Opt for internal transfer for same pay or choose a position outside of company for potentially more pay? Which would you choose under which situation and why?

For me, if I am used to the company culture and satisfied with my job scope, I would probably opt for a transfer to expose myself to various functional units in the company to grow my career prospect.. the only think that made me jump ship (touch wood) is when the working conditions are unbearable and having too much stress from work and bosses..

This all depends I would say. If you are young, go take up the next challenge & grab that job which pays you the highest. If you are in your mids, better to remain in your current job with the same pay which offers you a transfer. Realistically age do matters when you are applying a new job.

Go for the boss

If you want to learn something new or transition to a new role, it's usually easier for internal transfer because your current team mates and boss can vouch for you.

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The other thing which you may want to consider is the boss. For internal transfer, you will likely know how the new boss is like and his/her management style and if it suits your working style. For external, it can be quite unknown unless you know someone in there.

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Having good bosses and team leads can be quite underrated and never underestimate what good ones can do for your career or work-life balance.