Hiring an assistant (RW76, RW77, RL255)

When John tried to hire an assistant years go, he asked a woman he knew who worked as an office manager for help and the process got sort of hijacked by her appointing herself as his office manager. Then she hired an assistant, which means that for a while John had a manager and an assistant. Then the manager decided that John was an unresponsive boss which was not an environment she could thrive in, so she left unceremoniously and in a huff, leaving her assistant behind who at the same time became John's new assistant. As they had considered numerous applications during the initial hiring process, John had been kind of sidelined and his office manager had hired somebody who she liked. John enjoyed the service of the young woman for another year. Her name was Bailey and she did a lot of work for him, but John had big big plans. It included things like making merch and selling it, putting a store on eBay, putting together a Patreon or some kind of crowdfunding for his new record, or redo his websites. Those are tasks that are administratively impossible for John to do because he just cannot keep his mind on them and he cannot be bothered. (RW76)

Bailey was instrumental in putting together the live show that he did over the course of a year in Seattle and she got those coffee mugs with his face on made, primarily to sell them at the show. Eventually it became this all-consuming project for her. She stage-managed it and did all the other stuff that was on the list of things to do for the show, but it was hard getting many of the other things done the way they wanted, because doing a weekly show is not a small task at all. After a year, Bailey got into her car one night and drove away. She is living in some other state now and disappeared for a long time, even from the Internet. She was an adventurer and came from Colorado specifically to be John's assistant. (RW76)

A lot of the income that John would like to generate for his assistant would be income that would be derived from the projects they would be working on together. There is a large income stream of low hanging fruit available to John, mostly in the form of running a small enterprise by making things and selling things, generating content and giving people the opportunity to support or buy that content. But John needs help by someone who wants to do all that. He wants to pay them and in case of Bailey he was hoping they would have a diverse enough income stream to enable her having a good income. She ended up moving in with John's mom, because although they had tried a lot of things to compensate her, they didn't get it off the ground. The income they were making wasn't enough for Bailey to thrive the way John wanted her to. Today there are even more opportunities than 3 years ago! After Bailey left town, John immediately started to run for city council which was a money-losing proposition. After that, John was back immediately thinking about an assistant who wanted to develop his enterprise. He is working on music right now and is effectively going to run a small record label, making music, putting it online, giving people an opportunity to support it. All that requires trips to the post office, so in August of 2017, John was putting out the call again for somebody who is flexible, intrigued, capable and located in Seattle. Maybe they can even try working remotely. (RW76)

The main stumbling block is that John is not a very responsive boss. He doesn't like to get 14 texts a day about stuff. He likes to empower people and say "I'd like to have a challenge coin", because there are 20 opportunities in a typical week to give someone a challenge coin and it would be fun for them and fun for John. A listener had already designed a great challenge coin for him. The problem was that John would like to say "okay, make it and when the bill comes, I will pay it." He doesn't want to make any additional decisions in that middle part between agreeing on the design and when the finished coins arrive. John wants somebody who knows how to do that thing and it is their job to make all of these decisions. This is the thing about a good stage manager: When you have a bunch of people coming on and off the stage in the course of a show, the best stage manager is the one that you are not aware of at all until they are standing next to you, handing you a microphone and say "Okay, you are on!" After you did your thing and walk off, covered in perspiration and thrilled about your performance, that person appears again, takes the mic from you without saying anything and if they want you somewhere, they will move you there. There are other times when the stage manager is standing in the wings, whisper-shouting, stomping and complaining that everything is going wrong all the time, but that is bad stage management. This feels like show-business to people, but it is the opposite. (RW76)

The same is true in this dream relationship John is imagining where his assistant is invested in the job and in their relationship with John, but they don't need constant attention. His assistant needs to see this as an opportunity to lead this new business and learn the skills while John is also learning to run a record company and setting up a small enterprise that is selling a variety of goods in this new economy that is mostly online. John would like to record a song a week and make it available on the Internet, but that would be a component of some sort of crowdfounded creative product. Supporting listeners would have access to those songs and on higher levels there would be more perks like an iPhone-video of the song or handwritten lyrics. It doesn't have to be part of a Kickstarter, but it will be more of an ongoing process. People write John all the time saying that they would like to give him money for what he does, but there is not a single way to do it. There is not even a Paypal-button associated with him! (RW76)

Of course this would also be an opportunity to be creative, think of new stuff and get things made. Now three years later, John still doesn't have a challenge coin! He just got a challenge coin from a real admiral, which is so far his highest-ranking challenge coin. After doing 5 events together, he said that they know each other now and he shook John's hand and did the little palming. If only he had one to give him back, like "Nice challenge coin, Admiral, how do you like them apples?" John's design had a crow on it and a GMC RV and John doesn't even know if he can find that file now. Bill Brance back East did all this work for him pro bono because he is generous. A lot of people want to help, but we are all busy, like Dan could redesign The Long Winters website, but he doesn't want to, because he is a busy guy and has barbecue to eat. Merlin Mann designed the original Long Winters website just out of affection for him and John found $500 to give him, but Merlin made this website because he is a fan and he would typically charge $25.000 for a website like that, meaning that $500 is so out of the realm that he shouldn't even bother! Similar things happened a few times. That is John's problem! John wants to do all those things. He wants to wake up every day and make a 1 minute long YouTube video and just be producing content. He doesn't want to sit around and have all his deep thoughts go down the bathtub drain. He just doesn't know how to keep those comments and put them somewhere on the Internet. Maybe he should carry a recorder with him and record things as they come out and once a week he hands it to someone and they spend the time to go through it and act on anything good that comes out of it. But even that is more than John is capable of. (RW76)

After that story aired, several people contacted John on a variety of social media platforms, through email and through The Long Winters website and offered to be his assistant. Every single person who emailed was amazing! 3 of the 4 people live elsewhere and while they were not at liberty to move, they claimed that they can do a lot of things remotely. A 5th person was from a facilitation company and a procurement & distribution group who can make things and send them out. The problem is the step between himself and getting anything for them to make. One of the applicants is local to Seattle and they sound great, but now John needs someone to keep all that straight. It is very exciting and everybody is way more competent than John deserves, but there definitely seems to be some light at the end of the tunnel. All by way of saying: things are doing pretty good! (RW77)

Merlin does not like the fact that John is asking for assistant applications again. He had warned John about so many things before, he is like a personal Casandra and cuts out all the parts from the podcast where he's warned John about things. Merlin could make a supercut of all the times he said "Are you sure you want to do that? If that goes perfectly, that will make you happy? Are you sure?". When John starts a sentence with: "I've been thinking", Merlin immediately goes "Noooooo!". Nonetheless, this is the one that is going to revolutionize John's life! It will definitely not be somebody who is making too little money for them to really put their back into it. They will not half-ass it and really do it right so John doesn't have to do it again himself! So far, everybody who has replied seems like a very professional person with a lot of talents and skills! They are all legit! John has not gone deeper with anybody yet, he has just replied to their emails. Is there a window of "fancy-enough" through which those people should pass? Last time John got office manager applications from people at NASA who wanted to be his assistant. But that is the thing about the podcast: It is out there and people listen, sitting there under their own potato tree, saying "I'm just doing my thing!" (RL255)

Last time John was trying to get an assistant, she did a whole Dick Cheney on him and picked out herself. Cheney said at the time that the best candidate for Vice President was himself and when he became the Vice President, he started 60 wars with a man-sized vault in his office. It is still an incredible story to John that the entire Bush-administration existed. (RL255)