He returned to his native Villingen and went into partnership with a friend Ernst Huber which they called 'Kunstgewerblichen Werkstätten Huber-Flaig'.
This appeard to be not a total success and Waldemar Flaig left the business which continued under the name 'Huber-Roethe'. He moved to Meersburg on Lake Constance and startet a career as a Fine Art painter. He took lodgings in an appartment in the old palace. The 'Schloss' became a regular subject of his town paintings.
He become relatively quickly successful. He was able to exhibit in various galleries in southern Germany. Records show sales of at least 23 paintings in this short period from exhibitions in Wiesbaden, Mannheim, Friedrichshafen und Konstanz.
The years 1920-24 saw an early recognition of his talents. He worked on a series called 'Six Lithographs from Lake Constance', several Wood and Lino-carvings with various motives, Book illustration; 'Reiseschatten' by J.Kerner, Illustrations to the tales of E.T.A. Hoffmann and Grimms fairy tales. No original publications have been found, but sketches of the works have survived.
On 20th June 1920 he married Maria Thoma from Villingen, She was the daughter of Albert Thoma, a businessman and his wife Maria geb. Fallet, who had died 1904.
Waldemar Flaig now exhibited at his, so far, biggest exhibition in Konstanz in the Wessenberghaus.
In Oktober 1921 he showed his paintings depicting Don Quichote in Villingen. He added 12 Watercolours which have been lost and two further oil paintings with the same theme.
In December he exhibited for the first time in Baden-Baden.
A first setback came in 1922 and he become seriously ill with angina and the recovery took many months. Once recovered he painted his best self-portrait 'Selbstbildnis 1922', complete with cigarette.
He now expanded his horizon and with the help of Max Osborn, the editor of the "Vossischen Zeitung" he had his first exhibiton in Berlin at the renowned gallery 'Kunsthaus Gurlitt'.
May 1923 saw him undertake a first joint exhibition with the well know local artist Richard Ackermann.
And later that year he showed his work at the art centres in Konstanz and a exposition at the gallery 'Kunsthaus Schaller' in Stuttgart.
Flaig's growing repution led to an contract with the local authority in Friedrichshafen, to design "Städtisches (Inflations-) Notgeld". These where bank notes needed to keep pace with the hyper-inflation which was about to undermine the German economy.
The 24th October saw the birth of their first child. His son Hubert, would be killed in September 1943 on the russian front. The delight at their new addition his recorded in several works. The earliest oil painting is entitled "Mutter und Kind".
In Februar his mother died in Villingen. He was always close to his mother and her death is depicted in a sombre oil painting he called "Tod der Mutter".
Later in 1924 he continued with another exhibition in Baden-Baden.
Germany hyper-inflation accounted not only for his first scrap with poverty. His work continued to attract a good deal of interest, but the appetite and ability to pay for artistic works was much reduced.
He displayed a great deal of energy during this time and he began to live a more nomadic existance. Always with his small family, he started spending the winters in Germany's larger cities.
His instinct to spend the winter of 1924/25 in Düsseldorf proved an excellent one. He got to know the painter Gert Wollheim und of equal importance the russian jewish ballerina Tatjana Barbakoff. Two of his most lastings works are of her. He also renewed his friendship with Otto Dix whom he had met the previous year in Berlin.
Flaig began to develop new themes at this time. He worked on religious themes and produced a large numbers of works based on the landscapes in the black forest and around the lakes. His landscapes in particular often depicted a tougher, windier, colder style and this was unusual as the subject matter was traditionally portrayed as 'idylic' and 'gentle.
Flaig spent the first couple of months on the Italian Riviera, and moved between Rapallo and Genua. This was a very productive time and he returned with a good number of works: drawings, water colours and oils, all of them sold well.
He now started a new venture and over the next 3 years gave lessons to a young painter, who although disabled showed plenty of talent. He gave the lessons each year over a 4 to 6 week period in Hechingen/Hohenzollern. During that period he produced several distinct works: 'Hechingen im Schnee' and 'Schäferkarren, Rauhe Alb' as well as numerous drawings and water colours.
If that was not enough commitment, 1926 saw him sign up to the Friedrich-Theater in Dessau as a screen designer, painter and builder. There is a humourous series in water colour of his time there. He used his time during his stay in the Bauhaus centre to exhibit his works as part of the annual exhibitions of the Anhalt Kunstvereins. The exhibition was organised by the German 'Bund bildender Künstler, Dessau' which were embarking on the Bauhaus venture. Not surprisingly his portraits of 'Otto Dix' and 'Tatjana Barbakoff', received a lot of attention. 'Tatjana Barbakoff had been sold in a previous exhibiton at teh Kunstverein Konstanz for the Konstanz museum. This remarkable painting was later classed as 'entartet' and presumably destroyed by the Nazis. It has so far not been re-discovered.
In the spring the family returned to Meersburg and by the summer Flaig was exhibiting his work in galleries in Konstanz and Lindau. He then suffered his second serious bout of angina and took a long time to recover his strength and energy.
The red pen portrait 'Selbstbildnis 1927' shows him still suffering the effects of his illness.
Before the onset of winter the family returned to Berlin. Waldemar Flaig had found a position with the famous Universum-Film-AF (UFA) film production company. He worked as assistant to the filmarchitects Herlth and Röhrig. On 23rd November 1927 his second child, daughter Erika was born in Berlin, Droysenstr. 18. She features both as baby and growing up in some of his works.
He painted to classic portraits of 'Tatjana Barbakoff' one in a chinese the other in a russian costume. In the same period are drawings, sketches and red pen works featuring Berlin and his work with the UFA.
His stay in Berlin improved his finances and he returned for the third year to teach in Hechingen. Part of the work included journeys into the nearby Black Forest and he painted 'Schwarzwaldstrasse' and 'Schwarzwald bei Triberg'.
An exciting development was the founding of an artistic co-operation called 'Der Kreis', and they held their first exhibition in Friedrichshafen. Norbert Jacques, the novelist and screenwriter, most famous for the creation of the Dr Mabuse character who featured in many of his novels and films. He was a driving force behind the formation of Der Kreis. Flaig had met him previously and painted his portrait in 1927.
By the autumn of 1928 he was time to move back to Berlin as he had received a new contract to work with UFA. This was a busy time with exhibitions taking place in Berlin, Hamburg, München and Düsseldorf.
As his reputation grew he received an invitation from his friend Professor Karl Knappe to work on the artistic interior design of the ballroom of the ocean liner SS 'Bremen'. The work was in Munich and as he did not have an certain offer of a new contract with the UFA, he accepted this opportunity.
One opportunity led to the another; the painter Erich Glette was one of the designers on 'SS Bremen'. He had a commission to paint, together with Professor Knappe, the church in Döllnitz near Weiden, Oberpfalz. They asked Flaig, if he wanted to assist which he did. As late as 1965 the work there has remained unaltered.
Their collaboration continued and Prof. Glette und Flaig painted a Fresco in an appartment block in Munich, which was walled-up during the Third Reich and has remained undiscovered.
Der Kreis held an exhibition in early autumn in St. Gallen, Switzerland, and he managed, despite all his other engagements to show three paintings, two of which were sold on the spot.
The Family returned to Meersburg at the end of 1929 and Flaig was busy putting together works for a full exhibition by the Konstanz Kunstverein. It opened to excellent reviews on 1st February. However, sales were disappointing amid the increasing tensions of the german political landscape.
Nevertheless he managed a few different commissions. In Meersburg he decorated the Hunting lodge of the property developer Obser.
Similarly, he worked a new window on the staircase of the vicarage, which he had previously painted with frescos. The work was challenging transparent reverse glass painting. The composition is several religious motives. It is possible this work still exists.
Next, Flaig painted the mortuary in Meersburg. In February during the carnival period he painted the ballroom of two inns, the 'Wilden Mann' in Meersburg and another in Stockach.
By the summer of 1930 he received his next commission to paint the ceiling of a church in Hochemmingen/Baar with a 'madonna with rosary' motive
He began to struggle with these commissions, as his health deteriorated but completed the work. He also painted portraits of two patrons, Mrs Mauthner und Vicar Restle.
As well as several landscapes: 'Schwarzwaldtannen', 'Hochemmingen/Baar' and 'Mondnacht in Meersburg'.
Forced to stay at home he painted family portraits of his son Huber, his wife Maria in a red dress and daughter Erika, ill in bed.