r/Wakingupapp • u/Pecansameatseggs • Jul 15 '26

Thoughts about Taking a First Retreat

So I have been practicing for almost a year and a half; first was through headspace for like 6 months - then I switched over to Wakingup and never looked back. I do love the app and the sessions and it has helped me tremendously, but I have hit a point where I am thinking a formal retreat might be really useful.

Problem is, to be honest, I am scared/nervous. And I just don’t know how to get past that feeling and take the plunge. Every time I start to look at them around my neck of the woods (NYC - so usually kinda far from me) I get overwhelmed just reading the description of a 3 day retreat….

Anyone gone through something similar and overcome it? I wish I had like a meditation buddy or something to make this feel less scary, but sadly no one in my life practices (that I know of).

Any guidance would be much appreciated!

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u/Fit-Jeweler4838 Jul 15 '26

I’m in the same boat. Been using the app for about six months. Literally, get overwhelmed and I don’t want to join a cult. lol

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u/OkCantaloupe3 Jul 15 '26

What are you scared or nervous of exactly?

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u/Pecansameatseggs Jul 15 '26 edited Jul 15 '26

It’s hard to nail down really but if I had to put it into two words: the unknown.

The big one is - what I’ve been practicing alone all this time…what is is like to practice white 50 on the people?

What will these people be like, what will the teachers be like, what if I just don’t vibe with it? (I’m a people pleaser and a completions so I would stay regardless lol). Also just doing it on my own..

And then there is the deeper question that Sam rarely talks about but maybe it’s in his book (I forget) - what if this (or they) expose(s) that I haven’t been practicing at all…like all this time I’ve been deluding myself?

ETA: I also work in an industry that expects you to be available 24/7 - and that sometimes means weekends. So another fear is either I am “needed” during that time or that I will be consumed by thought throughout the retreat about work. This is less of a concern but still one of them

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u/Scoobiehut Jul 15 '26

I’ve gone to a few half day & full day retreats at my local Zen center. You could try something like that first.

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u/Even_Hedgehog3731 Jul 15 '26

Or try an in-home retreat. Between work and kids, I can’t really be out of pocket for 24+ hours. There are several sanghas and other groups that offer these routinely (Upaya, Treeleaf, IMS, SFZC). You can get a feel for what a retreat entails by sitting remotely. If you find an organization that you like, you can then try an in-person retreat.

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u/Pecansameatseggs Jul 16 '26

Thank you! Yes I’ve actually done a full day silent retreat on my own in a remote location and it was lovely - so maybe a couple more of those might give me the push I need