May 2022


Digital transformation is not about technology— it’s about change. And it is not a matter of if , but a question of when and how.

In What’s Your Digital Business Model?: Six Questions to Help You Build the Next-Generation Enterprise, the Chairman of MIT Sloan Center for Information Systems Research, Peter Weill and Research Scientist at MIT Sloan Center for Information Systems Research, Stephanie Woerner provide a framework for building next-generation enterprises in an age of digital disruption.

The authors highlight six questions that every organization should seek to answer in their bid to transform their organization.

I participated in my second marathon for the month of may after running the BMO Vancouver Marathon on May 1st, 2022. The Tartan Ottawa International Marathon 2022 was my second time running the Ottawa trail. I finished with a time of 4:37:39, an improvement from the Vancouver Marathon where I finished with a time of 5:00:31.

For the first time since 2007, a Canadian woman won the top prize for the women’s section. American-born Canadian long-distance runner Kinsey Middleton finished with a time of 2:30:09 and Ethiopian Andualem Shiferaw set a new marathon course record with 2:06:04, the fastest time set on North American soil in 2022.

Barack Hussein Obama II was born on August 4, 1961, in Honolulu, Hawaii. Obama served as the 44th president of the United States from 2009 to 2017. He is the first African-American president of the United States and a member of the Democratic Party. Obama had previously served as a U.S. senator from Illinois from 2005 to 2008 and as an Illinois state senator from 1997 to 2004.

Early Childhood

Barack Hussein Obama Jr. was born on August 4, 1961, in Honolulu, Hawaii. He was named after his father, Barack Hussein Obama Sr., Kenyan senior governmental economist who met Obama’s mother, Stanley Ann Dunham, while they were both students at the University of Hawaii. Obama Sr. got a scholarship through a special program to attend college in the United States. His parents married in 1961 and their union was dissolved in 1964.

Obama Sr. won a scholarship for a graduate fellowship in economics at Harvard University. He travelled to Cambridge, Massachusetts alone as the scholarship was not sufficient to support a family. After his degree, he returned to Kenya in 1964 to start work as a government economist.


Writing about his father in his autobiography, A Promised Land, Obama writes:

“Since I didn’t know my father, he didn’t have much input. I vaguely understood that he had worked for the Kenyan government for a time, and when I was ten, he travelled from Kenya to stay with us for a month in Honolulu. That was the first and last I saw of him; after that, I heard from him only through the occasional letter, written on thin blue airmail paper that was preprinted to fold and address without an envelope. “Your mother tells me you think you may want to study architecture,” one letter might read. “I think this is a very practical profession, and one that can be practiced anywhere in the world.”

“I DO KNOW that sometime in high school I started asking questions—about my father’s absence and my mother’s choices; about how it was I’d come to live in a place where few people looked like me”

In 1964, Obama’s mother met Indonesian oil company executive Lolo Soetoro in Hawaii, and they were married in 1967. The family left Hawaii and moved to Indonesia when Obama was six. He spent his early childhood in Indonesia. His half-sister Maya was born in Indonesia in 1970.

In 1971, the ten-year-old Obama was sent back to Hawaii to live with his maternal grandparents and attend Punahou, an elite college preparatory school to which he had attained a scholarship with his grandparents’ help.

“Despite the financial strain, she and my grandparents would send me to Punahou, Hawaii’s top prep school. The thought of me not going to college was never entertained. But no one in my family would ever have suggested I might hold public office someday. If you’d asked my mother, she might have imagined that I’d end up heading a philanthropic institution like the Ford Foundation. My grandparents would have loved to see me become a judge, or a great courtroom lawyer like Perry Mason.”

Education and Early Career

 After two years at Occidental College in Los Angeles, he transferred to Columbia University, where he studied political science and international relations. Following graduation in 1983, Obama worked in New York City, then became a community organizer on the South Side of Chicago, coordinating with churches to improve housing conditions and set up job-training programs in a community hit hard by steel mill closures.

“MY INTEREST IN books probably explains why I not only survived high school but arrived at Occidental College in 1979 with a thin but passable knowledge of political issues and a series of half-baked opinions that I’d toss out during late-night bull sessions in the dorm.”

Columbia University

“After my sophomore year, I transferred to Columbia University, figuring it would be a new start. For three years in New York, holed up in a series of dilapidated apartments, largely shorn of old friends and bad habits, I lived like a monk—reading, writing, filling up journals, rarely bothering with college parties or even eating hot meals. I got lost in my head, preoccupied with questions that seemed to layer themselves one over the next. What made some movements succeed where others failed? Was it a sign of success when portions of a cause were absorbed by conventional politics, or was it a sign that the cause had been hijacked? When was compromise acceptable and when was it selling out, and how did one know the difference?”

For three years in New York, holed up in a series of dilapidated apartments, largely shorn of old friends and bad habits, I lived like a monk—reading, writing, filling up journals, rarely bothering with college parties or even eating hot meals.

Harvard Law School

“And so it was that in the fall of 1988, I took my ambitions to a place where ambition hardly stood out. Valedictorians, student body presidents, Latin scholars, debate champions—the people I found at Harvard Law School were generally impressive young men and women who, unlike me, had grown up with the justifiable conviction that they were destined to lead lives of consequence. That I ended up doing well there I attribute mostly to the fact that I was a few years older than my classmates. Whereas many felt burdened by the workload, for me days spent in the library—or, better yet, on the couch of my off-campus apartment, a ball game on with the sound muted—felt like an absolute luxury after three years of organizing community meetings and knocking on doors in the cold.”

“Enthusiasm makes up for a host of deficiencies, I tell my daughters—and at least that was true for me at Harvard. In my second year, I was elected the first Black head of the Law Review, which generated a bit of national press. I signed a contract to write a book. Job offers arrived from around the country, and it was assumed that my path was now charted, just as it had been for my predecessors at the Law Review: I’d clerk for a Supreme ”

In 1990, Obama became the first African American president of the Harvard Law Review. After graduating from Harvard, he returned to Illinois to teach constitutional law at the University of Chicago and begin a career in public service, winning seats in the Illinois State Senate and the United States Senate.

All the best in your quest to get better. Don’t Settle: Live with Passion.

I remember where I was on November 4th, 2008, when then-Senator Obama was declared the winner of the 2008 U.S Presidential election,  becoming the first African American to become the president of the United States. Obama’s acceptance speech that night made me cry a lot; I had goosebumps hearing him speak and had renewed hope for the future and the power of possibility. The chant of “Yes we can” by those at the Chicago venue made it more inspiring. Obama started the speech with the following lines:

“If there is anyone out there who still doubts that America is a place where all things are possible, who still wonders if the dream of our founders is alive in our time, who still questions the power of our democracy, tonight is your answer.”

I fell in love with Barrack Obama during the 2008 election and I still get goosebumps and teary when I hear him speak. Barrack is one of my favourite living people for his audacity of hope, conviction, sense of purpose and charisma. I took me a while to finish “A promised Land” but it was worth the read.

A Promised Land is Barack Obama’s memoir that focuses on his tenure as the 44th president of the United States from 2009 to 2017. He chronicles his early upbringing, early political campaigns, family life, and his first term as president, and the book ends with the events leading to the killing of Osama bin Laden in 2011. I love Barrack so much that I bought both the 28-hours audiobook version and the 768 pages paperback version. I bought the book in November 2020 but did not get to reading it till around May-June 2022.

A promised Land is a great book that humanizes Obama and made me respect him more. Barrack writes about the challenges in his personal life, such as trying to deal with his smoking addiction, the rollercoaster challenge of balancing his political career with his marriage and family. He also spoke about how he got into politics as a way to inspire others and make sense of his mixed heritage. Barrack shared insights into the decision-making process of various tough decisions that he had to make as the most powerful man in the world. He describes the highs and lows, joys and frustrations, unpredictability, and tensions and how he navigated it with a sense of calm.

 The first volume of his presidential memoirs, Barack Obama tells the story of his improbable odyssey from young man searching for his identity to leader of the free world, describing in strikingly personal detail both his political education and the landmark moments of the first term of his historic presidency—a time of dramatic transformation and turmoil.

A Promised Land – Runaway Bestseller

According to Penguin Random House, the publishers of the memoir: A Promised Land sold more than 3.3 Million units in U.S. and Canada in its first month of publication. International editions have a combined 2.85 million copies in print, bringing the book to 7.55 million copies in print worldwide.

Published on Tuesday, November 17 2020 by Crown, the hardcover U.S. edition of President Obama’s critically acclaimed memoir now has 4.7 million copies in print in the U.S. and Canada, following an initial printing of 3.4 million copies.

Favourite Takeaways from Reading – A Promised Land by Barrack Obama

Seeking Refuge in Books

“Growing up in Indonesia, I’d seen the yawning chasm between the lives of wealthy elites and impoverished masses. I had a nascent awareness of the tribal tensions in my father’s country —the hatred that could exist between those who on the surface might look the same. I bore daily witness to the seemingly cramped lives of my grandparents, the disappointments they filled with TV and liquor and sometimes a new appliance or car. I noticed that my mother paid for her intellectual freedom with chronic financial struggles and occasional personal chaos, and I became attuned to the not-so-subtle hierarchies among my prep school classmates, mostly having to do with how much money their parents had.

And then there was the unsettling fact that, despite whatever my mother might claim, the bullies, cheats, and self-promoters seemed to be doing quite well, while those she considered good and decent people seemed to get screwed an awful lot.

“All of this pulled me in different directions. It was as if, because of the very strangeness of my heritage and the worlds I straddled, I was from everywhere and nowhere at once, a combination of ill-fitting parts, like a platypus or some imaginary beast, confined to a fragile habitat, unsure of where I belonged. And I sensed, without fully understanding why or how, that unless I could stitch my life together and situate myself along some firm axis, I might end up in some basic way living my life alone.”

Mother instilled a reading habit

I didn’t talk to anyone about this, certainly not my friends or family. I didn’t want to hurt their feelings or stand out more than I already did. But I did find refuge in books.

The reading habit was my mother’s doing, instilled early in my childhood—her go-to move anytime I complained of boredom, or when she couldn’t afford to send me to the international school in Indonesia, or when I had to accompany her to the office because she didn’t have a babysitter. Go read a book, she would say. Then come back and tell me something you learned.

Smoking Addiction and quitting

THERE WAS A final stress reliever that I didn’t like to talk about, one that had been a chronic source of tension throughout my marriage: I was still smoking five (or six, or seven) cigarettes a day.
It was the lone vice that had carried over from the rebel days of my youth. At Michelle’s insistence, I had quit several times over the years, and I never smoked in the house or in front of the kids. Once elected to the U.S. Senate, I had stopped smoking in public. But a stubborn piece of me resisted the tyranny of reason, and the strains of campaign life—the interminable car rides through cornfields, the solitude of motel rooms—had conspired to keep me reaching for the pack I kept handy in a suitcase or drawer.

After the election, I’d told myself it was as good a time as any to stop—by definition, I was in public just about anytime I was outside the White House residence. But then things got so busy that I found myself delaying my day of reckoning, wandering out to the pool house behind the Oval Office after lunch or up to the third-floor terrace after Michelle and the girls had gone to sleep, taking a deep drag and watching the smoke curl toward the stars, telling myself I’d stop for good as soon as things settled down.

“Sometimes it didn’t matter how good your process was. Sometimes you were just screwed, and the best you could do was have a stiff drink—and light up a cigarette.”

Finally quitting smoking

“Initially, the pool game had also given me an excuse to duck out and have a cigarette on the third-floor landing. Those detours stopped when I quit smoking, right after I signed the Affordable Care Act into law. I’d chosen that day because I liked the symbolism, but I’d made the decision a few weeks earlier, when Malia, smelling a cigarette on my breath, frowned and asked if I’d been smoking. Faced with the prospect of lying to my daughter or setting a bad example, I called the White House doctor and asked him to send me a box of nicotine gum. It did the trick, for I haven’t had a cigarette since. But I did end up replacing one addiction with another: Through the remainder of my time in office, I would chomp on gum ceaselessly, the empty packets constantly spilling out of my pockets and leaving a trail of shiny square bread crumbs for others to find on the floor, under my desk, or wedged between sofa cushions.”

Faced with the prospect of lying to my daughter or setting a bad example, I called the White House doctor and asked him to send me a box of nicotine gum.

All the best in your quest to get better. Don’t Settle: Live with Passion.

Gamification is the strategic attempt to enhance systems, services, organizations, and activities by creating similar experiences to those experienced when playing games in order to motivate and engage users. Gamification is a great way to motivate/trick yourself into achieving your goals. I have started noticing a pattern in my quest to execute my set goals. I have realized that goals that are attached to a form of play, fun, anchor or regimen are easier to achieve.

By gamifying my goals through the use of an app such as Strava (Leaderboard) for running, swimming and cycling, and Calm App (Streak) for meditation; I have stayed consistent with the goals that I want to achieve. The sense of completion with these apps is very fulfilling as the small acts of completing each activity are so gratifying. I meditate every morning for 26 to 30 minutes by listening to guided meditations from Tamara Levitt, Jhay Shetty and Jeff Warren. The streak and the minutes completed section of the app is one of my favourite things to look forward to daily.

In Learning to Lead: The Journey to Leading Yourself, Leading Others, and Leading an Organization, former chairman and CEO of Aetna, Ronald Williams shares his leadership principles for self-leadership, leading a team and leading an organization. Ron Williams is best known for his leadership at Aetna, where he transformed a $292 million operating loss into $2 billion in annual earnings. He serves as chairman & CEO of RW2 Enterprises, director for American Express, Boeing, and Johnson & Johnson. He holds an MS in Management from MIT Sloan School of Management.

Ron Williams is best known for his leadership at Aetna, where he transformed a $292 million operating loss into $2 billion in annual earnings. He serves as chairman & CEO of RW2 Enterprises, and director for American Express, Boeing, and Johnson & Johnson. He holds an MS in Management from MIT Sloan School of Management.

In Learning to Lead: The Journey to Leading Yourself, Leading Others, and Leading an Organization, former chairman and CEO of Aetna, Ronald Williams shares his leadership principles for self-leadership, leading a team and leading an organization.

If quality is your edge, you can’t compromise it.

Isadore “Issy” Sharp (born October 8, 1931) is a Canadian hotelier, founder, and chairman of Four Seasons Hotels and Resorts. Isadore started his career working with his father, Max Sharp, in the construction business.

The reason for our success is no secret. It comes down to one single principle that transcends time and geography, religion and culture. It’s the Golden Rule – the simple idea that if you treat people well, the way you would like to be treated, they will do the same.

In his memoir entitled Four Seasons: The Story of a Business Philosophy, 1 founder and chairman of Four Seasons Hotels and Resorts, Isadore Sharp, described his business philosophy, the founding of four seasons, and his approach to life.


success is not what you do on your own; it’s how many people have come along with you to reach higher than their expectations ever were.

In Four Seasons: The Story of a Business Philosophy, Canadian hotelier Isadore Sharp shared his life experience and the business philosophy that help him build one of the world’s biggest hotel chains: Four Seasons Hotels and Resorts,

If quality is your edge, you can’t compromise it.

Life happens to us all at some point, some of us are born poor, and dealt with childhood trauma, domestic violence, childhood sexual abuse, and addiction among other challenges. Your history is not your destiny. Where you are right now is who you are. We often mistake our life situation with our destiny but one of the greatest tools we have is our ability to change our course of direction at any point in time by deciding to. As American psychologist, William James once observed; The greatest discovery of my generation is that a human being can alter his life by altering his attitudes.

The greatest discovery of my generation is that a human being can alter his life by altering his attitudes. – William James

Your job and environment are not who you are. One of the most transformative questions, we all have to answer at some point is: “Who are you? Why I am here? The moment you answer these questions and really know what your purpose here is, you are going to go places.

  • Ursula Burns was raised by her immigrant mum in poverty but against all odds was named the CEO of Xerox, making her the first African American woman CEO of a Fortune 500 company.
  • Indra Nooyi grew up in India with humble beginnings but rose to become the CEO of Pepsico which is the second-largest food and beverage company in the world.
  • Viola Davis grew up in abject poverty, domestic violence, childhood trauma and brokenness but she overcame it all to become one of the most recognized faces on TV with an Oscar, Primetime Emmy Award and two Tony Awards becoming the only African-American to achieve the Triple Crown of acting.

How did these 3 inspiring women who grew up in challenging environments rise to the top of their professions against all odds and challenges stacked against them? They decided to take their destiny in their hands, they studied hard, built relationships, created their luck, prepared for their opportunities and executed relentlessly. Here are some great insights from the biographies of these 3 great women on how they did it:

In her autobiography, Where You Are Is Not Who You Are: A Memoir, the first African American woman CEO of a Fortune 500 company, Ursula Burn chronicles her story of growing up in poverty and the lessons learned on her path to greatness. She writes:

As a Black woman, I had to prove myself worthy of whatever position I was in because my coworkers would cut me no slack. I hadn’t slept my way up the chain. I wasn’t the recipient of preferential treatment. I wanted to make sure that the audience knew that I’d earned my position. To do that, I made sure they understood that I knew at least as much as anyone in the room. It was a defense mechanism against the assumption that I didn’t belong.

“My mother refused to have her children be defined by it. “Where you are is not who you are,” she told us time and again. I didn’t know what she was talking about.


Poverty has a pace, and the sidewalks were crowded with people rushing around in a frantic fashion, people racing great distances to save $1 here or there or hurrying to stand in line for a handout.

Indra Nooyi grew up in India and was named PepsiCo CEO in 2006 making her the first woman of colour and immigrant to run a Fortune 50 company.  In her autobiography, My Life in Full: Work, Family, and Our Future, she writes about her journey from rural India to leading a multinational company.

Mine is not an immigrant story of hardship—of fighting my way to America to escape poverty, persecution, or war. I don’t know what it feels like to be a refugee, homeless because my own country is in crisis. I spoke English. I had landed in the US with $500. I was at Yale. And I had the safety net of my family in India, a place that I was familiar with and loved and that would take me back.


“I had no money to spare. My scholarships and loans totaled about $15,000 a year, roughly evenly split, and I spent almost all on tuition, room, and board. I took a job working the front desk and the manual switchboard at Helen Hadley Hall three to four days a week, earning $3.85 an hour for midnight to 5 a.m. That was fifty cents an hour more than the daytime slot and $1.20 more than the minimum wage, which was $2.65 in those days. When the phone rang at reception, I’d buzz a resident’s room and put the call through to the hallway phone. All night, students ran down the hall in their nightwear and slippers to get their calls. I monitored the front door, sorted the mail, and did my homework.”


In Finding Me: A Memoir, American actress Viola Davis describes her roller-coaster journey from growing up in abject poverty to Hollywood fame. She writes:

“We were “po.” That’s a level lower than poor. I’ve heard some of my friends say, “We were poor, too, but I just didn’t know it until I got older.” We were poor and we knew it. There was absolutely no disputing it. It was reflected in the apartments we lived in, where we shopped for clothes and furniture—the St. Vincent de Paul—the food stamps that were never enough to fully feed us, and the welfare checks. We were “po.” We almost never had a phone. Often, we had no hot water or gas. We had to use a hot plate, which increased the electric bill. The plumbing was shoddy, so the toilets never flushed.

You know, when you’re poor, you live in an alternate reality. It’s not that we have problems different from everyone else, but we don’t have the resources to mask them. We’ve been stripped clean of social protocol. There’s an understanding that everyone is trying to survive and who is going to get in the way of that?

As the stories of these great women shows, your history is not who you are and with persistence and commitment, all things are possible. Inspite of their humble background, Ursula Burns became the CEO of XEROX, Indra Nooyi became the first African American woman CEO of a Fortune 500 company and Violas Davis became an Hollywood superstar despite the poverty, abuse and trauma of her childhood.

All the Best in your quest to get Better. Don’t Settle: Live with Passion.

American singer-songwriter and 11-times Grammy Award Winner Taylor Swift delivered the commencement speech to the graduating students of New York University. Taylor was awarded an honorary doctorate degree wherein she spoke about embracing your struggles and owning your mistakes.

Taylor Swift’s 2022 New York University Commencement Speech Transcript:

Hi, I’m Taylor [Applause]

The last time I was in a stadium this size I was dancing in heels and wearing a glittery leotard this outfit is much more comfortable. I would like to say a huge thank you to NYU’s chairman of the board of trustees Bill Berkley and all the trustees and members of the board NYU’s President Andrew Hamilton, Provost Catherine Fleming, and the faculty and alumni here today who have made this day possible.

I feel so proud to share this day with my fellow honorees Susan Hockfield and Felix Matos
Rodriguez who humble me with the ways, they improve our world with their work as for me
I’m 90 percent sure the main reason I’m here is because I have a song called 22. And let me just say
I am elated to be here with you today as we celebrate and graduate from New York University’s class of 2022.

Not a single one of us here today has done it alone we are each a patchwork quilt of those who have loved us those who have believed in our futures those who showed us empathy and kindness
or told us the truth even when it wasn’t easy to hear those who told us we could do it when there was absolutely no proof of that someone read stories to you and taught you to dream and offered up some moral code of right and wrong for you to try and live by someone tried their best to explain every concept in this insanely complex world to the child that was you as you asked a bazillion questions like how does the moon work and why can we eat salad but not grass and maybe they didn’t do it perfectly no one ever can maybe they aren’t with us anymore in that case, I hope you’ll remember them today.

If they are in this stadium i hope you’ll find your own way to express your gratitude for all the
steps and missteps that have led us to this common destination.

I know that words are supposed to be my thing but I will never be able to find the words to thank my mom and dad, and my brother Austin for the sacrifices they made every day so I could go from
singing in coffee houses to standing up here with you all today because no words would ever be enough to all the incredible parents, family members, mentors, teachers, allies, friends, and loved ones here today who have supported these students in their pursuit of educational enrichment
let me say to you now welcome to new york it’s been waiting for you.

I’d like to thank NYU for making me technically on paper at least a doctor [Applause] not the type of doctor you would want around in case of an emergency unless your specific emergency was that
you desperately needed to hear a song with a catchy hook and an intensely cathartic bridge section or if your emergency was that you needed a person who can name over 50 breeds of cats in one minute. [Applause]

I never got to have a normal college experience per se. I went to public high school until 10th
grade and then finished my education doing homeschool work on the floors of airport terminals
then I went out on the road for a radio tour which sounds incredibly glamorous but in reality it consisted of rental car motels and my mom and I pretending to have loud mother-daughter fights with each other during boarding, so no one would want the empty seat between us on the southwest.

As a kid, I always thought I would go away to college imagining the posters I would hang on the wall of my freshman dorm. I even set the ending of my music video from my song love story at my fantasy imaginary college where I meet a male model reading a book on the grass and with one
single glance we realized we had been in love in our past lives which is exactly what you guys all
experienced at some point in the last four years right. [Applause]

But I really can’t complain about not having a normal college experience to you because you went to NYU during a global pandemic being essentially locked into your dorms and having to do classes over zoom. Everyone in college during normal times
stresses about test scores
but on top of that
you also had to pass like a thousand
kova tests
i imagine
the idea of a normal college experience
was all you wanted to
but in this case
you and i both learned that you don’t
always get all the things in the bag
that you selected from the menu
in the delivery surface that is life
you get what you get
and as
i would like to say to you
wholeheartedly you should be very proud
of what you’ve done with it
you leave new york university
and then go out into the world
searching what’s next and so will i


so as a rule
i try not to give anyone
unsolicited advice
unless they ask for it
i’ll go into this more later
i guess i have been officially solicited
in this situation to impart
whatever wisdom i might have
to tell you things that have helped me
so far in my life
please bear in mind that i in no way
feel qualified to tell you what to do
you’ve worked
and struggled and sacrificed and studied
and dreamed
your way here to dare
and so
you know what you’re doing
you’ll do things differently than i did
and for different reasons so i won’t
tell you what to do because no one likes
that i will however
give you some life hacks i wish i knew
when i was starting out my dreams of a
and navigating life
love pressure
hope and friendship
the first of which is
can be heavy
especially if you try to carry it all at
part of growing up
and moving into new chapters of your
is about catch and release
what i mean by that is
knowing what things to keep
and what things to release
you can’t carry all things
all grudges
all updates on your ex
enviable promotions your school bully
got at the hedge fund his uncle started

what is yours to hold
and let the rest go
oftentimes the good things in your life
are lighter anyway
so there’s more room for them
one toxic relationship
can outweigh so many wonderful simple
you get to pick
what your life has time and room for
be discerning
learn to live
no matter
how hard you try to avoid being cringe
you will
look back on your life
and cringe retrospectively

is unavoidable over a lifetime
even the term cringe might someday be
deemed cringe
i promise you
you’re probably doing or wearing
something right now
that you will look back on later and
find revolting and hilarious
you can’t avoid it so don’t try to
for example
i had a phase where for the entirety of
i dressed like a 1950s
but you know what i was having fun
trends and phases are fun
looking back and laughing is fun
and while we’re talking about things
that make us squirm but really shouldn’t
i’d like to say i’m a big
advocate for not hiding your enthusiasm
for things

it seems to me that there is a false
around eagerness
in our culture of unbothered
this outlook perpetuates the idea that
it’s not cool to want it
the people who don’t try are
fundamentally more chic than people who
and i wouldn’t know because i’ve been a
lot of things but i’ve never been an
expert on chic but i’m the one who’s up
here so you have to listen to me when i
say this
be ashamed
of trying
is a myth
the people who wanted it the least were
the ones i wanted to date and be friends
in high school
the people who want it the most
are the people i now hire to work for my

i write i started writing songs when i
was 12
and since then
it’s been the compass guiding my life
and in turn
my life guided my writing
everything i do
is just an extension of my writing
whether it’s directing videos or a short
creating the visuals for a tour
or standing on a stage performing
everything is connected
by my love of the craft
the thrill of working through ideas and
narrowing them down
and polishing it all up in the end
editing waking up in the middle of the
night throwing out the old idea because
you just thought of a new or better one
or a plot device that ties the whole
thing together
there’s a reason they call it a hook
sometimes a string of words
ensnares me and i can’t
focus on anything until it’s been
recorded or written down
as a songwriter i’ve never been able to
sit still or stay in one creative place
for too long
i’ve made and released 11 albums and in
the process i’ve switched genre from
to pop to alternative to folk
and this might sound like a very
line of discussion
but in a way
i really do think
we are all
and most of us
write in a different voice for different
you write
differently in your instagram stories
then you do your senior thesis
you send a different type of email to
your boss than you do your best friend
from home
we are all literary chameleons and i
think it’s fascinating
it’s just a continuation of the idea
that we are so many things all the time
i know it can be really overwhelming
figuring out who to be and when
who you are now
and how to act in order to get where you
want to go
i have some good news
it’s totally up to you
i have some terrifying news
it’s totally up to you
i said to you earlier that i don’t ever
offer advice
unless someone asked me for it and now
i’ll tell you why
as a person who started my very public
at the age of 15 it came with a price
and that price
was years
of unsolicited advice
being the youngest person in every room
for over a decade
that i was constantly being issued
from older members of the music industry
media interviewers executives and this
often presented itself
as thinly veiled warnings
see i was a teenager
at a time when our society was
absolutely obsessed with the idea
of having perfect
young female role models
it felt like every interview i did
included slight barbs by the interviewer
about me one day
running off the rails
and that meant a different thing
to every person who said it to me so
i became a young adult while being fed
the message
that if i didn’t make
any mistakes
all the children of america
would grow up to be perfect angels
however if i did slip up
the entire earth would fall off its axis
and it would be entirely my fault and i
would go to pop star jail
forever and ever
it was all centered around the idea
that mistakes
and ultimately
the loss
of any chance at a happy or rewarding
has not been my experience
my experience has been
that my mistakes
led to the best things in my life
being embarrassed when you mess up
is part of the human experience
getting back up
dusting yourself off
and seeing who still wants to hang out
with you afterward and laugh about it
that’s a gift
the times i was told no
or wasn’t included
wasn’t chosen didn’t win didn’t make the
looking back it really feels like those
were as important if not more crucial
than the moments i was told yes
not being invited
to the parties and sleepovers in my
made me feel hopelessly lonely
but because i felt alone
i would sit in my room and write the
songs that would get me
a ticket somewhere else
having label executives in nashville
tell me
that only 35 year old housewives
listened to country music
and there was no place for a 13 year old
on their roster
made me cry in the car on the way home
but then
i’d post my songs on my myspace
and yes myspace
and i would message with other teenagers
like me who loved country music but just
didn’t have anyone singing from their
having journalists write in-depth
oftentimes critical pieces about who
they perceive me to be
made me feel like i was living in some
weird simulation
but it also made me look inward
to learn about who i actually am
having the world treat my love life like
a spectator sport in which i lose every
single game
was not a great way to date in my teens
and twenties
but it taught me
to protect my private life fiercely
being publicly humiliated over and over
again at a young age was excruciatingly
but it forced me
to devalue the ridiculous notion
of minute by minute
ever fluctuating social relevance and

getting cancelled on the internet
and nearly losing my career
gave me an excellent knowledge of all
the types of wine
i know i sound
like a consummate optimist but i’m
really not
i lose perspective
all the time
just feels completely pointless
i know the pressure
of living your life through the lens of
perfectionism and i know that i’m
talking to a group of perfectionists
because you are here today
graduating from nyu
so this might be hard for you to hear
in your life
you will inevitably
trust the wrong person
under react
overreact hurt the people who didn’t
deserve it
not think at all
create a reality where only your
experience exists
ruin perfectly good moments for yourself
and others deny any wrongdoing
not take the steps to make it right feel
very guilty
let the guilt eat at you hit rock bottom
finally address the pain you caused try
to do better next time rinse repeat


and i’m not going to lie
these mistakes will cause you to lose
i’m trying to tell you
that losing things
doesn’t just mean losing
a lot of the time
when we lose things
we gain things too
now you leave the structure and
of school
and chart your own path
every choice you make leads to the next
choice which leads to the next and i
know it’s hard to know
which path to take
there will be times in life where you
need to stand up for yourself
times when the right thing is actually
to back down and apologize
times when the right thing is to fight
times when the right thing is to turn
and run
times to hold on with all you have
and times to let go with grace
sometimes the right thing to do is to
throw out the old schools of thought in
the name of progress and reform
sometimes the right thing to do is to
sit and listen to the wisdom of those
who have come before us
how will you know
what the right choice is in these
crucial moments
you won’t
how do i give advice to this many people
about their life choices
i won’t
the scary news is
you’re on your own now
but the cool news is
you’re on your own now

i leave you with this
we are led
by our gut instincts
our intuition
our desires and fears our scars and our
and you will screw it up sometimes
so will i and when i do you will most
likely read about it on the internet
anyway hard things will happen to us
we will recover
we will learn from it
we will grow more resilient because of
and as long as we are fortunate enough
to be breathing
we will breathe in
breathe through
breathe deep
and breathe out
and i am a doctor now so i know how
breathing works
i hope you know
how proud
i am
to share this day with you
we’re doing this together
so let’s just keep dancing like we’re
the class of 22.

One night I had a dream…

I dreamed I was walking along the beach with the Lord, and
Across the sky flashed scenes from my life. For each scene I noticed two sets of footprints in the sand; One belonged to me, and the other to the Lord. When the last scene of my life flashed before us, I looked back at the footprints in the sand. I noticed that many times along the path of my life, There was only one set of footprints.

I also noticed that it happened at the very lowest
and saddest times in my life
This really bothered me, and I questioned the Lord about it.
“Lord, you said that once I decided to follow you,
You would walk with me all the way;
But I have noticed that during the
most troublesome times in my life,
There is only one set of footprints.
I don’t understand why in times when I
needed you the most, you should leave me.

The Lord replied, “My precious, precious
child. I love you, and I would never,
never leave you during your times of
trial and suffering.
When you saw only one set of footprints,
It was then that I carried you.