The first step is to notice the fear, give it borders and space.

You did that, as is proof from you reaching out, and wanting to overcome this. 

After you gave space to the fear, it prompted you to create clarity on what you are up against.

This you did precisely. You labeled it as a “fear from asking for help”.

You then asked yourself, “Where else is this showing up?” “What else does it look like for me?” and “What’s the deeper fear?”

These are great self-coaching questions you can ask yourself to go deeper with anything.

You came up with some more answers:

This shows up as a fear of asking for money, and a fear of appearing unsuccessful and needy.

(If this was a coaching session, I might ask you: What’s really going on here?  The point would be for you go yet deeper and focus on the core of all this, and see what deeper truth comes up for you in the presence of a powerful coaching conversation.)

Remind yourself that you’re not the first, nor the last person to face this challenge. And you’re not unique in struggling with this.

Often times we want to put our problems up on a pedestal of  “I’m the only one in the world with this challenge.” That angle is simply not true.

What is true is that you are 100% unique when it comes to your gifts, talents, and your unique DNA and mix of aptitudes, gifts and in your personal mission. That uniqueness is there to embrace. G-d needs you here – there is nobody on this planet like you – you are integral.

On the other hand, calling out your challenge as unique gives it undue strength – and weakens your belief in your natural ability to overcome it.

Let’s go one step further. This challenge is not only not unique – it’s the most common one out there.

Fear of social situations, also known as “social phobia” in more technical terms, is an incredibly common experience that affects somewhere around 1 in 20 people in a significant way. This type of fear is normally characterized by an overwhelming self-consciousness in social settings.

It’s important to highlight for anyone reading this that social phobias take various forms and can range from mild discomfort to paralyzing anxiety. The more stuck you feel, or suffering it is causing you, the more help I encourage you to seek to break free from this.

One particularly common way social phobia shows up: the fear of being judged by others.

And people will then avoid situations such as speaking in public, attending social gatherings, or even something as seemingly simple as eating in front of others.

So it’s normal to feel challenged by what others might think or more specifically, how they will judge you, perhaps as needy or unsuccessful – even thought it’s not true.

Now that you know what you’re facing – it’s going to be really valuable to lean on the skills, strengths and experiences you already have under your belt.

You asked for a strategy.

The truth is – you don’t need a new strategy when you already have ones that work.

In fact you have strategies that you’ve customized over your past experiences. And those will come in handy.

In your own words you shared, “I’ve already overcome different fears in my life.”

You have already overcome the fear of davening from the amud on Shabbos. You’ve also overcome the fear of public speaking. That’s no small feat, and I challenge you to find ways to remind yourself of that as you pass through this latest form of: “What will they think?”

If you’ve already developed the muscles and habits to daven from the amud on Shabbos in front of a crowd, and give talks to groups, then I am certain you can also overcome this fear of asking others for help, including asking for money.

You’ll want to ask yourself now:

If someone else asked me for help in overcoming a fear – what would I tell them?

Imagine your son comes to you and asks:

Ta, I really want to go chazzan at school but I’m so afraid of what my classmates might say. What if they laugh at me? What if they talk about me and how I’m no good?

What would you advise him?

You might tell him:

First of all, my dear son, I’m so proud of you for sharing this fear with me. And, great job giving it a name and putting words to all this. It’s so brave of you to bring this up, and to be vulnerable in sharing it. And what a great “want” you have – to be the chazzan, that’s holy work – good for you.

And then you’d probably advise him to take himself out of the picture while up there at the amud and focus on one thing:

My son, go give the people a nice inspiring davening.

And you’d probably share your own experience:

I was also fearful of this once upon a time. But when I stopped thinking about the fear of failure, what people might think, and making a fool out of myself, I actually started relaxing and that allowed me to do a great job!

When you’re ready to give it a try – focus on that – creating inspiration for the kehilla. Nothing else.

In the past, you have already overcome different fears in your life.

In fact, as a business leader you have leaned on what I like to call:

Creating a project or a challenge.

You have actually created daily challenges before: to see how many times a day you can do something in spite of the fear, such as making difficult calls (to teammates, clients and vendors), negotiating a deal, sales prospecting, approaching the “scary-looking person” at tradeshows and more.

So in the past you said: I will not let this fear stop me. I will turn it into a project, a game or a daily challenge to see how many times a day I can do something in spite of my fears;

You’ve done this before and you can, without a doubt, do this again.

So I’m curious, if you ask yourself this question what can you come up with:

What daily challenge can I create that gets me into action despite my fear of asking for help, asking for money or otherwise appearing unsuccessful or needy?

After you come up with your own answers, see if my challenge here fits with that. I challenge you Business Leader With a Fear of Asking for Help, to the: “BIG ASK” DAILY CHALLENGE.

Every day (Shabbos not included) your assignment is to make one BIG ask from anyone in your world: a family member, a client, a colleague, a vendor, or someone in line at the supermarket.

For example, you mentioned asking your father for $60 when you really needed $100.

So in this challenge, you might ask a client:

I’m working on a project/challenge from my coach to ask a big ask – every day. So I’d like to ask you: What would it take for you to send me 10 referrals before the end of the week?

Or, you might ask:

I’m looking for help with my start-up – I need seed money. Who do you know that would consider investing $10,000 to $100k into my business with a guarantee to double his return?

To make it simple:

The ask has to feel “BIG” to you.

So if you are used to asking for people to give you 15 minutes, start asking them for an hour or two.

If you are used to asking someone to pass the salt, starting asking if they will clear the table.

If you are used to asking someone for $100, ask them for $1,000 or $10,000.

Remember, my challenge is an add-on to whatever you feel is the right daily challenge for you.

I’m curious to hear what you come up with and how many BIG asks you can get in this month.