How To Win An Emmy – Ross Dettman

April 25, 2016



So you want something in life. How high will you jump? How hard will you drive? How much are you willing to persevere?

Let me share a story.

Remember back in Tiger Woods’ heyday? In 2001, he became the first player to win all four professional majors in a row. As Tiger rose in stardom, so did someone else—his caddie, Steve Williams.

Now I’d like to introduce you to a photographer named Ross Dettman. And let’s take you back to the time Ross was sitting in this famous caddie’s New Zealand home.

Ross was there on assignment for ESPN with the writer for the story, Wayne Drehs. The two were listening as Steve regaled them with various accounts of his life and career as a caddie. Steve, never short on confidence, shared success after success, and tied each of his anecdotes back to some picture or memorabilia that was sitting inside his trophy room.

There was the 1999 PGA championship flag, for example: Signed by Tiger, it said “Nice read on 17.” Tiger had a long putt and thought it was to the outside of the hole, but Steve was convinced it was to the inside. Tiger trusted him. He sank the putt. If that ball hadn’t gone in, things might have turned out very differently for Steve. There might never have been this interview with ESPN.

Ross and Wayne asked if they could take a peek inside the trophy room. But Steve wouldn’t budge.

“Absolutely not, it’s off limits to the media. Nobody has ever been in there except family and friends.”

Instead, he continued with his stories. The British Open. The PGA Championship. The Masters. And again, he kept tying it back to trophies, flags, golf bags, and pictures hanging on the wall, all of which were on display in his trophy room for nobody but Steve and a select few to view.

Wayne took notes as Steve recounted his various stories. But Ross could do nothing except sit there. And listen. And grow increasingly annoyed.

Finally, he couldn’t take it anymore.

“Steve. You’re going on and on and on about this fucking room. Wayne’s a writer, at least he’s got something to go on. But I’m a visual guy. You’re killing me.” And with that, the conversation was shut down.

Steve paused for a moment as he contemplated his response. Then he spoke.

“Alright then.”

And that was that. Steve let them inside his trophy room, and Ross had twenty minutes to shoot pictures of this room that nobody in the general public had ever seen.

I suppose if you’re on assignment shooting photos, you can take your time building trust and rapport. Or you can just be fucking blunt, mate. (You can find that ESPN story here: Bag Man)

Ross is not the kind of guy to beat around the bush. When he agreed to meet with me, I had lots of questions for him about making one’s creative passions a reality. After all, he has had an outstanding career. He has shot major sporting events, famous athletes and rock stars. He has won an Emmy.

So you can imagine I was caught off guard when his advice for people was: “You’ve got to be a realist. Follow your dreams, but you might fail. Have a plan B.”

Always the idealist, my heart sank a little. This coming from someone with his track record of success?

But like most things, there is always more to the story… some reason behind it, or some past secret.

So let’s rewind even further—back to where things started.

Ross studied engineering at the University of Illinois at Chicago. While there, he was hungry for the quintessential college experience—you know, the one where everyone gets suited up in their gear and heads to a football game to watch their college team play a conference rival. But if that were your desire, UIC would leave you wanting.

The closest thing UIC had was a Division 1 hockey team that was pretty good. The problem was that nobody went to games. It’s hard to get your “classic college experience” without cheering fans.

So Ross went hunting for an answer to why nobody paid any attention to the hockey team. It wasn’t long before he took a look at the school newspaper and happened upon his own answer. In his words, the photos in the paper sucked. There was nothing sexy or cool about them. It was no wonder that the paper didn’t entice people to venture over and check out a game.

Ross was determined to change that. So he started shooting photos of the games. He didn’t really have any experience, other than dabbling a bit with photography in high school. But that didn’t stop him.

In retrospect, his hockey photos also sucked, but they sucked less than the ones he was replacing. He continued working at it and honing his skills. It wasn’t too long before the school began to buy his photos and had him shoot other sports like gymnastics and baseball.

So it began.

But when Ross graduated from UIC in 1986, he quickly entered adult life. He got married, and he and his wife had twins. He didn’t want to be working in a cube in an office building, but the realities of his personal situation left him little choice. So he leaned on his engineering education and took his first real job out of school at a well-known architecture firm, Skidmore, Owings & Merrill.

But he kept shooting UIC sports on the side. While he was shooting at a UIC baseball game, one of the guys at the game asked Ross if he would shoot some pictures of his son, the third baseman. Ross said yes. This one small event turned out to be significant.

Later, that same father connected the Chicago Tribune to Ross when they were searching for a photographer to cover high school sports. The Tribune hired Ross as a freelancer. It was his first dose of serendipity.

While it seemed small at the time, whenever Ross was shooting at a game, people would consistently come up to him and ask “Who are you shooting for?” His response was “The Tribune.” That granted him instant credibility. It became the gateway to additional assignments.

By this point, Ross wanted to pursue his photography full-time. But he didn’t know how. His wife told him she was supportive if he could find a way to make enough money doing it. But he was a long way away from “enough.”

So he continued shooting sports on the side while working at his new full-time job for Premisys, a software consulting firm. That meant sacrificing family time on evenings and weekends, sleeping less, and almost no time for relaxing or spending time with friends. Also known as good old-fashioned hustle. And then something happened.

A trading card company out of Milwaukee that covered minor league hockey contacted a coach from North Dakota looking for pictures of some players for their trading cards. The coach told the trading card company that the school did have some pictures of the players they wanted, but that the school didn’t own the rights. So he put that trading card company in touch with the person who did own the rights—Ross Dettman. More serendipity.

Looking back on that event, Ross saw it as one of the luckiest of his lucky breaks. Why?

Not everyone in that coach’s shoes would have gone the extra mile to connect the company to the real owner of the images. Not everyone would have even understood that the school didn’t own the rights to the photos. But because that coach was who he was and did what he did, Ross now had a relationship with a trading card company.

And in 1994, that trading card company acquired a license to do NFL photos. They offered Ross the opportunity to shoot one season of NFL and college football games. He would make a few thousand dollars for each NFL game, $700 for each college game, and he would own the rights to all of his pictures.

But Ross still had his full-time job at the software consulting company.

Maybe what happened next was pure coincidence. Maybe Ross’ employers were mind readers. Maybe the universe was itching for Ross to jump head-first into full-time photography.

Ross’ employer sat him down for an unexpected heart-to-heart before he had time to contemplate the trading card offer. Their basic message was, “We need you to make a choice. Are you a consultant or are you a photographer?”

There was no ill will about it. The company just wanted Ross’ full commitment, and they knew they weren’t going to have it while he continued his aggressive after-hours freelance photography schedule. So pulling him aside and putting him on the spot seemed like the right approach to them.

Ross vividly remembers that moment he responded. There was no premeditation to it. Not even a conversation with his wife. The words just came out.

“I’m a photographer.”

And that was it. A feeling of empowerment washed over. There wasn’t even any fear. It felt like destiny. I’ve jumped in. If the water is ice cold when I hit it, I’ll deal with that. But I’ve jumped in.

Ross went home to his wife. She was mowing the lawn at the time. He gave her the news.

“I’m done at Premisys.”

The news went over like a lead balloon. Not being the risk-taking type, his wife’s first reaction was, in essence, “we’re doomed.” Their kids were in second grade at the time. Sure, he had one season of solid income lined up. But there was no telling what would happen after that.

All of this had come completely out of nowhere for her. The NFL opportunity had materialized out of thin air. The full-time consulting job had dissolved into thin air just as spontaneously. That’s a lot for anyone to take in all at once. But eventually she came around to the idea.

So Ross Dettman, part-time photographer, was going to have his shot at being all-in with his photography after all.

He began his first tour of duty shooting NFL and college football games. While he was shooting the college football games, he used the opportunity to take pictures of future stars. Later, ESPN The Magazine contacted Ross and asked to license a bunch of his college football images. And around this time, he was also hired as a freelancer by the Chicago Wolves.

So, after all of the hard work, patience, and serendipity, it felt like everything was falling into place. Things were finally coming together.



Until they weren’t.

The trading card company Ross worked for began to fail and pretty soon that gig evaporated. There was no more work for UIC either. And Ross had come to realize that ESPN The Magazine was exploitative. They would tell a bunch of different photographers to show up and shoot a game, all on their own dime, but only one photo would be chosen. That meant you would spend the money to shoot a game, but your odds of having ESPN buy one of your pictures was 1 out of 8 at best. It was a losing game and Ross knew it.

In a short while, Ross found himself pulling in a fraction of the income he was making before. He took any freelance job he could find, but his financial situation was worsening. He was sliding into debt.

One of the freelance jobs he took during this period was for a guy who acted as a broker between photographers and trading card companies. It was an extremely unhealthy working relationship. The broker was verbally abusive to Ross and regularly tore apart his work. Not only did it drain all the enjoyment out of photography for Ross, but it led to a lot of self-doubt. After two years of enduring this situation, Ross found himself on the brink of giving up on photography.

At the same time, his debt situation had come to a breaking point. Ross had thousands of dollars in credit card debt and was backed up against a wall. Completely out of options, Ross liquidated his retirement account to pay off the debt.

This was rock bottom. I’m hedging my future to put out a fire. 

It wasn’t like he was using that money for some investment for the future. He was using it to get back to “point zero.” This was tough on Ross. It was even tougher on his marriage.

Now would be a good time to circle back to what I shared earlier. Remember Ross’ advice to people? Here is the rest of it:

“You’ve got to be a realist. Follow your dreams, but you might fail. Just because you love something, it doesn’t mean you’ll be able to do it. Follow your dreams, but have a plan B. If you make something your profession, now you have to make money with it. There is pressure to that. You can find facets of your life competing with each other.”

This is advice from a successful photographer who has been out on his own for two decades doing something he loves. Equally so, this is advice from someone who was once on the edge of failure and watching the cracks form in the foundation of his family.

Dream-following isn’t child’s play.

Many of us will say we’re willing to make sacrifices, but that’s in the abstract. That’s when we’re still in a relatively comfortable spot, focusing only on the good parts of our dream, or on the bad parts of our current situation that we’re seeking to escape.

Usually there is some unconscious part of us that thinks we get to have some control over what we do and don’t have to sacrifice. But that’s not how it works. When sacrifice comes, it comes for what it wants, not what we’re prepared to give.

And when you’re beaten down, and you think you might be down for the count, there is almost no amount of encouragement that will get you back up on your feet to fight some more. Quitting starts to seem like it is the only sane option left.

Ross got right up to that edge. He was as close as a person can get to giving up.

But maybe it was a destiny thing after all.

After some time passed, ESPN The Magazine reached back out to him. This time, they were offering him legitimate assignments. Ross began shooting college football games, and with each successful assignment, he was steadily offered bigger opportunities.

One of those opportunities came in the form a phone call from someone at ESPN. They asked Ross if he would join the team responsible for shooting the Super Bowl. He tried to act calm and collected on the call, but on the inside he was like a five-year-old jumping up and down on the bed. The minute he hung up, he jumped up and down on the bed.

Ross’ career took an incredible turn. He went on to shoot more Super Bowls, the Stanley cup, and a string of remarkable special assignments and features.

There was Soccer in the Storm, the story of Bob Bradley becoming the head soccer coach of the Egyptian National Team. There was my favorite, Unity with the Universe, the story of a man named Tom Morgan, maker of some of the most expensive fly fishing rods in the world despite being paralyzed from the neck down.

And in 2009, Ross won a Sports Emmy for his work in No Love Lost, a series of stories about Chicago Cubs fans, from seven years old to over one hundred years old, and their continued commitment to a team that hasn’t won the World Series since 1908.

Ross’ career has continued to morph and grow. While he still shoots sports, his approach has evolved. His interests have shifted too—he would choose to shoot photos of a solo rock climber in nature over being out on the field celebrating with the winning Super Bowl team (“like a bunch of jackals on a wounded gazelle…”). He has also gotten into commercial work, shooting for brands like Nike and Hammer Strength. And most recently, he has been innovating with huge, high resolution photos, and outfitted the Chicago Cubs clubhouse with an expansive picture of the Chicago skyline that’s clear enough to see someone walking their dog in it.

In the evening, Ross might be capturing an image of a bloodied athlete in the heat of a competitive event. The next day, he might be staging a photo for New Balance.



Of course, none of this would have come about had Ross quit.

And he almost quit.

It happened around the time they cashed out the retirement account. At that point, when things were most difficult for his family, Ross had actually come to a decision. He was going to call off his full-time photography pursuits and go back to get a “real job.” So he went to his wife to tell her. He expected it to come as a huge relief to her.

And she said, “So now that it gets tough you’re going to quit? You can’t quit now.”


Ross was silenced.

In his words, “If I was a fighter, she tagged me on the chin with that and I was lying on my back staring at the ceiling. It was mind-blowing. It was the most inspirational moment of my life.”

At the point he was ready to throw everything away, that inspiration kept him going. It’s like the stars aligned. Things started to open up for Ross after that. That kicked off his career heyday.



These days, when he looks back on his career as a professional photographer, Ross sees a series of twists of fate.

  1. Had it not been for the father randomly asking Ross to take photos of his son playing third base, Ross would not have landed a freelance job at the Chicago Tribune.
  2. Had it not been for the college coach referring the trading card company to Ross, he wouldn’t have had the opportunity to shoot college and pro football. These photos got his foot in the door with ESPN.
  3. Had his wife not given him her inspirational gift, he would have walked away from it all.

To Ross, any of these events could just as easily not have happened—hence the need for a healthy dose of realism and a solid plan B. To Ross, his success was largely driven by good luck, even if he was well-prepared.

But I see things very differently.

When Ross was at Skidmore, he had a fantastic job. He was working for a prestigious firm on incredible projects. Yet something about it wasn’t enough. On some level, he found more meaning shooting pictures of a girl’s basketball game after work than he did working at the prominent architecture firm. It was so essential to him that he gave up his evenings and weekends, freelancing for five years on top of having a full-time job and a wife and twins at home.

After that, he landed another outstanding job, this time for a software consulting company. It was a progressive firm that treated him well, paid him well, and had perks that would make many people envious. Again, something inside compelled him to give up his evenings and weekends to pursue photography on the side, and he did that for another three years.

Sure, you could look at the little breaks along the way and chalk everything up to serendipity.

But to me, I see a decade of dedication. I see someone who busted his ass nurturing a passion on the side of an insanely busy life. I see someone who honed his craft day after day and never stopped pushing himself to get better.

I see someone who ran an ultramarathon at an 800 meter pace, and then ran another one.

That’s how I see it.

Have your plan B if you want it. But stick that on the shelf while you get out there and kick some ass on your plan A. Then do it again. Nights. Weekends. Whatever it takes.

It’s a simple recipe, really. Hustle like hell. Never give up.

Sure, you might fail. Or you might do something incredible.

♦ ♦ ♦

It’s the most important factor… maybe the only factor… successful people show up every single day. Read the next story to find out what this really means in How bad do you want it?

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Thank you Ross Dettman, not only for sharing your stories, but for turning the tables on me. Boom.

Follow Ross at Instagram: @RossDettman or visit him at his website