One thing that matters a lot is timing.

If I would have moved to Nashville 20 years ago instead of 10, my life would look VERY different. I would have probably been on the road with a country artist. I would have probably gotten good at playing sessions, and I would have probably been stuck in my way too much to start Soundstripe.

And If I would have moved to Nashville 30 years ago...or 10 years in the future?

Timing is incredibly important.

And you are most likely terrible at seeing the timing in the present. It's something that you usually have to reflect on.

But it's healthy to understand that what you want when you first start a project or career is not always the best timing.

I moved to Nashville to pursue being a session musician. I was completely convinced. But what I didn't understand at the time, was that the session world was declining in a real way. And it would have been my career's demise if I would have not been flexible with my dream.

So a conscious flexibility mixed with a staunch determination is often the secret sauce.

Because timing has a LOT to do with it.

When to Quit?

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?