I thought I would never sell my company. I started it as a hobby in 1997. When NPR did a story about me in 2004, I said I'd stick it out until the end, and I meant it.

In 2007 I did a ground-up rewrite of the website from scratch. And man, it was beautiful code. My proudest achievement of my life so far is that backend software. Wonderfully organized, extensible, and efficient: the culmination of everything I'd learned about programming in 10 years.

After a successful relaunch and Christmas rush, I was looking at my plan for 2008 and beyond. It was all stuff that would take a huge effort for little reward, but needed to be done to allow future growth. I had broken it into about 20 projects, each taking 2 to 12 weeks, and I wasn't excited about any of them. I'd taken it far beyond my goals, and realized I had no big vision for it being much else.

The next week, I got three calls from three different companies, each asking if I'd be interested in selling. I said no, as usual, since I'd been giving the same answer for 10 years.

But just to be open-minded, that weekend I opened my diary and started answering the question, “What if I sold?”

I had done this a few times in previous years, but the answer had always been, “No way! There's so much more I want to do! This is my baby. There's no way I could let go.”

This time it was different. I thought how nice it'd be to not have 85 employees and all that responsibility. I wrote how nice it'd be to get outside a bit and feel free from all that. I got excited about all the cool new projects I could do instead.

I realized the bigger learning/growing challenge for me was letting go, not staying on.

Surprised by this, I asked Seth Godin's advice. He said just, “If you care, sell.”

My lack of enthusiastic vision was doing a disservice to my clients. It'd be better for them if I put the company in more motivated hands that could help them all grow.

I called Jared Rose, my business coach, and asked him to grill me upside down about this big decision. “What other ways can you achieve the freedom you want, without selling?” After an hour of questions like this, we both came to the conclusion that I was really done.

Like any breakup, graduation, or move, you emotionally disconnect, and it all feels in the past. Like I was already on the highway with a little box of stuff, moving cross-country, with my old home long gone, never to be seen again. By the end of that day I was no longer [email protected]

Unfortunately, like a divorce, the paperwork took another 7 months. I let two companies bid, and ended up choosing the one with the lower bid, but that I felt understood my clients better. During the 7 months of never-ending due diligence, I had to keep my decision secret, since at any point if they tried to change the terms, I was willing to walk away and say nevermind. (Luckily the other company called me weekly to let me know they were still interested.)

But it was never about the money. The decision was done in that one introspective day of writing in my diary and talking with my mentors. I was completely unconflicted, and knew through-and-through it was absolutely the right decision.

I went to bed that night (January 18, 2008) and slept longer than I had in months. Then I woke up full of detailed ideas for my next company Muckwork, but that's a different story.

The reason I'm telling all this is because I've been asked the question a few times by other entrepreneurs, “How do you know when it's time to sell?”. My answer is really, “You'll know”, but I hope this detailed story helps illustrate that feeling.

(Huge thanks to Idea Sandbox for that brilliant image.)