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Deadline Schmedline

November 11, 2009

I seem to spend my entire life with exactly two groups of people – Starteruppers and Parents. There are very few differences between these two groups of people. They are both committed to raising things of their own creation, they are multi-taskers, they have their eyes on the future and they are madly trying to do too many things at the same time.

There is one primary difference, however, that I see almost universally. Parents know when something actually matters, and are able to let things slide when they don’t REALLY matter. Clothes on the kid matters, (clean clothes, less important.) Kid to school, and fed several times a day matters, (PBJ will work in a pinch, even if you intended to make port roast.) That pile of laundry? Screw it, it will still be there tomorrow, maybe even the next day and the day after that.

I cannot possibly list how many of my friends are perpetually stressed out about meeting deadlines within their startups. I have taken to asking them, “is that like food, or is it like laundry?” It matters, a lot. While deadlines, focus and momentum are of paramount importance in any business, they are often arbitrary, fuzzy and come with a cost. It is of vital importance that we learn, as “business parents” to tell the difference between an arbitrary deadline, a fuzzy deadline and a real deadline – and to be able to assess the cost and benefit of meeting the deadlines we set.

1. Real Deadlines are things that are created externally by market conditions. If, for instance, you are creating an iPhone app that helps people find the best locally grown peaches in town, you have a real deadline. You better be up and running by May, which will give you time to get PR and have a user base when the peaches ripen in June. If you miss it, you are done for another year. Peach season is a real deadline.

* Cost of Hitting Deadline: Hardcore crunch makes people tired, but because it is clearly finite, people can generally withstand it. You risk shot nerves and snark, but that often can be overcome with beer, pizza and the knowledge that it is temporary and will give you the reward of getting to market.
* Cost of NOT Hitting Deadline: Death.
* Benefit of Hitting Deadline: Life

Real deadline. Nail it.

2. Fuzzy deadlines are usually dictated by things like partners, collaborators and investors. They’re realish, but not usually life and death. Let’s say that you publish a digital magazine and you have a project lined up with a major national brand that will enable you to reach hundreds of thousands of new viewers. You create content, line up the plan, but for a variety of reasons, the deadline you set together just isn’t going to get hit. The plan is in place and you can hit it next month. Annoying and maybe heartbreaking, but what’s really at play?

* Cost of Hitting Deadline: If it is possible, it will require a lot of people working way too hard for something that they know could happen next month instead. The stress and ill-will is NOT easily overcome in these cases. The dialog between partners and collaborators will likely turn angry and nasty which may erode your future working relationship.
* Cost of NOT Hitting Deadline: Disappointment, which usually subsides with the time to sleep and play. Having to tell people that you’re going to be delayed, which is usually a big ego blow, but most people in business understand these things. Delayed revenue and traffic, which sucks.
* Benefit of Hitting Deadline: Progress, checking something off the list, traffic and revenue, momentum, the good vibes of getting it done. Those all matter greatly, but will still be there next month.
* Benefit of NOT Hitting Deadline: Sanity, goodwill, stronger working relationships. The time to get it done RIGHT rather than just get it done. The nebulous lesson that things can change unexpectedly and that you are strong and nimble enough to ride it out.

Fuzzy Deadline. Let it shift.

3. Arbitrary deadlines are, in my opinion, the things that kill most of us. An arbitrary deadline is a date that you circled on the calendar because you wanted to launch something at that time. For no real reason. You are launching a product that will help people wash laundry better than before, you chose June 16th because that is your mother’s birthday and that woman could wash socks like nobody’s business. Working backwards from that date, you decided that staff had to be hired by February 2. It’s Jan 15 and you still haven’t found the right people, you’re totally stressed, turning into an asshole and it’s getting ugly. (And everyone in your house has Swine Flu and you really don’t think you have time to care for them right now.)

* Cost of Hitting The Deadline: Losing sleep and friends. Making bad decisions because you’ve put yourself in a pressure situation that makes it hard to think. Your own health, because stress is bad for you!
* Cost of NOT Hitting The Deadline: None
* Benefit of Hitting the Deadline: Momentum and the undeniable “high” of being on your way. The ability to tell people that you’re on your way.
* Benefit of Missing the Deadline: Making better decisions. Being happy and sane, which, in turn, makes you a better person in your real life and your work life.

Arbitrary Deadline. Screw It.

Most of our business lives may not seem that black and white, but most of them are. Sometimes we are our own worst enemies, putting unrealistic expectations on ourselves based on arbitrary beliefs and the fear of being judged by others.

There are also VERY REAL things like budgets that get shifted when our deadlines shift, but those are fairly easily factored in when you step back from things. Yes, longer timelines mean longer burn – you should have factored that in, and there is always a work around.

But you have to learn to look at the human beings you work with as a limited resource, just like your bank account. If you exhaust, stress and deplete your human capital, you are just as screwed as if you deplete your bank account. If hitting deadlines depletes your human capital and does not ADD to your bank account and market share immediately, it’s probably not worth it.

If it is a race between human capital and cash capital, reallocate resources. Spend less money somewhere so that you have the luxury of making good decisions and creating a healthy environment. (Giving up office space, but keeping a great staff that can work remotely seems like a no-brainer.)

Ask any parent who opted to go see Where The Wild Things Are on Sunday afternoon with their kids rather than tackling the laundry. Or any person who let their marriage fall apart in order to hit an arbitrary deadline. The cost benefit analysis is big – and extends far beyond the lines on a P & L. (Unless we start adding “everyone hates me and there is a civil war brewing at the office” as an “L.”)

There are pros and cons to everything, and unless you learn to look at both, you’re likely to get buried under a mountain of your own dirty laundry and no one is going to want to help you.

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