About Raising a Glass: To Not Having It All Figured Out
What if we don’t need to have all the answers?
I’m Rob Flood, and this is Raising a Glass: To Not Having It All Figured Out—a conversational podcast exploring personal growth, authenticity, self-worth, and the uncertainties of everyday life.
Real life. Real questions. Honest conversations—and sometimes, no answers at all.
So grab whatever’s in your glass, and let’s figure it out—or not—together.
Episode 7: Not Sure Where Your Value Lies? It's You.
Ever feel like your worth is tied to what you accomplish or what others think of you? In this episode of Raising a Glass, we explore why our value isn't defined by our jobs, achievements, or ability to please others. Sometimes, we need to give ourselves a little more credit, a little less criticism, and remember that simply being ourselves is enough.
Raise your glass to recognizing your own worth! 🥂
20 Oct 2026
Episode 6: Reflecting Honestly
As we get closer to the end of the year, it's easy to focus on everything we haven't accomplished. But what about everything we have?
In this episode of Raising a Glass, we're talking about reflecting honestly on our progress, recognizing the little victories, and appreciating how far we've come—even if we don't have everything figured out.
Because reflection isn't just about what we could have done differently. It's also about celebrating what we've learned, how we've grown, and the things we've accomplished along the way.
And you don't have to wait until December 31st to be proud of yourself. 🥂
6 Oct 2026
Episode 5: The Freedom of “I Don’t Know”
There's a difference between having no direction at all and not knowing exactly where you'll end up.
In this episode, we talk about the freedom that comes with saying "I Don't Know!"
22 Sept 2026
Episode 4: Don't Leave Yourself Behind
Life changes—sometimes because we choose it, and sometimes because it chooses us. But adapting to a new chapter doesn’t mean we have to leave pieces of ourselves behind.
In this episode of Raising a Glass, we’re talking about the difference between growing and slowly disappearing from our own lives, how the things we love can evolve alongside us, and why sometimes the better question isn’t “Can I still do this?” but “What does this look like in my life now?”
8 Sept 2026
Episode 3: The Story You Tell Yourself
Have you ever decided how something was going to go before it even happened? We all tell ourselves stories about who we are, what we’re capable of, and what other people might be thinking—and sometimes those stories affect how we show up without us even realizing it.
In this episode of Raising a Glass, we’re talking about the connection between our thoughts and the way we show up in our lives. This isn’t about forcing yourself to think positively. It’s about noticing the story you’re telling yourself, getting curious about it, and leaving room for another possibility.
Your takeaway: The next time you catch yourself thinking, “I can’t do this,” “I’m going to mess this up,” or another thought that has already decided the outcome, stop and ask yourself: Is that a fact, or is that the story I’m telling myself? Then ask: Is there another story that could also be true?
Sometimes changing how we show up starts with questioning the story we’ve already written.
25 Aug 2026
Episode 2: Can I Be Authentic If I’m Still Figuring Out Who I Am?
What if being authentic doesn’t mean having yourself completely figured out?
In this episode of Raising a Glass: To Not Having It All Figured Out, I explore the relationship between authenticity and uncertainty—and why saying “I don’t know” might sometimes be one of the most authentic answers we can give.
Why authenticity doesn’t have to mean certainty
Giving ourselves permission to change and grow
Why changing your mind doesn’t mean you weren’t authentic before
Being honest about who you are right now
Learning to be okay with not knowing who you’re becoming
Maybe authenticity isn’t knowing exactly who you are.
Maybe it’s being honest about who you are while you’re figuring it out.
🥤 Grab whatever’s in your glass, and let’s talk about it.
Want to continue the conversation?
Join me on Authentically Rob on Substack: https://substack.com/@authenticallyrob
11 Aug 2026
Episode 1: Why Do I Keep Wanting to Start Things?
Why do some of us keep wanting to start new things—and does that mean we haven't figured out where we belong?
In the first episode of Raising a Glass: To Not Having It All Figured Out, I explore my own tendency to start businesses, create content, try new projects, and continually wonder where I fit.
Maybe trying different things doesn't mean we're lost. Maybe it's how we discover what actually fits.
And maybe we don't need to find the thread connecting everything.
Maybe we ARE the thread.
Grab whatever's in your glass, and let's talk about it.
11 Aug 2026
Raising a Glass Podcast Trailer
Welcome to Raising a Glass: To Not Having It All Figured Out.
A podcast about real life, real questions, and the freedom to admit that sometimes we simply don't have the answers.
I'm Rob Flood, and I'll be exploring life, authenticity, relationships, work, creativity, change, and everything that happens while we're still figuring things out.
Grab your coffee, tea, water—or whatever's in your glass—and join me.
We may not figure it all out. And maybe we don't need to.
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