Back in 1999 I was putting together a team and raising money for my latest venture—an Internet startup running a website to host construction project information. It was a crazy time and a very emotional ride because it coincided with a growing fissure between me and my business partners. We had disagreements over the management of our existing software company and thought spinning off this new venture would give us some space to work apart. This transition forced me into taking on new roles and there was money and my reputation riding on its success.

To make sure that I didn’t veer too far off course I hired Paul Lemberg, a business coach who I had worked with in the past and trusted. He required that I check in often via email and we always had a Tuesday call to sum up the past week and plan the next one. I hated these calls. Not that Paul was hard to talk to—he was great—but it was his job to fix what I was doing wrong, so the calls ended with me feeling like I needed to work harder and push myself more.

After weeks of doing presentations for potential investors and negotiating terms, I was pretty happy with my progress and actually looked forward to my upcoming Tuesday call with Paul. I bragged a bit about my week and how things were going and he asked, “How are you doing with the investor calls?” Feeling somewhat smug I replied, “I’m getting quite comfortable talking to investors.” Expecting a compliment, I was floored when he said, “Then you’re not pushing yourself enough.” Dammit. Why couldn’t he just have let me enjoy my happy place? As I recall, my response was a well-crafted and eloquent 30 seconds of dead silence. I proceeded to pick up the remaining pieces of my pride and worked to take his comment to heart.

I totally get it. I was getting too comfortable and work is not about comfort. It’s supposed to push you and make you better. That’s not to say that you can’t have fun while working, but if it’s effortless, then you probably need to take on a new, more challenging task and delegate the easy stuff. In the case of my investor calls, I was talking to the people I knew, the low-hanging fruit. These were good calls to make, but I needed to go further. I needed to get through these calls quickly and go after the bigger fish—the calls I wasn’t comfortable making. I was accomplishing just enough to make myself feel good about what I was doing, but not the work that would really make a breakthrough difference.

When I was first married, I had a job that paid the bills. Well, Judy usually made more money and paid more of the bills, but at least I helped. During that time I was constantly working evenings writing software. Sometimes it was shareware for the Mac and other times it was contract work to bring in extra money. These extracurricular activities inspired me in ways that my day job couldn’t. I felt limited during the day and free at night. I knew my day efforts wouldn’t blossom into anything more than a small annual raise. If I wanted to do amazing things, I was going to have to color outside the lines and push myself to be more creative with my time.

Because my wife was more responsible and had the stable career, I had the flexibility to spin many of my nighttime efforts into full-time ventures, which is why I’ve had five different startups over the years. It wasn’t always easy to write code until 2 AM and be ready for a Houston commute six hours later, but I wanted to be more than I was and do more for our future. I could see that my 9-to-5 job wasn’t my destiny. It didn’t fulfill me or stimulate significant personal growth. It wasn’t that I was bored, but it was more like feeling out of place—I could and should do more with my talents.

“I’m a lumberjack and I’m OK. I sleep all night and work all day.”

Both my sons are in their mid twenties and working long hours at fast food restaurants. When asked how things were going, my elder son quoted the above Monty Python lyrics. It made me chuckle, but it also concerned me because I know it’s all too true. I’m proud of them for their work ethic, but I want more for my kids. I want them to be more than what their work defines them as today. They have a poor work/life balance because a lower-end job is just not going to give them enough income to allow for more free time. This kind of job forces you to put in long hours to pay rent, utilities, and food expenses.

Not that it’s all about the money. If you can lower your overhead, you could earn less and do what makes you happy, like volunteer work, outreach, or teaching. It’s less about how much you earn and more about the satisfaction of working hard and producing something of worth. We all have stepping stone jobs—Taco Bell paid for some meals and books during my first year of college—but too often we settle for a shallow career. So many of us never reach our potential.

I’m blessed to be a fidgety type who isn’t risk averse. Merely collecting a paycheck doesn’t cut it for me; I need more. Running my own indie software company was hard work, but I had done it for long enough that it was comfortable. I was my own boss, which meant no one criticized my code and I drove the schedules. There was risk, but the majority of my mistakes were made in private. Taking a position at a company filled with brilliant individuals was pure disruption to my cozy life. It was easy being the smartest guy in the room when I was the only person in it.

Fortunately, this risk paid off and rewarded me with new career challenges and a brand new urban lifestyle. I didn’t know what would happen when I made this change, but I knew I was being handed a huge opportunity if I was ready to work hard for it. Pushing past the fear of looking like a fool was probably the hardest task.

I believe the trick to growth is to learn to enjoy being out of your comfort zone; teach yourself to crave a challenge and abhor too much time spent with the familiar. Amazing things happen when you open yourself up to change and the discomfort that may come with it. Life is waiting for you to wade into it. Come on in, the deep end is fine.