How many times, and for how long are you going to try, work, and fail before it's time really call it quits and move on?
I get asked this a lot. And this is probably the hardest business question of them all. At least the most painful.
It's extremely hard because there are two very real outcomes and usually always unclear:
1. You are say 2, or 10 failures away from a massive success. So just keep plugging away and you will get there. It's a matter of time and failed learnings that will make your 10th try a winner.
2. You are not going in the right direction at ALL. Best to quit and change directions while you still have your youth. This is the equivalent to me trying to be an NBA star but often it's not as apparent/pronounced. Usually, it's learning that starting a business is not really your cup of tea in the first place.
Years ago, Micah and I started a real estate investing business. It was a massive failure, despite all the work we put into it. It took a lot to call it quits but man am I so happy we did!
The one thing that always helped me was constantly having a true self awareness, a critical eye on what was working and what was not, even if I was the one to blame.
So don't be afraid to ask yourself the tough questions. It's often the best thing you can do for yourself. Where are you really at on the spectrum?