Recently, “telework” and “workcations” have become interesting topics of discussions in Japan; however, similar discussions were held in Japan around 1990. At that time, there was a focus on “multi-habitation,” but in reality, the concept of “multi-office” working (wherein a manager belongs to two offices, the head office or the parent company in the Tokyo area and the local branch or subsidiary) was considered more important. In this evolved “matrix organization,” where one lived did not matter, but where one worked did. Despite of the lessons learned from that period, teleworking has become synonymous with telecommuting during the COVID-19 pandemic. The same is true for workcation because it is excessively associated with the desire of the local governments to encourage people to live in their area. Like multi-habitation, the abovementioned concepts have to deal with the where to live factor. However, for telework and workcations, realizing a “multi-office” system is more vital than whether the work is done at or near home. This was the case 30 years ago and has remained so since the outbreak of the COVID-19 pandemic.