For five years, the New York University graduate had unparalleled opportunities as he worked under portrait photographer Ben Baker -- a man who has captured some of the world's most powerful people, notably Presidents Clinton, Bush, Obama and Trump.
As Baker’s first assistant, Dittmar worked on shoots all over the country. But after years of executing game plans, coordinating workflows, setting up and managing the office and handling scores of other responsibilities, Dittmar realized that he was no longer learning.
"At a certain point, I knew I had to make a clean break, and after the shoot in the White House with the Obamas for the third time, I felt ready to do that,” he told FOX Business.
For Dittmar, it was the only option.
“As soon as you start putting mental and physical effort towards a backup plan, that’s becoming your plan,” Dittmar explained. “Once you bottom out, then you quickly find a backup plan. But until that point, you have your plan and you're sticking to it.”
In 2012, he walked away from his position with Baker. It meant trading 90 percent of his income in a single day for the uncertain financial prospects of a career on his own.
Afterward, he worked furiously to generate cash, taking hundreds of client meetings while bouncing between bartending jobs, which were typically short-lived because he was out so often talking with prospective customers.
It wasn't long before Dittmar found himself forced to borrow money, which he said put a strain on his personal relationships. Living in New York, where high income taxes are coupled with some of the country's least affordable housing, only exacerbated the problem.
"I was ready to move on, but no one was ready for me to move on," said Dittmar. His break came with a call from The Washington Post, which was looking for someone to photograph the Tony Award-winning actress Idina Menzel as she prepared for the Broadway musical "If/Then," which debuted in November 2013.
“It didn’t matter what I had going on that day,” said Dittmar. “You need to be extremely prepared to be lucky. When someone asks you to do something, there needs to be no barriers to entry. Any excuse for someone not to hire you, they’re going to use.”
After that call, Dittmar returned to cold emails and endless meetings. They paid off. In the space of roughly two years, his workload shot up to roughly 80 jobs a year.
From working on Apple ads to photographing celebrities such as "Saturday Night Live" performer Kate McKinnon, comedian David Letterman, singer Al Green, Patriots quarterback Tom Brady and actresses Jodie Foster and Lupita Nyong’o, Dittmar has been sought out for a range of portraits.
And while his work is now recognized by some of the world's most prestigious publications, Dittmar acknowledged that he wouldn't be where he is today without someone willing to take a chance on him.
"I'm not the most talented photographer I know, not even close. But I work very hard and I have been available. More than half of it is being available,” he said.
“I got lucky to get the call, and I was prepared to make the most of it.”