🧢 Wearing the right hat: The identity shift needed to build real businesses

Throughout the years many of my clients have joked with me about how I exist in their head. They tell me that they can literally hear me. I often joke back about how I should figure out a way to charge them for all the free sessions they’re getting!

One recoined the acronym WWJD to “What would John do?”, as he found himself often asking this question when faced with a decision.

When I realised what this actually meant, I introduced the identity exercise to help stop people asking “What would John do” and instead to ask “What will I do” in the most positive of ways.

My clients were asking themselves “What would John do?” because they saw me as the model entrepreneur. I make good money, I have control of my time, I’m happy. They were using the questions as an identity crutch, a way to bridge the gap between who they are and who they want to be.

The identity exercise is simple:

1. I ask those I work with to outline things they think an “entrepreneur” does that are different to things they do. Sends “good enough” emails, for example.

   
   

2. I then ask them to write down why the difference exists.

   
   

3. Finally, we discuss this and then write what we will do differently, how we will enforce the difference, and in what order we will make the changes (some updates are higher priority than others).

   
   

All of my clients are entrepreneurs, but they don’t always see themselves that way.

Often, we have to hold multiple identities - a father, a friend, a son, an entrepreneur. Each of these identities are useful when used in the right context - but you don’t want to turn up as “you, the entrepreneur” to a conversation with your children, you need to match the correct identity to the correct context and ask how would the best version of you show up in this situation?

Issues arrive when you incorrectly match identity to context, and/or when past identities muddy current or future identities. In the instance yesterday with my client, Kaidi, she was previously a full-time academic. Kaidi the academic does things quite differently to Kaidi the entrepreneur.

Examples:

• Kaidi the academic might spend 5 hours researching something rigorously, but Kaidi the entrepreneur knows the value in making quick decisions and taking action.

• Kaidi the academic saves money and does things herself. Kaidi the entrepreneur invests money and pays for solutions that save her time and make her more money (return on investment).

• Kaidi the academic fears mistakes. Kaidi the entrepreneur embraces mistakes as useful data and a price worth paying for action.

  
  

Both identities are useful in the right context, but we need to know how to select the right identity in the right context.

A bit like Edward De Bono’s 6 thinking hats, we want to “put on” the right identity in the right context. In Kaidi’s case, I asked her to start stating it out loud. Which identity are we right now?

I’d encourage you to do the same. What identities do you have? How would an entrepreneur act differently to how you normally do? Which identity are you right now? Are you becoming the kind of person you want to be? How will you “put on” the right identity, the right hat, in shifting contexts?

When you start a business your identity changes - you become an entrepreneur. Your business reshapes your identity, but few people do this proactively.

What does your business say about you? E.g. you’re busy, you value work over your family, you prioritise bad customers, you’re a pushover, you don’t have boundaries, etc.

It doesn’t need to be this way. We can shift our identity and build our business to help us become the person we want to be. You can start today by giving my identity exercise that I mentioned above a go.

De Bono’s 6 thinking hats

What would John do? Mini montage (video, 61 seconds)

This point came from my newsletter Work Smart Wednesday, if you would like to read the other related points I made in that email you can find it here: https://worksmartwednesday.substack.com/p/work-smart-wednesday-july-30-2025

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