Dear _____ 

It is rare I read a letter more than twice. But I read yours a few times over. And I imagine I will yet read it a few times more. Because Unfortunately, I can relate to what you are describing all too well…

In fact, whilst it does not make it easier, I think you should know that whereas for younger Bochurim the most common emotional constraint low self-esteem/self-worth/self-confidence, for older Bochurim and Yungerlait that is often amplified by this feeling of ‘pressure’ that you describe. 

Unfortunately, it is challenging to empathise properly by this means of communication. Because by definition writing is ‘talking’ rather than listening…

How I would love to sit with you and Farbreng about this all night… for many nights… But our physical distance does not allow for that. So first let me tell you that if you find that this is hindering your day it is really important that you speak to someone local, face-to-face. 

Your pain is clear from your writing, and I am not sure if the first choice of response at this point are ‘words’, But the constraints being as they are, I will do my best to address your point by ‘talking’ it out in this way.

I often tell Bochurim that

The five most destructive words in the lives of most Bochurim are: 

By. Now. I. Should. Have. 

I know it may sound funny, but

one of the emotions that yield the least productive results is “Pressure”. 

When an individual is under pressure, feeling they must already attain their goal, the mind does what it always does when it is overwhelmed; The mind shuts down.

That is why, despite ample evidence to the contrary, your mind won’t see it. It will be in a constant panic, or worse, give up entirely. 

The older I get and the more I learn, the more I see the Chidush in Toras Chabad. The Alter Rebbe literally revealed a set of concepts that weave together to make a tapestry for life so all-encompassing, that it could only come from infinity. 

One of those Yesodos is that there are no ultimate goals, there are only ambitions.

You do not have a “Life’s Goal” – Hashem has a goal for each moment that He wants you to achieve. 

A Yid does not have a sum of achievements. A yid has a sum of moments, decisions, and internal struggles. 

There is no sum-total. There are unique moments. Each moment valued as a stand-alone entity. 

The Bochur complains that after all these years he wishes he could learn a Daf Gemora without an Artscroll. I understand the wish. I hope he can do that one day. 

But nowhere does it say that you must know how to learn a Daf Gemora on your own. 

What it says is that you must learn Gemora. 

Knowing how to do that would be nice, but if the pressure of ‘lack’ is causing further lack, then are you not allowing the lack of a side thing to become the most important?

The sum of those moments are overall achievements.

How can anyone fail before they die? Do you not have a job to do at this moment? על כל דחי’ ודחי’ שמדחהו – each time you push yourself to do the right thing you were %100 successful in that moment. 

I understand the feeling of disappointment in self for not having achieved more… but in my opinion, it is misplaced.

I will say it again, the question “Where I should be” is not a proper question. The only real question “What should I be doing now”?

The question of “Where I should be” is only to a tool to decide which area in life is most important to place your focus at the moment. 

I will never forget the Yid who told us his story. How the Eibishter Bentched his business and he did very well… How years later he lost everything and went bankrupt… only to have things turn around for him a few years later…. 

How did he have the strength to do it? 

Because years ago, the Rebbe told him not to look at the total he gave to Tzedaka, rather to look at each appeal on its own.

The Rebbe taught him to ask himself:

1. “Is this a cause I should support?”

Yes?

2. “Do I have the money in the bank?”

Yes?

3. Give. 

He lived my life that way ever since. In material matters as well.

“That saved me,” he told me.

“The day after the bankruptcy was final, I woke up and did what I had done for the thirty years prior.”

“I worked.” 

“Those first few months were humiliating. Bankruptcy is humiliating. But I never defined success by the bottom line.”

“I always just tried to use each hour wisely.” 

I understand your pain. But whilst it is hard to challenge emotion with logic, it is the only way I can do so via this means.

And so, when you feel the pressure of “Should be”

I can only urge asking yourself a different question: What should I be doing now? What can I do now?

And remember to blacklist these five words:

By. Now. I. Should. Have.

You are exactly where you need to be at this moment of your Avoda, and trying to assess where you would have been is illogical only עצת היצר trying to make himself look ‘Chassidish’.