I have seen (and received) a lot of advice on here for people who grew up distanced from their Jewishness who want to start practicing/observing that goes like this:

Start with something small, and gradually expand.

It's very practical advice, but I think it's not quite right.
Don't get me wrong, I think that starting a Jewish practice with simple things you know you can maintain is a great idea. Jumping into the deep end of a time consuming, lifestyle altering, intensely complicated practice is setting yourself up for failure.
It's the "gradually expand" part that I think is a little off. I think setting the expectation that the initial small, maintainable practice *must* expand is also setting yourself up for failure. It assumes, from the beginning, that what you want to do when you begin isn't enough
And it doesn't answer the question - what *is* enough? At what point do you get to stop saying "I want to be more observant" and start saying "I am observant"?
Personally, I think it's better (and I have had more success) with starting a practice I want to incorporate into my life for it's own sake, on it's own merit, without expecting it to be a step on the path to something else - maybe something else I'm not sure I even *want* to do.
You want to start lighting candles and drinking a glass of wine on Friday night to bring in Shabbat? Congratulations, you just incorporated Shabbat into your Jewish life. It doesn't *have* to lead to keeping shomer Shabbos. That's how you observe Shabbat, and it's good.
You want to stop eating pork? Awesome, do that, that's your observance of kashrut. It doesn't mean you *have* to stop mixing meat and dairy. It doesn't *have* to be the first step on your path to buying a second oven. Making that one change is already deepening your Jewish life.
The notion that incorporating any Jewish observance into your life should be a step towards a particular set of observances in a particular style of observance sets you up to feel inadequate and frustrated instead of joyful and excited about living more Jewishly.
It also reinforces the notion of a hierarchy of Jewishness, with Orthodox practice as the "most Jewish", and every other style of practice as incomplete or lesser. It's just not true. There are as many ways of observing as there are Jews.
It's much more important, in my not-a-rabbi opinion, to adopt practices you *want* to do, in a way that brings you joy and connection. Loving the practice you have is much, much better than having a ton of practices that leave you feeling frustrated and inadequate
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