Do you feel guilty selling?

How to go from feeling guilty about selling to feeling confident.

The word “sales” carries a negative connotation for a lot of people. The notion is that selling is unwelcome, involves deception, and is an adversarial process. Salespeople are slick, slimy, untrustworthy, etc.

For much of my career, people have told me that I would be really good at sales. I resisted those compliments, as I thought that sales was “beneath” me. Becoming an entrepreneur forced me (consciously or not) to start processing what was going on for me when I was in the act of selling, and I realized that I held a lot of these negative judgements about the sales process and salespeople.

I used to feel guilty selling things to people. I felt like I was scamming people out of something valuable (money) in exchange for something that I didn’t think was valuable (my knowledge and my time).

I don’t feel that way anymore.

The process of selling also involves confronting the emotion of fear—fear of rejection and fear of judgment. I’ll discuss that in a separate post.

The nature of guilt

I draw a distinction between shame and guilt. To me, guilt is an emotion we feel when we violate our own values and moral standards. Shame is something we feel when we violate society’s values or moral standards.

When I felt guilty about selling, I realized there were two things going on for me:

1) I felt like I was in violation of my own value of generosity: “I should be generous about helping people and not treat it like a transaction.” I did not want to be a stingy person.

2) I felt like what I was giving to people (my knowledge and my time) didn’t have real value, and exchanging something that has no value for something that has real value (money) is basically stealing. I did not want to be a thief.

Over time, my feeling started to change. The difference was I began to realize my own contributions were valuable.

Anger as the flip side to guilt

The flip side of guilt, in this case, is anger. Early in my entrepreneurial journey I would often offer things I knew to be valuable—usually for free—and people wouldn’t accept. My emotion there was usually anger: “This is free! And it’s good for you! Why aren’t you taking it?”

Their reasons for taking it or not are beside the point. Emotions are information. Anger, in this case, was an important clue that whatever I was offering, I did truly believe, deep down in my bones, that it was valuable. The anger was defensive, saying “you really are worth something.” The opposite of self-doubt.

This is a good form of anger!

If you feel this anger, I want you to listen to it. This is the anger that knows your true worth and knows your contribution. This is the same anger you feel when someone takes you for granted.

Eventually we want to move past anger into acceptance. Getting angry all the time isn’t helpful. Mostly, the lesson here is that not all people want what you want them to want at the time you want them to want it.

What if I don’t feel angry?

Anger is one clue. It’s not the only clue.

If you don’t feel angry, it’s possible (not certain) that internally, you really don’t believe that the product is worth very much. If you yourself don’t see the product as valuable, either:

1) you need to make the product better, or

2) you need to understand the product better to see if you really do have an accurate estimation of its value. Just because you don’t believe in a product doesn’t necessarily mean that it’s bad.

The latter is very important when you are the product—as an employee, a consultant, teacher, coach, writer, whatever. Listen for feedback:

  • I have 50%+ open rates on every single piece I publish on this blog
  • People have started to recommend me as a person to talk to for founders struggling with EQ issues in their business

That’s evidence that something I am doing is valuable to people. That external validation, alongside the internal anger, has helped me gradually dissolve the guilt.

Moreover, if you’re the product, you can always take steps to make yourself better. Do some professional education, practice a soft skill, read my notes… you get the idea 😉

The best salespeople

Effective salespeople are past both anger and guilt.

The best salespeople are the ones that truly, deep down in their bones, believe that the product or service they are selling will help the customer. These are also the salespeople that will tell the customer not to buy the product if they think it won’t help.

These people feel no guilt, because their desire to earn rewards for themselves by selling is paired with a genuine desire to help and a belief in the help they are giving. If they feel anything upon losing a sale, it’s sadness, because that means the customer will continue suffering and won’t get the help they need.

I suspect that this is also the attitude held by religious evangelists and missionaries. They are out there pounding the pavement, enduring constant rejection, and distributing holy books because they honestly think they are helping others.

Your journey as a salesperson is about accepting the guilt and the anger (and the fear, which we’ll talk about separately) and over time, transmuting them into fuel you can use.


Journal on this one morning, or discuss with a friend:


1.      Noticing—Guilt: What’s something that you feel guilty about offering to people?

2.      Noticing—Anger: What’s something that you feel angry about when people don’t accept it?

The latter is a product you believe in; the former is a product you don’t. The “product” can be yourself.


Ask one person you trust for feedback, with a focus on their emotional experience of being offered something (you are not looking for product feedback).

3.      Inquiry—Guilt: Does the product you feel guilty about feel like a scam to them?

4.      Inquiry—Anger: Reflect on the product that makes you angry when people don’t buy it. Ask them, if you were to refuse to buy this product, what might be going on in your life that would stop you from buying?


The exercise always concludes with action. This week is specifically guilt:

5.      Action—Guilt: What is a small, concrete step you can take to improve a product you don’t believe in? Remember, this product can be yourself.

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