During this period, VD Satheeshan embarked on his educational journey. He successfully passed the SSLC examination from High School in Panangad and subsequently enrolled at SH College, Thevara for Pre-degree studies. Notably, he was elected as the Arts Club secretary to the college union and served as a councillor for both the Kerala and MG University unions multiple times. His oratory skills were evident as he consistently emerged victorious in inter-university debate and speech competitions. In addition to his academic achievements, he held leadership positions, serving as the KSU unit president and Kanayannur Taluk president. VD Satheeshan also pursued a Bachelor's degree in Sociology from Kerala University during this period.
Continuing his commitment to education and leadership, VD Satheeshan joined the postgraduate diploma course in social service at Rajagiri College of Social Science, Kalamassery. His dedication to student politics continued, and he was elected as a councillor to the MG University union. Notably, he rose to prominence by being elected as the chairman of the MG University union. In parallel, he pursued an LLB degree from Kerala Law Academy Law College.
Building on his educational foundation, VD Satheeshan pursued a Master of Laws (LLM) course at Govt. Law College, Thiruvananthapuram. His leadership skills extended to a national level when he was selected as the All India Secretary of the National Students Union of India (NSUI). Concurrently, he started his career as a lawyer at the Kerala High Court.
This period marked a transition into politics for VD Satheeshan. He contested the election from the Paravur assembly seat, though narrowly missing victory. On the personal front, he married Lakshmi Priya, and they welcomed their daughter, Unnimaya, into their lives. Despite the electoral setback, he remained dedicated to his legal practice at the Kerala High Court.
2000-05
VD Satheeshan achieved a significant milestone in his political career by being elected to the Kerala Legislative Assembly from the Paravur seat. His leadership qualities were recognized, and he was chosen as the whip of the Congress Legislative Party. During this tenure, he successfully completed a large-scale drinking water project in his constituency, benefiting over 2.5 lakh people.
2005–2010
Securing re-election to the assembly, VD Satheeshan continued his role as the whip of the legislative party. He also played a vital role as a member of the opposition, raising numerous allegations against the government and its ministers while highlighting important issues in the assembly. One of the notable moments during this period was a public debate he engaged in with the then Finance Minister about the lottery scam.
2011–2015
VD Satheeshan's political career reached new heights during this phase. He was re-elected to the assembly and, as a testament to his leadership capabilities, was elected as the Chairman of the Public Estimate Committee of the legislative assembly. Additionally, he was nominated to chair the Joint Assembly Committee responsible for investigating allegations against the former Chief Minister. His influence expanded beyond the state, as he was appointed as the Secretary of the All India Congress Committee and also as the Vice President of the Kerala Pradesh Congress Committee. In collaboration with other MLAs, he initiated the Green movement.