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 💖,


The Keys To a Successful Marriage

Dear Grand Community,

Recently, my husband and I received a wonderful wedding gift, "Eight Dates: Essential Conversations For a Lifetime of Love", by John and Julie Gottman. I first read about psychologist John Gottman in Malcolm Gladwell's Blink. In it, he talked about Gottman's famous Love Lab where he studied thousands of married couples and, after only 15 minutes, determined with 90% accuracy if they would stay together or get divorced. The premise seemed wild, but through these interviews, he was able to identify negative communication patterns that predict divorce. He called them the Four Horsemen: criticism, contempt, defensiveness and stonewalling. It turns out that contempt is the most destructive of the bunch. They also discovered that low-risk couples maintain a "magic ratio" of five positive interactions to every one negative interaction during a conflict. Armed with this knowledge, we can discern that kindness, appreciation, and respect (the antidotes to contempt) are some of the keys to a long-lasting relationship.

What do you think are the key ingredients for a lasting marriage? What do you wish you knew about having a successful marriage? Please reply to me directly and let me know your thoughts.

If this is a topic on your mind, we're hosting our next Grand Session on 10/8 with our Grand Guide, Charlene Teare. She just celebrated her 23rd wedding anniversary and can't wait to share insights on what makes her marriage thrive. Learn more and secure your spot here.

We have two enriching conversations coming up this month as well: Living A Complete Life As A Single Person with Karen Wickre on 9/26 and a special collaboration with The Cosmos: Own Your Voice, Build Your Tribe with Melissa Andrada on 9/30.

We're always creating new Sessions at The Grand. Have a question you're navigating? Or, life lessons you want to share? Let us know by replying to this email. We're here to help you attend or host the session that's right for you.



Choosing to live life as a single person or with a partner

剩女. Sheng Nu. Leftover woman. It's a popular Chinese term for a woman who remains unmarried in her late twenties and beyond.

As soon as I hit my mid-twenties, "When are you going to find a boyfriend?" became a constant question from my family. I'd answer with a version of: "It's not important to me right now.” “I want to focus on my career.” Or, “I'm happy being single." My response was nearly always met with the same, cautionary warning, "Find one soon, you don't want to become a sheng nu."

Our culture positions couplehood as the norm, and the end goal we should all desire. The idea that someone would choose to build their life as a single person, and be capable of living a fulfilling one, is still foreign to many.

At The Grand, we want to reframe that narrative. Choosing to be single or have a partner is a personal lifestyle choice that can be manifested in countless ways. Each unique path is fulfilling in its own right, and we believe an equal emphasis should be placed on all of them.

This September, our Grand Sessions are designed to help you navigate which choice is right for you.

Living a Complete Life as Single Person on 9/26, led by Grand Guide Karen Wickre. At 68 and single for most of her life, Karen has passionately paved her own path whilst enjoying a long career in Silicon Valley. She is a master connector, most recently having authored a book on networking for introverts.

Join the Session

How to Find the Right Life Partner on 9/12, led by Grand Guide Courteney Kaye. Courteney is a relationship coach who's helped hundreds of people find their life partner. This session was sold out, but we just released two more tickets. Grab them soon.

We invite you to explore these topics, and look forward to hearing about your experiences making this decision in your own life. If you have a question you'd like answered or valuable insight that may benefit others, please join the discussion on Twitter and Instagram, and of course you can always reply directly to me here.

With 💖,


How To Find The Right Life Partner

Dear Grand Community,

I'm getting married this weekend. 💑It's happening! Many of my friends and family are probably letting out a sigh of relief. I think they knew deep down that I would eventually find the right partner, but it did take me a bit longer to navigate the entire journey. When I was a little girl and I would picture my future self, I thought for sure I'd be married at the ripe age of 25. But life happens, and there's no manual for finding your right match. I actually met my fiancé at a wedding and the night before I overheard a girl say, "if I were 30 and single at this wedding, I'd die". I was 31. People all around us have expectations and artificial timelines, but the most important thing is choosing the right person for you.

One of my favorite writers, Tim Urban, makes a good point in How to Pick Your Life Partner – if we're running a successful business, it's essential that we create a thoughtful business plan and analyze the business's performance diligently. However, when it comes to our love lives, society encourages us to stay uneducated and let romance be our guide.

"And when you choose a life partner, you’re choosing a lot of things, including your parenting partner and someone who will deeply influence your children, your eating companion for about 20,000 meals, your travel companion for about 100 vacations, your primary leisure time and retirement friend, your career therapist, and someone whose day you’ll hear about 18,000 times."

When he puts it that way, it really emphasizes the gravity of the decision, one that we should not take lightly. Going into this weekend, I feel lucky to know that I've chosen the right partner – we have an epic friendship, he feels like home and we can't wait to do this marriage thing together. If you're thinking about finding your match, join our upcoming session on How To Find The Right Life Partner (9/12) 🔎 with Grand Guide, Courteney Kay. She's a relationship coach and dating services veteran who's helped hundreds of people find their life partner. We'll discuss things like understanding ourselves better to identify our right match and meeting potential partners in real life.

Join us

We have just one more spot left for 🐣Making The Decision to Freeze Your Eggs (8/27). If you're actively thinking about this or curious to learn more, join us for this session with our Grand Guide, Niki Choo.

Finally, if you want to be a Grand Guide and lead a conversation on a topic close to your heart, please let us know using this form. Here's what one of our most recent Grand Guide's shared after leading a session:

"I love the community opportunity you're creating as I believe it is one of our most fundamental needs: belonging" - Kathi Shaw

Ok, gotta go write my vows now! 💌



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