Helping Alice
I have a sister.
Her name is Alice.
Due to circumstances, our lives developed in very different families and progressed along very different paths.
It has come to my attention that Alice is under a great deal of personal challenges in her life.
She’s family.
I want to help.
How?
Vignette 1 – The Support-Abandon Dilemma
Having learned that Alice is on the verge of eviction, I decided I would at least temporarily shelter Alice. I don’t wish to see my sister homeless. I’m happy to share a room with my partner for a month or two – we’d treat it as an exercise to grow our relationship, a win-win.
After a deeply meaningful reconnection with Alice, supporting her move-in, we set to understand the situation better. We learn that Alice had to move out of her home nearly a year ago due to it being a fairly toxic environment. We learn that Alice has been taking projects on and off, making about the amount one needs to survive and pay rent. By all accounts, it seems Alice is a remarkable teacher, able to instruct workshops at lucrative rates. The challenge, however, is trying to get reliable work that results in reliable income.
Intending to secure some upcoming jobs that are likely to work out, as well as the intent to get a full-time job if they don’t work out, we agree two months would be sufficient.
Some weeks pass. The various potential workshops have not progressed – they need more time. It’s apparent Alice is feeling more defeated. The overall experience is starting to wear on my partner’s life and mine. We’ve noticed that Alice tends to throw out the garbage when the bags are only half full. I really dislike this, because I have a pet peeve about how things should be used efficiently. My partner tries to calm me, saying Alice is probably doing this to show her appreciation by proactively taking chores, apparently finding this a non-issue. This got us into a fight. It reminded me of my partner throwing out a loaf of bread because it was “going to be moldy soon”. My partner reminds me that we are doing this because we are supporting my sister. I rebut that we shouldn’t be bending over backward to do so or we wouldn’t be able to sustain ourselves.
We value sharing emotions openly and do our best to give feedback where we can. As tension builds, we find that the three of us are having more and more conversations to talk about how we are dealing with the matter. Each time, these conversations reveal more of our experience and history. We shared with Alice the conflict my partner and I had, and Alice said she would try not to put out the garbage from a place of overeagerness. We learned that growing up, Alice’s brother has been repeatedly and publicly reprimanded by her parents. In a fear response to the humiliation she witnessed, she has grown up to be very sensitive about revealing any perceivable “wrongdoings”. My partner, however, is finding these increased conversations to be more uncomfortable – her career is in an important period and this is starting to be disruptive to her focus. I offer options where she doesn’t have to show up to every conversation and she agrees. Internally though, I feel conflicted because she’s the breadwinner at home, and I want to make sure I understand how she feels with some of the increased expenses that accompany Alice.
In one of these conversations that went especially deep into our history, Alice happens to reveal that she has a fair bit of credit card debt too and it often feels terrifying to look at those numbers. I was quite shocked. From what she reports, there is simply no way with her job prospects that she can afford debt payments on top of living expenses. I urgently reflected this back to her, leading to her panicking as a response – all I could do was help her process through her emotions. I bring this up to my partner, to her surprise as well. I mused about the idea that we could explore what portion of her debt we could, in theory, cover, but she was outraged at the idea and we had another big fight. Turns out, she has been feeling financial pressure, and her desire to have fewer of these Alice conversations was so she can focus on work to secure our financial wellbeing. Our relationship was under the largest strain it has ever been in.
As more weeks pass, Alice has secured even less work than before. My reflections made her realize that her financial situation was untenable, leading to a depressive state that made work difficult. Bizarrely, Alice restarted behaviors like throwing out the garbage half empty. If anything, it was more common now than it ever was, and our conversations only fixed symptoms but not the patterns. Always sharing the same room with my partner is also straining our relationship to a breaking point. Feeling defeated, I present the decision to Alice – she must move out. Feeling bad, I also connected Alice with a therapist friend and paid for a few month’s worth of sessions out of pocket, which Alice appreciated (but my partner didn’t). Fortunately, we were also able to find a cheap rental that she could just about afford relatively soon.
By the time Alice left, it had been five months.
Vignette 2 – Functional Support with Sensible Constraints
Many months pass…
My partner and I did not break up. In fact, with more space after Alice’s departure, couples therapy, and continued reflective dialogue between us, we felt like our relationship fortunately grew from the experience. We surprisingly learned that we broadly like sharing a room, arguably even more than having separate rooms. The lack of space forced us to look at how and why certain things we did annoy each other and how to create psychic personal space when there isn’t physical personal space.
Through the experience with Alice, we learned that boundaries are important to hold while supporting other people. This means we should set some pre-agreements about what extent we are willing to go for any given person. This also means we should keep more in mind that these initiatives tend to bloat in time and energy – that the other person’s (and our own) histories and trauma are often deeper and more complex than one might initially think.
We haven’t heard much from Alice. From social media, it seems she’s barely scraping by, but given our knowledge of her financial situation, that has probably only gotten worse. But, this isn’t in our control, so it won’t help to think too much about this.
This new approach has also borne fruit. There was a friend who had a parent pass away and was experiencing a hard time dealing with the emotional and logistical aftermath. We pre-agreed that we would devote about 3 hours a week to support them with this, including extra time cooking for them, but not buying them meals. Partially thanks to our agreements and partially thanks to us having grown as a couple, we were able to be greatly present and caring when we were involved. In fact, our friend reports a degree of appreciation that was surprising. They tell us that they wish there was more kind of help like this for people in general, and that for those three hours each week, they can expect real connection – to be seen and heard. We appreciate this greatly and it makes us want to do this more where we can, knowing that our relationship grows too each time. I love seeing the unique way my partner can solution for interesting problems and she loves seeing the way I make the other person feel seen and heard.
One night when we were having a dinner gathering with some close friends. One friend, Mike, brought up how his grandmother needed more care in old age, and he has been feeling conflicted about it. Mike described how the grandmother does not have many living relatives left, and few are in the circumstances to care for her, so he decided to take her into his home. Thinking back to Alice, my partner brought up how people with different lifestyles can create amusing kerfuffles when living together. Mike laughed in agreement and described how his grandmother insisted that you should save dish soap by diluting it with water, replacing all the bottles of dish soap with diluted bottles instead! Mike then shared how given the development of her health challenges, he’s thinking it’s time to move her to a long-term care facility. Another friend wondered if this would be socially isolating for her, and Mike sighed that he could try to visit her frequently, but the care she needs is simply beyond him. I asked if he has talked with his grandmother about it and he said no – that while he feels quite bad about this and will do his best to create a good long-term care experience for his grandmother, the decision is made. Understanding the necessity of boundaries, I nodded in response. However, I had a nagging feeling about this as we left dinner.
Returning home, my partner and I had a conversation about Mike and his grandmother:
“It’s kind of like Alice isn’t it?”, I said.
“What do you mean?”
“Well, you have someone that could use significant support and you have someone that wants to give significant support but is constrained. Even with the best of efforts, we have to form boundaries to make sure we don’t also sink along with the person sinking.”
“Yeah, it’s quite unfortunate.”
“Not just unfortunate, it’s more like ‘fucked up’ isn’t it?”
“Say more.”
“Alice is my sister. This is Mike’s own grandmother. Somehow we are to make a boundary with our own loved ones? Sure, they have their challenges and traumas and whatever, but … It’s like, when we talk about pre-agreements for helping people, does that apply to you too? Suppose you had cancer or some head injury, and it’s increasingly difficult for me to take care of you. Should I also have some hard boundary for when I need to just leave you in a hospital? I sure hope not!”
“Hmm… well if I was in a situation that really was going to collapse your life just because you need to take care of me, and the difference is pull the plug or not … perhaps… Most cases probably don't look like this though I guess. Suppose I become disabled, but still approximately functional, thinking that it somehow exceeded a boundary and you leave me, I feel very sad. If we were to separate, I’d hope it’s because we have been talking about it and have come to a shared agreement – a world where we both would feel immensely satisfied with the mutuality in the choice. Not without grief, of course.”
“Me too.”
“I suppose part of the assumption here is which unit is doing the supporting right? The modern notion of the “nuclear family” as a unit is not designed to deliver care that ancestrally was delivered through a tribe or village.”
“And that’s why we have institutions instead. Or rather, given that the institution that is “the tribe” is much less functional, we have other institutions to take its place. In this case, nursing homes for instance. However, while there are some advantages to having access to professional medical support, Care-as-an-act then has at least two levels of trust problems. The first is why should the care-receiver trusts the intent of a nursing home to care beyond profit. The second is the somewhat orthogonal angle of why should I, someone who cares about the care-receiver, trust the intent to care from the institution.”
“It’d be helpful if we knew the director of the nursing home. However, that doesn’t exactly scale as a general problem. We can’t know a nursing home director for Mike’s grandmother and a financial expert for Alice, etc. We also can’t expect every nursing home director to know everyone who needs to know them.”
“Ha, yeah, and if we are busy getting to know everyone, how can we still make an income that secures our own wellbeing? I certainly am not in that line of work, whatever that line of work is. Rather tricky that all of what we are talking about here has little professional relevance for either of us. This is at least part of what makes the boundaries strategy a functional approach right – we must prevent sinking ourselves while helping others. Which is quite the deal with the devil and surely doesn’t work out at scale: either help others insufficiently or both the support and the supported sink under pressure. Well, barring miracles or sainthood or something.”
“So it seems we are somehow categorically off. Between the two of us, we can only at best, support someone like Alice (and only a very few Alices) episodically. A “continuous” support that yields the kind of character transformation necessary, assuming it’s just the two of us, will only collapse ourselves.”
“All the while, Alice’s debt has probably increased substantially since we last met.”
Vignette 3 – Learning and Creativity in Tribe-ing
More months pass…
My partner and I have continued to wonder together about this issue. We’ve noticed that talking about these issues revealed even more about our own assumptions, about ourselves and each other. It gave us space to imagine scenarios that imply our futures, allowing us to model each other better and collaborate better in life and work.
We’ve even roped some of our friends into these musings too. It revealed many more examples of how people’s lives shared similar patterns. We learned that a few friends are having a lot of trouble supporting their children’s adjustment to school, and how it consumes so much of their attention that they can barely stay afloat. We learned that part of the reason Mike felt like he needed his grandmother in a nursing home was not only because of her health but because whenever Mike brought a potential partner home, his grandmother would always take over the conversation. Turns out, Mike’s grandmother was a former asset manager and had a habit of evaluating all of Mike’s dates on their financial literacy.
Everyone reported their own “Alices” and how it occupied all or nearly all of their attention.
As we learned more about different people’s situations, I realized that some of these cases latently link up to each other. Alice is a teacher that needs work and serious financial literacy. As it happens one of our friends still has a young child that needs daycare/early education and Mike’s grandmother is savvy in finance while actively needing social connection.
I shared with my partner that perhaps we can play a market-maker role and learn to facilitate these connections. Could we approach a more categorically appropriate solution to Care? It would move closer to solving a tribal problem with a tribal solution.
We discussed how simply linking people up wouldn’t so easily solve the issue. Alice’s financial problem isn’t only a financial one. Its roots are deeply psychic and emotional. Unless she overcomes a fear of looking at finances, no amount of knowledge will reverse a pattern of avoidance that recreates the situation again. This means that linking Mike’s grandmother can’t only be naively asking and expecting effective support. We would also want Mike’s grandmother to have some literacy in trauma and how to instruct Alice in a way that wouldn’t scare her off. This means a pre-condition where Mike’s grandmother would be willing to learn or talk about these things. Similarly, if our friend entrusted their childcare to Alice, they’d be counting on our endorsement that Alice is a good teacher. However, if Alice has a depressive episode again, we will introduce a new kind of turbulence to their already strained life.
Those conversations Alice, my partner, and I were having about our living situation have to be revived and revamped. Now, it needs to incorporate everyone for better-informed expectations while simultaneously not over-straining those, like my partner, who had limited bandwidth. If it’s successful, we should be able to lead to a world where Mike’s grandmother would have genuine care for Alice, a total stranger. Over time, this should even be an increasingly common experience.
Seemingly worth a try, I gave Alice a call.
It has been a while. Turns out she did find a full-time teaching job for a year. However, trying to introduce some new teaching methodologies into her job led to a lot of strain from the other teachers – despite positive student feedback. She both quit and was fired, after ongoing conflicts with her manager. The therapist somewhat helped during this, but ultimately, she couldn’t keep affording it and also found it insufficient for addressing her overall situation, including debt. As she describes all this, I hear a new kind of maturity in her voice. I ask about her finances now, and she reports she’s still struggling with it. Though there is a bit more stability during the year, she’s mostly making minimum payments on debts, so the interest grows, and she doesn’t know exactly how much debt she has now. Since leaving the job, she has restarted her own teaching business, and while unstable, she is still getting by.
I presented to her the idea of taking on a part-time gig in a small childcare arrangement and working with Mike’s grandmother. She was open to it.
From there, our conversations became more regular as we set up these arrangements. We’ve even decided to record some of our conversations to share with the parents, Mike, and Mike’s grandmother. It created an appetite for experimentation as Alice became more real as a human, setting up non-naive expectations, but also raising more questions for all of us to consider together. As it happens, Alice took on the childcare and more. Mike’s grandmother also connected real well with Alice. They decided that rather than immediately beginning to teach Alice about finances, Alice would teach the grandmother more about trauma education first, something she’s come to learn a lot about in the past year. The grandmother also valued it, because the more she learned about it, the more she could understand her own upbringing as she reflected on her final period of life. It was even semi-joked that Alice would probably end up inheriting Mike’s grandmother’s house rather than Mike himself.
Mike’s grandmother also had the realization that to the extent that she is confident Alice is becoming more mature financially, her high-interest debt forms a unique arbitrage opportunity. She could either buy the debt out herself and continue the loan with a lower but still lucrative interest or, better yet, sell it to other investors as a form of charitable investment. It also means that so long as we can “raise and educate” more Alices, she can take on more corresponding debt as a financial instrument. If there’s a large enough amount, she can even come out of retirement as an asset manager again and earn a commission on managing them in a new institution!
We are emerging a situation that could simultaneously:
Resolve a friend’s childcare needs
Resolve Mike’s grandma’s social needs
Resolve Alice’s economic needs
While being aware of the challenges of working with people with complex histories
While all parties are intrinsically motivated
While all parties are broadly not over-strained
While the children being cared for are raised witnessing this form of tribal solution
Actual, continuous, meaningful, and productive support seems possible.
Vignette 4 – A Possible Future of Real Intimacy
An intimate web of relationships is no easy thing. One simply doesn’t grow a tribe by just well-designed schemes and interesting connections.
There were hard times. Mike got into a relationship, and his new partner found all of this overbearing because of how much attention it took. It put a strain on Mike and his partner, as well as Mike and all of us. Alice hits some significant spells of depression coupled with suicidal periods, and despite them being shorter and easier each time, she still has trouble building out her business reliably. This at times also frustrates Mike’s grandmother. When my partner’s company lost its funding, our own financial struggles became difficult to work with, because we felt like everyone was already working with so much, and that it could also add pressure to Alice.
Nonetheless, it appears a fledgling culture is forming through our relationships, practices, and initiatives. While some friends grew out of contact, new friends came into contact. There was an ecology of practice.
While small, 5 figures worth of debt is being transferred within this little economy, facilitated by trust built on witnessing the quality of “education” delivered.
While early, there is now the strange habit of recording our conversations to pass to each other to talk about how we found each other’s conversations. It gives new perspectives on what would typically be considered social “dirty laundry”. It’s like a small media network with our private radio/podcast.
While few, children could be raised with a different experience of upbringing. One where they see the adults themselves as also constantly learning, both intellectually and emotionally. They’ll be growing up in an education orthogonal to whatever kind of formal schooling they may receive.
There are yet significant challenges beyond this embryonic culture’s capacity. As Mike’s grandmother enters the final stage of her life, how she is cared for in her dying process is a level of involvement still beyond our abilities. Many of us, like Alice, still haven’t figured out a path of livelihood that is both alive and meaningful. Much of the trauma and personal conflicts don’t necessarily all disappear in a few months. Real, actual children will also helpfully and proactively remind you that diapers need changing, lunches made, clean-ups done, and after-school programs signed up for.
While it took some time and ended up involving a lot more people and their lives, I think I’m finally able to have some sense of how to meaningfully and effectively help my family.


It must've been tough to know you wouldn't be able to support Alice, especially due to her depression, and I'm sure Mike felt similarly about his grandmother and her loneliness. What strikes me the most is that while for all the tragedy found in this recognition of our own humanity, it was also the recognition of our own humanity that became the solution. Upon coming to how "It was semi-joked that Alice would probably end up inheriting Mike’s grandmother’s house rather than Mike himself", I was brought to tears of awe, with renewed faith in the solace we can find in each other, and a sense of marvel at how this solace managed to extend beyond emotional comfort into real change happening. So often, stories that start like this are stories of how humans have human struggles, of the hardships we suffer through when there's a will but not a way. Yet you tell me that a mini but extraordinary ecosystem emerged that not just cares about what people have to offer the ecosystem, not just works for the people in the ecosystem, but cares about who they are as people in an ecosystem? Even as ethereal as such moments may be, even if they do not fix everything, they are no less profound: it must've taken connection and creativity, but also sincerity, hope, above all, *heart*.
thanks for writing this david. i found this delightful to read, and i admire what you and your partner did. i find it hard to imagine myself doing something similar, but it certainly feels a little less hard to imagine now.