, and creative ability. Imagination is key here. Seep into a dreamer’s frame of mind.

17. Systems shape who you are and shift your identity.  

I know I’ve read it again and again in James Clear’s Atomic Habits book that your actions will shape you into who you are, but it actually happened this year. I am in shock. I identify myself as a writer. A creator. I began systemizing my writing process and my creative process this year. Much of this system has been taking many many walks outside. Spending copious amounts of notes in my personal knowledge management system called my second brain that Tiago Forte taught me how to build in BASB.

18. People you surround yourself with matter so be choosy. 

When I started to become a writer, I needed to be surrounded by other writers who were in the arena taking action publishing. One that I have loved being a part of is Foster. I could look up to them to lean on them for support. Sure there are the folks in your life you don’t necessarily choose to be around but take agency over your life and who is in it when it is in your control.


19. Your health is your wealth, so invest in it- physically, mentally, and emotionally. 

Don’t feel the need to justify an investment in your health. I bought a $65 Hydroflask water bottle over the summer that felt absurd. It was an investment in my hydration that I still use almost every day as a reminder to myself of my health. How are you supposed to know what is going on in your head if you can’t reflect it outwards or communicate it? Therapists are amazing people who can help make sense of understanding these. They see things that you are too close to understand. Sounding boards are essential to externalize and understand what is going on internally. Maybe your consumption diet on the Internet needs to be tweaked to save your future self.

20. Go out on a whim to connect with someone. 

For Pete’s sake, my first time making money online was producing a wedding online over Zoom. I never saw that happening, but it did. Another one of my roles this past year was managing a career accelerant course. This all started over a random Zoom breakout room. That connection spiraled into much more that I’m beyond grateful for. You never know what doors can be opened from a new friend. Send the direct message on Twitter to take a conversation offline. 

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22. Embrace imperfections– they make you, you.  

They are not everything that makes you but acknowledge they are a piece of the pizza pie. They make us human and that is a beautiful thing to be. We are all born to be different, so let’s embrace that. Perhaps my genetics granted me grey early on. Yes, my eye vision keeps getting worse. Yes, I’m insecure of my stretch marks. Yes, I am beyond grateful that no one has to shake my clammy hands for job interviews. It’s okay that we’re all different. That can be celebrated for making us all human. Being human is cool. 

23. start Create that fucket list. If it’ll be a story worth sharing that you’ll be happy to re-share with others, then go for it. As 2021 rolled in, I was talking with my roommates about how two out of the three of us would die if thrown off a bridge and had to pull ourselves up. To change this, we ordered a pull-up bar for our apartment to started a challenge. I’m still the weakest of the bunch with the most room for improvement, but I am going to be able to do one pull-up before the end of this year. Currently, I laugh that I have seen zero progress in a month. Keeping it light makes it more enjoyable and funny.

24. True connection can be cultivated online. 

I think I counted myself having cried on Zoom at least four times this year with a room of people you think I’d call strangers since I hadn’t met them in real life before. Feeling this emotion along with goosebumps was a breakthrough to me. Yes, it is lonely to not have physical contact, but also technology is miraculous. Much that you don’t think can be felt across a screen actually can. 

25. Seek self-knowledge. 

Go take all the assessments in the world and try to find answers to describe yourself better, but don’t forget to have a magnifying glass on your own actions. I failed history countless times in school, but here I am writing historical stories for a podcast with timeless wisdom. I  never really liked science in school but now  I own my scientific mental model of life where I constantly hypothesize and see what I should change. As for me, I quit drinking caffeine in December and then alcohol in January. Trial and error and recalibrate where needed. Make rules for yourself to experiment and gain self-knowledge. Break them as needed.


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.

This essay was not written alone. Thank you to everyone who offered feedback. This includes: Gwyn Wansbrough, Ayomide Adebayo, Dan Hunt, Diana Hawk, Ergest Xheblati, Steven Ovadia, Jamie Russo


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