Last time I tried Keto, I was medically supervised and jumped straight into the deep end. I was absolutely miserable BUT I lost 9lbs in the course of 3 days. I’m conflicted, that was the first time I had lost weight doing anything.
So here’s the dilemma… I want to try Keto again but maybe not as harsh, just because I can’t put myself through that misery.
Any ideas to help me decide?
What made you miserable? Did you feel ill, or were you unhappy with what you had to eat?
My answer before even reading your post was “Yes. Always keep trying.” I’ve determined that response works unless you’re responding to someone striving to be a stalker, addict or serial killer. I guess if they really want it badly enough… I digress.
Yes, keep trying. Tell us more about what strict keto looked like when you were medically supervised and what you want it to look like now. Was it a combination between low carb and SAD? Was it too few of calories? Were you sick?
So don’t jump in the deep end. If you are not in a mad rush, take it slow and phase into it.
You know what needs to be cut out - sugars, grains, starches, fruit juices, highly sweet fruits, many root vegetables.
So start there. Cut out sugar for a couple of weeks. Cut out bread and pasta the next couple of weeks. Then cut back on fruits. Then move on to potatoes and rice.
Replace the foods you are cutting out, bit by bit, with the healthier low-carb vegetables like lettuces, other green leafy foods, broccoli, cauliflower, asparagus, squash, peppers. If needed, increase meat, eggs, fish consumption, and ease over into higher-fat meats (dark meat vs. white meat chicken, don’t trim fats from steak and pork, etc).
Mark Sisson has a good approach to get started here:
DietDoctor discusses several levels of low carb. Maybe start out with the Liberal low-carb level (50-100 grams per day) and then reduce to the moderate and then ketogenic as you get used to it and the food choices.
I was really ill. I had a major “Keto flu” as they call it. Let’s just say my mom was not happy. She hadn’t seen me that sick in a while.
Ok, that’s good, because it’s easier to fix. Keto flu is caused by an electrolyte imbalance because you’re losing a lot of water and salt when you start keto.
To avoid it this time start each day with two full teaspoons of salt in a little container. Throughout the day either eat that salt, or use it on your food. But make sure you’re getting all of it over the course of the day. And drink plenty of water as well. Also make sure you begin having that salt first thing when you wake up, at least a quarter teaspoon.
This is for Phase One - the starter phase. It’s still not complicated later, but this is the really easy to explain version which will help you no end.
Eat under 20g of carbs a day
Don’t worry about the scale - keto is a primarily a HORMONE-CONTROL diet not a WEIGHT-LOSS diet. If you eat right, the weight loss should come. But when it’s ready, not when you demand. Relax and trust the process.
Eat plenty of good food - fat and protein - while staying under 20g/carbs/day. Don’t worry too much about macros and calories EXCEPT carbs. Keep them below 20g/day. (Prioritize the protein - always start with protein in every meal, but don’t panic about it.) Your job is to get fat-adapted, so give your body the fuel you want it to use. Also, your appetite will vary - it’ll disappear, then it’ll come roaring back. Happens to most people, don’t sweat it.
ELECTROLYTES/SALT - KEEP THEM UP
Buy the meat you can afford - don’t stress about grass-fed, organic (con), etc… The worst meat is better than the best bread.
Fasting is a tool. Nothing more, nothing less. Works for lots, not for others. Don’t let tools tell you to use it before you’re fat-adapted and it makes sense.
This site has a search function (magnifying glass at the top of the page) and a newbies section - use them both, you’ll get a better variety of answers to your questions far more quickly that way. SERIOUSLY, THIS IS VERY USEFUL.[1]
That’s as difficult as it needs to be for a couple of months.
My good friend Terence (being friends with a Kiwi feels kinda dirty, but there you have it, keto makes for strange bedfellows) tells me this thing I have described above is called “dirty keto.” So yeah, do dirty keto, kids! 
Lots of Love, THE JUICE
[1]If you can’t find a useful answer after searching and reading for a while, we can help you a lot more if you tell us relevant data about yourself such as your reasons for doing keto, your weight/height/age/gender, a sample menu plan & any relevant health conditions.