Do you react to your world or does your world react to you?
Not only in the startup world, but in life, we are faced with uncertainties...about strategy decisions, rightness of fit regarding new hires, and about the future. There are natural limits to our ability to information gather, and so often times, we are faced with a gap--how much I know about this decision versus how much I would like to or even feel I need to know to commit to a choice. How you approach that gap is a major factor in how you wind up living your life.
Some people just do the best they can. They recognize the inherent imperfection in the system, work hard to research all the angles and then when they feel like they've exhausted all the angles, make a choice. They probably take longer than the average person but at least they feel comfortable with their choices. This type of decisionmaking probably works best in an established, stable environment--whether its a company or even whether its a relationship. In a big, established company, there are probably proven methods for gathering more data and there's little chance that waiting a little longer to make a decision is going to be the end of the world. Similarly, the distracting routines of an established relationship can often buy you some time to figure out the right next steps. And why wouldn't you dwell on decisions longer...you've got so much structure in place and potentially at risk...houses, kids, cars, just...stuff.
But in new relationships--ones with people, companies, markets, etc.--you often can't get more data and its possible that you can't even really afford to spend lots of time dwelling on decisions. That's because your relationship is really all you have. Routines are too new or maybe nonexistent, so you can't hide behind them. In a company, there may only be one relevent next step to think about, and all eyes are on you to make a call. This highlights the effect of how you make a decision can impact relationships, especially given the emotional investment that new relations and new companies carry with them. If you're too quick to make a call, and you appear to ignore th gravity of the decision, you could give the appearance of not caring or not being as invested as other stakeholders. Take too long and you'll cause doubt--especially among the people who have clarity of vision. If you're the last one to see what everyone else sees, how long will you continue to be seen as a leader?
This is where approach and determination play huge roles. It's difficult to me "more right" before you can see more about the direction of an outcome, no matter how much time you spend on it. That's why I've always spent a lot more time and energy trying to achieve success AFTER decisions have already been made. Whether you're choosing a certain visualization for your user interface or deciding to get into a long distance relationship, the one thing you can definitely commit yourself to is to make something work, regardless of what it takes. It's the freshman roommate approach. In college, you get stuffed into a room with a stranger. You have no idea if it will work out or not, what the person is like, what their habits are. That's the thing. I think if you take the perspective that their habits are unalterably x or y and that the outcome even depends on any of this information, you will ultimately fail. The reason is that if there's anything you can count on in life, its change and uncertainty.
The only thing you can do in the face of that is to decide, ahead of time, that you are determined to be successful. You will not move out mid-semester. You will not leave a broken UI up on your site. You will not let distance, emotional or physical, get in the way of building a good relationship.
That is not to say that you should bash your head against a brick wall over something that just isn't working, but I think a lot of times the reason why things don't work is because we're not open to them working. We want things to work a certain way, so we can't accept alternative outcomes. We can't relate to different kinds of people in new ways because of stereotypes. We aren't open to being moved and changed by others.
Its interesting that the more you think of life as static, of facts set in stone, of things inherently good or bad, workable or not, the more static you become...only finding success when you're able to put your square peg in a square hole. The more you think of life and your future as to be impacted you, the more you'll also be impacted and changed by life as well.