How Documenting Your Interactions With Others Can Make You More Successful

Sam Hickmann
4 min readJan 12, 2021

As an entrepreneur, I’ve met many people over the years, from investors to journalists, from customers to suppliers and from engineers to janitors. I always prided myself on calling them by their first name and tried my best to show them how important they are. Like William James, the father of American psychology, said: “The deepest principle in human nature is the craving to be appreciated.

However, I was facing a big problem: Over the years, my memory began to fade. When meeting with somebody I had only met a few months prior, I found it challenging to remember details about them. Therefore, my rapport with them was not as warm as I wished, and I felt like I didn’t get the full potential of the discussion.

I remember precisely when I decided to take action against my faulty memory. It was in 2016 during a meet-and-greet in San Francisco. I was chatting with John for an hour when he suddenly whispered into my ear, “No offense taken, but my name is Paul.” I was ashamed of myself, and I’m almost certain this mistake cost me a big business opportunity, as John — sorry, Paul — was the perfect prospect for my business.

Enter Moleskine

I read that, over the course of his life, David Rockefeller (former Chase CEO) wrote about 200,000 notecards to document his interactions with world leaders. So, I decided to buy a Moleskine notebook dedicated to taking notes on people. I started to populate the pages with everything that came to my mind. One page per person. I would write contact details, names of their loved ones, jobs, hobbies, food preferences and even bullet points on what we discussed when we last met.

However, I was quickly confronted with the limitations of a paper notebook. The notes started to pile up, and I was running out of space on each page. For instance, the person I documented on the first page of the Moleskine was full, so I had to start another page near the end. I needed to write “see additional notes at the end of the notebook” — not ideal. The second problem was that I was not always carrying my “people’s notebook,” so I wasn’t always able to review my notes prior to meeting someone, especially when the encounter was random.