The first word, and title, of our sedra is not a happy one. As the gemarra (Sanhedrin 106a) tells us, the word ‘vayeishev’ connotes and introduces a painful event. Similarly, Rashi (37:2) reveals that it was when Yaakov ‘wanted to sit in peace’ that the Yosef story (the brothers selling him, etc.) was thrust upon him. Why is sitting down so painful? The idea is that sitting down connotes a degree of stagnation.
In Judaism we are constantly seeking to spiritually grow; being still is not an option. This is one idea of the mizbeyach having a ramp instead of stairs. Just like a ball on a ramp either moves up or down – it cannot just stay there motionless – so too in order to achieve closeness to HaShem we need to realise that we cannot ever stay spiritually still; we are either moving up or down. This is why vayeishev connotes pain. For sitting down is the ultimate representation and manifestation of being still – not moving. Thus, sitting still is spiritually damaging, which can cause HaShem to send physical trials and tests in order that we move and become proactive in doing something to further our religious level.
So, on Yaakov’s supernal level, at some level he wanted to ‘sit back’ and enjoy a more comfortable life free from his past tragedies and pains.
But HaShem disagreed; this world is not for being comfortable, and so HaShem sent him the Yosef episode to test Yaakov and further his emunah.
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