I'll just come out and say it, picking out photos for your portfolio is damned tough. It seems like it should be no big deal, but when the time comes to make decisions on what photos to pick, paralysis strikes faster than a Cobra on a hot tropical day. Unfortunately, there's no anti-venom for portfolio picking frustration - but I can offer some tips to make the process less painful.
Drink Alone but Don't Edit Alone
My first suggestion is that you do not do this alone. You are a great and wonderful photographer - you are however a lousy editor of your own work. You're too close to it. Not only are you emotionally attached to the images and the process, you see the flaws and miss the impact that comes from looking at the work with fresh eyes. I also find that photographers look at their work from too narrow a perspective and don't see bigger trends that are right before our eyes.
Case in point, I was about to attend a portfolio review in Los Angeles with a number of big agency creative directors and art buyers. I was all set to show my usual portfolio, however a few days prior, a consultant friend suggested that I include a portfolio of my partying youth culture photos as well. Much to my surprise, the work was as big a hit, if not bigger, than than the other work I had originally intended to show alone. Moral: Always have someone else look at your work.
You Don't Need a Pro
Your helper can be anyone who you with a good eye and positive spirit. They must have an open mind and with some sense of visual literacy. An art director or designer can be especially helpful since they understand how images are used in media. If you're selecting images for a wedding portfolio, any woman who's ever been married or is planning on it is a likely candidate - after all, there's no better help than someone in your target demographic.
However, I don't recommend that that someone else be another photographer. Unfortunately, photographers in general look for the same kinds of stuff. They see the flaws and judge it through the prism of their own work and expectations. It doesn't hurt to get an opinion from a photographer you trust, but be careful. Any photographer you consult should have much more experience than you and have an open mind.
I actually had my portfolio critiqued by arguably the best photographer working in the world today, Nadav Kander. While I respected his opinions, I didn't consider them the last word just by virtue of the fact that he's a photographer dealing with the same stuff that I am - just on a much different level.
What About Consultants?
Consultants... this is always a tricky issue. Let me just say that they can help immensely. They can also be worthless. I've honestly had mixed success. As I pointed out above, sometimes the advice is helpful. On the other hand, I once hired a well-known and respected consultant to edit my book - only to receive a disastrous edit. The subject of hiring consultants is its own blog post so suffice it to say that consultants are no panacea for the portfolio picking malaise.
Here's my steps for perfect portfolio picking:
1. Include the Kitchen Sink
For your first/rough edit, grab every photo you think is interesting, portfolio worthy, good, worth a second look. Don't be afraid to include everything and anything that is worth consideration. At this stage, you're not being very critical. You're thinking outside the typical box as well. Experiment a little. If you have to think about whether you should include an image or not, include it. The way to break out of portfolio paralysis is to include everything!
2. Make 4x6 Prints of Your Selects
Prints are cheap these days so just send all of your selects off to be printed. For my recent portfolio edit, I ended up with a stack of well over 700 prints. Don't believe me, take a look!
3. In and Out Piles
Here's where you work with someone else. You should not be making the decisions at this point - although your input is necessary. The idea here is that you make a quick decision as to what stays in and what gets tossed. If there's any doubt, the image stays in. Do not get hung up on details or debate on whether the image is portfolio worthy. If there's a debate - keep it!
4. Lay 'Em Out
By now, you should have your selects down to a reasonable number, though not tight enough for a final edit. Here's where you lay all of your selects out on either a large table or the floor - depending on how many prints you're working with. The key is to be able to see all of the images at once.
5. Make Your Picks
Once you can see everything, begin picking out your favorites and then placing them in the order that they will appear in your portfolio or website. Again, you've got help here so you're not doing this alone. By being able to view everything at once, you can see the story of your work unfold before you. The good stuff will rise to the top - where you have images laid out - and the weaker work will stay put.
6. Be Tough
You've been a pretty easy reviewer up to this point. Now it's time to be a very tough critic. Only allow the best of your best to remain. People often ask how much work to show - my suggestion is that if you have ten great images, just show ten images. My 700 plus 4x6's got cut down to two portfolios of 15 images. Keep in mind that clients will not judge you based on your best work - they'll judge you on your worst. Better to show fewer images and let the client think you've got more great ones than show a bunch and confirm that you're actually quite mediocre.
Understand that people have limited attention span. Once you start showing dozens of images, the client pretty much tunes out. Each image begins to lose impact. If you have a lot of work to show, break it down into manageable galleries. For the record, a half-dozen galleries of 35 images each is not what I consider to be manageable.
7. Live with It
Once you have your picks laid out, live with them for a day or so. Let the photos soak in and see if they're working. Take a picture of the layout so if it gets disturbed, you know what photos where in what order. Portfolio picking should not be a rushed process - give it time.
8. Find a Tough Critic
Don't be afraid to get feedback, though always consider the source. Everyone is going to have a different opinion so don't make changes just because one person doesn't like an image or series. I've sat with art buyers and had one tell me that X image was the worst image in my portfolio then the next tell me that the same image was the best image in my book.
Case in point, after I finished my edit and had it up on the website, I had a close photographer friend give me some feedback. He didn't like it. Though I respected his opinion, I knew that, as a photographer, he was attracted to some of my more highly produced work. Next I sat with an art director friend and past client for his critique - fortunately, he loved it.
The fact that someone doesn't like a photo is not reason enough to remove it from my book. If someone was moved enough by my photo to say they don't like it, that means that there's something in the photo that's connecting with people. Most likely, someone else will like that same photo. The photos that I tend to ditch are the ones that no one comments on. Those are the ones that are boring people - and that's the last thing I want to do. (Obviously, if you get consistent negative feedback on an image, dump it.)
So far, I've come up with eight points. Now I know that every good list should have a full ten. But, in the spirit of only showing my best work, I've only got eight good ones so I'm going to stop right here. Good luck with your edit!