My Biggest Photography Failures and What I Learned


Success 1

“Success is a poor teacher. We learn the most about ourselves when we fail, so don’t be afraid of failing. Failing is part of the process of success. You cannot have success without failure.” – Rich Dad, Robert Kiyosaki

I was at a high-pressure shoot recently, and one of my clients was watching me make adjustments to my camera and lighting. They commented, “How do you remember all that stuff? You make it all look so effortless.”. The truth is that after thousands of photo shoots it has become second nature, but this wasn’t always the case.

Success 2 1

I broke a wedding.

Why am I always checking and rechecking exposure? Because I broke someone’s wedding. Yep, broke it.

The wedding was ten years BD (before digital) and very early in my career. I was so inexperienced that I didn’t realize the flash tube on my external flash was only emitting about 1/4 of its power and, as a result, I underexposed all the images by three to four stops. They could not be salvaged. I only managed to get one useable frame.

At the time, I just wanted to crawl into a hole and stay there, but this nightmare scenario defined the style of fill flash lighting I still use today.

I also developed a pre-shoot protocol that ensured I would never have this kind of disaster again. I always test all my equipment before a shoot and check and recheck exposure as I’m shooting.

“Fears are nothing more than a state of mind. Most great people have attained their greatest success just one step beyond their greatest failure.” – Napoleon Hill

If I had not experienced this crushing blow early in my career, I might have become more slap dash as a photographer and prone to more failures, steering my career to go in another direction.

Trevor Dennis

By Trevor Dennis

Why do I always use a light meter? Because I ruined the shot of my life by looking at my camera screen for the exposure and my hair light ended up being three stops over exposed. That shot should have stopped traffic. Instead, I lost a client.

Why do I back up twice while I’m shooting? Because an assistant (accidentally) dumped an entire shoot into the trash. I’m still in need of therapy over that one.

I’m proud to admit that I have failed spectacularly on countless occasions.

The aftermath was always the same. I’d have a complete meltdown and become a bit tired and emotional. I’d then spend a week at home curled up in the fetal position watching entire seasons of One Tree Hill and consuming my body weight in Nutella.


By Janine

As painful as each failure is, I learned something new each time, and I never made those mistakes again. They became burned into my brain.

“Failing is one of the greatest arts in the world. One fails toward success.” – Charles Kettering

You need to go out and fail, time and time again. Get up, cry for a bit, learn, grow, and move on.

At the time, these failures were devastating but I now know that my spectacular failures and toughest moments have been my greatest teachers and have molded me into the photographer that I am today.

I’m also proud to be part of a massive club of spectacular failures who have all gone on to achieve remarkable success.

Here are a few of my favorites:

  • Comedian Jerry Seinfeld completely froze during his first stand up gig and was booed off stage. He went back the next night was a huge success and went on to become one of the most successful American comedians in history.
  • Elvis Presley got fired from one of his first gigs and was told, “You ain’t goin’ nowhere, son. You ought to go back to drivin’ a truck.” Elvis Presley is one of the greatest recording artists of all time.
  • Oprah Winfrey (my hero) was fired from her television reporting job because TV executives thought she wasn’t fit to be on screen.
    She went on to create and star in “The Oprah Winfrey Show” the most watched talk show in the world, turning Oprah into a billionaire.
  • Winston Churchill failed grade six and lost every government position he ran for. He went on to become British prime minister at the age of 62.

Success 3 1

And one of my all time stories of how failure led to success is Apple founder, Steve Jobs. He was devastated after being removed from the company he started. Years later in a commencement speech at Stanford University he reflected:

“I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”

When he returned to Apple, he created some of the most iconic products in the world, including the iPhone, iPad, iPod, and he went on to become one of the richest men in the world.

“Never, never, never give up.” – Winston Churchill

Have you experienced any spectacular failures, and what have you learned from them? What are your strategies for coping with failure? I’d love to hear from you.

Gina is the author of four dPS eBooks including:

You can buy one for $19.99 or grab the whole bundle for only $49.99 (save 38%) from any of the links above.

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Gina Milicia has been a professional photographer for more than 25 years. She has photographed some of the world’s most high-profile people including royalty, billionaires and A-list celebrities. Often travelling the world, Gina also runs photography workshops and private mentoring sessions. You can sign up for her free ebook on "Portrait and Post Production Essentials" and see more of her work here. Check out her podcast “So you want to be a photographer” on iTunes.

  • Jake Tenenbaum

    I badly want a light meter, but work under SUFFOCATING budgetary restraints. I’m wondering if anyone knows of a TRUE low-budget alternative to the $200-ish meters out there.

  • Jake Tenenbaum

    I feel that right now, almost every shot I take is a spectacular failure. But I keep plunking away. I want very badly to be a professional photographer, and I figure the only way to do that is to keep taking pictures, study the masters and continually research the subject.

    I figure, right now, maybe one out of every 50 shots I intend to make is any good. But we’re usually our own worst critic in the “art world,” right?

  • Ken Lazar

    Hi Gina,

    Your openness and honesty about breaking a wedding is refreshing. I too broke a wedding. It was in the mid 1970s and I was four years into professional photography. I purchased a Mamiya RB-67 (still have it) for my wedding work. My problem, like yours was flash related but not with flash power but with shutter synchronization.
    The RB-67 is a leaf-shutter camera. Being in the business for over 25 years, I am sure you know what that means but for the sake of newer photographers I’ll explain. A leaf-shutter can synch flash two ways; one for flash bulbs with M Synchronization and one for strobes with X Synchronization. This design feature is because flash bulbs have a ramp up time to achieve full brightness and strobes are nearly instantaneous. M Synch will allow for this ramp-up time by opening the shutter a fraction of a second after the flash bulb fires and it is at full brightness–X Synch opens the shutter and fires the strobe at the same instant.

    I was using a flash (strobe) and the shutter switch should have been set to X Synchronization but I had inadvertently bumped the switch and was shooting in M Synchronization instead without knowing. It was a dark church and wedding ballroom all the images taken indoors came out terribly underexposed. Being set in error to M Synchronization, within a fraction of a second the shutter opened and closed then the flash fired; too fast for the eye to catch and the film was never exposed to a lit scene. When the proofs came back from the lab I instantly knew what had happened and my heart was in my throat. The very worse part was meeting with the bride and groom to explain it all.
    After throwing myself on the mercy of my clients, begging clergy and the catering hall owner to help me reshoot, paying to have new flowers made, dresses/gowns cleaned and tuxedos rented again I reshot the most important setups learning a very expensive lesson. I solved the problem with my gear by having a camera repair shop set the synch to X Synch and then had the switch removed so I could never ever put it in the wrong position again.
    All totaled, this simple error cost me about $850.00 in 1970s dollars. I’ll never forget lessons learned that day. I too developed a protocol to check all my gear carefully before going to a job. Something I do some forty years later.

    Ken Lazar

  • Gina Milicia

    Wow Ken, I felt your pain. Thanks so much for sharing that story. how incredibly generous of you to recreate the shots. That tells me so much about you and your integrity. I’m so pleased to read you managed to dust yourself off, learn from the mistake and no doubt go on to have a long and successful career. Congratulations.

  • Gina Milicia

    You are not alone Jake. Many artists feel this way and not just beginners. There are days when I think all my shots are rubbish and I should give up and get a day job.
    You are doing everything kind to yourself and acknowledge how far you have come. Keep going. Shoot everyday. You will be amazed how much your work will improve over time. Thanks for your honesty.

  • Gina Milicia

    You can get some amazing deals on eBay Jake. Check it out. I’ve had my Minolta light meter for 25 years and it’s still going strong.

  • You are not alone… I’m in a depressive phase so I can’t shoot anything too. But we have to keep the faith and insist in ourselves 🙂

  • Have you ever tried the option of smartphones apps ? I’ve seen some in my windows phone, but never gave a try.

  • Liz

    BIGGEST lesson to date – MUST HAVE multiple back-ups! One back-up is NEVER enough. Needless to say, hundreds of dollars and TONS of tears later, we now back up an excessive amount – 5 times.

    -We lost every picture we have EVER taken – including all of our personal travels and excursions.

  • A big THANK YOU for this article. I needed it!

  • Gina Milicia

    My pleasure Anna, I’m glad you got something out of it!

  • Gina Milicia

    Oh Liz, I’m so sorry 🙁 Thank you for sharing and I hope that your post will save someone else that heart break.

  • Gina Milicia

    Push through Luciano, back yourself. You are an artist and this means you are more sensitive than most people. I’ve felt the same way many,many times over the years. “This too shall pass”

  • Gina Milicia

    These look really good Luciano. I may test one for a blog post.

  • Stoffers

    Why pay for 5 backups when you can just use the cloud which will have all sorts of redundancies for you.

  • Scott

    I too have a Windows phone and my wife has an iPhone. I hadn’t thought of a light meter app. There are some decent photography apps for Windows phone, surprisingly. I’ll look into this too as it would be a valuable tool.

  • Scott

    I can attest to what Gina is saying, Jake. I personally use Pentax because I can use legacy lenses. I recently purchased a lens for only $14 on a whim and it’s quickly become one of my favorites. I also purchased old, used flashes that work great. Give it a try at a low risk, low cost level.

  • Scott

    I too wish to thank you. Even though we all know everyone has failures, it is very encouraging for someone as accomplished as you, Gina, to share your imperfect, human moments. As you know, those of us striving to make a living from our art tend to lift successful artists to even loftier heights in our minds.
    Ken, way cool of you to share that as well. Truly, it’s a great community here on DPS.

  • Gina Milicia

    Thank you Scott, that’s very kind of you to say.

  • Ken Lazar

    Hi Scott,

    Not to pontificate but there is so much to understand in photography if one wants to achieve a level of proficiency to make a living at it. One of the many ways to learn is to celebrate one’s mistakes and sometimes, like mine, epic failures that come along in a career. We are all human and all we can ever hope to do is to keep errors to a minimum and own them and make good on them in the best way possible for the client when they do occur



  • Chris

    It is easy to be very critical of your own work. It’s the same when we might hear our own voice from someone’s voice mail. Or we see a picture of our self. Your best photo could very well be the next one you capture.

  • Jake Tenenbaum

    Dude, I suffer from clinical depression, and one of the things that helps me combat it is shooting. So, get up, grab that camera, and get at it. If you’re anything like me, it’ll help far more than it hurts.

  • Jake Tenenbaum

    I hear that. And something that helped alot, finally installed Lightroom yesterday, and WHOA, is there a night and day difference. Not hating on myself as much now.

  • Jake Tenenbaum

    Thank you SO much. Intellectually, I know all that, and yet “hearing” more kind words from another person makes a difference. Thanks for caring enough to drop me comment.

  • Jake Tenenbaum

    I have one, but without access to a pro meter, I have no idea of the app is accurate or not!

  • Jake Tenenbaum

    I’ve been thinking about getting an F Adapter for me Eos, so I can start using old lenses.

  • Jake Tenenbaum


  • Jake Tenenbaum

    Took this over the weekend. I’m so glad I finally broke down and got a copy of Lightroom. Looks better at full RES.

  • Gina Milicia

    Love this Jake. Well done. I’m very excited for you!

  • Ken Lazar

    Hey Jake,
    Very nice. Moody… Ethereal… Haunting… This is a piece to really take pride in.

  • Jake Tenenbaum

    Thank you SO much!

  • Jake Tenenbaum

    🙂 Can’t tell you enough how much the kind words mean to me!

  • Bob Bevan Smith

    The Cloud may be fine for some things, but there is NO guarantee that you won’t lose the lot. My daughter on her overseas travel put all her photos into a cloud service, but that later went broke, and she now has nothing left.
    It is worth having at least one other backup, and with portable USB drives so cheap, you can easily make a home backup which you keep in some other location in case of fire, theft etc. Make an arrangement with a friend, neighbour or relative to store each other’s backup drives.

  • ShowHarmony

    We tend to learn from our failures and gain confidence from our successes. Main lesson: keep playing the game and you will surely learn.

  • Stoffers

    That’s why you go with a big player, Google, Microsoft, Apple. They are going nowhere, and if they do go broke, they will have plenty of warning before your cloud is gone.

  • cirripedia

    Gorgeous, so much depth. Warning though, don’t print it unless you have lots of ink on hand.

  • cirripedia

    I too have broken a wedding, my Wife’s Uncle’s wedding. Failed to check to see if the film was advancing on 35mm. Oops, a blank, unexposed roll of film that somehow I got 60 plus shots on. We all learn (never to shoot family member weddings)

  • Jake Tenenbaum

    Thanks! If I ever print this one, I’m getting it done out-of-house, because I don’t have a printer that would do this justice.

  • Jake Tenenbaum

    BTW, folks, I recently broke down and got a copy of Lightroom. Turns out that many of my spectacular failures were only semi-failures, or outright good photos, but I was using free post-software, and now I know why I shouldn’t have. Adobe, you the bomb!

  • Abiel rodney

    thank you …. the ending just made me pick up my camera again ..

  • Marc Pujol

    At every level of my life where I have been successful I leave behind a trail of learning experiences. Photography is no exception. Learn from the experience, analyze the series of events that lead up to the disaster, implement a corrective action plan (and follow) to ensure that stupid mistake never happens to you again.

  • People call it Africa, I call it home..(Dar es salaam)(Tanzania)

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