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Depends on what kind of person you are. Personally, in my decade of experience, I've worked roughly half of my career in agencies/freelance and a half in startups/big companies. Where you start doesn't really matter as much as what you learn from each opportunity. Each caters to a different working lifestyle as well as how much of a generalist vs specialist you can be. Here are some questions I recommend you consider when making your decision.
Am I interested in working on multiple projects at the same time with tight deadlines? Am I interested in selling my design work and the value that's tied to it in every presentation? Am I interested in creating ideas from the ground up? Am I interested in reimagining something that already exists? Am I interested in working with a new group of people every few months? Am I interested in working on something that I may not have contact with the dev team? Am I interested in working on a variety of projects (branding, physical, software, advertising)? Am I interested in being part of the Seal Team 6?... See more
Am I interested in working where people might not fully value design as much as dev or sales? Am I interested in working fast to validate something that may or may not eventually make money? Am I interested in changing direction on something I've put a lot of time and effort into? Am I interested in dabbling in front-end dev, design, and product management? Am I interested in getting paid less but have equity in the company? Am I interested in managing designers but still getting to play in the pixels? Am I interested in innovating on ideas big companies wish they had time for? Am I interested in more stability even if I mess up? Am I interested in being on the Police Force but also the SWAT Team?... See more
Am I interested in working on a very specific piece of an application with a lot of constraints? Am I interested in breaking up a design vision into bitesize releasable nuggets? Am I interested in collaborating with hundreds of designers to collectively make something together? Am I interested in well-defined processes and career ladders? Am I interested in managing other designers? Am I interested in getting a lot of access to mentorship? Am I interested in being part of the Navy?... See more