Went to 141 school/college to get ratings. Flight instructor and part 135 flying for 2 years while getting bachelor's degree.
flew in AK for 5 years for 121 cargo company. Went to a ACMI for 9 yrs, lost decade. Couldnt get a call so got masters in 1 year while at ACMI and finally got calls. Went to SW. Been applying here for 10 years before I got called.

Private in H.S.
ERAU
ACA
91 Department for 10 years. Great place to hang for the lost decade.
SWA for past 4 years. Wish I got here sooner. Drive to work and couldn’t be happier.

Around 2006 Finished my ratings
2007-8 Instructed
2008-2010 Spent time as an intern at FSI in various Citation sims.
2010-2019 Charter guy for 2 different companies flying all sorts of Citations, Hawkers and Falcons.
Started applying to SWA in 2014/15
2017/18 Became LCA/ACP
2019 Finally got the call to interview and got hired!

/Cliff notes

Awesome thread, many thanks to the OP.

I respect the dedication of you civilian guys, especially those that slugged it out during the lost decade. I don't know if I would have stuck it out. College - Marine Corps - SWA seems easy by comparison.

Of course you only remember the good times...

Haha! I did Army-SWA. Super easy, no hard work or sacrifice. Everything handed to me. Applied once. Invites to DAL and SWA. Went SWA. Glad to be here.
-Flag Tie Guy

College
CFI for 1.5 years
Regional for almost 11 years (had a 4 year plan...didn’t work out)
SWA (after 8 years applying)

True.

The Corps is where I wanted to go (with my friends) but in 1993 they were like “airplanes? Color waiver? GTFO.”

Timing is everything.

Small technical school in the Rockies for college, got my PPL there.

AF Flight School.

10 years on AD, got to see a lot of the countryside of Iraq & Afghanistan.

Reserves.

Offered a job by 4 big pax companies, 1 cargo company. Chose SWA. It’s been the best decision for my family, so far. Been here almost 5 years.

College
Flight instructed and flew tours 4 years til 2010 (latter end of lost decade)
Part 135 charter 4 years
Sun Country 1.5 years
Finally got calls from Swa and Delta. Chose Swa. Happy so far and living in base