Who's helped you navigate a big life decision?

When Anita and I started The Grand we asked our friends to nominate one person in their life who helped them navigate a big life decision. Our friends nominated their parents, their spiritual leaders, their eighth grade English teacher who inspired them to become a writer. Getting to know the life mentors who have inspired my friends has been my favorite part of building The Grand community. It's enabled me to create a more intergenerational personal board of advisors and deepened my relationship with friends by getting to know them from a new perspective.

As we approach Thanksgiving week, I'd love for us to reflect on the people who have generously guided us throughout our lives, and how we can honor them. Perhaps send one of your personal Grand Guides a thank you card to express your appreciation for the important role they've played in your life. Or consider nominating them to be a Grand Guide and giving them a platform to share their life experience and wisdom with a broader community.

Whichever you choose, here are a few prompts to help you express thanks.

Gratitude is always enhanced when made specific. Write them a note that includes:

  • A piece of advice they gave you that you reflect on often

  • An experience you shared that you cherish

  • A time their support made all the difference

Upcoming Sessions:

Modern Masculinity - 12/12: What does masculinity mean in the new context of society and business? How do you express your full range of emotions as a man? Join a group of men for a facilitated discussion led by Grand Guide Anthony Ware.

To Have Kids or Not - 12/18: Choosing to have kids is one of the biggest decisions we'll make in our lives. If you're exploring which path is right for you, and want to gain perspective from someone who consciously chose not to have kids, come to this session. Our Grand Guide for this discussion is Marci Alboher, a thought leader and former columnist for the New York Times who's written about what it means to leave a legacy in choosing a life without children.

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I'm grateful to each of you for your positive contribution to our community and our world. Thank you for being here.



What does it mean to be a man today?

I was recently in a coaching circle where one of the members of the group posed this question. He went on to share that this topic has been keeping him up at night – as an entrepreneur, as a father, as a husband. He was grappling with this and unsure about how to show up in his work and his life.

We were drawn to this question as a group because many others in the circle felt this way, and we explored it together. At the end, he was brought to tears and shared that never in his life has he felt more safe and seen than during this conversation.

In that moment, I realized that I've been fortunate to have a women's group where we talk about everything from our professional goals to our identities as women and more. But many men do not have a safe space for discussion like this.

At The Grand, we believe it's important for everyone to have a community for intentional conversation, so we've designed a special session to explore modern masculinity and what it means to be a man today.

I'm excited to have this session led by Grand Guide Anthony Ware. He is the Principal of AWare Catalysts, with a focus on helping startup founders create mental wealth to impact their lives and businesses. He shared with me that his journey has been a long one, but one that he’s proud of.

"I've evolved over the past 10 years to redefine what masculinity means to me in the new context of society and business, deepened my understanding of emotional intelligence and creating space for other people, and learned to be my whole self including the full range of emotions from crying to fear or joy.”

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If you're interested in this topic, you may also enjoy the round table conversation series, Man Enough. Each episode gathers a group of men to discuss how traditional masculine norms have influenced them throughout their lives, the impact they have on society, and how they're working to write a new narrative.

Upcoming Sessions

  • Reinventing Your Professional Self – Career Shifts Later in Life 11/12: Our increasing autonomy to craft our careers offers a window into greater professional fulfillment. Yet, for many of us, making career transitions often feels daunting. It doesn't have to be. Our Grand Guide Caroline Anzur has made a number of career transitions in her 30s and 60s, and is excited to answer your questions about this topic. Join us for this Session if you're making a career transition or thinking about one.

  • Exploring Adoption as an Option 11/19: Have you ever thought about building your family through adoption and wondered what the experience is like? Join us for this Session with Gigi and John Orta to hear about how they made the decision to adopt their daughter, navigated an international adoption, and built a wonderful family with both adopted and biological children.

Grand Insight

Traditions are some of the most meaningful ways to deepen our relationships and weave the fabric of our communities. The importance of creating them is one of the takeaways you shared from your Keys to a Successful Marriage Grand Session and inspired us to start a conversation about them as a community.

What are your most special traditions?

Let us know by replying to this email! We'd love to share your traditions in our upcoming newsletters so we may all support each other in creating more meaningful memories.

Here's one to start from Grand Member, Jenna.

  • Holiday Letters: Every Christmas Eve my immediate family gathers to write each member of our family a letter reflecting on the past year (i.e. I write each my mom, brother, and dad an individual letter). The letters span everything from that person's achievements to our gratitude for experiences we shared or times they showed up for us. We then read them out loud. We've been doing them for almost a decade and the tradition continues to create a special space for reflection and deep connection as we share what we admire in each other and are proud of, as well as openly give and receive our love.



Building a Family Through Adoption

I lived in three continents before the age of 5, and spent my childhood playing with kids of all different backgrounds. As a kid, when I thought about having children of my own one day, I pictured a family akin to the Jolie-Pitt clan. I loved the idea of having a home with a boundless backyard and all my kids running around playing with our St. Bernards. They'd be a diverse mix of adopted, biological, and fostered children, and we'd all go on grand adventures together and be one big, happy family.

As I've grown older and started to think about kids more seriously, my mental picture has become slightly more pragmatic: six kids is way too many for me, three feels more doable. I'd still love for them to be a mix of adopted and biological, but what is the adoption process actually like? How would I go about raising a family with both adopted and biological children?

Those are some of the questions on my mind, and ones I am eager to discuss at our next Grand Session with our Grand Guides, John and Gigi. John and Gigi are the parents of three beautiful children, and are both badasses professionally: John is the Head of Legal at Nextdoor and Gigi is an Executive Director at J.P Morgan. They had two biological children first, and as the kids became preteens, their family made the decision to adopt internationally. Now, eight years later, John and Gigi are excited to join us for a conversation and share their story of building their family. They'll talk about how they made the decision to adopt, navigated an international adoption, and built a wonderful family with both adopted and biological children.

Join the Session

Upcoming Sessions

  • 💸 How to Talk About Money With Your Partner 10/28 - Our Grand Guides, and husband-wife duo, Aditi Shekar and Dalmar Hussein will share how they've approached talking about money throughout their relationship, from the early days of dating to moving in together, adopting two dogs, getting married, and buying a house. Individuals and couples at any stage of a relationship are welcome to join us.

  • 💼 Reinventing Your Professional Self – Career Shifts Later in Life 11/12 - Grand Guide Caroline Anzur, has made a number of career transitions in her 30s and 60s, and knows first-hand that there are always more possibilities for each of us. If you too have been thinking about making career shifts, join us for this session.

Grand Insights

Living a meaningful life is consistently one of the most popular topics you're all curious about at The Grand. As we reviewed your comments, a particular question stood out:

Am I living a life I would be proud of?

There are only 69 days left in this decade. Your commitment to intentional living inspires a period of reflection on how we hope to seek meaning in the next one, and we wanted to pass along a few questions to consider during the last months of 2019.

  • What does your most fulfilling life look like in the next decade? What specific things would make it special?

  • What relationships bring you the greatest sense of fulfillment? How might you deepen them in the coming years?

  • When do you feel most alive? How might you prioritize creating more of those moments?

  • What have you always wanted to do or experience? How would it feel if you took the leap to try it?

We are similarly reflecting on these questions, and would love to hear which you're asking and answering too. Let us know by replying to this email.



Reinventing Your Professional Self

Career Shifts Later in Life

Financial Advisor.


Corporate Social Responsibility Manager.

Head of Knowledge.

Executive Coach.


I've made a few career leaps over the years and always remember the self-talk that coursed through my mind right before taking the plunge:

"I can't waste all of these years working on this to start something else now."

"I'm too old to make that transition."

"I'm not going to be good enough."

Thankfully, I was able to move past some of these negative thoughts by speaking with people who had similar experiences and maintaining the faith that no matter what happened, I'd be okay. Following my curiosity has led me to the most interesting career opportunities in my life; From working in Ecuador on a clean water project to leading an anti-child labor program with the government of Mexico in collaboration with MTV. More recently, it's led me to The Grand, and it's our ethos that ultimately helped me gain the confidence to take these leaps: Talking to people who've been there before.

That's why I'm particularly excited to share our latest Grand Session: Reinventing Your Professional Self – Career Shifts Later in Life, with Grand Guide Caroline Anzur, who made a number of career transitions in her 30s and 60s. If you too have been thinking about making career shifts, we'd love for you to join us for this session.

Join Us

Upcoming Sessions

  • How to Talk About Money With Your Partner. Our Grand Guides, and husband-wife duo, Aditi Shekar and Dalmar Hussein are excited to share how they've approached talking about money throughout their relationship, from the early days of dating to moving in together, adopting two dogs, getting married, and buying a house. Individuals and couples at any stage of a relationship are welcome to join us.

Grand Insights

It's been wonderful to see your conversations unfold after your September Sessions. We're grateful to highlight a few of your insights here, beginning with three valuable reads from Grand Guide Karen Wickre. Stay tuned for the rest on Twitter.

  • 45 Milestones You Can Have in Your Twenties besides Falling in Love "Finally doing something you’ve always wanted to do but initially avoided out of fear – scuba diving, voice lessons, exploring your spirituality. And finding that, even if it was difficult, it also brought you a level of happiness and thrill that you hadn’t felt in a long time."

  • The Difference between Loneliness and Solitude: "In 1957, the German-American theologian and philosopher Paul Tillich described this striking difference: “Our language has wisely sensed these two sides of man’s being alone...It has created the word ‘loneliness’ to express the pain of being alone. And it has created the word ‘solitude’ to express the glory of being alone.”

  • Morning Pages: These 3 Pages Might be Your Key to a Clearer Mind, Better Ideas and Less Anxiety "In order to retrieve your creativity, you need to find it. And it’s through this seemingly pointless process that you are able to find it. You discover things that have been hidden inside you and stuffed down in the business of life."

If you try Morning Pages, perhaps consider dedicating an extra page to exploring an inspiring insight shared by two Grand Members on living a values-driven life.

"It's a practice to clarify your values," they shared. Try creating and recalibrating your values by describing your perfect day.

As always, we are so appreciative of each of your invaluable contributions to The Grand.

We're excited to hear what you think of these pieces, and about your experience journaling should you decide to explore these practices. We're off to kick off our's now too.



How to talk about money with your partner

As an entrepreneur and former venture capital investor, it is my job to understand finances and have conversations about money. However, when it comes to personal relationships, I always feel awkward and often times anxious when discussing money. I never know when to bring it up or how to go about the conversation when in a new relationship, and more often than not, put off broaching the topic.

Having a regular dialogue about money correlates to a happy relationship. According to TD Ameritrade’s Love & Money Survey, 90% of happy couples discuss finances at least once a month, and on the flipside, 65% of divorces are attributed to money.

If ❤️ and 💰 are on your mind, join us for our next Grand Session on 10/28 with Grand Guides Aditi Shekar and her husband Dalmar Hussein. Aditi is the CEO of Zeta, whose mission is to help couples get smarter about money and have more successful relationships. Together, they'll share how they've approached talking about money throughout their relationship and how the conversation has evolved from the early days of dating to living together, adopting two dogs, getting married, and buying a house.

Join the Session

Upcoming Sessions:

  • 9/26 Living a Complete Life as a Single Person - People are increasingly creating meaningful lives without having a partner, citing benefits from the autonomy to pursue the experiences they desire to being healthier and having more friends. Join us this Thursday to explore this topic with Karen Wickre. Karen's enjoyed a long career in Silicon Valley, built a strong network of relationships, and lived a fulfilling life all while choosing to be single and not have kids.

  • 10/8 The Keys To A Successful Marriage - Gain firsthand insight on what it takes to have a thriving marriage. Our Grand Guide Rebecca Young has been married for 39 years, and will share her perspective on successfully building a life and family together.

I'm grateful for our Grand community and all of your efforts fostering knowledge and wisdom. One of my favorite reads this week was shared by Grand Member Aanchal DharA Couple in Chicago: A 1996 interview offering a unique glimpse into former President Barack and First Lady Michelle Obama's beautiful relationship.

As we grow The Grand, we're looking for hosts who are willing to offer their space for Grand Sessions. Do you have a cozy living room that can seat 8 people in San Francisco? We'd love for you to be a Grand Host. As a token of our appreciation, we'll gift you 3 months of complimentary Grand Sessions. Please reply directly if you’re interested, and thank you in advance for your contribution.

With 💖,


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