If I understand you correctly I think your whole plan has a few potential problems, to start with you will be flying back and forth between your work and wherever you are every 28 day and presumably leaving your bike there and picking it up again. Apart from the expense this will often be impossible as you will not be permitted to leave many countries without your bike.
Secondly this tight schedule leave no room for problems such as getting ill or getting stuck somewhere for whatever reason and being unable to get back to work, it sounds like one very stressful way of travelling which not what it should be about.
I would suggest that you do what most people do and either speak to your employer and get a leave of absence for a year or so, or just pack the job in a get it or another back afterwards, you will enjoy what should be the trip of a lifetime more without the hassle.
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