After working with him for a few months, my friend and mentor, Jeffrey Zeldman told me something I was not ready to hear. He said that I was too good for my employer and I should quit and start my own design studio. At the time I wanted to do just that, but I had a steady job that paid for all of our expenses while my wife finished her college education. At least that was the excuse I told myself and Jeffrey. While that was a reality, truthfully I was also terrified to leave full-time employment because I was scared to depend on myself.

It wasn’t until a year or so later that I finally had the nerve to baby-step into my design consultancy that I called Airbag. My wife, now graduated from school, landed her first job and that was enough stability for me to consider going into business. Like most folks starting out, I took on whatever work I could get my hands on, fueled by fears of financial ruin and career failure. I kept my head down and worked ten-to-twelve-hour days. In hindsight, it was absolutely the worst way to do business and did nothing for my physical and mental health. But that’s what you do when you start out, or so I was told by friends and family members who had established several of their own businesses.

Not anymore.

I’ve learned many, many, many lessons in business the hard way—death by a hundred small mistakes that add up and take their toll. Channeling these lessons, Ryan and I have designed a better way of working through the process of developing a successful business and it starts with some frank conversations at the very beginning.

Before we spend any time on developing your offerings or identifying target markets, Jump Ship begins by asking a series of questions about your intended quality of life. We guide you through exercises to document—put into numbers and words—how much money you need to make in correlation to what in life is important to you. Yes, we talk about money and your way of life right from the start. Our intent is to push you through moments of vulnerability and honesty not with us, but yourself.

I love that we're doing this because that data immediately provides clarity of your purpose and priorities. These inputs are used later to inform your offering(s) and sales opportunities—tangible goals and requirements for your finances and, more importantly, your quality of life.

Eighteen years ago I didn’t understand that self-employment shouldn’t be just another job. It should be an opportunity to create the life you want. A time to reassess what’s important and build a business from there. We spend a good chunk of time facilitating these conversations, in the beginning, to help others see and understand this perspective because we believe it’s key to building a successful business. I’m glad that I finally figured this out and that we don’t talk about the business you want to create until we help you figure out the life that you want to live.