Ask Faleskini - The Midlife Crisis Clarity Compass
This is the Ask Faleskini - The Midlife Crisis Clarity Compass podcast. All the Life Lessons You Need to Thrive in Midlife. This is your Guided Path from Chaos to Clarity, Confidence, and Purpose.
Peter Faleskini and his guests discuss everything midlifers are worried about or interested in.
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Ask Faleskini - The Midlife Crisis Clarity Compass
How Do You Stop Overworking Before Executive Burnout Destroys Your Life? Bill Gallagher
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Are you constantly busy, working 50+ hours a week, and telling yourself it’s a necessary sacrifice for your business or career? In this episode of the Ask Faleskini podcast, Peter Faleskini sits down with former CEO and executive coach Bill Gallagher to unpack why "busy is broken" and how leaders can escape the trap of chronic overwork.
Bill shares his personal wake-up call when his workaholic habits threatened his family life, and how stepping back for a full month's sabbatical in Italy didn't destroy his business—it actually helped it scale.
Key Takeaways in This Episode:
- The Cost of Overworking: How working past 55 hours a week leads to severe health risks and impacts over 745,000 lives globally every year.
- The "Busy" Addiction: Why busyness is often used as an escapism mechanism or a response to childhood coping patterns and fear.
- The Sabotage of Perfectionism: Real-world examples of how leaders burn out their teams, ruin marriages, and crash companies by trying to do everything themselves.
- The 1-Month Sabbatical Experiment: How preparing his team to run without him for a month in Italy resulted in tripling their store presence and leveling up leadership.
- Books vs. Coaching: Why reading business books provides the framework, but long-term coaching and accountability build new, lasting habits.
About Bill Gallagher:
Bill Gallagher is a veteran CEO coach with decades of experience helping founders, partners, and corporate executives scale their organizations without sacrificing their personal lives. He is the author of Busy is Broken.
- Website & Diagnostic Tool: busyisbroken.com
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Peter's books
The Clarity Compass
Stop Midlife Burnout, Escape the Matrix, and Resolve Faleskini’s Complex
Faleskini’s complex
Diagnosing the Systemic Costs of Midlife Crisis and Advancing Holistic Pathways of Resolution
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Welcome to the Ask for the Skinny Podcast with a guest. I'm proud to present Bill Gallagher. Bill, welcome to the show. Please tell us more about yourself. What is your story?
SPEAKER_00That's a long story. As I turned 62 this month, that's a long story. So I let me give you the story as it relates to the book, right? So I am a coach for CEOs, and that's because I'm a former CEO. And I coach CEOs and leaders, partners, founders across companies. The message, though, is really uh pretty broad. And I wrote a book about it that's coming out right now. Busy is Broken. Busy is broken. I think a lot of people understand right from the title of the book, like it's about something. We are all too busy, especially in places like the United States. Uh, busy, busy, busy. Busy is a kind of a cultural phenomenon. And even if you're not from the United States, it affects us uh globally in a need to drive to do more, more, more. Unfortunately, we know that it has personal impacts. You feel it, you you sense it for yourself. Um, and the research is pretty clear too. There's uh um a study by the World Health Organization back a few years ago who found 745,000 deaths a year came from working past 55 hours. So you know who you are. Even if you're working 50 hours, you're starting to show the signs of stress in your life. It starts to have personal impacts. The thing is, in business, what I told myself, what my clients tell themselves all the time is I'm making a sacrifice. We think it's only on us. I'm making a sacrifice to grow my business, to build my department, to do this thing. And we don't realize that not only is it having the personal impacts, it actually hurts the business also. And that's really what I saw for myself. You know, many years ago, long before I had that epiphany, I remember coming home one day late. Uh, I'd been working late, conference calls went late, projects went late, I was late for dinner. My wife was also an entrepreneur, but she prioritized more getting home for the kids. She got home, she had the dinner, the kids were done. I was late, I missed the dinner. I walked in late, I was still on the phone. I was on the phone talking, talking, trying to finish up, right? The client or vendor, whoever it was on the phone, I I have long since forgotten. Talked and talked and talked. I couldn't get off politely. Eventually I get off. 15 minutes goes by. I see them looking at me from the other room. I wave to them. Uh, once I hang up the phone, my wife walks over to me and she says, Look, if you are just going to be on the phone when you get home, we don't need you at home. And it was like a dagger to my heart, right? Like I was trying so hard to be there to be good. But even when I got home, I would take a few phone calls, I would handle a few things, I would look at my email, I would, I wasn't really there, right? And that's the first shot. And I still struggled with it for several years. But then um in uh 2008, I was running a jewelry business with my wife, and uh we were in a, of course, in a huge like period of difficulty and that kind of thing. 2008, we had the global recession uh brought on by the real estate crisis, but it affected everything because people stopped spending money. And so my jewelry was in, my jewelry business was in crisis, and in that year, as we thought about our lives and what we were grappling with, we remembered that when we got married, before we had children, long before all of that, you know, years earlier, uh, we said when our kids reached a certain age, we were going to take real time off. We were gonna go to Europe, we were gonna travel, we were spending months and months away. Except now I'm in a crisis. Now the kids are this age. It's time to do this. We said, we promised, and I can't get away. As a CEO, an entrepreneur in North America, I couldn't go away for a week without phone calls, emails, Skype, Zoom, like whatever. You know, I had things to do, and I couldn't really ever fully get away. Not for a week, not for two weeks, not for months for sure. Uh, so we see that, and I realize I have to do something. So we said, I'm going to get away. I'm going to go away. I'm going to do what I have to do. We'll do it really nicely with hotels, or we'll do it in um backpacking, camping, sleeping outside if we have to. And uh, but I had a year. So the kids are uh 10 and 12, they're gonna be 11 and 13. We're starting to think about our life plans. And so I started for a year to ask my staff, what are you gonna do when I'm gone? Next summer, we're going away. What are you gonna do? How will you handle this? So every time they brought something new, I said, next summer I'm going away. If this was next summer, how would you handle this? So I had a forcing function, an event that I committed to with my wife, no matter what, and we're going away. And and then I worked on it for a whole year. And um, you know, it was amazing. So it took repetition, it was actually only about 10 months uh of working on it over time, but it took real real repetition and focus. Come that summer, the summer of 20 2010 in June, the kids got out of school and we left and we went to Italy for a whole month. And in that time, the business increased, the staff leveled up. We in that time we tripled the number of stores that our product was sold in, we increased all kinds of things. Everybody did fine. I also had a great time. I got reports every day, every week, but I wasn't in phone calls and emails and things like that. I knew that everything was okay. I relaxed, I enjoyed myself, I had time with the family. Uh, I changed who I was as a leader. The business changed who they were and how they operated. And the old version of me didn't ever have to go back. So it took some time to make that kind of change, but it but it had a profound impact. Look, so the business went up, I got better, and that's part of what led me to then become a coach in a few years, is that kind of thing. Now, um, that was 2010, right? It's 2026 now. My son Jack is an AI scientist with uh Anthropic. I have a three-year-old granddaughter. My daughter is a uh art director, photographer, um, working for musicians and performers and in Los Angeles. The kids are grown. 27, 29. That time, though, you know, 11 and 13, sailing, driving, eating well, we have that forever. That not only benefited me and my life and my family, but also the business. And that kind of is what I I then went out to to coach. And and after some time, seeing my clients, both good and bad, I ended up writing the book, Busy is broken, to talk about that.
SPEAKER_01I I really like the concept, and I have so many questions. I would like to.
SPEAKER_00Sorry, I just went on.
SPEAKER_01No, no, it's it's great. You explained a lot, but um would you say that we are somehow addicted to being the busy? And this is busy, just additional addiction that we take on ourselves. And it's also an escapism in a way, because we are handy. Escaping the the real life being the busy.
SPEAKER_00Yes. Look, if the only hobby you have, or your main hobby is your business, you need a new hobby. Um, and and we lean into it and and it we inherit it. It is the culture we live in, it's the environment. In the United States, it started with the Puritan ethic. Benjamin Franklin said, time is money. We have the frontier mentality of keeping busy and surviving. We have the development of the modern factory, we have uh the um we have the 40-hour work week, but then we have management and and that kind of thing. We have Milton Friedman telling us to do more and be more efficient. And then we get our smartphones, we get um uh we get, and then the pandemic happens and work from home, work equals home, there's no separation anymore. All of that changes. You know, in some countries, I know you're in Europe, there there can be a little more protection of boundaries and personal kinds of things, but not necessarily among entrepreneurs, because entrepreneurs don't look to Europe and admire the productivity of the business. They look to the United States and they're like, oh, we want to be like that kind of entrepreneur. So wherever you are in the world, and in in Asia, we have the 996 phenomenon where people literally work themselves to death. So we have this thing, and we do it for lots of reasons. A lot of them are fear-driven. I'm afraid of failing, uh, I'm afraid of being enough. I don't know what else to do. Uh, I don't want to look at that, so I'll look at this. I know how to win at work, and I don't know how to win with that relationship or with my kid right now, so I'll just work harder. I had uh an executive tell me in a company that I was running some years ago, oh, my kids drive me crazy, but at work I know what I'm doing. And I appreciated her world because I could relate sometimes. It could be simpler.
SPEAKER_01It's interesting how uh we focus so much on the work, and we completely forget what is important in in our life because we just work basically to pay our um or most of the uh people who work to pay the invoices uh and all all the bills on the end of the month, but we completely forgot that that's uh that's not the reason.
SPEAKER_00You know, one of one of my clients a few years ago, this is a fairly tragic story. He um uh he he bought a company. It was the first time as CEO, and um he tried to work two, three hours a night, and he was strong, he was passionate. And so he was uh sleeping two, three hours a night and working and working and working and driving his company, but he was a perfectionist, he couldn't let things go. He was working too many hours, he was making his team crazy, um, confusing things, layering, reading not just one book or two books or whatever, but reading books like non-stop. And then he'd be like, oh, wait, we need to do OKRs. Oh, wait, we need to do radical transparency. Oh, wait, we need to do this or that. One thing after another, nonstop. And it made his team crazy, it made his team ineffective, it burned out his health. In the middle of all that, he got married and he started a family. But before uh the business failed, his family failed. So even after uh getting married, having a child, um, he very quickly tanked that, trying to work two and three hours a night. Uh and then soon enough, the business too failed. So uh he's at one of the stories in the book, Eddie ruined the company and ruined his life. Um, it doesn't have to be that way. I have other clients who are more like I was who had a wake-up call, who are like, oh, I need to make a change. And what I see again and again is if they do it thoughtfully, they actually make both their life and the business better, right? Uh one of my clients, um uh uh Tony Hartle, who we name uh and don't anonymize in the book, um, started his first company, he grew it, his marriage didn't last. He grew it, he sold it, he made some money. It was good. But he was trying to do every job, work impossible hours. He took 10 years off. He thought about it, he reflected it, he realized it was about leverage, about working with other people that really mattered. And when he started the next company and I started working with him, he worked differently. Today he has thousands of employees. The company is growing, it's tracking on a billion-dollar valuation in 100 locations now. Um, and Tony gets home most nights for dinner. He's there in the morning with the kids. He's there in the morning, he's there in the evening. He's making sure his second family doesn't pay the price that his first family did. And the fascinating thing is Tony's company is much stronger because his team has to do their job if he's not filling in for them.
SPEAKER_01Yeah. So uh would you agree that a lot of uh uh mistakes that uh we do in our business and life uh comes down to the unresolved uh childhood traumas and fears and grudges that we hold.
SPEAKER_00So time and again, the responses that we see to stress, to fear um are childhood-based patterns, right? And I'm not a psychologist, I don't have that particular background, but I know enough to see that the move that you did to get by in early school years and in your middle school years, those patterns you do again and again when life presents itself. So uh, but as your business grows, it's a different kind of world and you need to develop new patterns, not just go back to the ones you did as a kid, right? If the other kids in your study group didn't do their homework and you filled in for them on their assignment, that's great. It gets the assignment done, it gets you the grade when you're 12 years old. But when you're 35 or 45 and you're trying to grow a business, helping fill in the thing to get the project done doesn't build a business. It gets the project done, it gets you the sale, it gets you the client, it doesn't build a business that runs without you.
SPEAKER_01I I would agree with that. And I have a question uh for you. Uh you wrote the book and you're also a coach. So how far can a book take us? And when is the time to consider a coach?
SPEAKER_00Well, look, I I I am uh I've been using coaches, I use coaches today. I'm always looking for my next coach. Um, I I have worked through many coaches, I'm still in contact with my coaches. So I'm a big fan of coaches and I'm a coach for a living. Um, I would say the book gets us started. The book is where we pick up the stories, the book is where we see the model, the book is the source for learning, the book adds legitimacy, it gets you going. Then it's time to engage a group. Now, you can work on uh the concepts of a book with a coach specific to that book, or you can go take it to some other group, support group, or and work through something. But it's consistency over time and with other people that makes the big difference. So I designed my life and my job to step away and go to Italy, but it wasn't until I told my wife, my team, everybody that I was going to Italy and we work together. I had a coach in those days also who helped me with that work. Um, and I had my team surrounding me. So, coaches, your team, various kinds of accountability, not just a drill sergeant, but a structure of people around you that's pulling forth a new you, new patterns. Because those habits that we start as a kid, those are very easy, right? We go back to those unconsciously. So developing a new habit and even, you know, a year of work, it takes sustaining that over time. You will naturally go back for the rest of your life to some of those childhood habits.
SPEAKER_01Amazing. Bill, where can our listeners uh get in touch with you and uh where can they order your book?
SPEAKER_00Well, just go to busyisbroken.com. That's the website, and there's information, there's downloads, you can get stuff like that. That'll keep changing as the book comes out right now. What's on that website? But they can sign up and get on the mailing list, they can find out, they can get our diagnostic. Um, we have a PhD version of the diagnostic right now that's going for the my academic research that they can go do right on the website. And then they um can come to one of our events or have me come to speak at that. So busyisbroken.com is the website, and then of course, wherever you buy your books, if you go to Amazon, you can order the book right now.
SPEAKER_01Bill, thank you for all these insights. Thank you for sharing it with uh our listeners and uh thank you for being my guest tonight.
SPEAKER_00Thank you.