I would start with hauling all old bushes out of there ( but it might be good to have someone knowledgable come and have a look to see if ther is something worth saving that can be rehabilitated) then round up of the "grass/weeds".
But.....you need a plan! get some graph paper and make your self a plan...since you seem to know nothing you can simply say things like "small round evergreen shrub" or "tall arching spring flowering thing", or "neat small compact bush"....then take it to someone who will put plant names to your description.
Like most things, start with an outline... the main parts of the structure of your garden and then move on to the fill ins and the accents.
Have fun!!
Linda C

what I know now that I wish I'd known then:

Make your plan as Linda suggests, & put in your pathways first.

I've been digging stuff out for nearly a year because when I first started, I didn't allow for some way to get to the plants to take care of them!

about killing existing vegetation:

Once the plant has withered from herbicide, you still have to dig it out;
I've had good luck turning the ground to expose the roots to air/sun/heat, waiting a day or so for the roots to dry & shrink, & pulling them out of the soil.

saves a trip to the store & you can use your money for plants or compost!

Thank you, thank you!

I agree, linda. getting the bushes out will allow me to see the space clearly and draw up plans.

sylvia-

I love the "what I know now that I wish I'd known then"
It's so helpful.

What garden tools can you not live without??

I don't know your size age nor muscle mass....but I can't live without a small border spade...but if you are bigger, younger and stronger you might like a standard spade or a "tile spade" with a narrow blade.
I NEED long handled loppers....with the lever action that allows me to cut bigger branches than I should!
And a small hand trowel and a larger one....and a "bad knife"....an old narrow bladed kitchen slicing knife. Good for prying out weeds cutting up a clump of hosta or day lily, and loosening the soil and removing weeds in a narrow space.
You may want a garden rake and a spading fork.
Linda C

Thanks, Linda. I need to put together a shopping list. I know I have a hand trowel, somewhere. But none of the other things you mention. So sharing your tool list with me is very helpful. Thanks, again.

If you are going to be undertaking gardening as hobby (and watch out - it's very addictive), then I'd add to your list of tools:
- a pair of good quality pruning shears. Probably the most important gardening tool I own! And very necessary if you plan on growing roses.

- a garden fork. Like the border spade but with a forked end. Extremely versatile and useful for incorporating soil amendments, transplanting, dividing heavy clumps like iris or daylilies, or digging out the rooted remains of the plants you are eliminating. Other than digging new planting holes, I use my fork far more than my spades.

- a short handled rake. If you can find one with an extendable handle, so much the better.

- some sort of cultivation tool - circle hoe, hula hoe, three prong cultivator. You can either get these short handled for close in work or long handled. I have a selection of each. Invaluable for weeding in and around existing plantings.

- last but not least, a garden cart or wheelbarrow for hauling things around or transporting soil or mulch.

Added to Linda's suggestions (all of which I use regularly as well) this may seem like a long list but gardening is much like cooking - you need the right equipment to achieve the desired results :-) And having the proper tools makes the tough chores so much easier.

Personally I would not be too quick to take out overgrown bushes. Many overgrown shrubs can be easily rehabilitated, and if they are a nice variety you will save years and start out with a fuller, nicer garden. Is there any knowledgeable neighbor you can ask to see what they are?

Also, since you are a complete newby you can't be certain now how much you will take to gardening, and how much time you'll want to be spending. If you rip out everything you'll be putting yourself in the position of having to do a lot just to make it look decent. I'd start slower, myself.

One big mistake I made early on was simply selecting plants I liked, and not taking enough time to make sure they would grow well in my area, and in my soil. Look to see what everyone around you has and what they sell in the good local nurseries. Otherwise you may be throwing money out on stuff that won't do well. For example I tried to grow ericaceous shrubs that like loose, acidic soil in my neutral clay. No go!

Also, buy good tools! Even if you turn out not to be an avid gardener, the cheap ones will fall apart very fast. It's worth spending more and getting the best you can afford from a reputable source.

Wow! Thank you so much. I am about to head out on a little shopping trip and decided to check in to see if there were any other recommendations.

I have a friend who loves to garden. He told me my bushes are overgrown yews. They are beyond rehabilitation. They have taken over the front and up against my beautiful casement bay window. There are some other items I am not pulling, and will try to clean up.

So, I plan on getting a spade, long handled shovel, and a long handled cultivator tool... 3 prong? I think I'd use that. I'm still on the fence about a garden fork. And what sort of rake should I get? Thin steel? or something more substantial?
That'll get me started, I think. I sprayed the weed b gone this AM. Trying to get the yews out this week. Hopefully I can get started planting by the end of the week. Can't wait.

add to your shopping list: kneeling mat

Also, this is your first year. Clean up and condition your soil - if that's all you do this year, you are doing great. Make notes about sun hours/shade areas, etc. You may need that information next year when buying perennials, annuals, etc.

I personally would just take care of paths, pulling up weeds, unwanted plants/bushes and definitely make sure your planting areas have well draining soil - It is certain death to buy plants that can't drain well, especially during the winter (rotting can occur).

Be patient - also by the end of the season, you may be able to pick up perennials cheaper - Don't rush to buy too many things - you don't want them sitting in pots until you are ready to plant.

Most of all - and i stress this - WATCH YOUR BACK! Too many of us get overzealous and lift heavy bags, overdo the digging, etc. etc. If you watch yourself everyday, you can work everyday - Once you hurt your back, you could be out for weeks at a time.

Good luck - post some photos

Carrie

Chicago....yews are one of the shrubs that can be rehabilitated....cut them down to the size you want. Believe it or not, those brown branches will grow new green stuff....and you will be years ahead of planting little short ones.
Also I never ever use a cultivator...no hoe. That's what the bad knife is for. LOL!
And with lots of wood chips there will be no weeds!
Linda C

Oh, how I wish I had read the advice on watching my back and getting a kneeling mat. I spent hours today pulling up garlic mustard and something else that had taken over. Then I got a little crazy and tried digging up ivy roots. Oh yeah, that was fun. My mother, sister and I all bent over digging. I am so sore.
I don't think I want to garden anymore :(

I'm kidding... well, sort of. I just can't wait till I get to plan and purchase the fun stuff! I seriously considered tapping into my savings and hiring someone to handle it all. Too bad I have a kitchen and bath remodel that I need to pay for.

WHen you hurt from bending over, you do sort of think "am I crazy?" "I don't think I want to garden anymore", but believe me, you sound like you've got the bug and you will be out there - a bit more careful from experience, though -and you will learn to not overdo it - (Although, speaking from experience, it took me a long time to come to terms with learning to stop and not overdo).

Good luck - take pictures now - you will love looking back and comparing every year what you have accomplished. It's very rewarding.

Carrie