Episode 111- The Crossroads


Have you ever found yourself at a crossroads? A crossroads between one career and another, a crossroads between the old and the new. I want to tell you about my transition and how it came about and hopefully it might be able to help you if you’re in that spot. 

It was almost 5 years to the day that I’m recording this. Actually, about five years and one month. And I was presented a unique opportunity. I have been a photographer for the beginning for about 20 years up until that point, professionally but 17 years but I have been running my own business with my wife Elizabeth for 10 years. We’ve been self-employed and we built a great business. We were doing high-end weddings. I did a lot of professional sports. I traveled around the country shooting everything the you can imagine. But I was on this personal development age. It was something I wanted differently in my life in my work than what I was getting from shooting. What I found was, I eventually kind of grew tired of being behind the camera and I want to get out where I was involved with people more. I was helping people more, I was having more conversations. I’ve read a bunch of personal development books. I’ve been doing some coaching, I started writing a blog on it. I was trying all sorts of different things on the side of photography just to get my legs underneath me to figure myself out. 

So for 10 years prior, I have been following Dave Ramsey and using his financial advice to get us out of debt. That same amount of time. I’ve also been reading following Seth Godin and I’ve been using his advice to build our business. For a couple years before that, I heard this guy Gary Vaynerchuk and I start consuming his content as well. 

So one afternoon when I was online working, I found an inquiry for a job through some website and it was from the Dave Ramsey organization. They were coming to Pittsburgh to have an event and they were looking for a photographer. So I jumped on it because I really wanted to work for Dave and I wanted to meet him and thank him for everything he done for me. I really didn’t care about making the money from the shoot. I want to do shoot as a thank you and to hand him a handwritten thank you note for everything he had done for me. So I told him I was interested in the job and I know I was getting bid against by bunch of other people, but I bid the lowest price that you can bid,  $250 and I said in the form that I am bidding the lowest price possible cause I just want to thank you by doing the shoot for you. 

About a week later, I get a response back from one of Dave’s people. They say we love your work. We love to work with you. We actually have two events we’d like you do for us. So I was hired and the next thing I know Elizabeth and I are setting up lights in the backdrop of the Benjamin theater in Pittsburgh and we are about to hang out with Dave Ramsey and his daughter Rachel for the entire evening. I fiercely wrote out a thank you card for him and I couldn’t wait to hand it to him in person. But before we can meet David and take the pictures, a guy named Chris Medford comes up to me, he is the director for Ramsey’s events. Elizabeth and I strike up a conversation with him. He is a really nice guy and he is really interested in what we’re doing, seeing if we needed help with anything. And then we start asking some questions about how they’re doing and he tells about how busy they are because they’re doing this event in New York City and it’s Dave and Gary Vaynerchuk and Seth Godin. That event was a week away and they were scrambling to get everything done. I knew about the event and I want to go but I decided not to because I just got hired to photograph the Pittsburgh Pirates in the playoffs versus San Francisco Giants that same day. So after Chris mentioned the event, I blurted out “Oh yea. I wanted to go to that.” and Chris fully hear me and said “Do you want to go?” I paused and I changed and I said “Yeah I do” And he said I can get you a ticket. I said “Really? That tickets cost $800.” He said “I can get you a VIP ticket. Just reach out to my assistant and her name is Bethany and shall have the ticket waiting for you.” 

So now I’m at a crossroads, and this is the one I was speaking about in the very beginning. My life up until this point has been photography and I am hired to photograph this really big game in Pittsburgh. One of the few playoff games they’ve had in 20 years in Pittsburgh. It is going to be a huge event and something I tremendously look forward to. But on the other hand, I’m being given this fantastic opportunity. A VIP ticket with Dave Ramsey, Seth Godin and Gary Vaynerchuk. It wasn’t as dramatic then as it feels right now, but at that moment. It was a crossroads. Am I picking what I’ve done in the past and was going along fine or am I my picking what my future is? I talked to Elizabeth about it and we both agreed my future was in that direction, not in the photography direction, So I accepted the ticket and I turned down the shoot for the Pirates game and I made my way to the conference in New York City for The Business Gets Personal event. 

I went by myself because I didn’t realize when I got there that he actually give us two tickets, one for me and one for Elizabeth. But I only thought that he gave us one as did Elizabeth’s, that is why I was the one who made the trip. So I called her up and let her know. I said “You have a ticket too and obviously she could not get from Pittsburgh to New York City especially with our kids. I called a couple of my friends in New York and nobody can get out last minute so I wind up going by myself. And as I was wandering the hallways of the Rose theater, I heard conversation going on. It was really interesting and I interjected myself right to the conversation. There was these four guys talking and I got involved right away. I figured that I am going to make some friends while in here and I jumped right in. An opportunity happens when you put yourself into it because in that conversation was a guy named Ken Carfagna and Ken and I hit it off right away to the point that we just kept talking about the conference. We’d see each other in between breaks and we struck up an immediate friendship. I got to go the VIP event that evening with Gary and Seth and Dave and I got to drink wine with them in a winetasting contest, got to mingle and asked each of them questions. I got to meet Seth Godin that night, which eventually led to him endorsing my book when it came out two years ago. But what happened after that conference was even more remarkable. Ken and I stayed in touch. Not only that we stay in touch but we had weekly phone calls where we would “mastermind” the ideas we are working on. He was about to publish his book Arctic Land and I was talking about all the different ideas that I was thinking about that I want to build. 

So each week. Him and I masterminded on the phone and he was a former engineer so he loves to take note, I don’t take notes about anything. So he has emails of notes of every conversation that we had, about the topics we discussed and they’re all in the document that he created literally starting the week after that conference. The seeds planted that day, the mastermind that we did, the ideas that we came up with, from that day on, week after week, month after month. Literally all the seeds of everything that I do in business today. I now run a series of masterminds for entrepreneurs and freelancers. I wrote a book called Freelance To Freedom that Seth endorsed, that had stories from that particular event within it and we created a membership and coaching that come off the heels from all that. 

Quite literally, everything in our life turned around with that one decision. And yet understand that this isn’t turned around from things from awful to now they were good. This was actually a hard decision because this is actually deciding to leave from something that is going very good for something could be really great. It would have been very easy to say “No. I need to shoot the game. I need to keep doing what I’m doing. This has been working out all these years. I can’t leave all that experience and time behind.” But leaving all that behind led to every events that’s going on now. It has led to some that keeps growing and getting better and stronger. Even the ideas in the horizon dwarf the potential that I would’ve had if I stayed doing what I’m doing. And on a human and friendship level, Ken and I are best of friends. His wife Teresa and my wife Elizabeth are such close friends and our kids get along. Now we vacation as families together. 

So if you are at a crossroads, this is for you. The advice I can give from my experience is choose what your future is, not what your past was. I mentioned my book and if you’d like to download the audiobook for free. We give it all away. Go to totallifefreedom.com/F2Fbook. You could download the audio version of Freelance to Freedom for free. 

I’ll talk to you tomorrow!

Leave a Comment