When you reach the point of two lookups as opposed to a one-off, you don't want to repeat the same code. This is known the as the DRY principle in programming. As you will see below, the moment you add a second check, you want to refactor the whole approach because otherwise you will eventually screw up due to mistyping, and people will have trouble reading your code.
(There's nothing about two mostly-identical strings that says, "These are always supposed to differ only by this one character": they might as well differ by 100 characters. Totally identical strings in different lines of code also can't inform the reader -- which doesn't have to be someone else, it could be you a year from now -- "Whatever string you put in Line 2 must be repeated in Line 4.")
Another incredibly useful way to frame your thinking is the Zero-One-Infinity principle. For our purposes here, ZOI means that once you decide you want two lookups, you have to assume there will be a much higher number of lookups (maybe not "infinity" as the principle suggests, but the idea is "more than 1 = much more than 1"). ZOI means you should treat 2 as if it were 20, 200, or 2000. Imagine how crazy your script token would get if you copy-and-pasted-and-slightly-altered your code just 20 times. Obey the DRY principle accordingly.
## generic list-like string scanner w/selectable delimiter
#macro( listContains $haystack $needle $delim )
#if( $haystack.matches("(?i)(.*)(${delim}|^)\s*${needle}\s*(${delim}|$)(.*)") )
true##
#else
false##
#end
#end
## convenience call w/semicolon
#macro( semiListContains $haystack $needle )
#listContains( $haystack $needle ';' )
#end
## convenience call w/comma
#macro( commaListContains $haystack $needle )
#listContains( $haystack $needle ',' )
#end
#if( "#semiListContains( $lead.Interest__c 'Talent' )" == "true" )
Does contain Talent.
#end
#if( !("#semiListContains( $lead.Interest__c 'Performance' )" == "true") )
Doesn't contain Performance.
#end
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