*When did you know you should quit our job and go full time with your startup?*

This is a question founders get asked again and again — by the curious, by company “lifers” and “fulltimers,” and especially by those who have their own little start up in their back pocket. But I don’t think this is the right question, because it forces an irrational decision into a rational framework.

For many of us, knowing when to “cut the cord” and commit to our startup dreams is challenging. (Some of you, including, “Hasan Luongo”:http://gigaom.com/2008/03/07/the-dangers-of-a-startup-democracy/ and “Ravneet Grewal”:http://gigaom.com/view/question-of-the-day56, have written great posts about this.)

But I think the right question to ask is instead: “When did you realize you couldn’t go back?” At some point, enough critical factors or events will make it very clear that you have no choice but to found your startup — it’s a bit like getting stuck outside the breakers in a dingy, there is finally a moment when you realize you have to go out because you _can’t_ come back in. At least this is how it happened for me. It was a slow, progressive and yet _very convincing_ process. I’ll walk you through my experience _Blow-by-Blow_, and share the lessons I learned along the way.

*July 2004:*
I quit Yahoo! to co-found a consulting firm in the oh-so-hip discipline of “design thinking.” But consulting is an unnatural activity for a product person like me, so just five months after launching my consulting enterprise, I found myself moonlighting on reinventing new content management system (CMS) product with a Danish programmer named Lars.

*_Lesson 1: You can run, but you can’t hide from your true nature. Product people make products, be they engineers, designers or management. (Let the consultants consult.)_*

*April 2006:*
I found out I was pregnant. As the little person grew inside me, my interest in flying to New York for important meetings with important consulting people became steadily less interesting to me than sitting at my PC designing interfaces for our little CMS, by now codenamed _fennel_. But we discover quickly that there is no such thing as a “little” CMS. If I had sat up one morning and said, “Hey I think I’ll start a company”, I might have picked a smaller problem, like reinventing email. Our feature list kept growing and growing – of course we needed asset management, of course we needed inline editing. Eventually Lars figured out we had to cut features ruthlessly, if even if meant ripping up big chunks of code, or we’d be dead before we were live. I resisted for a bit. I wanted so badly to make something better than what was out there, and better somehow meant more features.

*_Lesson 2: You don’t always pick your product, sometimes it picks you. But don’t let it boss you around. If you’ve bitten off something to big to chew, spit it out and cut it up._*

*November 2006:*
I had my baby. Thank God Lars had also become a parent a few months earlier, or this might have been the end of it all for us. If we hadn’t been experiencing the same thing, I don’t think we could have understood what the other was going through. The skype calls took on a new tone “I’m tired.” “I’m tired.” “I need coffee” “I haven’t slept for three days.” Development slowed to a crawl.

*January 2006:*
I went by my consulting partners’ office to formally quit. In the process I signed away all the IP I had developed with them in order to get sole ownership of the IP I’d developed on _fennel_. It was an amicable discussion, and my (now former) partners offered to contribute to my baby’s college fund. _Notice I said “formally” quit. Sometimes I think I quit the day I met Lars in Copenhagen. Other times I pin it down to when I begged time off a consulting gig to work on fennel. Really, I’d been slowly quitting my day job for a year, I just didn’t notice it._

*_Lesson 3: When you notice that you are willing to give up things you normally would keep a deathgrip on, for the sake of your product, that’s a sign that it’s time to cut the cord. Having engaged in long legal negotiations with clients to keep rights over our insights, I cheerfully signed them all away in order to focus on my other new baby, fennel._*

*Spring 2006-Spring 2007:*
We spent the next year “almost launching.” We got our first online magazine onto the platform, but the status of “customer-ready” perpetually eluded us. We fought over business models, pricing structures and conference call times. Money was running low, and we had to pick up consulting gigs here and there to make ends meet. But it takes weeks to land a consulting gig , and they never end when they are supposed to, so I tended to avoid them. My husband grew anxious. My credit grew thin. Fennel didn’t launch. Finally, pushed by pressure from my bank account and lured by a former coworker at Yahoo!, I interviewed at Google. And interviewed again and again.

And then *I started work at Google*. Here is how it went:
*Day 1:* Orientation.
*Day 2:* Orientation.
*Day 3:* Meet your team and discover your little CMS company – now placed on hold – might have dreaded “conflicts of interest.”
*Day 4:* Break tooth. Go home. Soul search. Realize you can’t just walk away from your own company.
*Day 5:* Tender resignation from Google.

*_Lesson 4: They say money makes you do crazy things, but really it makes you do sane things — like take a job. But if you aren’t tough enough to spit in the eye of safety and success, you shouldn’t be an entrepreneur._*

As I walked off campus, debadged, I started laughing. Laughing loud, like a crazy person, like joker in the old batman series, laughing and laughing and laughing. My heart leapt out of my mouth and flew high above the volleyball court and the cross-current swimming pool. My heart flew high above the eight cafes with gourmet chefs, and the Segways and the Japanese toilets. It flew across the bay and into the sun where it was lit up with joy. I laughed because I had done something only an idiot would do. I quit a job others would kill for to do something that didn’t have a chance in a million to survive.

We launched a week later.

*_Final Lesson: When did I know it was time to quit my job and go full time with my start up? When I didn’t have any other choice._*