How to Stop Resenting People Asking for More

When you start a business, you end up giving a lot of yourself.

• You take the hit and accept a low salary.
• You work long hours, often at the sacrifice of your personal life.
• You deal with the worst problems you never imagined founders have to deal with.

And rather than get appreciation, you keep being asked for more.

• Your employees will come to you and ask for more money, more vacation days, and more time together.
• The investors you pitch will ask for more traction, better unit economics, and lower acquisition costs.
• Your board members will ask for more data, more analysis, and more growth.

You even expect more from yourself.

So you keep saying ‘yes’… until you end up giving too much.

The Request Trigger

At some point, requests start feeling different. Rather than hear an ask, you start hearing an attack:

• A team request for extra time off -> ‘They’re saying this is a s*** place to work.’
• A board request for data -> ‘They believe I’m a bad CEO.’
• An investor request for board rights -> ‘They don’t trust me to do the right thing.’

Of course, most of the time, they aren’t saying that. 

They’re just acting in their own best interest—and you can’t blame anyone for representing their own interests.

So where does this attack narrative come from?

If it didn’t come from them, it must have come from you.

Projecting Your Own Fears

Projection happens when your inner voice attributes your own fears and insecurities onto others.

On some level, you are deeply afraid of not being a good enough CEO. Or not building a good enough business. Or not building a good enough place to work.

The narrative you project onto them is a defense mechanism to stop yourself from directly feeling this fear. Instead, you feel anger or confusion.

And when you’re feeling these emotions, responding to the ask becomes a bigger deal than it should. It can feel all-or-nothing.

In the moment, the best thing to do is take a deep breath to calm your nervous system. However, I want to share something you can do afterwards that can help you regain your power.

The 100 Reasons Technique

One of the exercises I give my CEOs ahead of a fundraise is called ‘100 Reasons’.

The objective is to build the conviction needed to project confidence about your business, and not get derailed when you receive a ‘no’.

The exercise is simple: I ask them to write out 100 reasons they are building a great business that’s worthy of investment. Not 3, not 10… 100.

It works for two reasons.

1. First, it balances the negative internal narratives created by a deep fear of not being enough.
2. Second, it leads to new ideas on how to make the business stronger.

You might think this is about documenting reasons... but it's actually about creating them.

You have to be creative to come up with 100 reasons, and it forces you to examine your worth from many different angles.

And you can do the same exercise for any area where you tend to underestimate yourself.

• 100 reasons you’re building a great company.
• 100 reasons you’re a good leader.
• 100 reasons you’re a good friend.

If you’ve got a tendency to get triggered when people ask for more, you probably need a bit of a pep talk. This is how you give it to yourself.

Be Your Own Best Friend

When people ask for more, when we’re giving our all, it’s normal to want some recognition and appreciation.

But sometimes, you have to give that to yourself.

Until you fully appreciate who you are, what you’re building, and what it’s worth, you’ll always be susceptible to the Request Trigger.

But if you can take stock of your own value, you can start to hear asks for what they are: someone representing their own interest, and not a personal attack.

You must do the same: represent your interests, without attacking. Because that’s your right, just as it’s theirs.

Related Reading

• How to Use Nonviolent Communication in Difficult Conversations
• How Founders Lose Sight of What They Want
• How to Become More Confident at Fundraising

Originally published on January 7, 2026.