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I'm still at my first company after switching career in to development.

It's nice here, and the people including management are great.

But I feel I should probably move on for the sake of my career progression, but I'm scared to leave and find myself somewhere worse.

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Be very very sure of what this supposed "career progression" is before you leave something you enjoy.

If I hadn't moved to a new town, and if they hadn't also, I would have tracked down some of my old coworkers and asked them very nicely for a job. But we all 'graduated' and flew away.

I just worry that if I stay for years, and then for some reason do have to leave, it'll be harder to find a new job with my first as a dev having been at the same company for many years.

Generally I think long tenure is a positive signal, but you have to be growing. If you are growing and learning, and enjoying it, I recommend you continue to do so. Stop and smell the roses while you're at it.

In theory, skills are what matter, but I don't find that true in practice. Appearance matters more. A long tenure is a good look to most.

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