1. When did you realize you wanted to be a designer?

I sort of fell into it I guess. I always wanted to be a Disney artist and never practiced enough to hit that level. I used to say I was not good enough but now in my older age, I realize I just didn’t push myself hard enough then.

I was right on the cusp of digital design in the late 80’s and early 90’s and just went with the flow and loved it. I had a job at a great company with a fantastic culture (before that was a “thing”) but was feeling creatively unfulfilled and when the opportunity to leave presented itself I just went for with reckless abandon.

2. How did you get started and what was the biggest hurdle you overcame?

I look at my career in two or even three phases. Phase one was 20-37. I was married with a kid, freelancing and due to a unhealthy marriage I was an unhappy person. Phase two was age 37 to 41. I was divorced and had the chance to reinvent all aspects of my professional career and did just that.

So somewhere in there between phases one and two was the biggest hurdle. Having confidence and stepping outside almost 20 years of bad habits to show myself there was more out there for me. I am currently in phase three with the opening of my print shop and studio 2.5 years ago.

3. What’s been your most successful way of getting clients?

By far it has been word of mouth and just being someone in the community who has an open door and an open ear to help out where it is needed. My community helped bring me back from depression and I will forever pay that back so being present and giving with no thoughts about what I can get back (which translates into great word of mouth) has been the most successful way I have gotten clients.

Recently social media has really been doing well for me and I have been concentrating a lot of time on it. Especially Instagram.

4. How do you get clients to stay with you and use you for more work?

I am a nice guy and treat them well. I work with them and not for them so they see me as a trusted professional and by the end of a project hopefully a friend. Work with people who you can see as friends. That is one of my top new client qualifiers.

5. Do you ever have issues with clients paying late? How do you manage that?

Not really. I have my contract and processes setup to make sure I get paid before works starts and/or final files are delivered. Those are usually good motivators. I also stick pretty hard to those processes and have refused jobs based on companies wanting to pay no deposit (NEVER EVER DO THAT) or pay final invoices 30, 60, 90 days later. No thanks. I need to pay my rent and eat today for the work I did for you.

6. What does your typical work day look like?

That is what’s wonderful. There is no such thing a typical day. I design, I illustrate, I screen print. I do speaking events, live printing and community work. Every day/week hold so many new adventures!

7. Lenny Terenzi, any piece of advice/wisdom that you’d like to give the readers at This Design Life?

Just create. Lead a life of unlimted revisions. Have a million ideas and don’t know where to start? Divide them up and give each one a day or few hours and you will find that one sticks and you are off and running. Become part of your community. AIGA Chapter, start a meetup, Create the community you want to see around you. Support it and it will support you. Also, draw. As much as possible. Every day.


Lenny Terenzi runs Hey Monkey Design. A one-man creative and print shop that works with a network of other creatives. You can connect with Lenny on Twitter, Facebook and Instagram.

Chris Green

Chris Green at This Design Life
Chris Green is a designer and marketer. He runs an agency called Calloway Green and is also the founder of This Design Life.

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