The entrepreneur who was too organized to succeed

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This week’s question from our portal “Ask Us Anything” comes from Steven.

I was thinking about all the routines, processes, and checklists I have. I’m all about routines and structure. But I wonder – do those actually help? Although they’re good and give you guardrails, I’m wondering if they actually keep you in problem-first thinking. I thought, what would happen if I just blew up all of that and went freestyle the rest of the afternoon? That scared me to death. What do you think?

I think this works differently for everyone, but there is a point in time where structure needs to shift:

A structure isn’t meant to stay in the same place all the time. A structure is meant to move and shift with what you’re trying to create. It should be what you want to create first and the structure gets built around that, rather than structure first. If you’re structure first, that will limit you 100%.

It might be time for you to look at what’s working and what’s not working and do some house cleaning. If you don’t have white space in your calendar for creative thinking and for visionary thinking, that’s doing your business an incredible disservice.

In the book, “U Squared,” it says let it be easy, seek the elegant solution. If your structure is not producing the results you’re looking for, you’ve got to reevaluate. Doing the same thing over and over and expecting a different result is the definition of insanity.

That pushing – all of that is fear. One day you’re letting it happen, the next day you’re back pushing again. That’s fear, and that slows the process down.

What are you afraid of? If it doesn’t work, what happens? It doesn’t work, you start over, you recreate. So there’s nothing there to be afraid of. The fear is an illusion, it’s a ghost almost all the time.

You’re the leader. They’re following your lead. You just need to communicate with them: “Hey guys, I think maybe the structure is too constricting. You’re going to see me take a step back away from that and do some more creative thinking in the hopes that we get moving in the right direction and get the results we actually want.” Then let them give their comfort level with that.

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