Season two comes to a close with a reflective episode that aims to answer, "Do we now have a better understanding of failure?"Through reflection and a little bit of figjammin' and synthesizing the stories and lessons, we discuss three perspectives on the topic: 1. Failure, and how we define it, is personal 2. Failure isn't always apparent in the moment 3. We need to fail in order to evolve. Greg and Brett recollect stories from the season, provide some additional context and detail that's not included in the episodes, share more stories and anecdotes of their own, and leave us wondering...do we need to learn more? Should we do another season of stories? Give the final episode a listen, and reach out to us with your thoughts on failure, the podcast, and what you'd like to hear about in Season 3.

Have you ever done something nice for someone and been sued for it? It's not a common occurrence. So when it happens, you start to question how you're making decisions or how things went so wrong, not just legally. But, how can your goodwill, which is at your core as a human, be so exploited? In this episode, Wil Reynolds tells a story that sheds light on his guiding principles and how they've helped him to reframe issues and make solid decisions in his growing business, Seer Interactive. "This is just how I have managed the ups and downs of running a business with disappointments. Sometimes you have your heart stomped on a little bit by the people that you try to build up." - Wil Reynolds Yes, Wil gets his heart stomped in the story, but he's resilient, and while it was hard to find the lessons in the story immediately, they were right in front of him all along.

We begin episode six with what seemed like a benign situation turning into a chaotic mess that quickly leads to self introspection, and the feeling of failure. All due to a meeting. "It was like an escalating volcanic eruption. All of a sudden, people were arguing and now the room was fractured into two different arguments that are about stuff that I thought I had sorted out. I'm trying to get control of the room, but I am way over my head." - Scott Berkun In this episode, Scott Berkun shares a story about how he thought he had control of a meeting until he didn't, and then he realized maybe he wasn't prepared. It's a story (and a lesson) about preparation and facilitation that any project manager, leader, or master facilitator can relate to. And it just happens to take place in the golden age of Internet Explorer and Windows!

Has a situation ever made your altar ego come out? You know, that "dark" version of yourself that just is not taking shit anymore. You know the one. It's okay, it happens. We all deal with toxic traits from time to time. But what's behind those toxic traits? "So it turns out that instead of being a strong leader, um, I was kind of just an unpredictable asshole." - Galen Low In this episode, Galen Low opens with a personal story about how he had to be told about his toxic traits and how they affected his team. He tells the story of how it all went down but introspectively talks about what was behind that toxic masculinity—and there are a lot of contributing factors. Galen calls it a horror story, but it's a lesson we can all relate to. This episode will make you think twice next time you're dealing with toxic behavior in the workplace--whether you're Jekyll or Hyde.

Everyone hates a breakup, but we all love a breakup story. Especially if the breakup teaches you a lesson about yourself. In this episode, Margot Bloomstein joins us to tell the tale of falling in love with a client and their project and how that changed. We've all been there. You can fall in and out of love with a job, a project, a business relationship, or even a process. But how do you cope? And have you ever asked yourself, "What's my role in this failure?" "It's kind of like you're bringing your brain to it, but you're not bringing your heart to it." - Margot Bloomstein The conversation that spurs from Margot's tale touches on how we handle missteps or failures when working with others and how we try to cope with an imperfect situation and do our best work in spite of the circumstances. In the end, asking the question, "Is my heart in it?"

In this episode, Whitney Hess tells the tale of exciting projects, finding focus, and deciding when it’s time to slowly back away. The story is entertaining and interesting but also full of insights that may make you question how you define—or even experience—failure. "I've made many, many mistakes, but I don't hold them that way. I don't really have failure in my vocabulary." - Whitney Hess Whitney spent time before the interview checking her receipts. That’s right, she’s got details saved in email and she did her research to get the details straight. It makes for a great story, and there may be a happy ending…

If there's anything to be learned in this season of Sprints & Milestones, it's that everyone interprets failure differently. In this episode, entrepreneur and fine artist Tracey Halvorsen shares how a metaphorical grenade was dropped on her life and how she navigated it personally and professionally.

In the first official episode of Season Two, Brett and Greg sit down with Crystal Richards to hear her personal story of failure. This episode has a couple of plot twists, including the one where Crystal tells a second story! “Sometimes you're just that person that gets the wrath of people, and it's about all that you can control is how you react.”  - Crystal Richards The stories in this episode get to the root of many issues or failures: people and what happens when they release the Kraken. You must be prepared when they flip the script on you, whether it's a colleague, client, manager, or partner. Listen to this episode to hear Crystal's stories and lessons on managing difficult situations and playing it cool when you're under pressure.

After five long years, Sprints & Milestones is back with a new focus: failure. Spoiler alert: each episode in the new season focuses on stories of failure told by our fearless guests. We break those stories down to find common, universal lessons learned, as well as general themes about failure and how we all hold it differently. "If anybody out there somehow doesn't get something out of this, then um, consult your physician." - Greg Listen to this first episode and get excited with us about the journey we're on.

Season One of Sprints & Milestones was all about the principles of digital project management, taken from Brett’s book Project Management for Humans. In our final episode of the season, we respond to questions submitted by listeners.