I have waited for years to be "ready" and a month ago I decided I never would be ready and jumped ship anyway!
My version of achieving it was to buy a 10 acre run down holding with a pretty uncared for 1970s bungalow that even now the valuers and agencies recommend not to do anything to so that any potential buyer can just knock it down and start over
I don't like that it is beside a main A road but the upside is that I don't get stuck in snow and can always get out to visit the other 20 acres I rent a few miles away. I sometimes have to walk the last mile up there and back but that's another story
I had a secure full time job and was breeding ponies, had cats and enjoyed riding and showing the ponies as hobbies so it was worth my time and energy to be up at 530 midweek and drive those very long few miles to check ponies at the hill between doing the ones here and showering ready to commute to work by 740
The lot here had an open barn to come into for feeds or treatment but otherwise lived out and were hayed in the field - barrowing hay in wind, mud and rain after a long day isn't easy but it did get done - and I'm on my own, always have been so just get on with it. I also put in essentials like intermediate fencing and water supplies, central heating and a bathroom in the house, and put in a dutch barn with lean to and cattle gates to make flexible storage/handling/care facilities.
A few years back I started with a veg bed in the orchard and started making jam and chutney from the apples, plums and bought in easy things like rhubarb and green beans to start with. Experimented, dug out a new bed each year (with help!) and used some of the barn's winter deep litter to fertilise the veggies. Swapped veg and money for assistance, paid for fencers etc as needed, started to reduce expenditure, holidays included, as far as possible and started overpaying the mortgage when the rates dropped by keeping to the same high level I was used to. At one point I was paying 1/3 more than I needed to but it was easier to sustain an existing payment than get used to a lower one that might rise again!
Last year I had 3 family bereavements within 6 months and realised (amongst other things) how short and fragile life is and how you really can't keep waiting for the right moment. I had some slack with the mortgage, a small inheritance to live off and the opportunity to get redundancy money rather than yet more stress and illness. My health and fitness are the lowest they've ever been and there's a recession on but it was an opportunity unlikely to repeat itself and I no longer have a number of family concerns/ties that I had to worry about. So I went for it.
I have a number of skills to use off the holding, I ran 2 workshops on Saturday, which brought me some much needed cash and I've sold some things, reduced the work related costs such as commuting fuel cost, parking at work (cheek anyway £2.70 a day to be at work!), the lunches, lattes and mid afternoon chocolate crisis that working gave me, and I now sleep far better, get up at 530-7am depending on how long the cats allow, and am still blessed that the ponies are all out on grass and just need checking. The cat also had kittens and I sold them rather than give them away - some folk frown on this but every little helps pay for the cat food and litter I use.
There are now 4 veg beds, 2 still active and the freezer is full, apples still on the trees and I have a lifestyle I am loving. I want the chickens but fear I am better off buying eggs at the moment
and they and the sheep will probably wait til spring now.
If you have excess grassland then rent it for hay and take payment in made round bales you can store til you need them. Fodder prices are high now and higher in Feb/March so resell at that time if you don't need them. You'll easy manage veg, chickens and store lambs I reckon, and every bit of experience you get is invaluable before you depend on it.
I would say go for 2 full time jobs initially and build up the holding a little, then go for 1 day reduction from one of the jobs or whatever part time you can manage/negotiate to balance your holding needs. Look wherever you can consider moving to, look at living in slightly reduced quality housing in return for the land, and start now before you start to query whether you can really "afford" your life dreams. That is the start of the slippery slope and sometimes you just have to do what you need to do for your sanity and happiness
Sorry I'm rambling but I'm a passionate believer in living each year of your life to the full and having no regrets to look back on that are about limiting yourself with fear, only maybe a few about embarrassing yourself while you learn new things.