Going Trucking

Shalom Rabbi Lapin and Susan,

I am a 52-year-old woman, married for 27 years. My husband and I invested in our two daughters, homeschooling them while living on my husband’s income. Now both our girls still live with us. The oldest has her own job and does pay for her share of the bills including car insurance and phone bills, she is engaged and is planning to marry in the spring of 2024. Our youngest will be commuting to university majoring in music and psychology.

Seeing that I will now be able to return to work, I decided to get a commercial truck driving license. I enjoy driving and have earned $28/hr. as a food delivery driver. I couldn’t continue with it as my youngest daughter was going through emotional hurdles and I needed to be there for her. I really enjoyed driving a truck, but I also did not want to jeopardize my daughter’s well-being. I also wanted my husband and I to drive as a team. We’re both in our 50s and to strengthen our finances, I am thinking of returning to trucking. The main problem is that many of the trucking companies want me to drive on Shabbat. There are a few companies that will allow me to park the truck during Shabbat and some are willing to work with me on getting home on Friday before Shabbat.

I also obtained the Certification for a Nurse Assistant; however, the pay is not great. My husband and I aim to be debt-free with some investment property for retirement. My husband is earning a good income; however, it is spread thin as we are paying a few bills including my youngest daughter’s first two years of university. I am concerned about our financial future. During our marriage, I presented a few income-generating ideas to my husband but he is not one to take risks and so I am a bit worried.

I am currently working as a nurse assistant, but I must confess that my heart is not in it. The elderly couple I am assigned to take care of is very sweet, but my employer is paying me only $14/hour for four days a week. I could switch to caring for many patients at a time for $16/hour, but I feel this will be too taxing on me. I really don’t know what to do and I am agonizing inside.

I am currently reading your book “Thou Shall Prosper” and I will be purchasing the Financial Prosperity Collection in my next pay period. I really want to go back to trucking, but I feel guilty about having my employer assign another nurse assistant to the elderly couple. I also believe that as a nurse assistant, our financial progress will be stagnant. I have been depressed because I really don’t know what to do. I am concerned about our financial situation. Would you please shed some light on what I need to do?

Thank you for your time in reading this email.


Dear Sara,

Thank you for learning from our resources and we’ll try to answer your question. You are understandably anxious about your situation, and you want to move resolutely ahead towards a brighter and more secure retirement. However, don’t think that the steps you will need to take are going to be easy. You probably already suspect what some of these steps are, but you haven’t moved on them yet. This is because, like most of us, you have been hoping to be able to achieve improvement without any pain.

We do know people who have dramatically improved their lives and we also know people who experience little pain, but we know of nobody at all who has both improved their lives and also done so with no pain.

We haven’t spoken with your husband of course so we have no idea of whether the notion of sharing a trucking lifestyle with you is a dream come true or a hideous nightmare. We ourselves are drawn to the romance of a life on the road in an eighteen-wheeler big-rig. (SL: Not so much.) But your husband might disagree. If he is partial to the dream, well then, get on with it before you age out of the driver-hiring qualifications.

On the other hand, it is possible that he prefers to remain at his present job which you note is a good one, until he qualifies for pension or other benefits. We don’t know. What is lacking in your letter, Sara, is any information about these very necessary conversations with your husband. We feel that your letter reads almost as if you were a single woman.

Clearly a top-level board meeting between the two principles of your enterprise, namely you and your husband, is the first step.

The decision tree regarding your nurse assistant position is very clear. You are making $14/hour. Can you make more? Yes, if you move to the $16/hour multi-patient role. Obstacles to doing so: 1) Guilt about stopping to work for the sweet couple. There are many areas of valid guilt in all our imperfect lives, but this is not one of them. It is perfectly legitimate to change jobs for something more suitable or more remunerative. Give proper notice, fulfill your contractual obligations, and write the couple a warm letter wishing them well. Get rid of the guilt and go.

2) However, you mention that the $16/hour job might be too taxing for you. Settle that question, then you’ll know. If it is, you’re stuck where you are (Until you go trucking) if not, move.

Regarding your Shabbat question, you answered it yourself. When the time comes, apply only to companies that will let you drive in accordance with your religious beliefs. Again, we wonder whether your husband and you are both on the same page when it comes to Sabbath observance?

That leaves only one other issue that you brought into the question, that of your younger daughter. It seems to us that you perhaps ought to be establishing your financial security before underwriting your daughter’s university costs for two years while she dabbles in music and psychology. The costs are not insignificant while the benefits are quite the reverse. We said “dabble” because the odds are long against her being able to make a living in either music or psychology. Furthermore, a girl with some degree of emotional fragility does not belong on a university campus. Explain to her that unfortunately you and her father must establish your financial security before anything else and that you’d like her to find a job instead of university for the first year. We assure you that a real live job will do far more for her mental stability than the environment of a contemporary university campus with its outsize focus on therapy for everything.

Those are our recommendations, Sara, and we hope they are helpful. Looking forward to hearing back from you with a full account of how well everything is going.


Rabbi Daniel and Susan Lapin

A shameless plug

Join our daughter, Rebecca and son-in-law, Max Masinter, Wednesday night, January 10th, as they host a webinar sharing what they have learned over twenty years of parenting together. This will be a fun and relaxed evening for couples to gain skills and techniques to learn to work together, to support each other, and to parent as a team.

Click here for more info

This Ask the Rabbi is dedicated in memory of Pessi Cohen, 68, who lived on Kibbutz Be’eri and her family who were visiting her on October 7, 2023, brother-in-law, Zizi Sitton age 76, sister Hani Sitton age 73, and nephew Tal Sitton age 49 who were all massacred.

And with prayers for the safe release of all the hostages, among them, Tal Shoham, age 38. His wife, son and daughter (seen here), mother-in-law, his wife’s aunt and her daughter, were released on November 25 in a deal between Hamas and Israel. May he return to his family soon.

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