Leaping off a cliff head first

... and not knowing whether there's water at the bottom or large jagged rocks. And if there's water at the bottom, not knowing whether you'll find the elusive Jaguar Shark lurking below.

On Jan. 30th I sat down with my boss and handed him my letter of resignation. I was a manager in the IT department of the Indianapolis Star, a Gannett company, working with a great team of people and earning a respectable salary.

I had been given a lot of great opportunities there, and will always be grateful for that. Three years ago I was promoted and managed a team of people, 7 of 8 who were older than me, and 3 of the 8 who had worked at the Star longer than I'd been alive. I was the project manager or technical project manager for several 6-figure capital projects, learning a great deal about deploying and integrating enterprise systems. I was able to attend a 20-day management training program at Harvard, with speakers such as the CEO of Knight-Ridder and classes taught by Harvard Business School professors.

But even with opportunities like that, I still wasn't happy there. Sure, there were little things that I didn't like about the Star, but there wasn't anything major making me particular unhappy about the place either. I'd been doing a lot of soul searching over the last year trying to figure out where I wanted to be, and sign after sign kept pointing to one thing — it was time to leap off the cliff.

Before I came to the Star I was a partner in Bottled Software, a small software company in Indianpolis, and for about 4 years before that I had made most of my income from freelance software development. I went to the Star after Bottled closed because I wanted something more steady and wanted to experience working for a large company like Gannett. But I've never been able to shake the entrepreneurial bug, and I eventually realized a few months ago that I wasn't going to be happy in my career unless I was back working for myself full time.

So on Jan. 30th I took that leap, and yesterday, Feb. 24th, was my last day. I've been fortunate to have a couple freelance projects to start with, and have dusted off some product ideas, one of which I hope to have a beta launch of next week.

I'll let you know if I find my Jaguar Shark.

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