Planning ahead: chaos is dumb

The incomparable Mesilas Yesharim had strong thoughts about looking ahead and carefully considering your options.

One who goes through his life without introspection about whether his path is good or bad is like a blind man walking along the edge of a river whose vulnerability is great. He is more likely to face catastrophe than salvation. (פרק ב)

I see a need for a man to measure and weigh his paths each day in the way of great men of business who constantly organize their investments so they should not fail. One should set aside serious time for this so one’s assessment should be deliberate and not casual, for the consequences are great. (פרק ג)

Who’s going to argue with this point? Of course planning is important.

Here’s the thing, though. Devoting time to planning important decisions only makes sense when you’ve got important decisions to make. But what if your next steps are obvious to you? What if you’re not in the least bit confused or conflicted over the direction you should take in your life? Then now is a good time to worry. If you’re absolutely doubt-free you’re probably missing something important.

Life is complicated. What was right last year should be be reexamined now and what’s right for you is probably not Ok for your brother-in-law. One of the worst reasons for doing something is because “it’s what everyone else does.”

God chose for you a family, social influences, and a unique set of skills and aptitudes. Do you really think you can accomplish everything He expected you to do with them by carelessly imitating other people?

Want to intelligently chart a course for your future? Start by identifying your options. As a rule, the first thing I ask when talmidim request advice is “what are your alternatives right now?” Just by formulating an answer to that question, they’ll often recognize more choices than they’d previously acknowledged.

Never mind if some of the options seem far-fetched or are currently unpopular within your social group. You can always eliminate them later if you determine they’re not going to work - or they’re not a good fit with Torah values. But this has to be one conversation that’s not artificially limited by anyone else’s expectations. Don’t rule anything out before at least considering it.

Here’s what I really mean: Allow yourself to look beyond the narrow range of lifestyle choices currently popular in the yeshivishe world. Think big. Be ambitious. Commit to making the world a better place.

I hope it’s obvious by now that I’ve got nothing against institutionalized Torah study. If all the world’s kollelim were to suddenly close down, the orthodox community would effectively collapse within a few years: where would our rebbeim, roshei yeshivos, and top-level kashrus professionals come from?

But these essays aren’t talking about the needs of the Jewish community. Those are largely being met by the system the way it is now. Instead, I’m writing about the needs of individual members of that community. You. And the people around you. What are your needs and who is responsible for ensuring they’re satisfied?

Is there a difference? Isn’t what’s good for the community automatically good for you? No, it’s not. Take a moment to think about the words of one of the intellectual fathers of the modern yeshiva movement: Rabbi Eliyahu Dessler.

In a letter printed in Volume 3 of Michtav M’Eliyahu (pages 355-357), Rabbi Dessler explained why he opposed opening a degree-granting teachers' seminary for boys in Gateshead. While such an institution would surely have benefited individual talmidim, Rabbi Dessler felt that those benefits were outweighed by the risk that a single talmid with potential to become a godol might be distracted from his higher focus.

Here’s how Rabbi Dessler put it:

However, don’t think that they don’t realize that through this approach many (talmidim) will be destroyed, since they’re unable to survive such an extreme approach, and they’ll stray from the path of Torah. Nevertheless, this is the price to pay for creating gedolay Torah and yiras Shomayim…

We can see Rabbi Dessler’s overarching principle: the needs of the community justify at least partially abandoning the needs of the individual.

Perhaps Rabbi Dessler’s assessment of the situation was correct or perhaps it wasn’t - there were certainly those who disagreed. But his approach could only be applied to the community as a whole. I can tell you that if a talmid trying to work out his educational or career options asked me for my thoughts, I would surely do my best to give him the answer that best fit his needs. Anything else would transgress a Torah prohibition (see Vayikra 19:14 with Rashi).

So the questions you should regularly ask yourself involve how you - while remaining fully loyal to Torah values - can best serve yourself, your family, and - yes - your community. If the answer happens to also fit with the core goals of the yeshiva world, then great. But if it doesn’t, you’d be a fool to ignore your destiny.

What needs planning

Where do you start? Try making a list of what’s important to you now and what kinds of things you think will become important over the next few years. Perhaps it might end up looking something like this:

• What learning skills do I currently lack and how (and where) can I best acquire them?
• What specific Torah knowledge (seforim, mesechtos, etc.) would I most like to master over the next five years?
• Would I gain by focusing more attention on a specific area of learning (a specific area of practical halacha, b’kius, a particular rishon etc)?
• Based on my background and skills, what are my best career choices?
• How much income will I need to cover my anticipated living expenses over the next five years?
• Where will that income come from?
• What kind of chinuch do I want for my children?
• In which kind of community would I like to raise my family?
• How can I best serve my community (kiruv, Hatzala, chevra kaddisah, joining the board of a chinuch mossad etc)?

Those feel important, don’t they? But it would be so easy to blindly float through year after year without ever properly thinking through the “sugya” to discover the right choices. Which makes it fairly certain that, at least most of the time, the choice you just fall into will probably be wrong.

I’ll be coming back to some of those issues later. But, by all means, feel free to begin your serious thinking right away.

How to plan

Step one: gather all your information together. Make a new list with a separate column for each of your reasonable choices. Within each column, briefly note the consequences - both good and bad - that might be associated with that choice. Include costs - like how much money and time will getting to that particular goal require and what other important activities will it delay. And, of course, include the potential benefits.

Here’s a simple example to illustrate how it might work:

Where should we live?

Move to City 1	Move to City 2	Stay Here
More jobs	Cheaper houses	No moving expenses
Close to family	Paying kollel	Wife’s friends
Strong minyan	Good rav	No current income
High taxes	Far from family

You get the picture.

Now try to weigh them out against each other. You could, for instance, assign numbers that describe how important each particular point is to you. Positive points would get a positive number and negative points, obviously, a negative number. When you’re done that, add up the numbers from each column and see which gives you the highest total. There’s no guarantee that that will be the correct answer, but it’ll certainly give you some more to consider.

Or, in other words, perform a variation of what the מסילת ישרים called a חשבון הנפש.

Note: if you can’t figure out how to add positive and negative numbers, consider suing the hanhala of the mesivta you attended.

And, of course, talk about it with friends, parents, and rebbaim who know you well and understand your background. Your plans should be built on as firm a foundation as possible.