Interview with Chris Howland

Last year, I interviewed Chris Howland, founder and owner of Carillo & Howland Insurance (now Smith Brothers) about the eye-opening experience he’s had leaving the corporate world and making a go of it alone as a small business owner. It was an unexpected bit of enlightenment about ducking conventions and expectations alike, forming something new in the process.

Chris Howland found himself unhappy with corporate life and, at the age of 33, left his comfortable job, moving his family to a new town to start all over again, selling insurance on his own. The business started with only Chris, his wife, and his sister in law, but has since bloomed into something bigger. His story is informative and interesting, granting him a lot of wisdom to share.

I’ve taken the time to jot down some of Howland’s best bits of advice, talking about what makes them surprisingly effective. There’s always more to learn, especially when you remember to ask the right questions.

To start off, let’s look at perhaps the most universal statement made in the interview: “There is a difference between learning from your peers and following the herd.” This idea makes clear the distinction between doing what everyone’s doing for its own sake and actually taking lessons from what you see around you. Instead of doing what’s popular in your particular business avenue, try learning what led your peers to their various successes and failures. Get at the why and the how behind it all.

This leads to my next favorite moment from the chat, where Howland explained, “Ask why first. Why are we doing this? Why does this make sense? Then do the how we would do it, and what specifically we would do.” It’s a simple path laid out for any important business – or life – decision you could make. Once the why is figured out, the how and the what will follow. He reminds us, “People make an emotional connection with the why.”

It’s important to figure out your personal “why” because it will become the foundation for all that you do going forward. Why make a risk on your own when established corporations are offering jobs? The answer will vary for everyone, and it will be the key to deciding how your own business functions and what it does.

This pioneering spirit has its basis in a mantra that Howland kept in mind as he started his current chapter in life: “I’m going to abhor convention and expectation because I think those are two self-limiting models.” To some people, turning away from convention might seem like a road to failure; after all, conventions tend to form around what works. But what if the prevailing model doesn’t work for everyone? What if it produces one outcome, but doesn’t account for many other aspects of success? For anyone asking these kinds of questions, the answer is that convention isn’t a blueprint for happiness in life. It’s just a default mode of operation that can be left in the dust by those willing to think and try new ideas.

Speaking of success, Howland had a lot to say about that ephemeral idea. I asked him about it directly. “I’m very wary about saying, oh, I’m a success. Or this company is a success. I think that when you get to that point, your foot’s off the gas.” It’s another way of saying that we must always strive, always try, or we find ourselves coasting in the slow lane. It’s one thing to enjoy the perks that come with attaining goals, but it’s another thing entirely to sit back and relax once you’ve reached an arbitrary level of success. Coasting eventually leads to stopping, which is never good in the business world, or life at large for that matter.

Chris Howland had a lot more to say in the full interview, making it an essential read for anyone wanting to become a trailblazer out there. The full transcript and audio version will be posted for members. If you’d like to discuss this interview or anything else with Chris or myself, please head to the Technology Should be Simple Members Forum.