Selfless Giving Versus the Pleasing Prison

Kelly Teemer
Book Bites
Published in
4 min readAug 15, 2019


Photo by Erika Giraud on Unsplash

The following is adapted from You Don’t Have to be Ruthless to Win by Jonathan Keyser.

The business approach I practice and promote is built on selfless service to others with no expectation of receiving anything in return. Often, I do see my service returned exponentially, which is why I’ve been successful, but it’s important to maintain a mindset of selflessness to keep your motivations in check.

Many people do something that looks very similar to living the give-first mindset, but what they are actually doing is something called the pleasing prison.

Avoid Becoming Trapped

The pleasing prison is the place in our minds where we subject ourselves to doing only what will gain us the approval of others. When I wanted business before my transformation, I was stuck in this prison. I would take steps to make it look like I was giving to others, but what I really was doing was trying to gain approval, business, or favor from others by appearing to give selflessly.

The pleasing prison is creepy and uncomfortable for all parties involved. It is easy to sense, and it steals all the power from the giving. When we’re trapped in this prison, we live our lives trying to impress a specific group of people. We are inauthentic and motivated by the expectations we put on others, which is a miserable and ineffective way to live. People pleasers feel an inescapable desperation to gain approval, even to the point of compromising their values, integrity, and, potentially, even their closest relationships.

My escape from this prison took place when I began to give fully to others without desiring anything in return. I began to experience freedom — along with deep satisfaction, success, and meaningful relationships.

Know the Difference

The concepts of serving and pleasing may look deceptively similar, but they are miles apart in origin and in productivity. “People pleasing” typically comes from insecurity, fear, or personal, selfish ambition, and it is all about outward appearances. True service comes from a caring heart.

The two also produce different results in both the giver and the receiver, ending in either tension or gratitude. The two concepts feel different, not only to the giver but also to the receiver, even if only on a subconscious level. When people sense you are trying to manipulate them for your own benefit, there is tension. On the other hand, when people realize that you truly care about them, with no thought for yourself, they feel a deep appreciation. This is where having a solid foundation of give-first service becomes so important as you serve your team and, further, serve others in your life and business.

One of our missions at Keyser is to help our team learn the difference between selfless giving and pleasing. We constantly remind members of our team to be aware of which choice they are making in any given situation — giving and serving, or just pleasing others.

This distinction could come in deciding whether to give of your time and money to a nonprofit organization, helping someone with a few introductions, or giving someone a meaningful gift. We say, “Ask yourself, ‘Is this activity bringing me joy?’ If not, then you are probably acting from a place of insecurity, manipulation, or with an ulterior motive.”

Are You Serving or Pleasing?

Understanding the difference can be challenging. I have had people try out our system and then come back in disappointment because it did not bring them immediate financial gain. They will say, “I guess we just need to be patient.” Whenever I hear that phrase, I know that the person does not understand what we do. What are they being patient for? The reward? The payoff? If they have truly served or given to someone — genuinely and selflessly — the reward is contained in the act.

Look at your own motivations and actions to determine whether you’re in the pleasing prison. Ask yourself, “Is this activity bringing me joy?” If not, move from pleasing to serving. When you are taking steps to implement this methodology and find yourself impatient with the process, it means you need to step back and evaluate where your motivations lie.

To learn more about how selfless service can transform your business, you can find You Don’t Have to Be Ruthless to Win on Amazon.

JONATHAN KEYSER launched KEYSER in 2013 with the mission of reinventing and transforming the commercial real estate brokerage industry through selfless service. Representing thousands of companies globally across multiple industries, KEYSER is one of the largest and fastest-growing commercial real estate firms of its kind in the country. A best-selling author, national speaker, regular media contributor, and strong supporter of the Conscious Capitalism movement, Jonathan is actively working toward the upcoming launch of The Keyser Institute to inspire, train, and equip the next generation of selfless leaders.