My problem is so complicated I can’t figure out where to start

I had a terrible realization this evening that my life will not be successful unless major changes are made. Before I can explain how this realization came about I feel it is important to know about my family and me.

I come from a family that by the usual standards of measurement is educated. We were not wealthy growing up but we were not poor. My parents are divorced and remarried. My mother is a nurse. My father is a retired attorney. My sister has an accounting degree wand in her spare time oversees her husband’s dental practice. She is a stay-at-home mother. My brother is an attorney who now runs a day school and his wife is an attorney. My youngest brother is a dedicated Talmudic scholar. I have a B.S. in Management, a Master of Public Administration; I am one course shy of an MBA and have a JD (and have lots of student loan debt to go with it). I own my own financial services firm that I started two years ago.

My wife, Sarah, and her parents immigrated to the United States when she was 4. They had no college degree but have managed to work hard in their own businesses to create a nice lifestyle for themselves. She is the oldest of five. Her brother is a contractor with a degree in Construction Management and his wife has a bachelors degree but does not work. Her other brother is a financial analyst and is in the middle of an MBA program. His wife just graduated nursing school and is studying for the licensing boards. Her youngest brother has skipped college for the most part and dabbles in entrepreneurial efforts. How wife works as a paralegal in her father’s law firm. My wife has a B.S. in Psychology, attended law school for a year (left to take care of our son when he was showing signs of developmental delay) and is now in a nursing program and will graduate in December 2015.

We met in undergrad in NYC and after 7 months of dating decided to move to LA where we would finished school. At that time I proposed to her. We married a year later at 21 and 22. We had our first child 10 months later followed by our second one 18 months later. We had fertility issues and had to resort to medical intervention to conceive our third and fourth children. We have now been married for 12 years. We have 4 children. Our oldest and only son, Micah, is 11 and in 6th grade. My daughter, Ora, is 9 and in 4th grade. My daughter, Rachel, is 5 and in Pre-1st. We also have a 2 year old, Shoshanna, who is in a daycare run by her grandmother. We live in a three bedroom, two bath condo in a nice neighborhood near the school and synagogue. All of our school-aged children attend a private Orthodox Jewish religious school.

We attended undergrad and law school until I graduated in 2009. I started my own paralegal firm and worked for several attorneys with little or no success for a few years. After failing the CA Bar Exam four times I needed to find gainful employment outside the legal field.

From 2012 to early 2014 I worked for a real estate company. Despite the head of the company being a demanding and difficult person due to medical issues and mental illness, the first year was amazing. The pay and benefits were great. I had some autonomy in my work and was good at my job. The second year was terrible. The head of the company’s dementia worsened and he became intolerably abusive and tyrannical. He squandered all the capital and rather than end years of litigation with his son he pursued it to the edge of financial ruin. I had to make some legal maneuvers to settle with the son before it was too late. His conservator promised me payment once a settlement was reached but the man died before I was paid. The family threatened me with protracted litigation. We settled our differences. I walked away from the mess with a release of liability but also without an entire year’s pay.

I am now in debt to my mother-in-law nearly $40,000, we have student loans of $450,000 combined and struggle to pay for anything. We wait for 3 Day Notices before paying rent to give ourselves a better chance at earning the rent. Our electric bill is too much to handle and we are using a government service to help us pay it. Our cars are due for registration and I have no idea how we will pay that. The elementary school has allowed us to defer tuition payments until we can afford it so we now owe an additional $12,000+. This will increase as the new school year comes.
In the middle of my previous job’s nightmarish year I had started to venture out on my own with a financial services firm and with the legal matters behind me I started to put all my efforts into it. There have been good months and bad months. My business pays me sporadically right now as I work on finding committed individuals and get them trained and out into the field. The pipeline is there but not yet free-flowing. I am optimistic that I will be wildly successful. I just hope I don’t have to quit three-feet from gold.

We have a limited safety net. I lost all my savings. I want Sarah to work with me instead of her mother but she is afraid that we will not have money. What little she earns pays for the fuel in our cars and basic necessities. We are currently recipients of cash aid, food stamps and government medical insurance.

In the midst of all this chaos and turmoil we are trying to make our lives better and create real futures for our children. I am afraid we will not be able to afford to give our children a fair shot in life. I want them to have access to experiences and educational opportunities that right now are financially out of reach. I want my wife to have the assistance she needs to be more active with the children. We often turn down invitations from friends to go out because we cannot afford it. Those invitations are now drying up. People expect us to decline; they are not wrong. We are becoming increasingly isolated from our community, family and friends. We are not happy people and it is beginning to show outwardly.

This evening I realized that my children are either not intelligent or not being taught properly. I asked my daughter to clean up a card game and she needed to count the cards to make sure they were all there. She counted 49 but there should have been 50. She very innocently asked me if 49 was an even or odd number. I was completely taken aback by this question. She is entering 4th grade and I assumed this was taught already. I asked her to tell me if it was an even or odd number. She guessed even so I asked her to explain why she chose that answer. Her logic was that 4 is an even number so the whole number was even. I was furious at the school for this. How is it possible that she could make such a terrible mistake at her grade level. I immediately ran to the internet to find a solution and came across your blog. I must say that it changed my whole thinking on the subject. It is not the school’s responsibility to make sure my children know what an even number is and what an odd number is. It is my own. The struggle I am having now is how to make that a reality for my family.

In theory, we like the moral values and religious beliefs the school imbues in our children but are extremely disappointed with almost every other aspect of the school. Even the religious teaching has not lived up to our hopes and standards. The teachers are usually not accredited which is not a problem for us as so long as the teacher exhibits real ability to “teach” our children. The curriculum is constantly changing and is reinvented every year as turnover is high amongst teachers. Most teachers teach from the book and are not engaging enough. My children seem starved for learning opportunities in school. The focus is on homework and tests. Children that do not fit a certain mold tend to be left behind or the teachers have no idea how to teach a diverse classroom of different levels and styles.

The school received accreditation from the Western Association of Schools and Colleges (WASC). My wife was teaching at the school at the time so I was asked to participate in the process. I truly believed that what we were creating was a great plan for the school that would really make it an awesome place for my children to attend. We made sure that each subject had a scope and sequence. Each grade level was carefully analyzed to see if it built upon the previous grade and led to the next grade. Were the subjects appropriate for each grade. Was handwriting taught. Were computer classes offered. Art, physical education, math, science…

The committee came, saw and left. They made a flowery approval letter with a few suggestions. The following school year the curriculum was changed again and so everything we worked for was for naught. Computer classes were cancelled claiming the students didn’t take it seriously and the teachers did not actually teach it properly so what was the point. My daughter did not have PE for almost half the school year.

Our children would come home with homework and it seemed as if they learned nothing in school. How could they not know it? Didn’t they learn it in school? Homework is supposed to reinforce what they learn, not teach it to them. I was screaming and yelling at them to understand the information. At some point I gave up on homework. Why should I work all day and spend my evenings teaching? I was paying the school to teach them. I gave up caring whether their homework was completed or not. It was not worth it to me. I wanted more positive time with my children and less stress for all of us.

The following year I told the teachers that I would not enforce homework. If they couldn’t cover it in school it wasn’t going to get covered. Tests would be studied for and reports would be done but the day-to-day “make-work” would either get done or it wouldn’t. I wasn’t going to fight my children on it. I got a lot of push back for that. My children couldn’t make honor roll, they would fall behind, the teacher couldn’t assess what my children knew or didn’t know, in the real world a boss will give them an assignment, etc. This was a constant debate in my home and at the end of the day we had to do homework with them because if they were to be in the school they needed to follow the school’s system.

The school had a summer reading program. If the child reads a certain number of age/grade appropriate hours over the summer a “homework pass” would be granted for an evening of the student’s choosing during the year. If homework is so essential to the learning process, why reward a student with a pass?

Every completion of a chapter resulted in a class party or trip to the local 7Eleven. Food became a reward for everything. Learning was a means to an end, the end being food and prizes.

Proper behavior was maintained by threat of principal punishment or extra homework.
One teacher had Friday Fun Day. The whole day would be wasted watching Magic School Bus on the SmartBoard. Mrs. Frizzle wholly taught some subjects.

Micah has learning disabilities. He cannot sit for hours on end and he does not always connect the dots. His questions are strange and his answers usually unrelated to the subject matter. His comprehension is terrible. The class read a book together and all he could tell me about it was the stuff written on the back cover. He can spell and has a great vocabulary but cannot use it in a meaningful way.

He is acutely aware of his issues and has become an emotional and angry child. He is a different child when medicated but that is a double-edged sword because he is a different child when he is medicated. I feel that in order to bring out the best in him academically we are actually suppressing the best in him personality wise.

Ora used to be orderly and neat. She is now a slob. She used to care about cleanliness at home and in her schoolwork. Her handwriting was neat and legible. Now it is loopy, large and sloppy. She is messy and eats rather piggishly. Her manners have also suffered. She is rude and obnoxious to us. She cries a lot when she does not get her way.

A particular subject matter was difficult for her and oftentimes we did not do the assignments. I complained to the teacher about it and even offered ways to make the subject more on grade level. Somehow, despite not learning at all, Ora was awarded with a certificate of achievement in that subject matter. How bogus and patronizing that was. My daughter was so proud of it but we were not.

Rachel is an animal. She has always been more adventurous and has never stopped moving since the day she was born. She jumps and climbs and is very assertive. This is a positive in that she is a natural leader, takes risks and is extremely active. This is also a negative as she is completely non-conformist and does her own thing even when it causes everyone around her problems. She learned how to escape a 5-Point harness car seat at age 3. She absolutely refuses to wear a seatbelt in the car (we stop 100+ times on the way to anywhere we go). She does not go to sleep until she is completely worn out, sometimes after we have fallen asleep ourselves. She does not clean up after herself and jumps from activity to activity. We are not sure how this will be handled as she gets older and more expectations are placed on her behavior wise in school.

Now that a new school year is upon us, we began to clean out the backpacks from the last year and see what supplies we would need to replenish. We found many workbooks that were empty or incomplete. Apparently they did not get to those topics during the school year. Half the cursive letters Ma’ayan needed to learn in order to write all her reports in cursive (mandatory for 4th grade) were unlearned. Basic skills like telling time on an analog clock, money and counting by 5, 10, etc. were shaky at best. Which brings me back to tonight. This is the final insult I can take.

I immediately went online and looked up homeschooling. We both know it is the right thing to do for our children. I found a blog on However, we do not have time to teach our children the way they ought to be taught in school. We would have to buy textbooks and read lesson plans and work through it all with them. How can that be done with children on different levels and of such varying ages? I’m mediocre at math. My wife has mediocre written grammar. I am impatient and she has no time. I have even less time or maybe she does. It depends on the day, week or hour.

I have a somewhat flexible work schedule. I have certain tasks that need to be done and one evening a week it is mandatory for me to be at my office. Prospecting, hiring of new associates in my firm, coordinating my schedule and those of my associates, client meetings, paperwork and financial education are all ongoing and daily activities. If I don’t work we don’t have cash flow and cannot pay for basic necessities. This is improving but still tight and not as consistent as a 9-5 would be. I am an entrepreneur by nature and would rather struggle for my own benefit than struggle for someone else’s. For the most part I can work from home if I discipline myself.

My wife is a nursing student and has to be in school every Monday and has a clinical every Wednesday for 12 hours. She also has to study. Due to our cash flow crunch she has been moonlighting in her mother’s daycare. She has zero flexibility with her schedule right now but plans to work three night shifts after graduation so she can be home more with the children.

The children start school at 8:30am. Their school is not co-ed so there are two buildings to drop off at. We are usually late and I do not drop them off until around 8:45am or sometimes closer to 9am. Mornings are chaotic and it doesn’t seem to help much if we prepare the night before.

I like to get to the office by 9am and Sarah usually has to leave at 6am to be at the hospital by 7am or 7am to be at school by 8am. She needs to be at the daycare by 8:30am so she leaves by 8am on those days. This means I have to get all four children out of bed, dressed, have lunches made, make sure everyone looks normal and has shoes on by 8am. Someone inevitably forgets something. I forget my own things. In short, every morning starts out with a lot of order barking and stress.
Pick up varies by child. Ora gets out at 3:45pm, Rachel gets out at 4pm and Micah gets out at 4:30pm. This means I need to leave work by 3:30pm and do not get them home until close to 5pm. At this time we argue about homework, cook dinner and eat. Then at 7pm we argue about showers and brushing teeth and bedtimes. Micah thinks he should stay up later. If we let him Ora gets jealous and won’t go to sleep. Rachel is an animal. Shoshannah will generally fall asleep but if there is too much chaos she needs to be cuddled with in our bed. Hila will either fall asleep on the living room floor, outside our door, at the foot of our bed or on a decent night in her room.

When arguing with my wife about the idea of homeschooling and how it would work she believes we cannot do it at this point in our lives. We have too much going on in our personal and professional lives and too much economic hardship. The most we can do is supplement what they are learning in school. I agree that if they are in school we need to supplement because they sure as hell are not getting any education at all. Essentially they are in overpriced babysitting facilities with pseudo educational activities. However, by the time we get home and get everything settled it is already bedtime. I am not sure when we would supplement. We already try to have educational conversations at dinner but the children lose interest before they put the first bite of chicken on a fork.

We try to keep the condo clean but the children don’t seem to help us at all. Then we spend our evenings cleaning up after them. It is the worst on weekends. Saturdays are usually spent at synagogue in the morning and home in the afternoons. Dishes pile up and toys are left all over the place. We have run out of energy to keep up with the mess they are making. Did I mention that Rachel is an animal, Ora is a slob and Micah is indifferent. Shoshannah just is. My home office is a messy jumble of personal papers, business related documents, office supplies and computer equipment. Usually it is the worst after the cleaning lady comes on Friday. She just piles anything she doesn’t feel like putting in its place on my desk or in a laundry basket scattered all over the condo. Laundry piles up faster than we can wash it.

I do not find time to study religious texts or pray as often as I should. Even when I do find time to pray it is harried and meaningless; just rote reading of Hebrew words. I know what they mean but I don’t feel the meaning. I do not enjoy holidays or Shabbos. They are expensive and only remind me of all the work I cannot do. We do not have company as often as we would like because our home is not tidy. We can hardly afford to feed ourselves so how can we feed others? Food is more expensive because it has to be kosher. Eating out is more difficult because it has to be kosher.

We are overwhelmed and failing to be at our best. We are failing ourselves. We are failing our mental and physical well being. We are failing as children. We are failing as spouses. We are failing academically and professionally. We are failing as friends. We are failing religiously. Most importantly and as a direct result of all our failings, we are failing as parents.

We realize that we need to change something. Our disagreement right now is how drastically we need to change things. It is a chicken/egg argument. I believe that if we get my business to be more consistently profitable our home lives will become easier as I could more easily delegate the mundane household chores to hired help. I could delegate much of my administrative work to an assistant. Sarah believes we need to straighten out our home before my business can succeed. This requires chores and dedicated family life planning times and a regimented schedule.

After doing some research I am now convinced we need to overhaul the whole system at the same time. The logistics of this seem impossible. We cannot afford to do it but we cannot afford not to.

How do we do what is best for our children with all these problems? I am convinced that we will be better off and I will be able to be more focused and productive if we homeschool the children. The time wasted and energy spent on stressful schedules would be better used in productive and meaningful endeavors personally, professionally and educationally for us all. Michal is too scared to even try, as failure would be ruinous to everything. I cannot do it without her buy-in.

What should we do? Where do we begin? I could not sleep until I got all this down. I am up at 4am writing this letter. I suppose the first step has already been taken. We agree there is a problem and that homeschooling is the ideal. We need help getting there. I like your approach with no set curriculums but have no idea at this point how to implement such a system. Our oldest two have lost five years of potential learning in a school that did not even come close to our expectations and now we have below grade level children. I am afraid for our next child in line to face the Russian roulette that is their school. Is the timing wrong? Should we wait until Sarah is done with school and our professional schedules become more controllable and predictable? Any guidance you have would be appreciated.

16 replies
  1. Penelope Trunk
    Penelope Trunk says:

    Here’s a plan. Don’t skip any of the steps.

    1. Stop paying back your debts. The only thing that will happen is you will have bad credit. You absolutely cannot fix your life if you pay back your debts.

    2. Stop criticizing your children. They have two parents who are a mess emotionally and financially and your kids are merely reflecting that back to you.

    3. You need to focus 100% on figuring out how to earn more money. You are easily overwhelmed and cannot focus on more than one thing.

    4. Your wife will do fine homeschooling. She doesn’t need textbooks or supplies. Just an Internet connection just an iPad for each kid. You will save lots of money so she can stop going to school.

    5. Your wife should focus on getting confidence with herself and the children. She should read my blog about how to homeschool. She should focus on the kids and not worry about money.

    6. Your job is to earn money. Do not tell your wife how to care for the children. Do not tell her how to homeschool the children. Just tell her she is doing a great job.

    7. Reassure your wife constantly that she does not need to earn money. Remind her the cost of childcare and private school is pretty much equal to the after-tax income she’ll get as a nurse. So she’ll have more money if she homeschools than she will if she works as a nurse.

    Good luck.


  2. Pirate Jo
    Pirate Jo says:

    This entire letter is bullshit. What, exactly, is his wife’s name and the names of his children? Shame on you Penelope for pimping this made-up crap. How much did you pay one of your lackeys to write this imaginary nonsense?

    • Pirate Jo
      Pirate Jo says:

      I apologize for being rude, and Penelope maybe you didn’t pay someone to write this. But I still think this letter is made up. The names of his family members keep changing throughout, and there are other parts that are just too outrageous to be true.

      I suppose there’s no rule saying every letter in the Mailbag has to be genuine, and even works of fiction can provide good examples, in this case of what not to do. But I wouldn’t get too worried over this guy’s plight, because I don’t think he actually exists.

    • Penelope Trunk
      Penelope Trunk says:

      Not only is this letter not made up, but I get like five of these a week. The reason the names keep changing is that he asked me to change the names and I couldn’t keep track of everyone.


      • Pirate Jo
        Pirate Jo says:

        Well, again I apologize for my initial rudeness. The explanation about the names makes sense. One other thing that made alarm bells go off was the student loan debt of $450K. I find it hard to believe people even qualify for that much in loans. From what I have observed, borrowing limits max out at around $60K, so even with two people it wouldn’t be half that much.

        The saddest thing is that anyone could spend that much (or however much) on “education” and still emerge with equally horrible family planning and financial planning skills. It’s like they’ve never balanced a checkbook.

        Given the hole they are already in, your advice for them to stop paying on their debt is probably a good idea. They just don’t have the money to feed themselves and still cover that kind of debt. (Four kids … four???) But an earlier commenter was right, too. Stopping the debt payments will free up some immediate cash for them, but they will never be able to discharge student loan debt, even through bankruptcy. The government will be deducting it from their Social Security checks eventually.

        • jessica
          jessica says:

          Of course they need to pay their student loans. Just not today tomorrow next year or probably 5 years out. They don’t pay them, the kids will get them.

          It’s just incredible to me that the poster can’t stick with any one career. They do not have the time or resources to be choosy. They need to put their head to the ground and get a good paying job, stick with it, and develop a side income.

          leave the mom to tend to the kids, stop paying private school.

          It’s that simple.

        • Amy
          Amy says:

          Student loan debt has been a quandary for many people. They can acquire hundreds of thousands of dollars in debt, and that debt compounds, increasing their debt.

  3. jessica
    jessica says:

    I think this guys problem is continuing to think his world is about to be over in every way possible. I don’t know how you can accumulate that much debt, except through indecision and lack of commitment. If there is anything the poster needs right now it’s commitment to solving his problems one by one. I would get an in person counselor to help guide this process.

    Also, read 7 habits of highly effective people. I think it will help.

  4. Sarah K.
    Sarah K. says:

    First of all, Penelope, I’m sometimes amazed that you consider yourself to be so brutally honest. When it comes to most of your Mailbag answers, you are quite a bit more non-judgmental than I am or most people are.

    Personally, I can’t help but think this guy has his head stuck in the clouds. He has this bourgeoisie vision of the perfect life and the perfect family, and he’s so determined to hold onto it at all costs that he’s plunged himself into debt to do it. Dude, if you want to fix any of your problems you are going to have to let go of your overbearing ideals and focus on the way things really are.
    And as much as this statement won’t help, the fact that you rambled on for so long including every detail means you must have thought you needed to do so to attempt to make excuses for everything. Admittedly at this point I’m not even sure what that “everything” is, but I’m guessing you do know.

  5. Stacey
    Stacey says:

    I don’t think being honest means being judgemental.

    I think the reason the mailbag is so well liked is because it’s like getting a coaching session for free.

    We can all see parts of ourselves in different issues and PT cuts through the emotion and judgement and is very straight forward and non judgemental. It makes it easier for readers to learn to cut through their emotions when making decisions.

    When I read an answer to a mailbag question, I feel like I have another tool to make better decisions in my work and home life.

    That said, I don’t always agree with an answer, but I feel they’re almost always 95% on target.

    • Melissa
      Melissa says:

      I agree with you. I was born a judgmental person. I’ve had to work very hard to become an honest person.
      For me, an important part of honesty is being true to my values. I want to be compassionate even when I would rather be dismissive.

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