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An acquaintance needs to find a decent-paying job in her field, because she and her husband have no savings and her husband has a life expectancy of around two years. She is 50 and they have two teenagers. The family has expenses of $60K/year, but he earns less than that so has been getting money from me and friends. I don't have enough money to support the family after he dies. She had a well-paying job in the human resources field up until she got married and moved out of the city.

She doesn't drive (she has taken the driver test and failed), and there are no relevant jobs near her house. (There are retail jobs nearby, but she says the sidewalks are dangerously icy in the winter. This also prevents her from getting to a bus stop.) She doesn't want to use a taxi or Uber or Lyft. As she puts it, "I won't get into a stranger's car". No examples were offered about issues getting into taxis in the past.

How can I talk to her about these fears, and encourage her to step outside her comfort zone so she can get a job?

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Have you considered the possibility that her fears have nothing to do with Taxis or icy sidewalks, and instead are more about the fact that in ~2 years she's going to be a widow and also financially responsible for the entire household? Compound that by the fact that her chances of walking back into a "decent-paying" job in HR are slim, verging upon none.

I'm not suggesting that she's lying about her fears, rather that she is instead focussing on substitute fears because the real issue is too big for her to handle. I'm not judging her for that - she's in a truly horrible position and any one of the challenges she's facing would be potentially overwhelming to anyone.

As such I really don't think that attempting to tackle the taxi issue directly is going to get anyone anywhere (no pun intended) as even if you resolved it her mind will likely throw up another spanner in the works in order to protect itself from facing the unpleasantness of her situation.

If she isn't already I strongly suggest that you advise her to seek professional help (therapist, support worker, counselor) to help her deal with the situation.

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TL;DR: Listen to your friend and understand their situation, and propose solutions. If the friend refuses all the solutions you both have thought of, change the topic and remind them that it's not efficient to spend more time on something they're not willing to change.

Disclaimer: I do not know the entirety of the situation, so I am making a few assumptions here, correct me if I am wrong.

Assumption: You have talked to this person before about helping them get a job, hence the response you got about the fact they won't get into a car with a stranger. In this case, you are basically asking them to step out of their comfort zone, which can be tough.

I would suggest writing a short letter to the person explaining:

  • Why you want to help them get a job
  • Why you think a job would benefit them
  • Why you feel that the person can succeed in the job
  • Why the person can get past the roadblocks of transportation and figure out how to get to the job- give them solutions, like you have tried before. Other solutions might be carpooling, or trying the taxi with you for the first few times (if you can manage it)

I also think it's important to be encouraging when interacting with them, but try (we're only human, we can make mistakes) to make sure that what you say isn't pressuring your friend more than they can handle. (For example, if your friend refuses to talk about taxis, don't push them into trying a taxi with you if they absolutely cannot stand it)

After sending or giving the letter or note to your friend, let them have time to think about it. (This can be anywhere between a few hours to a week or two, it depends on the relationship between you both, which I don't know)

If they bring up complaints of wanting a job and not having transportation, you can refer back to the note, and say something like

I was wondering what on this note isn't working for you? Let's talk about it.

Can you give me any examples of why you absolutely cannot do these transportation options?

What are some solutions that could be implemented by changing only a little thing? What little things can or can't be changed?

What are some solutions that could be implemented by changing a big thing? What big things can or can't be changed?

The questions here are guidance questions for helping you and your friend figure out what options might be best for you both.

If your friend refuses to change anything, you can say that

Okay, I'm glad we had this talk, if you do not wish to change anything, you can refer back to this conversation and think about the options we discussed and any changes that could take place. When you are ready to make any changes in these approaches, let me know. Otherwise, we will be rehashing the same thing over and over. I would rather help you [do something else] (maybe job or hobby related) for the time being to keep spirits up.

If they approach this conversation again, let them know you have discussed it before, and you're ready to help when they are ready to change something. If they want to gain attention for that one thing, ignore it. It helps them realize that the only one to make any changes in their life is themselves, not others.

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