The Guilt Monster

I was talking to a friend of mine who is a CEO and Founder of a successful business. They’ve recently released themselves from the day to day running of that business. They haven’t sold it, they still own it, but they have managed to ‘let go’ of the reins, becoming a ‘hands off CEO


My friend mentioned the guilt they feel when they do non-work related things which are fun. I can relate because I remember feeling this way when I was running my previous business and I managed to get on top of things and ‘let go’.


When I went from an 80 hr to a 14 hr working week, it allowed me to learn to fly helicopters and race cars, have lunch with my wife and go on breaks away. I felt incredibly guilty doing that while the business was making a lot of money and other people were doing all the work. I really struggled with the reality of life as a ‘hands off CEO’ and I think this is quite common.

I used to put fake entries in the calendar so people thought I was at business meetings, when I was actually having fun. Or I would be mysterious about what the calendar entry was, because so many people in the business could see my calendar. I remember one occasion when I put mysterious things in my calendar and rather than assume I was having fun, someone thought I was meeting someone to sell the business. At that point I hadn't even thought about selling the business!

When my CEO friend and I decided to try and work out why we felt this way, I started by asking him ‘what do you think other people at work really think when you are off having fun?’. He said he had spoken to this business partner who was still working in the business doing long hours and told him he’d been doing all these fun things. His business partner said “that’s brilliant isn’t it?”


I quizzed him further about it and asked ‘how do you think the rest of the people at work feel about it, do you think they think “look at that bastard out there having fun” ’ and he said “no I don’t think they do, they think ‘good on him’ or at least the ones that matter do”. So we pushed the point of what makes us feel guilty and came to the conclusion that it’s not really about other people’s perception, it doesn’t really matter what they think or even if you know they think that. As Eleanor Roosevelt once said “You wouldn’t worry what others think of you if you realised how seldom they do.”


People have this mentality that their self-worth is driven by working hard. That’s what we are taught, it’s how we are brought up; you work hard, you do well! You justify doing well by working hard and then when all of a sudden you decide not to work hard anymore you have no basis to value your self-worth. It’s really difficult to come to terms with your new reality.


We discovered the problem was that our self-worth was driven by us working hard and that’s our own internal judgement not the people around us.


You feel like if people knew they would be resentful but actually the majority of people don’t feel like that, certainly the people that matter don’t feel like that. People that matter think ‘he’s worked hard, he’s done well, taken opportunities in life, taken risks and now he is getting his reward’. They genuinely feel like that which is an interesting perspective. But we make ourselves feel guilty by imagining they are judging us.


There’s a little guilt monster inside you. The issue is in your own head, it’s not in anyone else's head.

The solution

Accept that that guilt monster exists. It’s there because of the way we were brought up or something that was instilled in us at an early age. It’s served its purpose having successfully pushed you to improve and succeed through fear, anxiety and guilt and now it needs to go!


Positive Intelligence’ refers to this saboteur as “The Judge that beats you up repeatedly over mistakes or shortcomings, warns you obsessively about future risks, wakes you up in the middle of the night worrying, gets you fixated on what is wrong with others or your life. It’s your greatest internal enemy’’, and encourages you to name your guilt monster to weaken its power and makes it easier to identify when it’s in play and to accept it’s not correct and to ignore it.


Go out and do the things that you really want to be doing and when that guilt monster comes and says ‘you should be working and not having fun’, identify it and think of it as a separate person in your head, like a saboteur in your brain as opposed to you. Gradually this will steal the guilt monster’s credibility and undermine its power!