You can use mailmerge to do it.

A standard label merge will place a NEXT field in each label but the first
which causes the merge to move to the next record.
If you want four labels each from the same record, then you have to remove a
few next fields.  So if we are to assume that your database contains the job
names and you want four labels for each job then you would create something
along the lines of

Label 1 {Mergefield JobName}
{Mergefield Estimate}

Label 2 {Mergefield JobName}
{Mergefield Closeout}

Label 3 {Mergefield JobName}
{Mergefield Correspondence}

Label 4 {Mergefield JobName}
{Mergefield Other}{Next}

Label 5 {Mergefield JobName}
{Mergefield Estimate}

Label 6 {Mergefield JobName}
{Mergefield Closeout}

Label 7 {Mergefield JobName}
{Mergefield Correspondence}

Label 8 {Mergefield JobName}
{Mergefield Other}{Next}

Repeat this sequence until the page is filled.

If the second label line is to be plain text then a slightly different
approach is required

Label 1 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Estimate"}

Label 2 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Closeout"}

Label 3 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Correspondence"}

Label 4 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Other"}{Next}

Label 5 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Estimate"}

Label 6 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Closeout"}

Label 7 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Correspondence"}

Label 8 {Mergefield JobName}
{IF{Mergefield JobName}<> "" "Other"}{Next}

Repeat this sequence until the page is filled.