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NYC Branded Lifestyle Portrait Photographer | This is where I share with thought leaders and other high-level entrepreneurs how to present themselves powerfully, purposefully and authentically in their image content on their websites, social platforms and sales vehicles.

Be Playful To Get Serious Results From your Photo Session...

Have you ever been so engrossed in thought over an upcoming event or activity that your thoughts eventually began to steer you towards the dark side, where anxiety and doubt begin to run havoc on your confidence, to the point that you almost talked yourself out of participating altogether?

Yeah, I’m guilty of that, maybe once or twice in my life — or hundreds of times, but who’s counting, anyway?

It’s a fairly common, and unfortunate, mindset many of my clients possess going into their photo session. They’ve visited and re-visited the experience in their minds, and each time, it resulted in a total horror show where they end up producing zero usable shots, look unbelievably ugly and old in every image, and completely wasted their precious time and hard-earned money.

Mind you, I didn’t even get a chance to turn the camera on and this is what I’m going up against!  Shesh!

Fortunately, I’ve been able to talk many a client off the emotional ledge, brought them back down to reality, and, ultimately, left them excited and pleased with the results of their session.  And how did that happen?  The moment that they decided to take the whole process so seriously and they tapped into their silly side.


Prior to every headshot shoot, I request that each client look directly into the camera, and I ask them to “make the stupidest face that he or she can possibly think of right now,” and, honestly, I’ve seen some pretty awesomely weird expressions.  

Here are a couple:

Of course, I don’t ask them to do that for my own personal amusement; rather, I want to use this silly exercise to break that silent tension between them and the camera.  Not only do I want them to purposefully move some muscles in their face, get them loose, and used to taking direction from me, but I also want their minds to enter a playful state, quiet their doubts and anxiety, and have them more focused on the present moment, instead of what they conjured up in their mind about this experience in the days leading up to this session.

The best part about letting loose and playing along with my request is anonymity; these pictures will never be seen by anyone other than the client and myself, unless he or she wants to post them (which has happened on more than one occasion!), or I’m allowed to post them socially.  Since the stakes are pretty low, the benefits from the exercise are really high.

Although this is not intended to lead to any potential keepers, it does lead to the type of mindset that will lead to a slew of great images that capture authentic aspects of each clients’ personality.

Another fun game I often like to play with clients that I learned from my mentor, Peter Hurley, is word association; I throw out a phrase or emotion and ask for the client to present that emotion with his or her facial expression.  So, if I asked for the client to produce a look of “happiness,” he or she will provide me with his or her interpretation of a “happiness” expression. 

I tend to avoid simple emotions like that; generally, I often freestyle whatever comes to mind and that compels the client to play along.  They usually burst out in laughter, since, most of the time, I have no idea what is to come out of my mouth, and I tend to say completely nonsensical things.  It’s this uncertainty that maintains the client's engagement in the process and not thinking negatively and self-consciously.  Again, the game itself won’t necessarily produce the solid keeper images – it’s the moments in between those silly expressions that do!

That’s when clients truly get comfortable, get loose, forget what they were anxious about in the first place, and that’s when their authenticity brightly shines through.


Although this is only one of several techniques employed to coach clients to their true, confident and approachable selves; when they allow themselves the chance to tap into their inner child and let their responsible and sensible adult guard down, it inspires them to forget about all their hangups leading to this moment, and inspires them to deliver boldly on their time and financial investment — and have some fun in the process!