The Italy Test: Could You Leave Your Business for a Month? 695

Can you get away? Like really get away? Get away, no phones, no email, no Slack, no messages, no WhatsApp. Can you get away or can you only like move your body but still be somewhere else? That's the question that I'm grappling with this week that I think is interesting to me, that was interesting to me, that still affects me today and the CEOs that I coach. So, That's our topic today. Hey everybody, I'm Bill Gallagher, scaling coach, host of this Scaling Up Business podcast. Show comes to you every week, 700 or so episodes now. Find them wherever you get your podcasts, all that. So, this is from a series of podcast episodes, solo shows, that are drawn from my book, Busy Is Broken. You can order it right now. As I release this episode, I am not here, but I'm probably getting on a plane or arriving in Greece as this, where I step away for 5 weeks to do research on my PhD related to the topic of the book, to finish the promotion for the book, which is due coming out now. So you can order the book, BusyIsBroken.com, Amazon, wherever you get your books, that kind of thing, go find it there. So, is AI and your team helping you or is it just giving you more things to do? Is it unburdening you and letting you think and live a great life, or is it just more things for you to supervise and shackling you? So that's my question today. In 2009, I realized something, that I couldn't get away. My business was really challenged at the time in 2009. I don't know, maybe yours is challenged today too. In good times and bad, it can feel like we're particularly challenged, no matter whether we're on the upslope or the downslope. I was in a rough spot in 2009 when I realized that I couldn't get away then, and I couldn't get away even in any good or bad times. And I realized that because that was the year that as we looked ahead to 2010, and you know, we're always— you probably do the same thing. You are looking at where you are now and looking at where you want to be in a year. I realized in conversation with my wife that this was the year that we said we were going to start to get away. We'd said long before we had kids that when they were like 10 to 14, before they got into the teenage years where they didn't want to talk to us anymore, but they were old enough to remember things, we were going to take serious time off. We were going to travel with them, particularly internationally, and expose them to the kinds of things that we had so valued from our growing up. So 2009 is there, and even in a good time, it was hard for me to get away. I would be on the phone, I would be on emails, on Zoom, or whatever the equivalent— back then it was more like Skype— but I would be on calls, meetings, things like that all the time. And in 2009, I was running a company that was particularly hard hit by the recession. So we were kind of on the ropes. So we're on the ropes, we realize this is the time we're supposed to get away, and I can't ever get away. I can't get away in good or bad times, right? We don't have AI. I do have a team at that point, but I'm in a strategic bind. So my wife and I looked at each other and we're like, well, we said that we're going to get away, and the kids and our family and that experience is more important than anything else. So next year when summer arrives, right? 2010, June of 2010, we're gonna go away for the summer. As soon as school gets out, we're gonna take off and we're gonna be gone. And, um, we'll do that with backpacks and sleep in parks or cheap places, um, uh, or we'll do it in hotels and, and live well depending on what we do with the business this year. So I realized that and we picked our place. We decided Italy was gonna be our destination. Uh, we considered a couple places, but Italy is where we ended up with June of 2010, we're going to Italy. It's now like fall of 2009, and I realize I have some work to do. I'm not only working on getting the business stable and healthy again with my wife— we worked together in those days— but I'm also then grappling with what's it going to take for me to be a different kind of leader. Now here's the interesting thing to notice. In those years, in those days, I had the structures. So, you talk about your who, I had my who. I had a team of people capable. I had operations and production and sales and service and accounting and finance and controller and I had all the roles. I had the plans. I had the dashboards. I had the daily huddle. I knew and was doing most of the Rockefeller Habits more than maybe many of you are. So I had all those things and yet I couldn't step away. Why? So if you have people and you've given them things to do, that's delegation, that's your who, that's setting up that thing, focusing on your unique ability, right? And yet, why are you still sometimes the bottleneck? Why are you still so essential? Because you're probably a micromanager. It could also be that you're a bit of a perfectionist, and it could also be that you can't get your head outside of the business, you're always in the business. So micromanagement, perfection— after the basics of delegation, there's micromanagement, there's delegation, there's delegation first, then there's micromanagement, perfectionism, actually letting things go, and there is then getting your head outside the business. Going to Italy would get my head outside the business, but not if I was on phone calls and email and messages and Skype or Zoom or like whatever at the time. So I had a question for myself in the mirror, but also for my team. So I announced to the team, "Hey, come June of next year," you know, now I'm announcing this fall of 2009, "June of 2010, I'm gonna go away. What are you gonna do about this situation," whatever it was, of the thing of the day, "when I'm not here, when Lori's not here? How will you handle this if I'm not a meddling in your micromanaging kind of boss?" I didn't call myself a micromanager exactly, I just I related to it— I don't know, they might have— but I related to it as I was helpful. I think by and large we had trained each other, right? So very often they wanted me involved in things. They, you know, if you come to me and I tell you what to do, then who's responsible for the course of action? Me, right? Not you. So it relieves some responsibility in some ways. It's also stifling if you're honest. But, um, but so a lot of people They were comfortable with that. But now for about 10 months, I kept asking the question, "What will you do when I'm gone? How would you handle this if I wasn't here?" I asked that question many different ways. I was going. I told people I was going. I planned the trip. I had tickets for the trip. I started to get things that were really concrete. It was in my calendar. I announced it. I was spending money towards doing it. I was really committed. I told the family that I was doing it. We told the kids. We started to get excited about it. So I'm getting ready to go and I'm training the forcing action of that caused something to shift. And then I, in addition to telling them that, pushing back, I also just gave myself little reminders like be curious or ask how they would solve a problem, ask what issues, what options they see. So I said, how are you going to handle this when I'm gone? I'm going to be gone. You're going to need to be able to do this thing. What ideas do you have? What risks do you see? That was the whole kind of conversation. 9, 10 months. Um, well, it worked. Um, so June comes and we take off. Uh, by that time we'd spent that time like pushing back and making the plans. We knew what to do. They had all the things that we had before, but now I was disengaged and they'd taken some time to grapple with, and I'd taken some time to get comfortable. We went to Italy. It was awesome. Jack had just turned 13. Sophie was 11. We went sailing. We drove around. We stayed up late. We played. We laughed. We lived like Italians. We had great meals. That was awesome. Today, Jack's 29. I have a 3-year-old granddaughter. He's an AI scientist at Anthropic. Sophie's, uh, 26. She'll be 27 soon. She lives in Los Angeles. She does, uh, direction and management for, for musical artists. She goes on tours. She's been recently working with a guy named Artemis. She's done all kinds of work with really cool people. Um, you You know, they're busy, they have their own lives. She lives in LA, Jack lives nearby, but he's busy with his life. And we'll never have that time again. But I had that time and the business got better. So I go on the trip and it's awesome. We play, we do all kinds of things. Every day I got a picture of the whiteboard and some comments about the daily huddle. Once a week I get a little more detailed dashboard and some commentary about the weekly meeting. No phone calls, no interventions, no emails, no special meetings. I didn't do any of that stuff. It worked okay. The team leveled up, I leveled up. The old Bill, the one who had to be in everything, never came back. When that trip was over, I came back to the business. I started taking long lunches with customers, employees, that kind of thing. I changed the way I led forever. You know, there's backslide, there's moments of things where I do stuff. There's moments where I'm not perfect. I didn't become superhuman and start to glow and elevate. But I was really— and it led to my being able to go be a full-time coach without actually selling that business. We changed the business. Lori changed the business after I left, but the business continues. So I didn't have to go back to doing it. That meant I could do other kinds of things in my life. The team could step up. They could be— some of them, one of them went on to start her own company. It's a cool company out in the world. Another went on to take executive positions in, in other businesses and moved on. So people moved on and grew and, and evolved from that thing. But I also moved on and I became a full-time coach and then went on from here. So there's something beautiful about that. It takes asking a couple questions. First of all, what's your Italy? Where would you go? What would you do? What kind of life would you have? Maybe you don't want to go to Italy or Bali or somewhere like that, but it could be that very often there's a marquee, kind of a, like a long significant trip, but it doesn't have to be that. Maybe you want to sail across an ocean. Maybe you want to take your family off somewhere. Maybe you don't have a— maybe you're past that. Like, what is it that you want? What is the life you want that you can't get away from work long enough to actually have, and you have that as a someday when I retire kind of a thing? What is that? When are you going to have that? So first of all, what is your Italy? What would you have in your life that you can't have because the way your job exists today, that you think you could only have after you sell the business? What's that? Then, what would break if you just took off today? If you just did that tomorrow, what are the things that would break? So where would you go, what kind of life would you have, and what would break if you just did that tomorrow without any preparation? Those are interesting questions. I think it'd be useful to share the answer to those questions with somebody else. Share it with a partner, a forum mate, um, an accountability buddy, a coach, um, your spouse, um, your family. Share with them what kind of life you'd have and what you'd want for yourself, your life, your Italy, um, your goal, like from a personal standpoint. And then Share with them what you think would break if you did it tomorrow, not a year from now. Then I suggest you actually declare it and talk to your team about where you'd like to go, what you'd like to do, and start to ask them, what would you need to do so that I, you and I could get to that place? How would you need to step up? What would, like, how would you evolve? That is kind of the work to do. Figure out where you want to go. Let some people know what it looks like for you, what your life— if it's not going somewhere, what does your life look like? And think about what would break, and then start to deal with that. Like, declare it, book it, commit it, um, or at least talk about it. And I mean, the, the stronger, more committed you are, the more powerful it'll be. And then start to grapple with what would be most likely to break, and then begin to go to work on that, right? I took 9, 10 months of repeatedly asking, "How will you handle this when I'm gone? How do we begin this?" So, 9 to 10 months. It helps if you have a coach, it helps if you have an accountability, forum mates, a buddy, something like that to keep that alive. But your family and your team can help you keep it alive as well. So, family, team, start to go to work on that thing. They want to get to that place, not because they care that you go to Italy or Hawaii or wherever it is, They care about the company growing. They care about their own careers stepping up. So, that's the opportunity for you. That's my challenge for you this week. I hope that's helpful. Enjoy that. In the next solo episode, I'm going to talk about a guy that I worked with the last couple of years who did it one way. He made some money. He grew his business. He sold his business. But it cost him some life, energy, time, and some family. So big life fan, and there was a lid on the business. And then he, he took 10 years off. He rethought about it. I started working with him on the second company, and the company is more than 10x bigger than the prior one had been, and his family is in much better shape. So the team's better, the business is much bigger, and his family's in better shape. That's our story next week. We'll talk about Tony Hartle and the Crunch Fitness franchise business.. So, till next time, keep scaling, keep thinking about what it is for you, right? You want to give things away to the team. You want to let AI free you up. You want all of those kinds of things, not just more stuck in the business. Hope that's helpful. We'll talk to you again next time. Keep scaling.