Instead of doing your landscape all a once, try doing just one project a year, picking something you can do yourself or with the help of your spouse. (You could even try to get your teenagers involved: good luck with that!) If you stick to a modest-sized project, you won’t feel overwhelmed and you’ll quickly discover you already have most of the tools – and indeed, often many of the materials – on hand.
But where to begin? Of course, that’s your decision, but it’s usually best to start by solving any underlying problems that will affect your future plans. For example, poor drainage is not going to go away on it’s own, and yet adding drainage pipe to a damp area is inexpensive and quite doable… if you take care of it yourself. A wobbly or damaged walkway is something you could fix on your own and is doing so is vital for safety (and insurance) reasons. A steep slope may need terracing (you certainly won’t want it covered in lawn or it will be dangerous to mow!) and installing a wall is a vital step that does take quite a bit of energy. Or get rid of that patch of invasive plants by cutting them down and covering them with old carpet until they die from lack of light.
None of these projects really improves the esthetics of your property per se, but once you’ve got the hard slugging done, you can move on to beautifying in following years. A flower bed here, a vegetable bed there, a bit of trellising, etc. You’ll be amazed at how quickly you create the landscape you’ve always dreamed of even if you only do one project a year… and when you step back to admire it, you’ll be proud to say “I did it myself!”