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A Fundraising Cheshbon Hanefesh For Jewish Leaders Serious About Growth

When a business owner works on their productivity, vision-building, or professional skills, they’re… building a better business.

When the head of a Torah organization works on those same things, they’re increasing the amounts of Torah, kedusha, and chizzuk they can bring into the world.

Bottom line: If you’re a Jewish leader, investing in your personal growth isn’t just “self-development.” It’s avodas hakodesh. It’s a responsibility to Klal Yisrael.

So here’s something I call a Fundraising Cheshbon Hanefesh — a self-assessment to help you reflect, reset, and reignite your productivity, purpose, and fundraising power.

How to Use This List

  1. Print this out or open a doc and type directly into it.
  2. Run through the questions quickly, jotting down the first answers that come to mind.
  3. Then revisit them when you have more time and dig deeper.

Here we go:

1. Self-Mastery & Growth

- What’s working really well right now?

- Write three habits, tools, or people that give the biggest payoff.

- What are you most proud of accomplishing this year?

- What are your three greatest strengths – and how are you using them?

- What’s one mistake or failure that taught you something valuable?

- What’s not working – and what single change could improve it?

- What fears or limiting beliefs are holding you back right now?

2. Vision & Mission Ignition

- When you picture real success for your organization, what do you see?

- Are you on fire in your mission – or just going through the motions?

- What shift in mindset or behavior would reignite your fire?

- What habits or routines keep you inspired and connected?

- What one thing blocks most of your success? If you removed it, big results would follow.

- What can you do to remove that blocker?

- What first, concrete step will you take today?

3. Productivity Accelerator

- If you could accomplish only one thing in the next 12 months, what would it be

- Where are you overspending your weekly hours?

- Where are you underspending them?

- What one adjustment will free more time for the work that matters most?

- Which new skill do you commit to acquiring this year to gain a new level in your work productivity?

4. Fundraising Game-Changer

- If you were a wealthy outsider, would you make a major gift here? Why—or why not?

- If the answer is “no,” what must change so you’d feel eager to write that big check?

- Could you confidently ask for a gift five-times larger than your current top donation? Why—or why not?

- What one barrier makes that ask feel unrealistic?

- Would a gift that size genuinely surprise you? If yes, why?

- What single resource, mindset, or action will let you play at that higher level?

- What specific step will you take today to set this in motion?

Wrap-Up

How was this process for you?

  • Which question hit hardest?
  • Which one made you smile?
  • Hit Reply if you'd like to share what came up for you — or if you'd like help taking any of this further. And please do let me know what success comes from the work you just did.

Hatzlacho Raba,

Avraham

Copyright © 2025 Avraham Lewis & Co.