Why you can’t enjoy your holidays

A few summers ago, I was on a driving holiday in Scotland. Glorious. Driving through the dramatic landscapes of Skye and Inverness… I felt like I was on Route 66 or something. (Not that I’ve never been on Route 66. It just felt a little otherworldly.) Apparently, it rains a lot in Scotland. Not this […]


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The “multiple avatars” problem (and how to fix it)

If you’ve been in business for a few years, you likely see a number of types of customers inside your business. For example, in my language business, StoryLearning, we have customers learning with wildly different goals: Some for workSome to keep their brains healthySome to speak with their partner in their language To make matters […]


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Are you a pillow kisser or a business owner? (How to tell)

Question: How do you know when an online business has “grown up”? Answer: When their ideal customer lands on their website and says: “Holy s*** — this was made for me!” Like these emails that Uncle Olly receives regularly: When you can get reactions like this, selling your stuff is easy and effortless. But getting […]


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The real reason I went “all in” on this newsletter

When I started this newsletter in January 2023… It was mostly for fun. I wanted to do something creative again. I had stuff to talk about from 10+ years of running StoryLearning. And I’ll be honest… It was nice for my ego too, to see my personal brand out in the wild, spouting my sagacious […]


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The dark side of being “good on calls”

I have this friend. Brilliant coach. Clients are queuing up around the block to work with her. She’s completely maxed out. Can’t fit another soul into her calendar. When I asked her about her secret sauce, she shrugged and said: “When I do sales calls, people just love me. They know I can help them […]


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The measure of the man…

This is not the email I expected to write today. I thought I was going to write “launch email 2” or whatever. Instead, I find myself scrambling to fix things going pear shaped. But rather than run from it… I’m going to confront it head on. . . . So, yesterday, two things happened: Now… […]


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