When in your life did you feel the most disappointed?

For me, professionally, there was one huge disappointment when I was a construction estimator and worked several weeks to bid on a very large public works project. I prepared the multi million dollar bid package and drove to the 10:00 AM opening. Walking through the parking lot I noticed one of our competitors asleep in his car and woke him. We walked in together, turned in our sealed bid envelopes and waited in the auditorium with all the other contractors.

The trustees came in at 10:00 and opened the bids, 16 in total. The first 14 opened were slightly higher than mine. Then they opened mine and I felt good, very sure I had won. Then they opened the last, the guy I woke up, and his bid was $1,015 less! Second place is first loser. Very very disappointed.

I never told my boss that I woke the winner up.

/r/AskOldPeople Thread