I've long agreed with this blogpost's premise that signing NDAs is almost always pointless, because ideas are so cheap:
If you’ve ever tried to bring even one venture to market, you know perhaps all too well that ideas are just the starting point, and take by far the least work, time, and capital.... Gary Vaynerchuk said it perhaps best in his talk at the 2011 Big Omaha: “ideas are shit, execution’s the game”.
But Leila Johnston has recently gone one step further, and in a turnaround from her previous opinion, asserted that focussing on ideas can be actively harmful, even when you can just about manage a prototype's worth of execution before moving on:
... What you have to do, if you’re the sort of person who likes to feel brave and excited and creative, is switch off that part of your mind and knuckle down. You have to learn to be a sales person before all else. You have to shut yourself up, with all your passions and drives and intuitions, and get into the cold, hard, number crunching part of your brain. You have to do the best for your charts, not for your pleasure centres.
There's another blogpost to be written about how the ability to start all over again, and not be penalized it, is a function of privilege, although I think is implicit in what Leila says. A good measure of how that privilege has worked out for you historically is how wealthy you are now, by means other than all your ideas you'd like to try out: if you want to tinker in your spare time, you have to hope either your nest egg or your full-time job pays for that, while still leaving you with enough energy and zest to still be able to make things at all, let alone make them fast.
With that balancing act in mind, I think it's worth moving away from the either/or dichotomy at the heart of Leila's post, to envisage instead a spectrum. At the one end, this might involve providing boring administrative services for creative types (e.g. being an agent), through really nailing the admin for your one single Dragon's-Den big idea, through having a select number of projects which you develop just enough of a network to be able to market and eat economy beans, to at the other end gaily pouring every penny you have into prototype after prototype. Once you picture that spectrum, or even a multivariate graph of decision after decision, then you can start making choices based on how important big and continued success is, and how much your heart really lies just in the making and tinkering.
As soon as you move away from the boring admin, though, I agree almost all of us are taking bigger risks than we realise when we read Pinterest posts about following our dreams. Even if you make (some) admin effort, how well any given idea is accepted by the prevailing culture depends on so many factors that it's as much an art as a skill. Some people, and then only for certain lengths of time, manage to get their ideas to align so closely with the zeitgeist, one after the other, that they need almost effort to get them adopted (some people are also quite skilful, so that even their shoddy prototypes have the heft of a polished, finished product. I'm looking at you, Bowie.) Other times you can feel like like cartoon Calvin, trying to sell his kicks in the butt, wondering why the people who need them don't (think they) want them, when society as a whole is crying out for more people who deserve it to get kicked in the butt.
Throughout all of this discussion I'm torn, because on the one hand I think (permission to) play is tremendously important and so often lacking in what we do with our lives. All of us wage slaves have working lives full of mediocre and understretched drudgery, and a habit of making things fast can bring out the playful in such people. But I'm also starting to become attracted to the idea of tackling the unglamorous first, in a poorly-defined meaning of that word, that tries to describe society's reaction to things, rather than the things themselves. I think the unglamorous, very broadly, is where social good and fulfilment tend to be found.
Right now our society as a whole, but especially our SV-influenced tech filter bubble, values the glamorous, yet needs the unglamorous, without really realising it's confused in that way. Hack days on completely new projects, often only fleshed out on the day (days whose combined efficiency is I think unproven) are glamorous; triaging small bugs on existing projects with traction (with an observable beneficial effect over time) is unglamorous. And you only have to have someone faintly competent be assigned to manage a previously unmanaged project, to know that unglamour sometimes feels surprisingly like water on parched earth.
Knowing how to put together a schedule, and keep calendar appointments reliably: unglamorous. Always having enough envelopes in the house: unglamorous. PHP: unglamorous. The North.... Well, that's another discussion in itself, isn't it? But the unglamorous feels to me like a signpost to fulfillment; and to fizz with ideas is to most definitely be glamorous: so you can see where this is headed, I hope.
(The trick of course is finding a way to turn the unglamorous into the glamorous; or, at any rate, turn the unglamorous into play. I'm working on that, OK?)