A Level Deeper

Ah, retirement. How we view it and the way we plan for it (or don't) can have a really big impact on our working lives. In this final episode of the series, we'll hear from: - Demetrice Dawkins, a financial advisor, to understand the basic mechanics of retirement - Adam Harper, someone who retired at 37, who tells us if it was all worth it - Gail Goodman, someone who is beyond typical re...

One of the most asked questions when it come to work is about money or passion—which one should be prioritized? In this episode, we'll seek to gain some perspectives on that question. Listen to my conversations with Brittany Denam and Ryan Monte as they reflect on their experiences on both sides of this coin and share how different events and experiences have changed the way they view work. I...

Chris Young is a professional backpacking guide located in Arizona. Didn't know that was a legit career path? Yeah, me neither... and it's awesome. Chris shares the story of how his professional came to be and like most stories we uncover on this show, it's one packed with tons of substance, hardships, and meaningful life lessons. Find Chris on Instagram @foreveryoungsadventures. No...

Dedra Janvier just spent Summer 2024 hiking 2,650 miles from Mexico to Canada on the Pacific Crest Trail—alone. In this episode, we go inside Dedra's 5+ month experience hiking on the trail and all the things she encountered and had to overcome along this incredible journey. Be careful, this one might just leave you inspired to go conquer all of your dreams. Follow Dedra's journey: Insta...

It feels impossible to do a series about work and not look at the question: Should I quit my job? It’s a question that keeps coming up in different ways, for different reasons, and if you’re tuning in, maybe it’s one you’ve been asking yourself, too. In this episode, we'll try to look at this question from different angles and hopefully make it more approachable. We’ll unpack those nagging do...

After 34 years in the military and 18 years in the education system, Roy Webb tried to hang it up and enjoy his retirement. Key word: tried. In his retirement, Roy has been a volunteer, a bus driver, a blackjack dealer, and more. What Roy has found in his retirement is that there's incredible value in community and he's returned to the community he loves to give back in some incredible w...

You know the advice, "follow your passion" or "if you are passionate about it, you'll never work a day in your life"... is that good advice? Should we try to turn the things we are passionate about or our hobbies into our work?  Today, I'm excited to share conversations with people on both sides of that equation. Alyssa is a former advertising professional who turned...

You grow up, go to school, start your career, work for 40 years, and retire as soon as possible, right? For decades, that seems like it's been the path that so many of us are prescribed to follow. What if there's a different path? Today, I chat with a couple of coaches, Gina Marotta and Mitchell Martin, who work with people to navigate their careers and their relationships to work. I ask...

It’s estimated you’ll spend roughly 90,000 hours working in your lifetime. That’s 1/3 of your entire life. If you’re anything like me, you’ve probably asked, “What am I working for?” Maybe you’ve thought about quitting your job, changing careers, altering your relationship to work, or trying not to let your work rule your life. If that’s the case, this series is for you.  In this series, we’ll exp...

Alyssa LaHaie is an author and, if you ask her, it still feels weird to say that. Alyssa recently completed her first novel ahead of her 30th birthday and is in the process of trying to get it published.  This episode is about pursuing a dream, overcoming self-doubt, finding creativity and motivation, and pushing past what other people might think of you for trying something new.  It's one of...

Mitchell Martin is a former Chiropractor who now lives in Puerto Rico and serves as a men's coach and liberation guide. Liberation from what? Well, addictions, generational patterns, harmful habits, and so much more. Mitchell shared his perspective on what it takes to build a life with more ease—and why to stop asking "How?". We talk about light—both how to harness it to benefit you...

Everyone dreams of spending their winter in Alaska, right? Well, folks, it's true. After spending the summer in the 49th state, Eileen and I will be calling Alaska home for the next 7 months and experiencing our first winter here.  Today, I'll answer questions like: are we insane? I'll rewind our Alaskan adventure and take you through what made us decide to stay here for the winter....

Healing may not be easy, but it's a journey my guest, Robert Joseph, believes is necessary for so many of us to connect to our truest selves—and something greater. A cybersecurity salesman by day and a spiritual guide, healer, and men's coach by night, Robert shares how both of these things co-exist and complement one another. Robert pulls back the curtain on his own healing journey—a jo...

The world lost a bright light when we lost our friend, Nick Mundy—he had been valiantly fighting cancer for many years. Nick joined me on the show in the fall of 2023 and I was immediately struck by his story, perspectives, and message to "Live and Love Boldly". This episode is dedicated to Nick. I felt compelled to re-share our conversation because I believe we can all benefit from hear...

Jenni Adishian would prefer you ask her about WHO she is, not what she does for a living. Sure, partly because she's changed the path of her professional course a few times, but mostly because she doesn't want to continue to place labels and bounds on herself around the person she is and the things she does. Much like me, Jenni has spent much the last few years traveling in vans and plan...

If it takes two to tango, well, it can also take two to start and run a successful business for 9 years. Today, I'm joined by Steffani Traskos who serves as the other half of the leadership of Nakee Butter, the company that Evan Weber (last week's guest) started 9 years ago. Steffani called her own shot by asking to join Evan in the business soon after it started and has been with him ev...

Ah, happiness. It seems like we're all seeking it and yet how often are we really aware of if we have it or why we don't? Today, I'm joined by the founder of a product called Nakee Butter, Evan Weber. Nakee Butter is a spread with benefits—think of something like peanut butter but even more delicious and infused with superfoods. In our conversation, Evan takes an honest look at the...

Hey folks, this week I'm sharing a conversation I had with guest and friend of the show, Angelo Santiago, on his podcast, We Are the Men. This episode was first published on his show under the title: A Meaningful Life through Deep Conversations with Chad Miles. On the show, we talked about this podcast, why I started it, and some of the things I've observed and learned about people from...

What are you willing to sacrifice in order to make a retirement dream a reality? My guest, Adam Harper retired at 38 years old and now lives in Costa Rica with his wife and children.  In this episode, Adam shares his journey of going from a teen who lacked confidence and direction to the retired man practicing surfing and dedicating time with his family. We talk about the mindsets that lead to ach...

Creating a meaningful life does not happen by accident. I believe that creating a life you love living is a very intentional act. Recently, I've been finding myself reflecting and feeling immensely grateful for the unique life I'm living and, my friend, I believe that's possible for you too.  So today, I want to share my recipe for a meaningful life. Using some of my own stories as...

When you think about your most true self, what comes to mind? Maybe it's the goofy, quirky, child you remember being growing up or the artist or creator you've once been in your life. And how is that version of you different than how you find yourself showing up now? I'm joined by Jill Bourbonais, an IFS-informed enneagram coach who works with clients to help them understand and hon...

Dr. Jonathan Brajtbord is a board-certified Urologist, integrative physician, and men's lifestyle expert—and he lives on a 24-acre farm outside of Boston, MA. How cool is that combo? In this conversation, Dr. Jonathan and I talk about his path to becoming a doctor and why, of all fields, he chose to become a urologist (his answer makes so much sense). We talk about Dr. Jonathan's human-c...

Bre Wolta, a relationship clarity coach, dropped by the studio (its virtual) to chat about how to identify toxicity in relationships and more importantly, how to get out of those situations and into healthy ones.  We talk about Bre’s story of starting to accept who she is and how we can all use re-parenting and parts work to bring a never level of acceptance towards ourselves. Then, we dive into a...

Miles Santo is a Dentist and a Men's Coach - an intriguing combo, isn't it? We talk about that. We also talk about the idea of thinking for yourself—why don't most people do it and if that's the case, where do we start?    Miles takes us back into his journey of choosing a career path following in his father's footsteps, what happened when he got small glimpses of thinking...

Christine Reed is a thru-hiker, author, adventurer, and storyteller at heart. This conversation was a blast as Christine and I jammed about sharing our stories and the properties of effective storytelling. We talked about the idea of forcing our creation to become something that makes money and how Christine ended up as an author (she didn't even like writing). Lastly, Christine takes us thro...