I am a bike and hike guide in rural Japan. I had a request to do a three-day guided trip in Tokyo for a family of six. I declined.

Me: “I do not do Tokyo. I haven’t been there in years, plus there are plenty of tour guides who live there and know the area.”

I then tried to find someone for her, but since it was around the New Year’s break, none of the other private guides were available. She begged me to help her. I helped her (for free) with planning for transportation and presented various options of things to see (which I took right from the other tour guides’ itineraries listed on the web), and she still wanted me to go there, a couple of hours away.

Okay. I broke down. I figured I could get a paid trip to Tokyo and visit some friends.

One of the things she mentioned was seeing Sumo. There were no Sumo tournaments at that time, but I made an appointment to visit a Sumo practice stable which is only available to foreigners if they have a Japanese-speaking guide with them. They could not have gone alone.

The rules at the stable are:

• Be on time! This group royally screwed that up.

• It is not for gawking; it is for true Sumo enthusiasts. The stable let us slide on this one.

• You have to stay until the end. This means a few hours of watching Sumo drills.

About thirty minutes into the practice, the woman came to me.

Client: “I think my children are tired. Let’s go.”

Bear in mind that these were all adult children.

Me: “No, we can’t. It would be rude, and they have a rule.”

Client: “But the kids look tired.”

Me: “Okay, I will ask.”

I went over to the teacher and pretended like I was asking him if we could go, but I wasn’t. Instead, I just made them wait an extra hour and sit through the experience they had asked for and that few foreigners would get to experience.

Then, we went to the highlights of Tokyo. One was a big temple that is very famous, so it has lots of tourists.

Client: “Ugh, this is too touristy. I want to see the real Japan. Can’t we go to Asakusa?”

Me: “Oh, I’m sorry, maybe you couldn’t hear me before; Asakusa is where we are now.”

I went out of my way to find out-of-the-way places with character to eat where I was sure there would be no other foreign tourists, but she vetoed me.

Client: “No, we want to go to this famous place we saw in [Travel Guide].”

Of course, it was a kind of theme restaurant aimed at foreign tourists, who were 90% of their clientele. They got back to the hotel, and she asked me:

Client: “What is the plan for tomorrow?”

Me: “I thought we would walk from here to Shinjuku and pass through some interesting areas along the way. Some are crowded and popular with tourists but also very popular with the Japanese people. It is well worth it.”

Client: “We can do that by ourselves — unless there are any secret areas?”

Me: “No. I am afraid that there are not any real ‘secret’ places in Tokyo. If it is interesting, someone has written about it, and you will find tourists there. We can go wander through some small quiet neighbourhoods, and I can almost guarantee that you will not see many foreigners, and if you do, they will be locals.”

Client: “Is it in the guidebook?”

Me: “No.”

Client: “Well then, what is good about it? We can do that ourselves, as well!”

Me: “Okay. I agree. I will tell you what I have planned for the next two days, and I am sure you can do it by yourselves. There is plenty of English-language material in Tokyo for tourists. Let’s just say goodbye here.”

I fired my clients, and unfortunately, due to being in a rush in the morning to get to the Sumo, and just not being able to get a chance for them to get cash to pay the full amount for that day, I had to leave with only the deposit.

Luckily, the deposit covered my transportation, and there are cheap capsule hotels in the area.

The day after I fired the customers, I did exactly what I would have done with them, and I loved it. A few weeks later, my family and I had a stopover in Tokyo, and we did that same walk, and they loved it, too.

Client: “Write ‘X’ but circle it. Circle it so that it shows it’s not so important.”

Me: “But a circle would make it stand out.”

Client: “No, no, not a circle — a circle like you use when something’s not important.”

My patience is ebbing.

Me: “We can put it in parentheses… Is that what you mean?”

Client: “No, like the little circles that are on the nine and the zero on the keyboards.”

Me: “Yes, those are parentheses, like brackets.”

Client: “Yes, yes, brackets. That’s what I meant, but just not so square. More rounded.”

A client wanted me to help him change domain registrars. I helped him through the process, and the five-minute tutorial turned into a thirty-minute ordeal as he questioned the security of every step.

Me: “There, done. Now just enter your card details.”

Client: “No. I don’t trust the website.”

Me: “Then you can’t transfer your domain! Don’t worry. The site is very reputable.”

Client: “How on earth do you know? I’m a businessman; I need to know who I’m dealing with.”

Me: “They have an SSL certificate and half a million customers. I use these guys, and I trust them with my card details.”

Client: “Then we’ll use your card details.”

Me: “But why would I pay for your site?”

Client: “I think that’s only fair seeing as you’ve taken up so much of my time. Every second I spend on this, I’m not working on my core business, so I’m not earning money.”

A client called yesterday and asked if I could do a “quick” logo for him. He said he just wanted something with a palm tree and a warm color palette to advertise his beachside restaurant. Normally, I would reject a job for a “quick” logo because they take time and research to complete, but I’d worked for this client several times before, so I gave him a quote and started to work.

After I sent him three comps in oranges, reds, and yellows featuring sunshine and palm trees, he texted me.

Client: “I don’t like them. They look like Miami!”

I rolled my eyes before texting him back.

Me: “Sorry you are disappointed. That is your font I was working with. It is definitely an art deco font, and yes, Miami is very art deco.”

Client: “Is it going to cost more to get a couple more samples? The black letters are way overpowering, too.”

Me: “Yes, it is going to cost more. If a customer in your restaurant was still hungry, he would have to pay for more food, right?”

He didn’t reply right away.

Me: “So, do we want to ditch the font, then? Maybe you could give me a call?”

I haven’t heard back from him.

I was working with a major credit card company over an eight-month period where I was making them a series of marketing materials. Early in the process, I had a conversation with my direct contact that went something like this.

Me: “In order for me to follow your brand, I will need a copy of your brand book. Can you send it to me?”

Client: “We don’t have a brand book, but here are some of our colors, and you can look at our website for more inspiration.”

The entire time working with them was a complete migraine. They would have a certain visual concept at the start of each project and then change their opinion multiple times throughout. It got to the point where I stopped following what I thought was appropriate for their brand and just tried to make the multiple voices happy.

Sure enough, on the last project I made for them, several revisions in, I got this email.

Client: “The last revision you sent us was off our brand. Please refer to the brand book I have attached.”

The brand book was dated before I had started working with them. 

They are no longer my client.