Should you follow your boss to a new job is a rather subjective poser. There are bosses, and then there are BOSSES. I have known people who worked for the same person throughout a career. I have known people who stayed with the same company for many years and had multiple bosses, some better than others. There are bosses who can enhance your knowledge, appreciate what you do for them, and allow you to stretch and grow; but there are also bosses who stifle personal growth and only care about their own advancement, sometimes at your expense.
Your immediate supervisor is a boss but not the boss. Some companies have a strict caste system while others do not. If one works for a company that does have a rigid social structure, it might be quite flattering for the boss to ask you to come along. Should that happen, though, you may be fairly certain that the boss is thinking of himself rather than you. It would behoove you to consider location, expectations, salary and benefits very tediously before deciding to go.
If following your boss means relocating yourself and/or your family, there needs to be compensation for moving as well as a rather substantial raise. Moving always proves to be more costly than one expects.
There are jobs and careers where following the boss is not at all out of the ordinary. A prime example is coaching. Often when a new head coach is hired, whether it be high school, college or professional ranks, the new coach is allowed to bring all or part of his/her staff. I worked as administrative to a secondary principal who loved to open new schools, and as it happened, our school district was one of the fastest growing in the State. I followed the principal to two new schools after the initial one. I did not have to, but I would have probably followed him to the moon. We worked well together, and he was an exceptional principal. He was the exception in my life. There have been other bosses through the years that caused me to sigh with relief when they left, even if they were moving on to greener pastures and gave me an option to go with them.
Do not follow anyone for any reason unless you are genuinely happy working with and for them. No amount of salary is worth being miserable. Things do not always look the same underneath the surface; sometimes you are better off where you are. Is there opportunity for advancement in your current situation, or where you would be going? Is the cost of living higher or lower in a relocation situation? Is the new environment more congenial than the current one? It is never an issue to be taken lightly, because every major change in life, especially career choice is a building block to your future, whether your choices are good or bad.
Finally, consider whether or not you might eventually have the opportunity to move into the position that he/she is leaving vacant. That might be worth staying for, if it happens to be something you would enjoy doing. I have had to make that choice and did move into that position with no regrets and miles of opportunity.
Do not limit your long distance vision. Look at all the options and make an educated choice rather than an emotional one.
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