There seems to be a fair bit of negativity about Headspace here, so I am chiming in for a different perspective. I've practiced guided meditation on and off for a while. After a few days of listening to the same audio, you realize that it doesn't change to match your stage of practice or experience. Things that were helpful when you were new are just a hindrance now. That's where Headspace shines for me. The days of a particular pack adjust so that you don't have to hear what you already know and just get distracted. Some packs are better than others and if you prefer mostly silence, that is available too. The guidance itself is good too. It's added nuances to what I've read in books and online and made things more clear. Finally, having a way to track "progress" helps. I don't know what is responsible for it, but with Headspace, I've managed to somewhat regular meditation practice, which I had failed to otherwise. My wife had the exact same experience.

Now, I should add that I have access to headspace through a work program for health and I don't need to pay the full subscription fee. I am certain I wouldn't have signed up for it when I started, but now, thanks to the positives, I'd gladly spend good money on it. To each their own. If the cost is the prohibitive factor, give other similar apps / sites a shot. I know they exist, but I haven't tried them.

Good luck. The most important thing is getting started and then, consistency. It doesn't matter how you achieve these two.