Seth Godin has the idea that one should fail, and fail often, if one is going to succeed.
That said, it is important to fail at the appropriate scale.
To craft a proper strategy, one should set up opportunities which are (perhaps) likely to fail, where the failure won’t be a complete disaster, taking one out of the game altogether.
Here is Seneca on Peace of Mind:
It is above all things necessary to form a true estimate of oneself, because as a rule we think that we can do more than we are able: one man is led too far through confidence in his eloquence, another demands more from his estate than it can produce, another burdens a weakly body with some toilsome duty. Some men are too shamefaced for the conduct of public affairs, which require an unblushing front: some men’s obstinate pride renders them unfit for courts: some cannot control their anger, and break into unguarded language on the slightest provocation: some cannot rein in their wit or resist making risky jokes: for all these men leisure is better than employment: a bold, haughty and impatient nature ought to avoid anything that may lead it to use a freedom of speech which will bring it to ruin. (trans. Stewart)
The take-home is that every one of us has our own particular limit, exceeding which we are likely to fail. Putting ourselves in situations where this sort of failure is going to bring us complete shame will give us the sense that we don’t deserve success.
Instead, Godin argues about strategy:
“A plan might come with a guarantee: 'If we do this, we win. ' A strategy, on the other hand, comes with the motto: 'This might not work.' Strategy is a philosophy of becoming, a chance to create the conditions to enable the change we seek to make in the world.”
He argues that any successful strategy must begin with a sense of empathy — if your idea isn’t going to genuinely help people, it isn’t a good idea. From there, it is important to make reasonable goals for how you can legitimately rise to whatever challenge is necessary to actually make that idea happen without self-destructing.
If I am struggling with sobriety, and think that I’m going to just magically step up and manage someone’s social media campaign, without the proper program and assistance, that is a recipe for disaster. It will lead to me flailing and burning out, and my client being angry and unhappy and in turn giving me bad reviews, making it impossible to build a client base.
If I instead find a proper volunteer opportunity with a group of people who understand my condition, and for whom whatever little bit I can offer is legitimately appreciated, I can learn to grow out of my selfish inconsistency and slowly learn what it is to grow and build something together, confronting fear while developing skills and gaining experience (which will likely generate more and newer types of ideas and opportunity).
I hope that this might be of some small use to you.
Aspiringly, Aaron