In the summer of 2007, I filed paperwork to form a business. I had no idea what I was doing (evidenced by the fact that I later had to hire an attorney to correct said paperwork), but I wanted to formalize my freelance work, and to legitimize some of the projects I had been working on. A little over a year later, I put in notice that I’d be leaving my job to work full-time for myself my business my clients.

March 1, 2014 marks my fifth anniversary of being self-employed. Naturally, I started thinking about all that the business has to show—all of my bragging rights, really. Then I started recounting all of the struggles; building a business around creative services is incredibly fulfilling, but it can also be unpredictable and exhausting, and mine’s given a few scars.

But instead of nostalgia, or a list of accomplishments or lessons learned, I’ve created five portraits of people I look to for inspiration—friends who’ve paved their own path, and who I respect for their tenacity, humility and outright hustle.

Jay

Trunket & Brooklyn Carry Co

Five-Years-Jay-Chowdury

Harris

Underground Eats & Damashek Consulting

Five-Years-Harris-Damashek

Justin

Plowshares Coffee Roasters & Natural Thrills

Five-Years-Justin-Rodriquez

Ryan

Ryan C. Jones Photography & An Unlikely Scene

Five-Years-Ryan-Jones

Daniel

Daniel Topete Photography

Five-Years-Daniel-Topete

Thanks for your friendship, collaboration and insight, fellas. And special thanks to my clients, employees, collaborators, and everyone who has been a part of this venture. I’m extremely grateful.

(Note: I acknowledge that this list is short, all-male and NY-centric. I wanted to show diversity, but can’t fully cover that in five portraits, but starting here gives me an excuse to continue the series.)