Everything is normalized in the glow of hindsight.

It’s a core survival instinct to rationalize the failures of our past as guidelines for the future. And nowhere is this more true than reflections on startups we just couldn’t make work.

There are endless posts on learning from the pains of failure, but few touch on the decision to quit itself. To those of us that have been there, that’s the inscrutable and tough one.  No matter who you are, how experienced you may be, this process is never completely rationale and always mired in pain and trauma.

This comes from the very nature of the startup dynamic I think.

By dint of what we do, we make the unimagined real. On a daily basis we work in an environment where the reality of our vision is invariably at odds with the realities of the marketplace.

We work in a perpetual state of suspended disbelief, rationalized through sheer drive and vision.  Every day is a medley of ups and downs, internalizing this over and over again making it hard, almost impossible at times, to decide when enough is really enough.

This came back to me with painful clarity the other day.

I was sitting at Esther’s wine bar in Santa Monica and was overcome with a wave of regret over my decision a number of years ago to shutter my passion project, thelocalsip, a community platform for the wine community and retailers across the globe

I so loved this idea.

This is the launch post, oozing with confidence and passion.

As I look back, I realize that my decision to close this down was shortsighted. Yes, wrong in the clear light of reflection.

Not that it was bound to succeed certainly, but because my criteria for the decision was incorrect. That years later, there is still a nagging personal ache in this area and a market hole that is still wide open.

I decided to close theLocalSip not because there wasn’t interest, there was. Not because there wasn’t value certainly. But because I simply couldn’t make the model work and as a bootstrap side venture, it needed economics of some sort to continue.

What I failed to acknowledge then that I understand now through experience, self-reflection and mentoring others, is that when we look at the hard realities of the marketplace, it is not a test of the model as much as it is whether we believe that our visions of value still holds.

Even in the face of market economics.

I’m not a P & L denier by any definition but in this instance, and in many facing entrepreneurs, it’s whether we still, even in the face of poor market fit and struggling to make payroll, believe not necessarily in the product but in the core need of people within the market that we were driving towards.

In a discussion with a buddy the other day, he took the other side of this argument. That execution not ideas matter. That not vision but market fit is what drives. That if you can’t raise the funds, that is a sign that you can’t sell the dream.

There’s truth here of course but everything aside, in the loneliness that only founders and CEOs understand, you need to come to grips with whether the passion of your drive is the archetypical Koolaid of self-delusion and should you just keep doing it. Or rethink it. Or is it time to close it down?

No matter how clear the learning is when looking in the rear-view mirror, nor how many times you go through it, it remains a struggle at this inflection point regardless of how skilled you are at managing your own emotions.

No matter how many times you have been in this hyper emotive state before.

I listened to an excellent Tim Ferris podcast on this topic recently, a compendium of stories from well known entrepreneurs on the topic ‘when to quit?’.

The one theme that stuck with me was—make a decision whether it is product that has failed, the market that has turned or whether your vision itself is still a driving force.

If it is the later and there is no market vision fit to boot, you learned something and move on.

If not, dig deep to see whether you have the poise and perspicacity to continue to work on the vision in some way that connects core belief to a still yet to be proven market.

Closing a company is a serious act of finality. Realizing that you need to rethink or redo or reconfigure, quite another.

Some people view the world as a series of great ideas with failed executions. Some as a race against market share and capital burn.

I’m prone to believing that the very best execution on a less inspired and internalized idea is a sure road to nowhere. And that vision, truly visualized yet still inchoate is not something to let go of so easily.

It took me a while to internalize this.

It’s a truth that mollifies the crazed highs and lows of startup existence, somehow making them more palatable. And something that should be of use to startup founders who are always dealing with this.

And for me personally, it makes me wonder–just a bit–whether I should brush of that theLocalSip database and give this passion another go.