To fear the opportunity of an occasion to make merits, to do not follow an arosen kusala-citta (one of non-harming, non-disputing, renouncing, giving), is what the Buddha had called something that needs really to be feared, avioded.
As good householder sees here: as soon as starting to rationalize, giving doubt changes, all good gained decays, and another seldom opportunity fades, and not sure if another arises, as it's stream had died off by not nourishing it, giving into.
So it's actually this which should be feared, or better to give into what's not cutting of bad (a-ku-sala). What isn't given, hold on, is lost.
The earlier one goes into the holly life, the lesser his many risks to never be able, got caught along the way, and the lesser the changes to bend straight again.
It's not possible to increase chances by taking and trades in the world, such is just the way of excuses made up by defilements.
Nothing to mention if one with doubt seeks advices by doubters, a prisoner asking prisoners how to escape... kind of association is ones gain or lose.
The Sublime Buddhas teachings are full of mentions of failing people and the reasons why.
And, as mentioned: It's very needed having and maintaining a relationship (with a person who have great qualities, one more advanced in real liberality, Nissaya) because it bonds one to desire toward liberation, leading to an end of suffering.
AN 1.071-080: Kalyāṇamittādivaggo: Good companionship and others contains the particular answers from the source of Unbond.
[Note that this isn't given for stacks, exchange, other world-binding trades, but for an escape from this wheel]