I've been meditating now for 150 days straight, but even before that I was a fairly regular meditator for many years, I had just never kept up with any sort of meaningful streak every single day. My current momentum started from a difficult period in my life and even once that difficulty subsided, there was still a desire to keep going with the streak. 150 days later and I'm still happy to maintain it, but figured I'd write down a few insights I've gotten from this whole period.
For most of my meditation sessions, I've used Headspace. I've worked my way through many their programs, finished Headspace Pro(which incorporates more silence week on week), their daily sessions and have just used it as timer when I didn't want to hear anything.
Over time, I've tried to reflect heavily on what has worked for me and what hasn't.
I've meditated on trains, planes (and automobiles in fact) and everywhere else in between and while it's great to be able to meditate anywhere, I do have to say that I found my mind definitely casts itself into that relaxed awareness far more easily in the right space. At home, I put some effort in. My flat has wooden floors, so I have a pretty comfy mat with a pretty solid meditation cushion on the floor. During the early morning sessions I often light some incense and a candle.
This is something I never really focused on before, assuming that I could just focus on my breath and those aids were just hippie nonsense, posing as a mindful person. For me nowadays it's whatever can best help me get into a quiet, contemplating, curious mind. So ignore that self-critical part of yourself that might judge for some incense, or a particular post, whatever gets you in the zone and practicing every day.
The best time I've found to meditate is first thing in the morning. That's what I've worked out but it may be different for you. When my mind is still relatively quiet, I move around a bit to get some alertness and then sit in silence, it's also a wonderful way to start the day but isn't always possible.
If you have to meditate in strange places, the best thing you can do is spend a minute or two just focusing cultivating a genuine curiousity about how you're feeling right now, like ask yourself "How is my breathing?", I've found it helps me keep focused and not take the practice for granted and get more value out of it.
The same is true after meditating, I spend a minute or two just basking in the feeling after a meditation and resolving to try maintain it for as long as I can, which is admittedly, not always very long.
I have also found however, that when I meditated just in the morning, the relaxed, wise energy that came with the practice faded quickly. I started incorporating meditation into various parts of my day. Headspace has a commuting meditation, as well as a walk in the park. There's sessions dedicated to various issues you might have at work, mindful computer usage etc. I've tried a lot of these and I can't recommend any one of them more than any other. They all sort of provide the general benefit of making you aware of your monkey brain and might help to stop feeding that side of you when you get caught up in things.
From my own perspective, I gained a lot of insight just trying different things out, all the while still maintaining my morning practice.
Another thing I can recommend if you have an Apple Watch is the Breathe App. It's a simple timer that vibrates in such a way to help you time your in and out breaths. This is called rhythmic breathing and it's great.
There's a talk on YouTube here, that might help convince of you of the value of rhythmic breathing(including measuring the heart rate of a poor guy dragged on stage). It's pretty convincing that rhythmic breathing is definitely something worth trying, there is also probably some alternative you could use on a Phone, I've just found the Apple Watch app is discreet and convenient, so I can do it on the train or work and no-one would even notice I'm simply focusing on my breathing rhythm.
Another sales pitch for rhythmic breathing, when I found my mind was too active and jumping around while I meditated if I switched to rhythmic breathing for a few minutes, I could more easily focus on the original meditation I wanted to work on. This was particularly helpful when I woke up after a stressful dream and my mind was still racing.
This might seem obvious, but on those days where I was feeling pretty lazy, I would attempt a meditation in bed, rather than get up and do it. It's a pretty bad idea and you might as well not bother and get a couple of extra minutes sleep. Seems obvious but it can be a pretty easy thing to convince yourself to try in a half awake state.
Most of the meditations on Headspace are heavily guided, you can choose to go along the Headspace Pro pack(which I do recommend after a while) or the timed Unguided Meditation, but beyond that most involve a lot of listening to Andy guiding you through the exercise and for the most part I find this great. However, I did notice the difficulty ramping up when I tried to simply sit quietly.
During my 150 days I went on an introductory meditation retreat for a weekend. No screens whatsoever and a lot of (surprisingly enjoyable) silent periods. When I arrived I felt like meditation was something I was good at and wouldn't have any problems with the prolonged silent meditations. Boy was I wrong. While Headspace is great at practicing with meditation, just a silent meditation of just you with your own thoughts is still definitely a more challenging experience. Far more noticing of discomfort, a louder mind with no voice to guide it, I frankly struggled sometimes, but in a way the reward. was much greater. I felt like I had delved deeper into facing the monkey mind despite the challenges i faced. Silent meditation is not something I think I could do at home every day but I do think I'll push along with headspace pro again and find more time for silence.
Sounds similar to the previous lesson of incorporating it everywhere but not exactly. You can focus on the breath everywhere, but you can also focus on different activities. You really can meditate while walking, cleaning, cooking, eating, basically just focusing on your life with a easy relaxed awareness supported by some sort of regular focused meditation would give everyone a huge boost in contentment. Don't get too hung-up on the breath, at the same time those other "mindful moments" certainly are a little more difficult to maintain and I am certainly not there myself, but it is something I try to aspire to each day(when work and life don't get in the way).
One of the lessons I learned very recently was to slow down, this message came to me during my meditation retreat. The long periods of silence and no technology created an environment that cultivated an excellent setup to meditation practice. When I say this, I mean that feeling of easy awareness really stuck with me for far longer. Our lives are often incompatible with a mindful attitude, but that content, easy feeling I felt during the retreat motivated me to start taking a hard look at my own life and perhaps eliminate as much "busyness" as I could to cultivate a similar feeling. This realisation has come recently and am I certainly only a beginner at this, but will share any insights and things I've tried that have/haven't worked.
If you constantly expect meditation to show you something about yourself, or provide that warm fuzzy feeling you will often be disappointed. If there's any expectation to hold it's that you will always find the truth in meditation, and that truth can be extreme pain or the height of pleasure.
That's all I can come up with for now, but the best advice I could probably offer from a wise cartoon monkey(10 points if you get that reference), which is, "Every day it gets a little easier. But you have to do it every day. That's the hard part. But it does get easier.".