*This week’s issue of The Joint Account is brought to you by Steward!*
It’s not hard to see why many couples avoid estate planning. Talking about money—today, in the present sense—is hard enough. We often encourage couples to focus on positive shared goals for their future and then back into what they need to do to accomplish them. Good vibes only.
But estate planning doesn’t feel that way. Talking about what happens if one of you dies or becomes incapacitated can feel morbid, emotionally charged, or simply overwhelming. We remember the heaviness of preparing our first estate plans after Hazel was born. It drummed up all sorts of emotions about our small, incohesive family support system. At first, we weren’t aligned about who would do what in the event we both couldn’t care for our kids, and addressing this complex issue on top of every other thing we had going on felt insane. We didn’t push it off, but oh man, we wanted to.
David Meister is the CEO of Steward, a modern estate planning and trust administration firm that combines technology with human expertise to help families protect what matters most. He totally understands the predicament couples face when adding these decisions on top of *waves hands around* everything else.
He points out that it’s not just a fear of death or injury that drives couples away from the hard conversations but also fear of conflict and having to address the power dynamics in your relationship; namely, who has more of a say in financial decisions or who comes from generational wealth that could influence these decisions. David so aptly notes, and we agree, that beyond the fear associated with estate planning, couples also have to look their values straight in the face.
If you’re not aligned, that’s a really hard thing to do.
Proactive estate planning isn’t just for the ultra-wealthy, and it isn’t just about dividing up assets, despite that common misconception. David wants couples to understand that it’s about making sure guardianship for your children is clear; healthcare wishes are documented; probate delays are avoided; and beneficiaries match your actual intentions. These are issues that affect almost everyone.
A main reason we wrote the last section of Money Together is to help couples reframe their fear of the unknown and embrace the fact that we really don’t know much of anything. We don’t know what will happen in one year; let alone, forty years. The irony here is that at some point in time, most of us will get sick. All of us will die. Any certainty we believe around these things is an illusion to help us cope with our discomfort. Therefore, preparing for anything is better than selling yourselves on one version of how things go, because that’s just not how life works.
David believes that modern estate planning needs a reframe. Instead of just thinking about death, we should think about it as finding care, clarity, and control—for ourselves and the ones we love.
Similar to what we preach about kicking off money dates with your spouse, time, place, and entry points matter when you’re talking about legacy. It feels like a big topic until you make it smaller.
“Take the time to discuss shared goals in a low-stress, casual environment,” he says. “This can be over happy hour or at your favorite coffee shop. Consider the bigger questions of ‘What do I want my legacy to be?’ or ‘Who do I want to be taken care of if I’m not here?’ and then drill down from there. The more intricate planning details can be filled in later with a professional guiding you.”
Another great place to start is with a more proximate question (or at least, one that feels that way). What happens if you just…can’t manage your bills for 90 days? Or you’re out of commission for a couple months?
David suggests you create a quick ten-minute list of your 4Ps:
People
Property
Passwords
Preferences
If you just spend ten minutes jotting down the basics for your partner and keeping that somewhere safe, that’s awesome. You’re off to the races. You don’t need to get it all done at once.
That being said, waiting until you’re in crisis mode to formalize your estate plans will make those decisions and logistics exponentially harder, and often, more expensive. We often talk about the importance of planning before you’re forced to react. The options will never be as good when your backs are against the wall. Douglas has seen it firsthand in practice. I’ve seen it in the couples we’ve interviewed for our book.
Steward includes all estate planning document families need, which include:
Revocable (or living) trust
Pourover will
Healthcare proxy
Power of attorney
Assistance with deed transfer
Trust funding
When you work with Steward, you get the help you need from a professional with the efficiency you want. You start with a consultation from a dedicated Concierge to evaluate your needs. Then, you go through a digital onboarding process supported by AI and your concierge. Your attorney then reviews your documents, meets with you to review them, make any adjustments, and answer questions. Steward then sends a mobile notary to execute the documents and help move any assets into your personal trust.
Later, there are also moments in life that warrant revisiting your estate plans. Similar to how your financial decisions change as your lives change, you don’t really get to make your selections once and be done (sorry about that). Revisit the plans with a light touch every year, even just during one of your quarterly money dates. David suggests that couples should strive for same week updates (!) to their estate plans when any of the following life events occur:
Just remember, you don’t have to resolve everything in one sitting. What matters most is that you start and keep going. Estate planning is about so much more than legal paperwork. It’s about taking care of each other, ensuring clarity for those you love, and building a shared vision of the future you want.
We’d like to thank David Meister and our partners at Steward for contributing to this week’s newsletter.
On that note, Steward has graciously offered to purchase a copy of Money Together for any readers of The Joint Account who sign up for a consultation with them between now and our publication date of October 28, 2025!
Also, we are so excited to have David team up with Douglas for a free webinar on couples and estate planning on Thursday, October 9th from 1-2pm EST. All registered attendees of the event will also receive a free copy of Money Together, courtesy of Steward!
We’ll remind you as it gets closer, but why not register today?
I wrote about vacationing with friends last month. And well, we’ve just returned from our annual August pilgrimage to the Jersey Shore, where we spend a week in a rental house with close friends and then a couple days with my dad and stepmom. As we head into a supremely busy season with the launch of our book and much more, I know we’ll look back on this time of togetherness with nothing but love. Right now, though, I am very excited for a couple nights’ sleep in our own bed before we hop a plane across the country on Sunday.
BTW, who else is attending Future Proof in Huntington Beach from September 7-10?
We’ll be signing the first IRL copies of our book and sitting in conversation with Caleb Silver from Investopedia! Let us know if you’ll be there, and if you see us, you better say hello :)
TJA in the news
Big firm news for us. Our wealth management firm, Bone Fide Wealth, just announced our transition to Altruist, where we’ll be able to deliver modern, intuitive, and accessible service to our clients. We couldn’t be more proud of the work our team’s put in to making this move work or more thrilled for what’s to come. Read more about it here.
Money Together: have you pre-ordered your copy yet?
Our upcoming book, Money Together: How to find fairness in your relationship and become an unstoppable financial team, arrives on October 28, 2025. If you enjoy The Joint Account, we’d be incredibly grateful if you pre-order from your preferred retailer. Imagine if every one of our subscribers ordered early…that would mean the world to us.
Also…
Are you a financial advisor? Would you like a free chapter of Money Together? Well, we’d love to send you one. All you need to do is e-mail us your request and the name of your firm. It’s that easy!
Shameless plugs
The book site is LIVE! Click here for more info on Money Together and how to have us come chat with your organization!
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We’d love to hear from you.
Find us on social: @dougboneparth + @averagejoelle :)
The content shared in The Joint Account does not constitute financial, legal, or any other professional advice. Readers should consult with their respective professionals for specific advice tailored to their situation.
It's all "rainbows and unicorns" until you have to talk about inheritance.
The possibility people will agree on a common goal can be slim in many situations with extend family.
With immediate family can be sensitive.
Trying to separate emotions and money is tricky, so the goal needs to be clear as day.