Press Pause to Take Accountability: Jon Sheldon on Ego, Vision, and Misalignment

What happens when something you believed would succeed… doesn’t ? 

In this episode of Time To Press Pause, Ellen Williams is joined by Jon Sheldon, founder of Bellewood Coaching, who shares a humbling and deeply honest press pause story about accountability, ego, and misalignment. 

After years of success in real estate investing, Jon made a decision that looked right on paper, but slowly became unsustainable in real life. 

What followed was a difficult realization: the problem wasn’t the market, the property, or the people involved. The problem was his lack of focus and accountability. 

This conversation explores what it really means to take ownership, not just of success, but of failure and how pressing pause can help realign your time, attention, and intention. 

In this episode, you’ll hear: 

• How ego can quietly drive misaligned decisions
• Why vision without accountability eventually breaks down
• The cost of assuming past success guarantees future results
• How to recognize when something no longer supports your life
• Why pressing pause is sometimes the most responsible leadership move

This episode is a powerful reminder that real growth begins when we stop deflecting and start owning the truth.
 

 
🔗 Learn more about Jon Sheldon and Bellewood Coaching:

👉 https://www.belleauwood.coach/

 👉 https://www.linkedin.com/in/jonathan-sheldon-82760a51/

 🔗 Learn more about Ellen Williams:

📘 Ellen Williams upcoming book (pre-launch):
 Creating Time: The Key to Productivity and Peace

 👉 https://shopbooksdirect.com/product/creating-time/
 
📰 Subscribe to Ellen’s newsletter for updates on new episodes and the book launch:

 👉 https://www.thesalientstrategist.com

👉 https://api.transpond.io/form?am=42668&fid=49041&host=true 
 

Transcript

 
Speaker 1
 
When I started really thinking about it, the saying that made me really press pause on this pretty large aspect, financial aspect of my life, was the enemy is me. I had done this to myself.
 
Speaker 2
 
Welcome to Time to Press Pause, real-life stories from the C-suite. I'm your host, Ellen Williams, CEO of The Salient Strategist and author of Creating Time, The Key to Productivity and Peace. And today we're talking about the importance of introspection and understanding how much of a role you play in the consequences, good and bad, of your own life. My guest is John Sheldon, founder of Below Wood Coaching. John's a leader, growth, and small unit coach who helps high performers lead with authenticity, operate in alignment, and grow with purpose. His background as a Marine Squad Leader and Fortune 500 Sales Executive shaped how he approaches clarity, discipline, and resilience, especially under pressure. Now, he works with individuals and teams to build performance systems that scale sustainably without losing what matters most. John's coaching is grounded in stoic, calm, radical honesty and a belief that real growth starts with owning the truth. Welcome, John. I'm so excited to have you here today on Time to Press Pause.
 
Speaker 1
 
Thanks so much for having me, Ellen. It's a pleasure. I'm excited for our conversation.
 
Speaker 2
 
I am as well. I want to thank you for reaching out to me. And asking to be a guest, that is not a common occurrence, although I encourage listeners to reach out to me. I'm always looking for guests. John, I was really happy to get your e-mail, and I'm really looking forward to your press pause story.
 
Speaker 1
 
Yeah, and again, thanks for having me. It made so much sense. It seems like these types of conversations, the ones that you're having and the one that your podcast is based off of, really aligns with a lot of the work that I do in my business. I just felt compelled that, yeah, pretty cool. And I'm excited to share with your community.
 
Speaker 3
 
Fantastic.
 
Speaker 1
 
Have at it. Gotcha. Yeah. So the press pause story that I have, I've got, I've had a bunch in my life, but the one that I think resonates mostly for me right now is actually a really humbling one. And the reason that I picked this one after I got your e-mail was Just when I was thinking through hey, what are some of the big moments in my life that I had to really reconsider what I was doing and press pause. This one that happened to me in the last two years just really jumped out because at the end of the day, this one taught me more. And we can get into that in a little while. But essentially to give some backstory, right now I'm a professional coach. For the last 15 years or so before this, I was in financial planning in various roles, owning my own team to becoming the director of sales for another company. I ran into a really good situation when I was in college and was fortunate enough that the owner of the house I was staying in with one of my best friends, he was getting out of real estate. So he was going to be selling all of his properties. And he and I were pretty close. He was probably 10 years older than me. So he was a great example of someone that was living this multifaceted professional lifestyle. He talked to me a lot about real estate and I was like, sure, this sounds great. So when he left, he actually offered me the house, turned out to be a great deal and turned into a long-term rental, made the improvements, had the vision that I had for the property, sunk some money into it, all paid off, increased the rent, had great tenants, multi-year tenants for years and years, they wouldn't leave and it was awesome. Flash forward six years after owning that property and having some really good success in it. And again, this is happening behind the scenes. Stop over there like once a week, you'd have to do your emergencies and it had a couple of emergencies that have to do with nothing crazy. But then COVID hit and all of a sudden, especially in upstate New York where I'm from, which was a pretty real estate depressed market, we were still buying houses for mid one hundreds, skyrocketed like lightning bolt. And I know that happened a lot, but from what I understood from the reading I did, Rochester and upstate New York was hit in a good way for real estate investors, at least looking to sell in probably the best way possible. So ended up getting enticed honestly by the money, not by the ease of use, like the, I call it the fair poor property. The fair poor was hands off. And I had to stop over there basically once a week to mow the lawn, which took me eight minutes. And got enticed by the money that I could sell the house for and the profit that I would gain. Still wanted to stay in real estate. And this is when I'd been staying in Airbnbs since 2013, which is a pretty early adopter of Airbnbs. I always thought it was cool. I remember the first one. Alan, I know that you're from New York. I remember the first one that I went to was in New York and I was like, how is this a, how is this apartment $140 a night? This is insane. I'm all in on this, right? So really got enticed by my experience working in that world or just experiencing that world. And so I ended up selling this really good Investment that I had used for a lot of things in my life had supplemented my income when I was starting businesses. It was great and was like, all right, a little more stable. Now let's jump into something that maybe we'll make a lot of money. And so I actually ended up buying a glam ground in the finger lakes. Ended up being a pretty cool situation where a house Airbnb came with it had this great plan. I crunched the numbers. I. I did everything that I thought. I consulted with not only one, but probably 4 real estate professionals, even though I had been doing it for a decade. I was like, yeah, I want to make sure I'm doing this right. And everything checked out. And what I think of it is I had the vision down. I crossed the T's and out of the I's, or at least I thought I did. So fast forward, we get through closing. I had this idea that, hey, you know what? Glampground is 3 seasons. And if there's people in real estate right now, you're probably going to be laughing at the rest of this. I was like, it's three seasons, so I'll renovate the house. I'll put the money that I was going to put into the glamp ground, into the house instead, turn that into an Airbnb. So that can go all year round and that'll fund the glamp ground. I had this vision that was gonna happen. It didn't work out that way. The renovation and furnishing the Airbnb itself took a lot more time and a lot more money than I was expecting. Glamground had to be put on pause for a long period, extended period of time, was not making any money. The Airbnb was barely breaking even at a maximum, right? Even in the summertime, it was only having three or four good months at a time. And it came to this realization after we kind of let it settle in for the first year. I was like, okay, maybe this is a little bit different, but then year two was really similar. And it was honestly starting to put some pretty big hindrances on my life because it was not even breaking even at this point in time. And this is where the big press pause moment came in because I was under this impression that I was maybe this good real estate investor. Again, I had been doing it for a decade. It was really profitable. That first house I had, I literally never paid a mortgage payment on it. The tenants paid for that plus a good chunk of money on the outside. I was like, man, this is the best thing ever. Ended up selling it for way over what I thought it was worth. I was like, man, this is amazing. And then it was such a kick in the teeth to then have this property that was an hour away from my house that I had a property management company for that was supposed to be handling this whole thing. And they are, they're great, but that it was just wasn't working and I couldn't understand why that was. Where I had to end up press pause was really on the vision of what I had created. What were my miscalculations potentially? Internally, I was questioning like, how is this missed by everybody? Are the pictures not good enough in the property? Are we not giving out candies or personal touches that are giving better reviews? Why are there, is there a ladybug problem for heaven's sake, right? What is going on with these things? And almost getting to that, that almost like victim mentality in my brain of Hey, This is not your fault. You crunched the numbers. You had the vision. This should be working. And I remember just coming to the saying that I had to say to myself, it was, it came actually from this book by Ryan Holiday called The Ego is the Enemy. When I started really thinking about it, the saying that made me really press pause on this ask, this pretty large aspect, financial aspect of my life was the enemy is me. I had done this to myself and there was a very specific reason for that. Right. And so I had to take this time and it was a pretty significant time. I actually went into. the reclusive state around the property in general. I didn't want to talk about it with anybody. I went even further on the wrong side of things. I don't want to spend any time doing this now because it's such a waste of my time. I can't believe I wasted all this money, time, and energy on this thing. Now I don't even want to talk about it. And That's almost exactly the opposite of what I teach people, what I coach people to do, and what I believe that you should be doing. And it was this really deep part of inflection or introspection, really, that was the enemy was me. I was I in the cause of this. And one of the things that caused me to press pause was that I just didn't pay enough attention to it. I had set the vision up. It really was. I had plans for the Glam Crown. It was gonna be this cool thing. Bands were gonna play there. People were gonna stay there. It was gonna be this nice thing in the hills of the Finger Lakes. I can't believe I owned 22 acres in the hills of the Finger Lakes. This is crazy. And it was just crumbling around me. And the reality was, I didn't take accountability for what was happening. There were so many things that I could have done that I shook under the rug because I thought that just the vision was gonna take care of it. that I had hired the right people to do it. And they're great people and has nothing if they listen to this, both my real estate agent and my property manager, nothing on them at all. At the end of the day, it was 100% on I lost focus and I had zero accountability. So the end of the story is I pressed pause still actually in the process. Half of the property is now sold. We're trying to get rid of the other half of the property currently right now. And the press pause, I'm actually in the middle of it right now, to be honest with you. But it's this lesson that I've learned. And the press pause for me is, what importance do I put in my life? I started a new business. I've been professionally coaching for four years, went on my own as my own business last December. And all of them, again, all of my time and energy now went into that. This big hands-off approach. I only have so much time and energy for a couple things, especially in my professional and personal life. And getting an alignment into what those things were, getting so stressed out about all the property and trying to balance both of these things where one is thriving and one is absolutely sinking. And the pride that came with it, that ego that came with it of I can do it all, I can do both. But I wasn't giving every aspect of both the attention or accountability that it deserved. This entire journey for me has really changed my mindset on this thought process I have around just what are our blueprints, what do you need to succeed? Why did this fail when I've done honestly so many things so great in my life? And there was one thing, and I've mentioned it five times now, was accountability.
 
Speaker 2
 
John, thanks so much for sharing all that.
 
Speaker 3
 
It's definitely a unique story on this podcast.
 
Speaker 2
 
We haven't had anyone talking about real estate. So I love that we have a slightly different perspective. A couple of things I definitely want to get back to. What I heard was I was really successful at this thing and just a bit of an assumption that I would be successful again, even though it was a completely different type of property, it was a completely different market. It was like, it was that, hey, I've done it once. I can do it again. So I appreciate the fact that, number one, you're still in your pause, but even in the midst of your pause, you're you were willing to come on the podcast and talk about how introspective you've been and the lessons learned already, that even though your pause isn't quite over. So I appreciate that. Ego is the enemy. What I really like, and let's talk a little bit about this, as a leader, I think this is important. You talked about how you had a vision but eventually took accountability for not really communicating. Can we dig into that a little bit?
 
Speaker 1
 
Yeah. Yeah. And I think, I'll go back before we dive into that. I think the mental pause for me is over. That's where I thought of this story. I think one of the biggest pieces of this puzzle is I don't think that it was clear of what my personal vision and how this property was supposed to support that vision, because it just, it didn't even from day one when you, when I really look back at it. Like it did on paper, but within the first 90 days, it didn't. It was very obvious that it wasn't going to. I think that's the piece that I didn't communicate. And some of the work that I do now too is emphasizing you need both, right? You need a personal vision and you need a, and if you're a business owner or if you're in any type of job too, make sure that is supporting what you want because you only get one life. So it's the deepest and earliest lesson that I've probably learned. from my time in the Marine Corps was you get one shot at this. And so I'm very fully invested in starting with personal visions and then moving into how does that support a business vision or how are those two things connected? Because if they're not, you have a massive amount of misalignment there. Yes, this is a good conversation. If I had viewed them more as teammates instead of, hey, I pay these people. If I had viewed it more like that, I probably would have been a lot more willing and probably conscious about sharing, hey, this is what I need this property to do for my life. This is why I bought this thing. And I view them like that now. And again, that's one of the things that came from this is like, if you're going to do work with people, make sure that you're viewing them as a team member. I love that you brought the word leadership up in this because I don't think I would have thought of that. Because actually, honestly, I will send them this podcast. I want to get their opinion on it. At what point in time did they feel like, man, you probably should bail on this outside looking in without even knowing my personal vision around it. So it's a good lesson in communication with others too. It's how you build your circle of advisors, right? Your personal circle of advisors.
 
Speaker 3
 
So I have two comments on what you just said. One, years ago when I was with Constant Contact, which comes up a lot in this.
 
Speaker 2
 
Podcast, we went through a process of, I think it's like the seven whys. And my team, who were not Constant Contact employees, they were independent businesses, they had purpose. And for me to be able to support them, I would ask, why are you in business? Why are you supporting Constant Contact? Why? And you get the, I like helping people and that's cool. I like e-mail, but that's cool. But when you really dig, you get to that personal vision. And I remember one of my team said, I want to buy a Corvette. And I was like, there's the why, right? That's what's motivating you. So how do I help you do that? And it turned into a very different conversation versus how do we meet your goals or your quota way up here. Now I'm down here where it really matters. Let's talk about that. That was something I learned that I think is relevant to what you just said. John, you have given us so many lessons in your story, so I have one last question for you. What advice would you have for other leaders as to when they would identify it's time to press pause?
 
Speaker 1
 
I think that if you can't put, and it means something different to everybody, and I want to make sure that's clear, but if you can't put time, attention, and intention behind something, that might be the sign to say, this is, we should, I should press pause on this. That's not just a business. It's not a real estate. That's life. If you can't put all three of those things into something, you might need to press pause.
 
Speaker 2
 
I appreciate your time, attention, and intention. I think that makes a lot of sense. And it also takes some introspection and being present to be able to come to those conclusions. Thank you again for being here, your lessons, your wisdom, your stories. multiple stories within your pause. I appreciate everything you shared. And I'm so happy that you were here today.
 
Speaker 1
 
Thank you again, Ellen, for having me on. And I hope that anybody listening can take something away from this, whether they're in real estate or not, it doesn't really matter. Again, that's not my profession. It's just a hobby of mine. But these lessons are, I think, universal. It's universally changed the way that I view a lot of things in my life now.
 
Speaker 2
 
Thank you for listening to this episode of Time to Press Pause. 

If you're interested in learning more about John, visit bellewood.coach. 

That's B-E-L-L-E-A-U-W-O-O-D.coach. 

If you're interested in learning more about me, visit thesalientstrategist.com. 

And be sure to sign up for our newsletter so you get the most updated information about my new book. 

And please listen again wherever you listen to your podcasts.