Inside Colin's Head

We're about to make a major shift in how our product works. It's crazy how many times I work feverishly hard to build something and even as I'm finishing it up, I realize that I'm going to have to start all over. It feels like a Tibetan sand mandala (http://en.wikipedia.org/wiki/Sand_mandala). Just when I thought we'd reached a point of product maturity, we find ourselves staring up another mountain.

I can't tell you how frustrating this is.

But the product is telling us where to go, and it seems counter to my core software philosophy to ignore it. Shit, most good ideas come from the rethinking of an old one. And I can't ignore the fact that as great as our product is, I still haven't felt it click.

So as I curse the massive effort I have in front of me, my future self I think is smiling widely at the inevitable turn that had to happen
(and glad he doesn't have to do the leg work). One step at a time is the only way you can move forward. So here goes my thousandth step and looking to the next thousand ahead.

I've philosophically thought about the effects of routine on human life, but recently I've felt an experience-based insight on the subject.

First I should describe my work style and its general lack of routine. As a founder of a tech startup, I work odd hours sometimes and share ultimate responsibility for everything we do. The nice side of this is that no one tells me what to do, and the tougher side is that if I don't take action, things don't get done. I don't have an exact work schedule, though I usually work during the daytime on Monday, Wednesday, Friday, Sunday, and parts of Saturday. I do side consulting work on Tuesday and Thursday each week at a client's office and every once in a while I pick up a contract that I can work remotely on. The roller coaster of working on a startup leads to days of absolute intensity and occasional stretches of days when there is nothing at all to do. My philosophy is strike when the inspiration is hot (and get a ton of shit done) and when it's not, slow down and enjoy the non-work side of life—whatever time of day it may be.

What I've noticed in myself every once in a while is a brief desire to be a nameless cog in a system where everything is nice and regulated. This is of course exactly what I'm fighting against by running my own businesses, but every so often this feeling is undeniable if not terribly strong. I'm thinking: "Someone tell me what to do." "Give me the safety of a system that's bigger than me." "I want to wake up to an alarm and get home at the same time each day." "I want measurable success and fewer chances to make mistakes."

This is so not me. And I think these moments signify how routine fulfills something so deep in human nature that it can challenge other factors that make up your state of mind. Your job may be shit. Your boss may be horrible. You may not be appropriately respected for the work you perform. But at least you have a routine you can lean on to remind you that life keeps on chugging and everything's going to be at least moderately pleasant. It feels good to be busy, whether or not what you're doing is valuable work.

Routine isn't in itself a bad thing. Routine keeps you organized. Routine can keep you sane. My belief is that we are animals at the base level and routine is just built into our blood.

I guess I'm just saying it's important to figure out when you're letting routine keep you from acting.

What are the most important personal characteristics necessary for being successful out on your own? After having a passionate drive (I'm iffy about the word ambition), patience might be number two.

Patience is the trait that builds confidence safely: with good doses of humility.

Patience allows you to be optimistic while keeping reality in full view.

Patience is the mantra of the long-term-oriented person, which is where big ideas happen.

The energy of starting something new is incredible. It gives you laser focus and a healthy, hurried efficiency at achieving your first milestone. Often times though, it also allows you to build delusions which, when unchecked, can damage your delicate sense of clarity. When doing your own thing, you're forced under this simple rule: doing work does not equate to success. You may be doing brilliant work. In a normal employee scenario you may be indispensable. On your own, however, you're subject to new laws of physics. Or more accurately, you're subject to almost no laws at all.

In my opinion, patience is the metronome that keeps you on a successful track, surviving the ebs and flows and ups and downs that are absolutely inevitable. It keeps you from taking drastic measures when you really should just wait it out. It encourages quality. It keeps you in a balanced state from which all decisions become more level-headed. This in turn leads to being able to better trust your instincts, which has an unending stream of payoffs.

In comparison to many of the other critical personal characteristics (optimism, talent, industry knowledge), patience seems to me to be one that can be grown most easily. Being patient begets stronger patience.