In short
Episode topic: The “25th Hour” idea—leaders waste about an hour a day by giving away time to unnecessary meetings, events, long conversations, vague language (“maybe/sort of”), and fear-driven overcontrol. The fix is “manage you,” not everyone else.
Guest backgrounds
Neil Shore is founder and former CEO of Trident Digital, now an executive coach and author of The 25th Hour (launching Aug 11). Jason Pfeiffer (Entrepreneur Magazine editor-in-chief) hosts.
Key claims
Fear (of firing, judgment, optics, being seen as weak) triggers “swirls” (ruminating thoughts like “I should’ve said/done…”). Leaders also make time-wasting decisions based on catastrophic narratives. A “1% bucket” exercise helps purge low-probability fears; if a real performance issue arises, separate “devil” fear from the “angel” governor and address the actual problem.
Notable examples
A client spends seven hours instead of minutes because they didn’t ask a clarifying question; a text chain with Jason’s son escalates due to unclear intent; a unicorn CEO fears board firing despite a 1% probability, wasting time anyway.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Time Management Dilemma
0:56 to 2:06
Discussion on the struggle to find time and the impact of unproductive habits.
“horizon3.ai slash problem solvers and request your free Node Zero demo.”
The Time Management Dilemma
2:13 to 4:32
Discussion on the struggle to find time and the impact of unproductive habits.
“Get more with Northwest Registered Agent at northwestregisteredagent.com slash solvers free.”
Understanding Our Own Obstacles
4:32 to 7:05
Neil Shore discusses how individuals create their own time constraints through fear and indecision.
“Neil, why do we get ourselves into this situation in the first place?”
Effective Communication Strategies
7:05 to 10:12
Exploring how asking clarifying questions can save time and improve communication.
“been teaching now for years is how you manage you.”
The Impact of Fear on Decision-Making
10:12 to 14:00
Neil explains how fear leads to poor decision-making and wasted time in professional settings.
“Now, days later, we get to laugh about it, especially because this is what I do.”
Overcoming Fear-Based Decisions
14:00 to 26:03
Discover how fear influences our decision-making and time management.
“Please tell me and do it in the way of a question like, I'd love to learn more.”
Transcript
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2:16Jason Feifer:Get more with Northwest Registered Agent at northwestregisteredagent.com slash solvers free. Good things can happen even from the worst case scenario like getting fired. I can't begin to tell you how many times I've heard from people post them getting fired about what a blessing it was. It was a bad fit. It was a round peg in a square hole type situation. Running a business means solving problems. I tell you how the smartest entrepreneurs do it. Hi, I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and this is Problem Solvers.
2:57Jason Feifer:I'm gonna admit something to you. I shouldn't admit this to you, but I'm gonna do it anyway, and my guest will hopefully have to forgive me, which is that I prepped for this podcast episode that you're about to listen to like two minutes before it happened. And the reason for that is because I don't have the time, guys. I don't have the time. I am stretched so thin. It's one thing after the other. There's no time to think about anything. I am just constantly scrambling around. At the end of the day, my to-do list is longer than it began. I'm sure that is you too, right? You think to yourself, wouldn't it be great if there was another hour in the day?
3:29Jason Feifer:Well, actually, wouldn't it be great if there was like 24 more hours in the day? But I would settle for even one more. How do we get there? How do we get even into this problem where we feel like this in the first place. That is what I'm going to talk about today, which is the only reason I felt comfortable talking about how little I prepped for this. And that's because I am here with Neil Shore. Neil Shore is the author of a book that is really going to promise exactly what I desire, The 25th Hour, How to Thrive and Gain Ridiculous Amounts of Time by Getting Out of Your Own Way. Neil is going to tell me and you how we are in our own way.
4:04Jason Feifer:Neil is the founder and former CEO of Trident Digital. He's an executive coach and now the author of this book. Neil, welcome to Problem Solvers. Thank you for solving my problem. Thank you, Jason. What a great intro that is. And we'll have to find a way to get you your 25th hour in real time. Let's do it, please. And by the way, in case anyone's actually watching this, instead of listening to it, you will see that I'm hunched over this laptop on a couch because I'm at my parents' place. It's a mess, guys. It's a mess. Neil, why do we get ourselves into this situation in the first place? The title of the book here is suggesting that we, founders, operators, are just getting in our own way constantly.
4:46Jason Feifer:What do you mean by that? That's because we do. So it's really not about extra time. It's about the time that you are giving away. And it's about the extra meeting, the participating in events that you don't have to, the long extended conversations, not being definitive, using the kind of maybe sort ofs, which means that it's unclear. And if you take a look at the aggregate, especially as a leader of all of that and how it comes together, it is proven through decades of doing this that we give away at least an hour a day. Huh. What do you think is underneath that? I mean, you described a whole lot of things that I relate to, just getting involved in things that we shouldn't, having conversations that go on too long.
5:35Jason Feifer:Like, what is underneath this? Is it just a lack of focus or something else? So primarily, the biggest driver of this is fear. So it's our fear of getting fired. It's our fear of the judgment or the board member that is going to create a hassle for us or the employee that is going to respond in a certain way. And so we overcompensate and therefore create so much additional complexity because our fear systems get activated. And then we start to control it. So it's that Slack message that becomes a whole Slack chain that winds up, instead of it just being one quick little blurb, it winds up being 15, 20, 30 responses magnified by the amount of people that are in the chain.
6:26And then we're chasing our tail. Well, what then winds up happening is what I refer to as the swirls. The swirls is when your mind just keeps going. I should have done this. I could have said that. I meant to do this. And then we start to completely attack ourselves about how we're bad at what we do or whatever it is, which crushes our time. So the idea and the whole premise, and again, this has been proven by decades of work with some of the world's brightest and craziest CEOs is you manage you. So instead of trying to manage everybody else, the principles and the concepts that I write about in the book and that I've been teaching now for years is how you manage you.
7:08And it just changes the entire game.
7:11Jason Feifer:So what does it look like for you to manage you or for me to manage me? So for you to manage you means that depending upon the circumstance, but let's just say that something came up and immediately you're looking to get defensive or respond or engage or wind up using time to justify. At CLA, we're in your corner and on it. We coach tax strategies and Little League First Base. We help you adopt AI data tools and we adopt rescues named Buddy. We walk your factory floor and jog the local 5K. though sometimes we walk that too. Wherever you're coming from, we're right there with you. Wherever you're going, we'll get you there.
7:59CLA, CPAs, consultants, and advisors. Learn more at claconnect.com slash with you.
8:06Jason Feifer:This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+. It would look something like this. Pause just for a couple seconds. Figure out what the intent is. What was the intent?
8:38Was that person's intent really to insult me? Was their intent to actually ask me this question? Or are they just looking for some attention? Is it a really hard problem and complicated? Am I going to respond in a detailed way because I want to feel good about myself and therefore I want to feel relevant? All these different scenarios come up. So just solve for the intent. After solving for the intent, ask a question. It's one of the most powerful tools we have. Just ask a clarifying question. Hey, I'd love to understand more about what you're trying to achieve. I had a situation just last week with a client who wound up spending seven hours, seven hours, that's not an exaggeration, on a topic that had he just asked a simple clarifying question about what the person was trying to achieve would have been about a five, maybe seven minute discussion.
9:34It became a runaway freight train. And Jason, this happens all the time. And funny enough, I do it myself I had a situation just even personally With one of my kids the other day An adult son who I made a comment to He misunderstood the comment I thought I was clear And had I just picked up the phone And made a very quick phone call And explained my intent It would have been five seconds Instead, it became a dramatic text chain Which I engage I teach this and I did it anyway. And it was a massive erosion of time, hurt feelings, etc. Now, days later, we get to laugh about it, especially because this is what I do.
10:20So we all have these moments. It's not preventable. We're human. But the idea is really you manage you and just pause, figure out the intent, ask a question and solve it.
10:33Jason Feifer:You know, Neil, so much of solving the greatest problems in our lives come down to extremely simple things. And that is why you just saying like, look, if you just ask the right question, ask a clarifying question, you can save yourself so much time. It doesn't sound revolutionary. And yet we don't do it. And so I always love to try to understand the reason we don't do it. You had said fear. And so I want to run a hypothesis by you. As you were talking, I was thinking, well, what is the fear-driven reason to not ask the question if that is the thing that is going to create such a boundary between us and our time.
11:12Jason Feifer:And what I came to was, and tell me if I'm wrong, is, you know, the reason why if somebody asked me something at work and I didn't ask a clarifying question and it then took up a ton of my time, the reason that I would have been afraid to ask that question would have been because either, number one, I didn't want to reveal to the person that I didn't know what it seemed like they thought I knew or that I should know. Or number two is that you don't want to take up more of that person's time. Like you're afraid of being an imposition to them by saying, actually, can you just spend an extra five minutes with me?
11:52Jason Feifer:I know you're really busy. I know maybe you, you know, if we're talking about like corporate ladder stuff, I know that you maybe are a step or two above me or something. But I, or if you're an entrepreneur, you know, you're talking to a client, you don't want to take up your client's time, but whatever the case is that you don't want to be the imposition. And so you would rather fall on your own sword here and let them go along with their day while you spend some time trying to figure out what it was that they want. Am I right about those things? So you're right. Ish. So you said, tell me if you're wrong.
12:23So I'm not going to tell you you're wrong, but here's what I'm going to tell you. Yeah. The fears that you talked about in your number one, the optics of it is positively true. We get very concerned as senior leaders, we don't ever want to show weakness. We don't ever want to use too much vulnerability. And the truth is professional vulnerability is a massive leadership characteristic. So by saying, hey, I'd love to understand more about that, please explain, not only makes the person engaged and not only makes them feel good about it, but it is clarifying. But yet so many senior leaders just won't ask the question for the optics exactly as you explained.
13:12The second part of it is where I would reshape that just a little bit. It's, yes, the seniority levels and people not wanting to press on their bosses. That is for sure true. But it's all that qualifier. You know, it's above my pay grade or I'm not the smartest person in the room. If you calculate the amount of time with qualifiers that take place, I observed a meeting just a couple months ago where every person, there was 11 participants in the room and every person had a qualifier. It's those dilutive statements You know, I may not be the smartest person in the room Well, if you say that, I'm going to believe you're not very smart And so therefore don't say it And by the way, you are smart So even those little statements take time They're distracting They're intended to be humbling But actually they're minimizing And we don't ever want to minimize, period It's a massive use of time And it's just not necessary So how we then fix it is just recognize, you know, I don't know that.
14:25Please tell me and do it in the way of a question like, I'd love to learn more. Or actually, I didn't know that. Please explain. That honesty is far more humbling than it is to use that chest thumping or some other ways that we were talking about before.
14:41Jason Feifer:You know, Neil, you also write about how fear doesn't just hold us back from getting the information that we need, but that we also waste a lot of time by making fear-based decisions. Can you unpack that? We tell ourselves some crazy narrative, right? Crazy, crazy narrative. So if I deliver this project early, I'll get promoted. Or if I answer my board members on a Sunday night at nine o 'clock when I'm supposed to be having family time, then they will like me better. And the reality is that we forget or we don't know, we're not trained to ask ourselves the question, what's the worst thing that can happen?
15:25So if we don't do this, what's the worst thing that can happen? Or if we put boundaries in place, I'll have this to you tomorrow morning. In most cases, people are just trying to get something out of their mind or off their desk or inbox into your inbox. And we create these narratives about the catastrophe situation. I love these because I've lived it. And that's how I've created most of the tools. And just one great example. I work with a CEO of a unicorn, like absolute thriving company, just raised significant money. and he lives in fear of his board firing him. So he's the founder of this business.
16:16They just raised hundreds of millions of dollars of capital at a very multi-billion dollar valuation. So by all external measures, crushing it. And if a board member asks a question, the narrative that crosses his mind is, doesn't like me, doesn't trust me, going to fire me. It's going to affect my options. I mean, literally the swirl is unreal. And so the exercise there goes something like this. What's really the catastrophe? Okay. My, my fear is that I'm going to get fired. And then we probability weighted. Okay. So in this case, um, let let's, we'll, we'll, We'll call him Mr. X. I'm not using any names.
17:05We'll call him Mr. X. Mr. X, what is the probability that you're actually going to get fired? Let's just look at the facts, minimize all the emotion, take all the fear out of it. What's the probability?
17:13Jason Feifer:And you said, 1%. I said, great. So 1%. That's probably right. I would say the same. I know your board. I know your sponsors. Probably 1%. So if I offered you an investment opportunity and two of them, two options. One had a 99 % probability of being successful. The other one had a 1 % probability of being successful. How much time would you spend on the 1 % probability? And he said to me, zero. Why would I ever spend any time on a 1 % probability? Of which then I said to him, well, great. Why are you spending any time on the 1 % probability that you would get fired? And when we can go through rational exercises around things like the irrational, which is the swirl that fear system activating, it changes the time profile because then we pause.
18:10We go, yeah, so right now I'm thinking this, guys, I'm going to get fired. I'm not getting fired. And we just purge that narrative from our mind. We get refocused, and it captures tons of time.
18:21Jason Feifer:It's like being aware of classic psychology, loss aversion theory, right? Our brains are programmed to protect against loss more than to seek gain. So we are constantly assessing what we have and what the risks are of losing it, which then can absolutely hold us back from actually just building upon it. I would say, I agree with that. And if we say it in the definitive, it is. It's not that it can. It does. There's zero cases in my entire practice, whether it's a student or all the way through retired CEOs of very large, notable companies that haven't faced this exact same thing. Sometimes it manifests as imposter syndrome.
19:06Sometimes it's just incredible amounts of fear. It comes through in different shapes and sizes and colors, but it is always there. I lived it myself. I literally, in building Triton, I wound up eroding enormous sums of time, including giving away weekend time and some precious family time and coaching my kids' baseball team with a headphone in on phone calls because I wasn't managing myself. And the fear of me not being present in a meeting and people interpreting that I'm not interested or that I, that I am absent caused me to do some crazy things that were massively stressful and eroded a lot of time.
19:50And the truth is nothing bad would have happened.
19:54Jason Feifer:Nothing bad would have happened. Right. How do we know that nothing bad is going to happen? I mean, the exercise that you just went through of the probability is very useful, but it also requires a real trust and belief that nothing bad is going to happen or being in a true 1 % situation, right? I mean, that example that you gave is really great and I love it because it's humanizing somebody at that particular moment in time. They've raised all this money. The company is on a rocket ship and they're still asking themselves, am I valuable or do people perceive me as valuable? Am I going to get canned?
20:33Jason Feifer:Which I think about all the time too myself. I'm in very, very positive situations, obviously at Entrepreneur where I'm the editor-in-chief, but also I work with a lot of different companies outside of Entrepreneur. I have a lot of relationships. People pay me money for lots of different things. And I get in bed at night and I think, have I done enough lately for XYZ person or thing? Or are they starting to wonder if they're wasting their money on me? So, um, so, you know, maybe like speak to the person who doesn't feel like they could put a 1 % chance of things going wrong. And maybe they're like, I don't know, maybe it's 50 50.
21:08Jason Feifer:I have no idea where I'm at. And you still want to give them the confidence that things are not going to go wrong. You need to focus on how best to use your time. Okay, so there's two ways that I like to look at this. One is, let's call it the 1 % bucket. That's where I refer to it metaphorically as like the devil and the angel that should sit on our shoulder. So the devil becomes our governor. That's the person that starts giving us that narrative. It's the person that's just chirping at us, the version of us that's just chirping us about all this bad stuff that could happen. that is incredibly low probability.
21:49And we have to just fire the devil. We have to just flick it off our shoulder, go away. I have one client that said to me, well, I can't fire my devil, so I'm just gonna send my devil on vacation. But I go through an exercise where we literally fire the devil. And firing the devil is very symbolic of I am no longer gonna allow that narrative to govern me. And when we become extremely aware of it, And when we manage ourselves, you manage you, it winds up making massive, massive differences. The second prong to that is when we as leaders are acting that way, other people on our team start acting that way.
22:29So you can tell people how to act or you can manage yourself and people follow the leader. It's just natural the way it happens. The second part of it to what you were asking is there are times where our performance is low or that issues come up or things happen. And when they do, those are the meaty topics that we have to get into where I could get fired or there is a real performance issue. When we can separate it from the devil and the angel. So the devil is giving us all his fault in there, but the angel is the one that is the real governor, the more appropriate governor. And in that governor governor situation, it could be, hey, we have to solve for this.
23:14Oftentimes, we don't have the space to solve for it because we're so riddled in the minutia and the little things. So when big things do come up, our capacity is constrained, we're fatigued, we're exhausted, we're in that hamster wheel or that churn, so we don't give ourselves that space. When the big meaty things come up, you rally the team, you solve problems, you win the crisis management, whatever the case Maybe every case, of course, is a little bit different. And if you get fired, you get fired. In most every case, someone is employable. They're good at what they do. They have great characteristics.
23:50I can't begin to tell you how many times I've heard from people post them getting fired about what a blessing it was. It was a bad fit. It was a round peg in a square hole type situation. Their fear systems didn't allow them to move on. All different kinds of scenarios. but good things can happen even from the worst case scenario like getting fired or losing a client. In your case, when you were saying, you know, the swirl that you're going through about, can I be doing more? Maybe just limit it. Okay, I'm going to take five minutes and swirl. And I'm just going to be in my, I'm going to let my devil govern me for five minutes.
24:31And you literally set a timer and you just swirl out for five minutes and you cap it. And then when the five minutes hit, it's over. And when you're managing you and you can follow that process, you're literally putting yourself in a five minute time spin or five way instead of hours, which can just, you know, become very negatively contagious and get out of control.
Read the full transcript
24:55Jason Feifer:I really love that. Neil, I really appreciate how you're taking these very, very human things and turning them into something that feels structured and almost physical. I can move it around. I can put it on a desk. I can look at it. And quantifiable because this is ultimately not just about how we feel. This is about how we're managing the day and you can't get more time back by doing that. So let me say once again the book by Neil Shore is called The 25th Hour. How to thrive and gain ridiculous amounts of time by getting out of your own way. Neil Shore, thank you so much for joining me on the show.
25:30Thank you. I'm excited. The book is launching August 11th. I'm a first-time author, and I'm really excited about it. And I've had my swirl moments, but we'll talk about that in a minute.
25:39Jason Feifer:I agree. And you will have more because book launches, they are extraordinary swirl events spoken from experience. I am seeing. And thank you so much. Really great to spend time with you.
26:04at CLA we're in your corner and on it we coach tax strategies and little league first base we help you adopt ai data tools and we adopt rescues named buddy we walk your factory floor and jog the local 5k though sometimes we walk that too wherever you're coming from we're right there with you wherever you're going we'll get you there CLA CPAs consultants and advisors Learn more at claconnect.com slash with you.
From the publisher
Executive Coach Neal Schore says that fear-driven habits are quietly
stealing at least an hour from your day, every day. Drawing from
decades of coaching founders, operators, and unicorn CEOs, Neal explains
how anxiety about being fired, judged by boards, or seen as “not
enough” leads to endless Slack chains, diluted meetings, and mental
“swirls” that crush focus and time. Neal and Entrepreneur
Editor in Chief Jason Feifer unpack why good things often start with
worst-case scenarios (like getting fired), how to stop overcompensating
out of fear, and why managing you—not everyone else—is the only
way to reclaim your calendar. He shares practical tools from his new book, The 25th Hour, like the “clarifying question” that can turn a 7-hour crisis into a 7-minute conversation, the devil/angel metaphor for fear versus real performance issues, and a simple five-minute “swirl limit” to stop catastrophic thinking from hijacking your nights and weekends. If you’re a founder or senior leader stuck in loss-aversion, overcommitting to boards, or living in constant “what if I get fired?” mode, this conversation shows
you how to get out of your own way, protect your time, and even see job
loss or client churn as the start of better fits—not the end of your
career.
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