In his latest book, Side Hustle, Chris Guillebeau writes about "that guy" when it comes to asking people for help. He highlights two examples. The first is about someone that reached out to him on every social media platform within the same hour with the same message. He added a message at the end to say that he just wanted to make sure that Chris saw his message. The second is about a person who kept following up with Chris on a favour he had requested twice a day.

Both of these, as well as many other such behaviours, are thoroughly annoying. These are behaviours that can put off even well-intentioned people that want to help.

I've been on the receiving end as well as the delivering end of such behaviours, although I have learnt my lesson and haven't been "that guy" in several years now.

When we are in need of help, it is very easy to have our worldview centered around us and have unreasonable expectations on those we are seeking help from.

When you're asking for help, make the other person feel good, don't guilt trip them or put pressure on them, and thank them for their time irrespective of whether they do or do not end up helping. Always assume the best intention on their part.