From 1990 to 2013 he was the director of the "Nikola Marinov" Art Gallery - Targovishte. Since 2002 he has been an associate professor, and since 2006 - a professor of painting at the "Bishop Konstantin Preslavski" University of Shumen. His creative biography is extremely rich with numerous participations in group exhibitions, plein airs, conferences, as a member of juries and as a manager of art projects. He has over 80 solo exhibitions and participated in more than 100 international exhibitions, plein airs and symposiums, the most important of which are: Festival of Arts in Cannes Sur Mer, France (1984), Salon d'Autumn in Paris (1990), plein air "Process - Space" (1986-1993), International plein air and exhibition in Pulawy, Poland (2013), representative exhibitions "Contemporary Bulgarian Art" in Moscow, Rome, Caracas, Warsaw, Madrid and other cities.

Dimitar Cholakov has received recognition and awards for his achievements, some of the latest are: International Painting Prize "Micetti", Italy (1988), Prize of the exhibition "Man and the Sea", Varna (1992), the Grand Prize for Painting from the National Competition for Painting, Sculpture and Graphics of "Allianz - Bulgaria" (2008), the Grand Prize for Painting "Ludogorie" - Razgrad (2013), the Bulgarian Art Gallery Award "Petko Zadgorski" in the exhibition "Watercolor 2020" in the name of Nenko Tokmakchiev, Burgas (2020), the Grand Prize "Sirak Skitnik" - Sliven (2022), etc. He was awarded the prestigious Painting Prize named after Vladimir Dimitrov - The Master for 2023.

He lives and works in Targovishte and Shumen.