Ok, some people who dive in and try things don't succeed. But do any people who don't dive in and try things succeed?
Yeah, if you try you might still fail. Most intelligent people realize this is a possibility. If you don't try you will definitely fail though.
Don't we all have some high school friend who didn't really work hard on anything and got pretty high scores on everything, somehow got offered a good job by some friend, smoked weed, went to parties, never worried much and seems to be quite successful or at least quite happy?
I think that's the main problem with all these discussions about success and growth and stuff - it is all anecdotal evidence and nothing more. No real science here and it can hardly ever be.
Failure is the mother of all learning.
The more you fail, the more experienced you are (it's almost an equivalence relationship that grows in time with effort, attempts), the more you become likely to 'succeed' at that thing. I don't know of any other way.
If you need investor money for a fast growth company, are not sure whether you can get it, but dive in, you might fail when nobody invests. If you realise that finding and convincing investors is a roadblock for you, you can choose to save more before starting, pick a slower growth approach or different goal or different funding model which doesn't require investor money at all and sidestep the problem.
There’s certainly a time and place for both approaches and people have their work ‘style’ preferences. This is also a big part of why most productivity software, todos, checklists is generally not for me. I lose too much productivity just by using the tool.
Edit. I should add context. I don’t work as a dev. I’m in Corp finance. This worked for me as individual contributor, mid manager and now in a leadership role. As IC it was how I worked as manager it’s how I delegate as leader it’s how I motivate my team. Again, I’ve had to take the other style at times. It’s not natural for me. Feels like a waste of time in effort not to waste time. I see the benefit of it at times. And I’ve been impressed by some people’s experience in doing it that way. (Eg. a relatively quick successful ERP implementation at a large company is a marvelous thing to witness).
To me it does; diving into water is the alternative to going in slowly and cautiously; your talk is more like "look before you dive" - and discussing by mixing metaphors won't clear anything up. You plan, anticipate roadblocks and judge how much you can overcome them in advance, and adjust the plan. To me, that's not diving in, even if you do it quickly; "Diving in" would suggest that you first learn about the roadblock when you get to it and then your progress stops until you overcome it or can't.