I am new to strolling magic. I want to end a set with a bill switch but am having a hard time figuring how to get the tt on while talking to a small group.
I could turn around and do it, but there must be a better way.

Normally I keep the mismade dollar in the tt and hold it in place with another tt.
If I try to put in on using one hand in my pocket it seems the potential is there for the bill to fall too deep into the tt or fall out. Any suggestions.

How about paper clipping it to the inside of your pants pocket. That way the paperclip is holding the thumb tip AND the bill in place just under the lip of your pocket. So now your whole hand doesn't have to go inside the pocket...just your thumb. A lot of people casually put their thumbs in their pockets while standing. It is very fast and it works. Give it a try

If that doesn't' work, just try putting it in your pocket but glue a small bit of sponge in the bottom of the TT. That way the bill CANNOT fall in too deep. It stops at the perfect spot and you won't have to worry about it.

Maybe try the Jay Sankey assassins pouch, it allows easy loading of a thumb tip, but may require the cover of a jacket it attached to our belt, or if you had the item on a table, center pouch on pad and in the action of moving out of the way load the thumb tip. It's a super cool item.

Unless you are using a jumbo or extra large TT,Ther should be no worry about the bill falling to far into the TT.In my experience a regular size TT holds the bill perfectly.[If you are using an oversize TT because you have a thick thumb,Bobby's suggestion with the sponge is a good one].

You may be thinking too much about being caught [Magicians guilt]. As long as the bill is oriented properly in the TT, just casually put your hand in your pocket casually and slip it on.
Remember... folks have no idea about what you are going to do... so don't feel guilty.
Of course after the TT is on, good TT management is important. TT handling takes practice and doing like anything else.

Stand in front of a mirror go through the exact motions dozens of times until you can do it smoothly. You will be looking at what your spectators will see, and if you proceed casually...all will be well.
[Also, never glance at the dirty hand, or they will too]

Best,
Rich

Get the book Switch, by John Lovick. It gives you many different switches to look at, some without the TT and it gives you ideas for keeping the money in place.

Ammar on his tape gives advice - put a paper clip that secures the bill to the TT. When your hand goes into the pocket and the thumb into the TT, the second \ third finger flick off the paper clip.
I always do this to secure the bill in place.

Good luck.

Learn the no TT version of the Koslowski. Jay Marshall would kill with it.

Assuming you want to do a TT swich, (and not the no TT version as suggested)...
I search in both jacket pockets, and sometimes trouser until I "find it", no more, no less. Agree with Rich above.
If the Bill has fallen out - put it back in while still in the pocket...!
If you happen to put on "backwards", and you are working tables, you can re-align it while walking around people. Remember - they do not know what you are about to do, so manage the people to suit your problem.
Do not be so scared - it's a "Nike" move - Just Do It.
The Sankey DVD has a gazillion very different plots for the TT, using standard Vernet and the Koslowski Switch. I never switch the bill, just move some sharpie'd text from one side to the other while doing origami.....
Good luck.
Bruce

Use a vernet finger tip instead.
they are tighter and thinner and your thumb only goes in a small way. its so tight that the bill says in position and the tips of my real thumb is "on the money" every time.

and I can get it on my thumb - in perfect position in a split second - the time it takes to dump a deck in my pocket.

they also have the advantage that - anyone who knows of a thumb tip looks at the base of the thumb for a join/mis matched colour - but never look too see if the tip is over your nail - I think the finger tip used as a thumb tip is the best for every trick - huge capacity, very easy load and unload and its blends in with your cuitical - people don't see it even when looking for it.