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Drawing from personal experience:
Worked at a small agency. Loved the hustle. Hated tiny client budgets.
Moved to a global agency. Loved the resources. Hated the politics.
Moved to freelance. Loved doing my own thing without red tape. Hated the unsteady work. If you can, secure as many projects as you can before you leave and even start working on them before you go solo. There are times where months went by without any work for me. I still was able to balance highs/lows for 4 years.
Finally landed back at a small agency because at the end of the day, I wanted to be challenged by the work and not the personalities.
Ultimately, I think it's about you and what you thrive on. So many amazing, creative and smart folks love agency environment and others the opposite. You may have to try few things before you figure it out but otherwise you won't know.
It's the cheesiest but smartest thing I learned from someone: lead with your passion and what moves you.
Left sapient and went to Skyscanner....haven’t looked back since.
I have been in agencies as a strategist my whole career, until now. I went into television- it's a good transition since you have experience with branding and strategy. Now I do digital media, which is extremely strategy related and I use a lot of my experience, if not all. I am personally never looking back, the lifestyle in TV outside of agencies is incredibly fitting to my lifestyle.