You could call it my $10,000 mistake. I’ve worried that that’s what you’ll think. I’ve wondered if what I’ve done was stupid. I’ve thought and felt many things while I struggled through this decision.

I recently took a new job, and I left my old job right before my old company paid out their annual bonuses. I say “right before”, but I didn’t know exactly when bonuses would be paid. Still don’t. I asked a couple of people that I knew, and the closest I got to a concrete prognostication was a friend who told me “Either the first or the fifteenth (of March)”.

If I had known the exact day bonuses would be paid, I would have declared that as my last day at my old company. But I didn’t know the exact day. In hindsight, I should have asked, “What day should I choose for my last day if I want a 50% or greater chance of getting my bonus?”

While interviewing for my new job I thought it would look better if I said I could start right away. But interviews aside, I was ready to move on and wanted to start this new job as soon as possible. I had outgrown my old job a while ago, and when they asked if I wanted to start on March 4th, I said yes.

But I wasn’t locked into the 4th. I could change it - push it back a few weeks no question asked, and push it back a month if I had a good reason. I asked my wife what she thought. I told her I could start later if she wanted to ensure we got the bonus from my old company. She said she would be happy either way and told me that she knew I’d been waiting to do something new for a long time. That was our first conversation.

After that first conversation with my wife I started asking friends at work if they knew when bonuses would be paid. I wanted to give my wife another chance at choosing the bonus, knowing the exact day it would be paid. But as we’ve established, nobody I know knew the exact day. I asked her again about changing my date of departure, and again she told me she didn’t need the bonus and would be happy with whatever I chose.

I decided to stick with March 4th as my start date, but I couldn’t stop thinking about it. Because it would be rational to stay until bonus time. I made a good living at my old job, and was going to be making even more at my new job, so I didn’t need the $10,000 bonus. But even if you don’t need $10,000 it’s hard to convince yourself that you don’t need $10,000. And a voice in your head will remind you that your peers will criticise you for leaving $10,000 on the table.

I thought over my decision multiple times, but I always ended in the same spot. I wanted to move on immediately, and I didn’t want to wait in uncertainty. So I gave up $10,000 to start a new job a little sooner.