I met Abby a million years ago when she hired me to help organize her dining room. We hit it off and have stayed in touch ever since. Abby is an an award-winning Fortune 200 leader-turned-entrepreneur; author and speaker; and expert on deliberate living. I’m chatting with her today about her book Money and Love, her decision-making framework, and how to run an effective family meeting.
What prompted you to write your book Money and Love?
It was inspired by a course my co-author, labor economist Myra Strober, taught for 40+ years at Stanford Business School, called Work and Family. I took it with my then-boyfriend when we were both second year MBA students, and it gave us what I call “radical permission” to broach intimidating topics (such as money, career, and kids) – topics I’d never discussed with other boyfriends, despite living with one previously!
After we graduated and got married, we returned to Myra’s class as guest speakers for nearly a decade as we climbed our respective career ladders, had kids, and navigated the many issues we’d covered in class. The further out we got from graduation, the more we realized the course had set us up for success and changed our lives for the better.
When Myra retired in 2018, she shared that she was planning to write a book based on the course. About a year later, I asked her, over lunch, how the book was coming, and she told me she hadn’t written a word. When I suggested that she needed an accountability partner, she proposed I be her co-author – and right then and there we resolved to write the book together (thereby violating our first principle that big life decisions shouldn’t be made in an instant)!
What are the most common big life and relationship decisions you come across in your work and research?
Many relate to romantic love: is this “my person”; should we live together/get married (and if so, how should we divide chores); should we break up/get divorced. Others relate to other family members: should I have a child; how should I combine career and family responsibilities; how should I care for aging relatives. Lastly, the perennial question: how should I decide where to live and when to move.
Why do you think decision-making is so hard, even paralyzing for people?
I love the way philosopher Ruth Chang defines a hard choice in her TED Talk – a choice becomes hard when there is no “best” option – because each alternative being considered has positive attributes, they each come with different benefits (and costs). Layer onto that the fact that we’re not just calmly choosing between options…these are stressful decisions that cause us to wrestle with our insecurities and fears (including the dreaded FOMO) at the same time. No wonder they inspire a fight, flight, or freeze response!
So what to do instead? There’s no silver bullet, but following a trusted, evidence-based decision-making process can help. One that doesn’t tell you what to do but guides you through the steps involved in making more informed decisions. Things might still not turn out the way you hoped, but having a trusted process helps avoid what Annie Duke calls “resulting,” which is where you judge the quality of your decisions based on their outcomes.
Can you tell us about your decision-making framework?
A framework wasn’t part of Myra’s course, but we developed one together because we found that people tend to make decisions either too quickly or overanalyze them to death. We wanted to help people cut through the complexity, slow down their decision-making (without tipping into analysis paralysis), and feel more confident about their approach.
Our framework has five steps, and we call it the 5Cs.
Clarify what’s important to you: understand what you truly want vs. don’t
Communicate: open up a dialogue with others affected by the decision
Consider a range of Choices: broaden your perspective to increase your options
Check-in with trusted resources: ask around for advice, guidance, and resources
Explore likely Consequences: weigh the short- and long-term effects of different options
These are laid out linearly, but it’s really an iterative process: you clarify what’s important to you at the beginning, then re-clarify as you get more information along the way. I picture it in a circle, like this:
Since the book came out, we’ve heard from many readers about how the framework has helped them make difficult choices: a mid-career executive who used it to make a big career pivot; an early-career entrepreneur who ended a relationship with one person (because they had different goals) and started one with another; and a 90-year-old who relied on the framework to make complex end-of-life decisions and discuss them with her adult children. Myra taught her class to people in a narrow age range (primarily their 20s), so it’s been especially gratifying to hear how useful our framework has been to such a broad group.
What should a couple should consider when one partner is considering a major career change?
There are two dimensions to consider: time horizon and degree of positive/negative change.
As humans, we have a powerful short-term bias, so while we’re good at considering the consequences over the next six months, we may need prompting to consider how this change might play out in the medium-term (>six months to two years) and long-term (>two years).
We also have a powerful negativity bias, which means we’re better at seeing negative consequences. We need to trick our brains by asking ourselves “what can go right?” to consider the positive consequences. In terms of the potential negative consequences that are surfaced, couples should discuss how to mitigate them. Of course, no one has a crystal ball, but we should do our best to ensure that everyone affected by the change can at least live with the result.
You write about how relationships are a form of wealth—can you explain?
I love this phrase, coined by leadership coach Michael Melcher in his excellent book Your Invisible Network. Both Michael and I believe relationships are everything. In fact, my book, Money and Love, helps people put their most meaningful relationships at the center of their decision-making – and their lives.
We typically think of wealth as being connected to tangible assets, such as our bank accounts or home equity (since those are easier to price and measure), but intangible assets – including our personal relationships – are equally important forms of wealth and have a direct impact on our tangible assets.
I’ve experienced this firsthand. In the 2+ decades of my career I spent working for others, all my jobs came from warm introductions from my network. Now that I work for myself, I rely on my network to source speaking, coaching, and consulting opportunities and to run my business (for example, I met my attorney when we were both working for the same company).
As we live longer lives, we’ll need to navigate more career pivots and reinventions; having a healthy and diverse network is key to weathering all the twists and turns.
The great thing about relationships, as Michael Melcher says, is that they’re a form of wealth that’s under your control. In this time of stock market volatility and overall economic uncertainty, focusing on shoring up your relationships is a smart investment.
What’s the most common life decision regret you’ve witnessed in your research?
The most common regrets are the ones related to things people don’t do. Daniel Pink wrote a terrific book called The Power of Regret, for which he collected thousands of regrets from people in more than 100 countries. When he analyzed this data, he identified four core categories of regret:
Foundation regrets - not being responsible when it comes to education, health, and money.
Boldness regrets - not taking a chance or a risk that could lead to growth.
Moral regrets - not doing the right thing.
Connection regrets - not prioritizing relationships with family and friends.
We conducted our own survey for our book, and the two of these that showed up most frequently in our research were regrets connected to boldness and connection (those relationships again!).
To be clear, the point of life is not to avoid regret. The key is not to let our regrets haunt us; instead, try to harness them as learning opportunities that help us grow (I know, easier said than done!). Our regrets have a lot to teach us, if we’re willing to listen.
The next time you have a big decision to make, you can use the strategy of anticipating regret. This involves mentally time-traveling into the future, imagining you’ve made the decision, and predicting if you regret it or not. You can do it as part of the last C of our 5Cs framework (Consequences), which encourages you to play out the potential consequences of a decision across different time horizons.
This isn’t a sure-fire solution, because research shows we frequently overestimate our regrets (which can lead us to act too conservatively). But when used appropriately, the idea of anticipating regrets — especially one of the four core regrets — can be a valuable tool in your decision-making toolbox.
What is your formula for running an effective family meeting?
Do it regularly (every week or every other week)
Keep it relatively short (half an hour, max)
Have an agenda, but don’t be afraid to improvise
Make sure everyone’s voice gets heard
Incentivize participation by pairing it with a treat
We have ours on Sunday nights. First we review what happened last week: we cover what went well and what didn’t go well. Then we look to the coming week: we identify anything we want to work on as a family; discuss the schedule; and surface any requests people have (right now, getting a dog comes up repeatedly). We end with a “family meeting treat.” The treat itself varies – sometimes we test out new dessert recipes before we make them for company, other times it’s a tv show we all enjoy.
What’s one small but powerful shift someone can make today to improve both their financial and relationship well-being?
This will not be a shock based on my above answer: schedule a recurring meeting!
I’m a big fan of the strategy of automation (something you wrote about recently), or said another way, “set it and forget it.” Having a recurring meeting with someone important to you is powerful because it ensures you prioritize that person and the well-being of your relationship.
In addition to family meetings, my husband and I have a weekly meeting we call “TCOB” (Taking Care of Business). It’s primarily focused on logistics, but we also rely on it to raise other topics: fun topics, such as vacation planning, and less fun topics, such as estate planning. We don’t always tackle the big topics right then and there, but if they come up, we make sure to schedule a separate time to discuss them.
Having a standing meeting on the calendar may not sound sexy, but it actually is, because it ensures two things:
That these topics are discussed and not ignored; and
That date night is reserved for genuine connection instead of logistics, grievances, and other mood-killers
Instead of (or in addition to) a significant other, you can do this with anyone who affects your well-being. For example, I know siblings who meet weekly to discuss what’s needed to care for their aging parents.
If you don’t already have a standing meeting on the calendar with someone whose well-being is connected to yours, reach out to them right now and suggest that you set aside some time to have your first one. Why not this weekend?
What is your actual morning routine?
Get up before my kids (easier than it once was, since they’re 12 and almost 10).
Meditate for 10 mins. I use the Insight Timer app, and the Brick device helps me avoid checking email or other apps afterwards.
Move my body for 30 minutes (I still love and use Peloton!)
What book(s) are currently on your nightstand?
I am an avid library patron, so there isn’t enough space for my books on my nightstand (my husband jokes that I’m running a small library branch from my side of the bedroom). I usually read two at a time: one non-fiction book (for daytime) and one fiction book (for bedtime). Right now my non-fiction book is The Mindful Body by Ellen J. Langer and my fiction book is The Magnificent Ruins by Nayantara Roy.
One self-care tip you follow religiously?
I have become hyper-vigilant about sleep, especially since entering my 40s. Most nights, I’m off screens by 9:30 and in bed by 10. Also, getting dressed in real clothes, even when I don’t have anywhere to go. Wearing “hard pants” most days during the week keeps me honest.
A life hack you swear by?
Red lipstick! When I’m feeling off, or I need to look put together, or both, it does the trick. My favorite is from Gen See (this one) – it’s magical.
How do you fuel your creativity / productivity?
I’ve written before in my newsletter (here and here) about how Alex Pang’s book Rest changed my perspective – both about the important role rest plays in stimulating creativity and what constitutes deliberate rest. Since reading the book shortly after starting my own business, I’ve changed my approach, taking more walking meetings; making time for weekly tennis lessons in the middle of my workday; and building better boundaries between work and rest.
How do you recharge when it's all too much?
Time in nature:
Weekly: a short hike (a 7 minute walk from my house)
Monthly: a longer hike as a family (these hydration backpacks and post-hike ice cream bribes have done wonders for our kids’ willingness to go on them).
Annually: an unplugged weekend in Tahoe. No devices (for anyone) – just time in nature, board games, and one another’s company.
Favorite or most used app on your phone?
The Streaks app. It’s where I log my meditation sessions and other foundational habits that keep me grounded, and it syncs with my Apple Watch to track how many steps I take and my workouts.
Favorite gift to give?
My go-to gift for teachers and others is to make granola (I swear by the Lazy Day Granola recipe from my friend Genevieve Ko’s wonderful cookbook Better Baking), put it in a mason jar, and tie a ribbon around it. Voila!
Easy weeknight meal?
We eat a lot of vegetable-forward meals and are currently loving recipes from Hetty Lui McKinnon’s Tenderheart. I’m obsessed with her recipe for crispy sheet pan noodles with glazed tofu (gift link to recipe). But full disclosure: my husband makes 99% of the meals in our house, and yes I realize how lucky I am!
Thank you, Abby! For more like this, make sure to check out Abby’s book – Money and Love: An Intelligent Roadmap for Life’s Biggest Decisions. You can also explore her website and subscribe to her excellent newsletter Practically Deliberate.
**My new goal setting mastermind retreat on the California coast is FULL. Click here to join the waitlist for future retreats and in-person events.
Currently Reading: My UK publisher sent me a copy of Happy With Less by Helen Chandler Wilde and I can’t wait to dig in and share my takeaways.
Listening: Megan Rapinoe and Sue Bird chat with Adam Grant about pursuing excellence and knowing when to quit on the ReThinking podcast. Listen here.
Fewer, Better Faves: I have outdoor entertaining on the brain. Obsessed with these sweet scalloped plates, this plastic-free outdoor dining set, and this candle with a cult-following.
NEW: 1:1 Strategy Sessions: Laser-focused coaching sessions (book publishing, pr, marketing, goal setting, and productivity). Info Here.
For the Entrepreneur: Start or scale your business with my mentorship program for creative entrepreneurs - Info Here.
The Get Organized Master Class: Learn how to edit, organize, and elevate your home like a pro. Info Here.
For Curated Product Recs: My fewer better faves for your home, life, and wardrobe. To the Recs
I’m looking forward to reading. Gosh Abby you have a wonderful amount of energy and verve. I am exhausted at 66 from maintaining and rebuilding constantly my yoga business. FYI I love Tanis Fishbin on Insight Timer for her Yoga Nidra. Is your meditation guided- if si anyone special? Thanks!
This is a fantastic interview. I took away some great ideas...including a new red lipstick option! Thank you!