Caleb Masterson: A Boston Inspiration

Hi I’m Caleb, I am 22 years old and live in Boston, MA. In the near future I would love to pay off the rest of my credit card bill and travel to Germany.

What are a few things that motivate you when you’re down? My friends and partner, Andrew, are what motivate me. I have depressing periods but having relationships with people around me and being able to go out for a cup of coffee, or a walk in the park, is so important.

What is something that inspires you & why? Living simply and organized helps me recover from the outside world and inspires me to take on more of what life has in store for me.

If you could recommend a movie, website, song, or book for others & their inspiration, what would it be & why? Documentaries. Andrew got me to watch a few documentaries and they are so eye opening. Human Planet and Planet Earth are my favorite because the documentaries give you a huge amount of information in an artistic way.

Tell me about a time when you’ve had to overcome something? How did you fight your way through? Coming out as gay was a huge obstacle to overcome. I was so nervous that I was going to be treated differently, and some people did treat me like that, but for the most part I got to see how people love when you are honest with them. It takes your relationships to a deeper level.

Do you have a goal list? If so, what are a few goals you would like to accomplish, small or large? I have learned that when you make specific goals they tend to work out differently that you had planned. For most people this is ok, it makes me anxious. So I tend to make my goals specific enough to have direction and broad enough to let it happen the way it is going to happen. I would love to live in Copenhagen, speak German and Danish and design my own house.

You recently stopped pursuing photography, if you’re comfortable talking about it, why is this & how have you pushed yourself forward without it? It was hard to admit that I wasn’t passionate enough about photography to make it a career. I still enjoy it in my everyday life. I was discouraged for a while because I had literally moved to Boston with two suitcases to pursue photography. Everything happens for a reason, and I started noticing that the opportunities in my life were so much better in reality than I had imagined and that I could hold on to photography and still pursue other things.

Where do you see yourself in 10 years? 10 years from now I would like to own/start my own business. I am not sure what type of business, but something creative and meaningful. Andrew and I would like to have kids by then, but 10 years seems light years away!

You recently moved to Boston, how has this decision changed the way you see the world? Boston was the best decision I have ever made. I bought a one way ticket, had $800 (not enough to even pay first and last months rent for an apartment here) and I just told myself “I will make this work.” I see the world as a place of unlimited opportunities that I have to be open enough to learn from and accept that I don’t know everything.

If you could motivate or inspire someone with one paragraph, what would it say? All I would say is this…Take life one day at a time.

Leave a Comment