Kat O’Sullivan (Email | LinkedIn) is a professional keynote speaker who loves encouraging people to say “Hell Yes” to the seemingly impossible, knowing that it’s going to be both disruptive and magical. She moved from the US to Mexico about a year ago to create a new, fulfilling life and adventure for herself and her husband. 

I’ve loved working with Kat because of her deep engagement with my process, and her complete willingness to show up and be fully present, authentic and vulnerable. I believe you’ll be able to see that in this interview. 

This blog post is a summary of the interview (edited for clarity) with the full video at the end.

How did this whole “move to Mexico” thing happen?

Well, everything I’ve ever done in my life of any significance has also been something that was seemingly impossible. In each case, it has been transformative for me! So, most recently, during the middle of the pandemic, I decided that I wanted to make more time to do the things that I love, without worrying about how to pay for it. 

At the beginning of COVID, everything got disrupted and my business shrank. I got to a point of utter frustration because I was doing the same things over and over and nothing was working. One day, my husband innocently asked me if I needed anything, and my answer to myself was: I want a new life!

I realized I had been going on autopilot for a while at 100 miles an hour, in the wrong direction! My husband Michael is 18 years older than me. He’s been retired for quite a while. I have my work. If we were to enjoy any sort of retirement together, it required a dramatic shift.

I came across an article about a woman that retired to Mexico on $1200 a month, and decided to do some research. It required selling our house, cars and boat in North California in three months! We made the decision in July 2021 and moved on October 10th! It was unrelenting, but also a blessing to not draw it out over a long period of time. It was disruptive, emotional and difficult to let go of our whole life here – my husband had been in that house for 38 years and I had been for 28 – since we got married. There was a lot to let go of, but also a whole transformative process. 

While I’m definitely not retired from my work, I was able to retire from what I was doing that wasn’t working for me, rather than doing the same thing over and over expecting different results. As successful as my previous career was, and as much as my clients loved me, it became more blah blah blah to me, and that’s not a good place to be in. So I had to give myself permission to do something different and make a leap of faith. We’re still figuring a lot of stuff out, a new and amazing culture, a whole new language, a different bureaucracy, but we definitely do not regret making the move. 

What an incredible story! So what got you interested in a photo session?

I’ve been going through a program for training speakers (HPS) to create a script that reflects what I want to communicate to people. As I was doing that, I realized I want to make a shift from a corporate business brand to a personal brand, which are very different things. I’ve always been averse to talking about myself and self-conscious about being photographed. While I’m very bold about doing things in business, when it comes to me personally, it’s a very different story!

The process of creating my speech helped me ground myself: Who am I? What’s my vision? What’s my purpose? How do I want to communicate that? I’ve been doing that through my keynote script, but then I realized that I needed a new website – a whole new personal brand. 

When I saw your photography, it struck a chord. I felt that you were able to capture the essence of people that you were photographing, and after talking to you, I thought the timing was perfect. I was flying in from Guadalajara to Philadelphia to do a video shoot of my speech anyway. I have worked with photographers before and there are a lot of good ones out there with their process, posing and all that. But with you, I love that none of your photos look ‘posed’, and it felt like talking to someone who gets me. I also love the fact that you used natural light so effectively in your sessions. 

How do you perceive the distinction between a corporate vs. a personal brand?

A corporate brand is all about work. What services do I provide? How do I provide it? It’s more informational. It can be more than that, but you’re focused on the credibility of the business, the service, the product and so on. Obviously, if you’re the CEO, you represent the business, so some of the brand has to be focused on you, but the context is still the business.

On the other hand, in a personal brand, the context is me! My personality, my style – it has to be authentic because I want to attract like-minded people who value who I am and how I go about what I do. It’s very personal and vulnerable. That’s a keyword: vulnerable. You can hide in a business. You cannot hide in a personal brand. 

Focusing on my personal brand has helped me really show up. As I’ve been working on my keynote in my HPS speaking course, especially while we filmed the promo video, I got a lot of feedback from people appreciating my vulnerability and relating to my sharing in a very personal way. It’s very different from someone coming up to you after a business presentation to talk about the results of a business. It feels much more personal and vulnerable.

What was the creative and planning process behind the photo shoot like for you?

Check out Kat’s entire board on Pinterest

The idea of a mood board terrified me at first! I had a lot of resistance. I didn’t know anything about Pinterest, so that was intimidating. That being said, once I got started and searched for stuff on the site, things started coming together and I got addicted! One idea would trigger another and then another. I went through things that were meaningful to me and brought them in as well as possible props. It was really fun and almost ridiculous.

I started my search using keywords that were meaningful to me. But in order to do that, I first had to get clear about what those keywords were! Once I came up with half a dozen keywords, I searched them individually and in combination with each other. For example, I put in words like “Joyful” and “Playful” and started adding in everything that came up. Just like the process of creating a speech or writing a book, I gave myself the freedom to add anything in there that caught my interest at all, and then whittling it down, taking out less interesting or duplicate items. 

I also loved your suggestion about taking into consideration my keynote script and the emotional journey that it reflects. As I was reflecting on my speech, I realized that I completely missed capturing my emotional state at the start of the speech, because I was so focused on the end result of the journey – where I am now. So I had to go back, and that required me to get real and vulnerable with myself and think about my entire emotional journey!

What was your experience of the actual session?

I was definitely concerned about wardrobe issues since I was traveling for the shoot, but I was able to resolve those before I got there. What terrified me was the idea of posing, which has been a challenge for me in photo shoots before. 

Having Crystal (Creative Director) doing some initial breathing and grounding was super helpful. Because of the environment that you and Crystal created, it felt completely natural! I loved the process of talking and thinking through my script, and actually performing and embodying it. There was also so much permission to try things, maybe things I wouldn’t have thought of, and to have fun with the props. I feel like we captured the right images for all of the outfits and props and embody my core value of playfulness!

What did it feel like to see your photos for the first time? Any reactions from friends or family?

I was blown away! I was so grateful that we were using natural light, because everything does look natural and you really captured the light well. I also love having all of this variety, the different flavors of shots – with my wardrobe and all of my props. Interestingly, I would have never thought of the outfit with the sun on it as a good one for a business headshot, but in a personal brand? It works so well! I also thought we had a lot of fun with the glitter. Even though the way I had planned it didn’t quite work out, we ended up doing something crazy like dumping it over my head, and that worked!

I’m excited to see how my designer uses these photos in my website and brand. She was over-the-top excited when I sent her the gallery. Her first reaction was: OMG, this is amazing! She has a lot of shots to choose from. I’ve done photo shoots where you only have a limited number of photos you feel good about. In this case, there really isn’t a single photo which I wouldn’t want to use. I’m just curious about which ones she pics. 

My family and friends love the photos and they all said: Wow, you’re really photogenic. They’ve overwhelmingly agreed that the photos capture who I am and my unique style. 

Would you recommend this experience to a friend or colleague? What would you tell them?

Absolutely, I’ve already referred people to you, and I wholeheartedly recommend the experience. You want somebody who’s going to “get you”, create the environment for you to show up in a way that’s really authentic and vulnerable. You want to work with a team that’ll create a safe space for you. The overall experience was so positive and unexpected in a positive way. You’ll be doing yourself a disservice if you don’t work with Raj to do your photo shoot and capture who you are and what you’re about!

Video of Kat’s interview (30 min)