In 2018, when Darren Marshall took over as CEO of Smith Teamaker, his goal was to take the company from high-end boutique to major retail force. However, that kind of change doesn’t happen without some tough and painful decisions that left everyone wondering ‘is this worth it?’ But, as Darren and his head teamaker, Ravi Kroesen discovered, it was worth it--because if it weren’t for that “pain,” they wouldn’t be prepared to pivot and be one of the few companies now experiencing unprecedented success in the middle of a pandemic...

Thirty years ago, Scott Showalter wanted to be a classical pianist. But when he realized that despite his skill, life as a working artist wasn’t financially viable, he left music to get an MBA--a decision that decades later led him back to music, as CEO of the Oregon Symphony. And now he's in the position of dealing with the same questions he faced as an artist. The only difference: this time his answer doesn't just affect him, but 100s of people, including musicians, whose future depends on his decisions...

How do you know when it's time to 'throw in the towel'? It's a question most of us face at some point in our lives, especially when it comes to relationships and jobs. And, it can be even more complicated when dealing with money, as "giving up" has huge implications for our financial stability and physical survival. But what if giving up isn't the only option? Or rather, what if it makes sense on paper—like it did for chef Reem Assil, who opened a restaurant during a pandemic—but it isn't something you're willing to do?

If you could either retire at 35 or 65, which would you choose? What if retiring at 35 meant working long hours at a burger joint for two decades, and retiring at 65 meant working twice as a long, at a job you love, as an attorney? Suddenly the decision isn’t so easy. However, for Matt Bath and Sue Ra, this isn’t a hypothetical situation – and they wouldn’t trade their choices for anything.

If there’s one thing Jagpaul Badhesha learned as a farmer, it’s that you don't take money for granted. While Jag wouldn’t trade his family's 1,000-acre operation – or the personal satisfaction of a hard day’s work – for the world, it comes with incredible amount of responsibility and massive financial pressure.