Odds and Opportunities
How? is the Wrong Question
11 Insights from Michelle Obama’s Becoming that WILL make You a Better Person
Only 14 US Presidents and 11 First Ladies have served two terms, and only five US Presidents and four First Ladies are still living. It seems impossible, doesn’t it?
“Barack and I were joining a strange and very small society made up of the Clintons, the Carters, two sets of Bushes, Nancy Reagan, and Betty Ford. These were the only people on earth who knew what Barack and I were facing, who’d experienced firsthand the unique delights and hardships of life in the White House. As different as we all were, we’d always share this bond.”Michelle Obama
We are always so eager to align ourselves with others, to join clubs, to find our people, to identify as part of the cool kids. And, on the other hand, we naturally think of ourselves as special, unique, or as having extenuating circumstances. Maybe we believe that our career is a big deal or that our kid has exceptional talents. Perhaps we have a title, or a background, or a history that sets us apart.
My husband’s dream job is to be the voice of an NBA team. There are only 30 teams and approximately 74 million working men in the US. I didn’t include the nearly 66 million working women, because a woman has never held that role. While not all working people aspire to be play-by-play broadcasters, of the 30 team jobs theoretically available, most are filled by someone who will hold the job for life. No one who lands that job is eager to vacate, and some play-by-play broadcasters can be the voice of a team for their entire careers. All that to say, turnover is low, and the odds are not in his favor.
But what do the odds have to do with it? I mean, really. What are the odds of President Barack Obama? Of President Donald Trump? Of Oprah? Or Queen Elizabeth II? Or, for that matter, Meghan Markle? People overcoming the odds is invaluable to the human experience.
When something is important enough, we go for it, no matter the odds. Sometimes, it’s not about winning or achieving the goal anyway. Sometimes, it’s about becoming the person you must become to give yourself the best possible chance of success. Then, no matter the outcome, you’ve won.
It’s one of the reasons I was so eager to read Michelle Obama’s Becoming. I was excited because I love her; her story is impressive, as is her willingness to share her evolution. The timing was also a draw. She and her husband were in the White House from 2009–2017, which corresponded to ages 34–42 for me. Those were the years we got married, survived cancer, and became parents. Until Becoming, I thought we had a lot on our plates.
Let’s go back in time for a moment. During the 2008 presidential election, we were putting the final touches on our wedding in Vail and our honeymoon in the Mediterranean. I had a vague peripheral sense of the historic nature of the pending election, was a big fan of Hillary Clinton and Barack Obama, and felt a general sense of optimism, both about our lives, and the progress of our nation. Still, I wouldn’t have considered myself particularly politically motivated and I wasn’t paying full attention.
On our honeymoon, we spent a month touring Mallorca, Tunisia, Dubrovnik, Corfu, Nice, Eze, Monte Carlo, Malta, Taormina, Olympia, Santorini, Rome, Barcelona, Florence, Pisa, the Almalfi Coast, and more. It was by far the biggest trip of our lifetimes, and we were kids in a candy store, soaking it all up, marveling at historical wonders, exotic sites, and basking in the sun and romance.
We were also missing out on the 2008 Democratic National Convention in Denver, our hometown.
And since it was 2008, connectivity was not at all like it is today. Take a look at those stops. A lot of our destinations were remote, or even off the grid. We had Blackberries with international roaming. Still, we rarely checked in, were hardly on social media, and most of the news programming we saw was local, or BBC, which meant a uniquely international take on the US presidential nominees. There wasn’t as much vitriol if you’re wondering; that was the most apparent difference.
At the time, it didn’t seem that important. Looking back, and certainly contrasting it to the previous and upcoming US presidential elections, I realize how informative, and how pivotal it was to process it from a distance, with a little healthy emotional detachment.
Ok, that was a lot of lead up. I wanted to set the stage and remind myself, and all of you, just how fast life goes, how much changes in a blink, (Obama to Trump, and everything else changed from 2009 —2020), and how, at the same time, we can just bob along in our inner tubes, floating down the river of life, letting the current control our direction. While it’s not all bad, that approach may leave us feeling a little like life passed us by or that we missed the moment, or moments, a series of opportunities to do something amazing with our lives.
If nothing else, the thing that stood out to me in this book was how much Michelle and Barack packed into their years. Their lives were full before the White House, but during those eight years, they lived several lifetimes. Like I wrote about here, we had a relatively full decade, and it is laughable in comparison. Not that I’m comparing (see #9).
“Time seemed to loop and leap, making it feel impossible to measure or track. Each day was packed. Each week and month and year we spent in the White House was packed. The velocity was too great, the time for reflection too limited.”Michelle Obama
Her pace is staggering, and I’m sure she could have shared so much more. After all, her husband’s most presidential moments, the historical activities, and behind-the-scenes details were mostly not included, and still, the pace was breathless. How intentional was she to write it down, to make notes and capture photos, and document it in some way to be able to recount it and turn it around in a book so soon after it happened? Bravo, and thanks.
Breathless and scrutinized by the way. Imagine being on that world stage, having to perform every waking moment, and God forbid, if you misstep, the world will judge you, and your family, gender, and race, by extension. I feel like a football interviewee cliche when I say this, but my hat’s off to you, Michelle, you played a helluva game. Your poise, strength, tenacity, and endurance are the stuff of legends.
So going with that analogy, let’s breakdown her playbook and apply the lessons, so we too can have amazing lives. It’s not too late, by the way, for any of us.
1. When you find yourself in the enviable position of being flush with opportunities, take full advantage. Don’t hesitate, don’t overthink it, don’t squander it. Just capitalize.
“There’s something innately bolstering about a person who sees his opportunities as endless, who doesn’t waste time or energy questioning whether they will ever dry up.”
Barack and Michelle said yes to so many things. They said yes to what was outside their areas of expertise, beyond their comfort zones, potentially out of reach, past what they saw modeled, what they knew how to do, plan for, or manage. They set precedents and paved the way. Imagine that for yourself.
I’m a coach. Everyone wants to know how. A gentle reminder: How is the wrong question. No one can tell you how. You are you, with your talents, gifts, beliefs, constraints, examples, and principles. There are billions of variables that make up your life and your journey. You are going to have to find your way.
You can take advice and apply lessons and learn from others, and it may smooth your path, but even if you did exactly the right thing at precisely the right time, just as so-and-so did it, there’s no guarantee that it will turn out the same for you. So, stop asking how and just go. Find your way. Take action, baby steps if you must, but move towards what you want, say yes to opportunities, and figure it out as you do it.
As Marie Forleo says, you win, or you learn. There’s no failure. As long as you are alive, keep going.
2. Becoming a mother means discovering superpowers you didn’t even know existed. Once identified, use them.
You are a better, more fierce, more capable, more resourceful, more conscious version of yourself. Don’t let anything or anyone influence how or when you show up as your full, newly realized self.
"Also, importantly, they were working moms. They were unapologetic about prioritizing the needs of their children, even if it meant occasionally disrupting the flow at work, and didn’t try to compartmentalize work and home the way I’d noticed male partners do. I’m not sure compartmentalization was even a choice, given that they were juggling the expectations unique to mothers.”
There are consequences to becoming a mother. It’s irrefutable. Until women collectively take the perceived disadvantages and turn them into advantages, until we show up wholly as our sovereign selves, embracing our motherhood as essential to and enhancing our work, and lives, we can’t win.
3. Working and parenting are frequently at odds, but they are two of the best things you can do, so there’s that too.
It’s messy; it’s imperfect and real. Do the best you can, and be brave enough to do your way.
“Each one of these women was educated, ambitious, dedicated to her kids, and genuinely as bewildered as I was about how to put it all together.”
Stay-at-home parents, work-from-home parents, parents with office jobs, travel jobs, nannies, grandparents, sitters, and daycare — it takes a village. Yet many of us don’t have a village, but we still strive to do work/life balance the best way we can.
Give others the benefit of the doubt. Assume everyone is doing their best. See others, not as they are, but as they want to be. Reflect their best selves to them so that they can be that person, and you can too.
4. When we make choices for our lives, there’s always opportunity cost at play. Even if the costs aren’t visible, or when the upside seems too good to be true, costs are invariably a part of the equation.
And often, the only way to increase the margins is to sacrifice some short-term gains for long-term success. See your life play out in its entirety and choose with the long haul in mind.
“We can afford this.” What (Barack) meant was, it would be costly. For me, it was like spending money without knowing your bank balance. How much resilience did we have? What was our limit? What would be left in the end? The uncertainty alone felt like a threat, a thing that could drown us. I’d learned that planning and vigilance mattered a lot. It could mean the difference between stability and poverty. The margins always felt narrow.”
We aren’t all born on third base, or even second, or first. Some of us don’t even know how to play the game. Sorry for all the sports references in this one. In my defense, we just watched The Sandlot again.
Rest assured, you don’t have to know everything to make a plan. You don’t have to know how to do the thing you want to do to make a plan. You simply set your sights and take steps, and reach out to people and learn as you go.
Imagine what’s possible over a lifetime and look for an edge. Anytime you can level-up, level up. Learn, connect, and see where it leads. Be open. Don’t wallow or stew. You likely won’t see or feel the incremental growth while it’s happening, but when you look back, holy shit, you’ve come so far. Anticipate the joy of realizing how far you’ve come.
5. Again, have the long-view in mind in a “The best time to plant a tree was 20 years ago. The second best time is now.” sort of way.
“We were planting seeds of change, the fruit of which we might never see. We had to be patient. I found it demoralizing, infuriating, sometimes crushing.”
We may not all have the platform she has, we may not have the impact, but we are raising children too, right? By default, that makes us equally invested. We have neighbors, families, colleagues, and friends, and we all share the same planet and air, don’t we? We are bound to the same future.
Even when everything seems demoralizing, infuriating, and sometimes crushing, as it increasingly does, we can do something today, tomorrow, and every day, to plant the seeds of a better world. We must.
Making the world a better place often means starting close to home. Meaningful change is rarely instant or sweeping, but it can start a butterfly effect with the potential for so much more.
6. Think good thoughts. Attitude is a choice. Happiness is a choice. Worthiness is a choice.
Roald Dahl says, “Good thoughts will shine out of your face like sunbeams and you will always look lovely.” My brother says, “We achieve victory when a change we make to ourselves leads to change in our environment.” Be the change.
“Am I good enough? Yes I am.”
“Are we good enough? Yes we are.”
Michelle repeated that mantra when she got stuck, was out of her depth, or when facing a fear, knowing she would stall if she didn’t keep going.
Having a mantra is more powerful than you think. Yes it seems deceptively simple, gimmicky even, but try it. Observe yourself for a week, noting your self-talk, thoughts, the words that show up when you get scared.
If you don’t believe you get scared, pay attention to when you get angry. Anger is fear. Then determine the theme of your words and craft a mantra to counteract your fear.
I can’t speak for Michelle, but “Am I good enough. Yes I am.” to me is a rallying cry for worthiness. It’s yes, I was born in a hopeless place, but I’ve found my way here, and I know I am smart enough to figure out what’s next, so let’s do this. Her version captures what she needs to hear, what she needs to feel, to stay in the game. It changes her in the moment to change her outcome.
7. Follow your instincts (in the form of beliefs or passions) and occasionally take a moment to evaluate what your pivotal moments were. Reflect to understand.
When did you do something, or choose something or someone, that irrevocably altered the course of your life?
“Was it the day I’d finally walked away, convinced I’d find something more fulfilling? My mind sometimes landed back where I’d gone to be with a Barack as he spoke to a neighborhood group that was struggling to push back against hopelessness and indifference. I’d heard something familiar articulated in a new way. It was possible, I knew, to live on two planes at once — to have one’s feet planted in reality but pointed in the direction of progress. You got somewhere by building that better reality, if at first only in your mind. Or as Barack had put it that night, you may live in the world as it is, but you can still work to create the world as it should be.”
“I’d known the guy for only a couple of months then, but in retrospect I see now that this was my swerve. In that moment, without saying a word, is signed on for a lifetime of us, and a lifetime of this.”
I was sitting in a meeting at HBO’s Headquarters in New York City, across from Bryant Park, listening to Roger talk about our new original programming slate. These monthly meetings were the ones we looked forward to the most. He used to travel to all the regional offices showing clips. He had an internal newsletter detailing his adventures at TCA events, visiting the sets, meeting with the production teams, and sitting in on the executive strategy sessions. His role was pretty incredible, and his behind-the-scenes scoop was riveting. We used the material for sales and marketing, of course, but also to maintain our insider street cred.
One day, I was daydreaming about my boyfriend during his presentation. Roger was introducing a show, I can’t remember which one, and was talking about love, about writing about love, about portraying love on screen. I was getting serious about my boyfriend at the time, but wasn’t sure. Roger said something that led to a realization, and here we are 11 years later, happily married.
It’s a silly story, but in retrospect, I too, now see that this was my swerve. It was the moment when I decided to go from not sure to sure, to be all in. That led to a lifetime commitment and every amazing moment since.
8. Isn’t that the heart of the matter? We judge women for their complexity because we secretly seek the freedom to reveal all our sides too?
I watched Miss Americana, Taylor Swift’s Netflix documentary, and enjoyed it. Sure, I was annoyed by the incongruence of her immaturity and platform, but I loved her evolution. And when I dive a little deeper into my annoyance, it’s mostly jealousy I feel. Jealousy that I don’t make as big of a difference, mixed with regret, that I don’t get to be silly and frivolous anymore.
Ironically, it’s the very thing she’s fighting for, too. “I wanna love glitter and also stand up for the double standards that exist in our society,” she declares. “I wanna wear pink, and tell you how I feel about politics. And I don’t think those things have to cancel each other out.”
Her team cautions her, citing the Dixie Chicks controversy, to keep her in line.
The Super Bowl halftime furor was more of the same. Two women were unapologetically enjoying their power, beauty, and athleticism. They owned their bodies and the moment, and we couldn’t handle it. They didn’t fall in line. Oh, and by the way, if you are part of “we,” it wasn’t for you.
“Over the course of nearly seven years now as First Lady, I’d been struck again and again by both the promise and vulnerability of young women in our world. Barack and I were committed to changing the perceptions about what made a young woman valuable to a society.”
“I’d been mocked and threatened many times now, cut down for being black, female, and vocal. I’d felt the derision directed at my body, the literal space I occupied in the world. I’d watched Donald Trump stalk Hillary Clinton during a debate. I can hurt you and get away with it. Women endure entire lifetimes of these indignities. These things injure us. They sap our strength. Some of the cuts are so small they’re barely visible. Others are huge and gaping, leaving scars that never heal. We carry them everywhere, to and from school and work, at home while raising our children, at our places of worship, anytime we try to advance.”
“And I will always wonder about what led so many women, in particular, to reject an exceptionally qualified female candidate and instead choose a misogynist as their president. It wasn’t ideal, but it was our reality — the world as it is.”
The SuperBowl halftime show, the presidential election, and #metoo is a microcosm of what we are reconciling as a country. The idea that women are people, as diverse and complex as men, and that one woman, or one moment, doesn’t define any other woman or any other moment, isn’t new, but it’s hard for some to accept.
J-Lo and Shakira don’t need you to take them seriously. They also don’t care if you think of them as sex objects. What they were doing was for them, and it had nothing to do with you.
When the Chiefs run a play, do you ever think, if he really wanted me to respect him as a quarterback, he would have never thrown the ball that way? When the 49ers lose, do you think, well that reflects poorly on all men?
9. There is no ideal. Not a perfect woman or man, not an ideal marriage or ultimate job. Every single time we compare, we fall short.
We never compare ourselves to who has it tougher or who is failing. We always compare in a way that leaves us wanting. And that version of comparison, which is the only version of comparison there is, is judgment. It’s us judging ourselves for our perceived inadequacies. It’s imposter syndrome, and we all have it.
“The power and truth of that moment stays with me to this day. So many of us go through life with our stories hidden, feeling ashamed or afraid when our whole truth doesn’t live up to some established ideal. That is, until someone dares to start telling that story differently.”
Just by being who we are, by showing up wholly, the world eases up a bit. If we all are who we are, then we have to accept each other as we are. If there’s no ideal, we can all breathe a little easier. Michelle showed up for us, she blew up the model, which was an illusion, and we all get to exhale because of it.
10. Perspective, my friends, is everything.
“I had nothing or I had everything. It depends on which way you want to tell it.”
Michelle Obama had a rough start and many rough patches too. And yet, there was an undercurrent of hope and optimism throughout her story. It wasn’t just because, spoiler alert, there’s a happy ending.
Again, I can’t speak for her, but I got the sense that she was hopeful and optimistic, and when she didn’t have the strength to be, her husband gave her his strength and optimism.
If that isn’t the best defense for marriage, I don’t know what is. Pick a person who gives you what you need to carry on when you can’t. There will be times that you will need his strength. He will rely on your toughness too. And, please remember, strength isn’t always carrying the load, sometimes it’s just a matter of shifting perspective, reminding each other of all that you do have.
11. It was the right title and the right story, at the right time, and we were all feeling it.
There’s a famous scene in Jerry Maguire when Tom Cruise wins back Renee Zellweger, which we all love, because “you complete me” and “you had me at hello” and Cameron Crowe, and well, for a million more reasons.
But let’s be honest, Michelle had us at “becoming” for some of the same reasons.
“At fifty-four, I am still in progress, and I hope that I always will be. For me, becoming isn’t about arriving somewhere or achieving a certain aim. I see it instead as forward motion, a means of evolving, a way to reach continuously toward a better self. The journey doesn’t end. It’s all a process, steps along a path. Becoming is never giving up on the idea that there’s more growing to be done.”
“I’m an ordinary person who found herself on an extraordinary journey.”
Is Jerry Maguire the best movie ever? No. Not even close, but it was the best movie the first time we saw it. It captured a moment we wanted to hold on to. Michelle Obama’s book does the same. It’s not the best, but it’s satisfying, and it captures another moment we aren’t ready to let go. We saw her evolution, and like Taylor Swift’s, it was provocative and bold, and also, it moved us because what she shared, we could see in ourselves. We are becoming too.
She’s also wrong though. She’s not an ordinary person who found herself on an extraordinary journey. She’s an extraordinary person who found herself on an extraordinary journey. All of us are extraordinary (all of us!), but how many of us will have the courage to live extraordinary lives?