#1355: “How to stop helping a former coworker.”

Hi Captain,

About 5 years ago I (she/her) helped a coworker Lauren (she/her, fake name) get out of an abusive situation. As I got to know Lauren, it became apparent she had no family support. As a traumatized teenager with 2 kids, she needed lots of help and I often gave her small amounts of money.

Years go by. She only reaches out when she needs cash. During COVID her requests escalated.  I’ve offered other forms of help (driving her places to apply for benefits; getting her kitchen set up so she doesn’t have to rely on takeout; etc) and Lauren refuses. I was poor for years and I know that there are practical ways to reduce expenses and that they are not always doable or the long term way out.

I recently had a baby, I’m frustrated with Lauren, and I want to stop or drastically scale back on giving her money. However, I know I’m the only person she can ask, and I don’t want to cut off that avenue completely. In the past when I’ve said no, I direct her to local sources of help.

I’ve saved for years. If I wanted to, I could set her up with a car, and apartment, and pay for a few semesters at community college. But then I’d be out of savings, and frankly, not sure it would help her long term.

I don’t think Lauren is lying to me about what she spends the money on and I know her need is genuine. But I’m just so irritated that she chooses a $20 Uber ride instead of a $3 bus ride and then can’t feed her kids. I feel like a condescending ass even typing that. Obviously the $17 isn’t going to magically make everything ok, but it will help her in the immediate short term.

I’ve never criticized her financial habits. I understand she basically has to live crisis to crisis, and it’s hard to think long term under those conditions.

So these are my questions: How do I compassionately tell her to only ask for help if she’s exhausted all other avenues, and to only expect $20 every 6 months? How do I deal with my guilty feelings about being able to do more and choosing not to? 


I think any kind of “helping” relationship works best when the person doing the helping understands their own limits and the person asking for help can be sure of where they stand. On the helper side, the help you can offer may not be what the person needs, but if you try to meet their need at the expense of your own capacity (or, let’s be frank, enthusiasm), it’s a bad bargain. When you need help, it’s vulnerable to have to ask, and there’s so much fear and shame on both sides of the transaction (fear of asking for too much, fear of being drained dry or not having enough to meet the need, fear of too many strings attached, fear of being judged, fear of being refused and having to start the whole humiliating process again while the crisis deepens). Ambiguity, shame, and guilt all breed more fear, so anything that lends clarity to the situation is probably useful, even if what becomes clear is “No, this won’t work.”

So, if what you really want is for Lauren to stop coming to you for money, it’s time to be honest about that. “Lauren, I’m sorry, I can’t help out with cash like I used to.”  It doesn’t sound like you have a friendship (“She only reaches out when she needs cash”) and when you do give her money you feel resentful and judgmental of her choices. Your financial priorities have undoubtedly changed with the arrival of a new baby and the chaos of the last year. If Lauren knows the answer is “no,” she can make another plan to get what she needs, and she can stop placing further pressure on your relationship. However, I do not suggest that you create additional conditions or strictures around asking for money in the name of compassion. This lady has enough hoops to jump through already to access help, so either say yes wholeheartedly, or say no.

Like you, I live in this time of crowdfunding for basic necessities and mutual aid as the only aid that is ever coming to people in crisis, and it’s easy to get both overwhelmed and overextended. One thing I do, in addition to routinely supporting some fellow creators and making small contributions to a few local organizations every month, is have a little account that is separate from my main household, checking, and savings accounts. Every time I buy something with my regular accounts, the sum gets automatically rounded up to the next dollar and the change goes into that account. Every time I get paid from any source, a tiny percentage also goes into that account. From there, the account functions as “mad money,” where, I can treat myself to takeout, spring for that taxi instead of the two buses, or buy that ebook that just went on sale even though I already have so many books. It also functions as my “no questions asked” mutual aid fund, where, if somebody close to me asks for help, they can have whatever’s in the account, no questions asked. If the account is depleted when the ask comes in, then I don’t have it, so the answer is no.

We’re not talking princely sums here, mainly what’s useful for me is that I know I can afford to part with it without running additional calculations.. I don’t lend money as a rule, since if I can’t afford to give it away I definitely can’t afford to be without the money AND take on the additional mental & emotional friction of a debt. Starting when I went away to college, my Grandma Louise used to send me $5 or $10 in the mail, along with clippings from the Worcester Telegram & Gazette about the dangers of smoking or drug use or walking home alone at night, and strict orders to “treat myself to a little something.” The gift wasn’t just the money (or real-time documentation of 1990s moral panics), it was the explicit permission to use her gift to make myself happy. Grandma’s surprise gifts and this little account both remove friction. The question of “can I afford to help & how much?” is easily answered with a balance check, and the question of what it’s for is moot. Is it *really* an emergency? Is $20 or $40 just “a drop in the bucket?” Will the person make “good choices” with it? Don’t know, don’t care. Sometimes I have it and sometimes I don’t, and when I do, it’s a gift in every sense of the word: a) A gift to me, to be in a position to give for a change, and, b) Not mine anymore once I give it away.

Letter Writer, if you would truly be happy to give Lauren $20 every six months, what happens if you make that your plan? No to emergency requests, yes to tossing a $20 bill into a pretty card and mailing it to her now and then with some well-wishes, no strings attached. It’s easy to see how this relationship has calcified into only being about crises & helping over time, so maybe if you contact her when it’s not an emergency it will reset things a little bit. Or, put aside a few dollars in a “Lauren” fund every month without telling her. If she comes to you with an emergency, pay her out of that, and when it’s gone, it’s gone. If she doesn’t, at the end of the year, gift her whatever has accumulated, or roll it over until it’s enough for a down payment on a reliable car or somesuch. Lauren might be bouncing from crisis to crisis and unable to budget long-term, but you aren’t. Think of it as removing friction, where you can still help her to the extent you’re comfortable, in a way that’s sustainable and predictable for you.

It’s probably easier and less fraught than trying to set a lot of conditions around when Lauren is allowed to ask for help (only if it’s truly an emergency, only if she’s exhausted all other avenues, only if it will reflect well on her long-term planning skills). It’s a subtle distinction, and there’s no obligation if you’re truly really ready to be done, but transitioning “help” into a periodic gift that you give because you want to might make everything feel less fraught.