The Mindful Midlife Crisis

Episode 63--Escape the 9-5 Grind with Brian Gallagher (aka The Simple Man Guide)

June 15, 2022 Billy & Brian Season 5
The Mindful Midlife Crisis
Episode 63--Escape the 9-5 Grind with Brian Gallagher (aka The Simple Man Guide)
Show Notes Transcript

This week, we talk to Brian Gallagher.  Brian is a former Corporate American turned Global Citizen. After a career in finance, several years as a fitness studio owner, and giving away 99% of my belongings, Brian left the traditional path to see the world and live life on his own terms. Brian created Simple Man Guide, a personal brand dedicated to helping others leave the corporate world behind, simplify their lives, and regain power over their most precious asset - time. Brian is currently living with his girlfriend in Amsterdam, and he is working on his 1:1 coaching program, Take The Leap, which helps others fund their corporate escape, ditch their 9-5 grind, monetize their favorite skills, and live their dream life.

We ask Brian:
--You left the 9-5 grind a few years ago.  Walk us through that.
 --When you look back on the 9-5 grind and when you talk about that with your clients, what are a few things that come up as far as things they’d like to never do again? 
--What’s the danger in, “Well, I’m unhappy at my job HERE, so I’ll just get another job doing the same thing somewhere else”?
 --How has the increased demand for working remotely shifted the way you work with clients?  Do you think working remotely frees some people up from the 9-5 grind, or is your goal more to liberate people from Corporate America?  Like, what do you have against Corporate America?!
 --One thing you continually stress, which I think is extremely responsible of you, is that if someone wants to escape the 9-5 grind, they need to sit down and REALLY take a look at what they’re financially responsible for before just saying, “Fuck it! I’m out!”  What does that process/conversation look like with you?
 --So you and I are very similar in that neither of us have ever been married or have children.  As someone who struggles with impostor syndrome, I’m wondering how often “You just don’t get it…I have a family” comes up in a conversation.
--What are some other self-limiting beliefs you hear from your clients and how do you navigate those beliefs with them?
--What’s the best part about what you do?  Where to next?  

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Brian Gallagher: I really love being able to see the light bulb going off in people’s heads, like figuring out what they want to do is definitely attainable if they just stop and think about it. I love that red light analogy, Billy, like, yes, I want people to slow down, stop, think, and question everything. Question why they’re going to go right and run to another corporate job. Why is that? So thinking about those things and helping people stop, slow down, and think, that’s one of the biggest things I love about what I do is seeing that light bulb go off in someone’s head.


Welcome to The Mindful Midlife Crisis, a podcast for people navigating the complexities and possibilities of life’s second half. Join your hosts, Billy and Brian, a couple of average dudes who will serve as your armchair life coaches as we share our life experiences, both the good and the bad, in an effort to help us all better understand how we can enjoy and make the most of the life we have left to live in a more meaningful way. Take a deep breath, embrace the present, and journey with us through The Mindful Midlife Crisis.


Billy: Welcome to The Mindful Midlife Crisis. I’m your host, Billy, and, as always, I’m joined by my good friend, Brian on the Bass. Brian, how you doing over there, man? 


Brian: I’m high caliber today, Billy. 


Billy: Ooh, high caliber. Why are you feeling so high caliber today? 


Brian: I’m above the line. I’m a cut above. I’m reaching higher. I’m doing better.


Billy: Than ever before or just the normal?


Brian: No, just better.


Billy: Okay. Yeah. 


Brian: That translates to high caliber, I guess.


Billy: Our goal is to just get 1 percent better each and every single day. Isn’t that sort of the theme of our podcast right here is to try and get 1 percent better each and every single day?


Brian: Our listeners we’re hoping get 1 percent better every day. That’s the stuff. We’re hoping to take them with us.


Billy: Absolutely, and the way that we do that is we bring on high-caliber guests, like our guest today. Our guest today is Brian Gallagher. He is a former corporate American turned global citizen. After a career in finance, several years as a fitness studio owner, and giving away 99 percent of his belongings, Brian left the traditional path to see the world and live life on his own terms. Brian created Simple Man Guide, a personal brand dedicated to helping others leave the corporate world behind, simplify their lives, and regain power over their most precious asset: time. You can actually follow him on Instagram at @simplemanguide. Brian is currently straight east of me in Mérida, Mexico, working on his one-to-one coaching program, Take the Leap, which helps others fund their corporate escape, ditch their nine-to-five grind, monetize their favorite skills, and live their dream life. Welcome to the show, Brian Gallagher.


Brian Gallagher: Thank you, guys. Quite an intro. 


Billy: Yeah. Yeah, it’s important to sell yourself. It’s important to showcase your many attributes and your many talents and your many accomplishments so we might as well get them all out there. So, Brian, one thing that we like to do is we like to have our guests talk about the 10 roles that they play in their life. So, what are the 10 roles that you play in your life? 


Brian Gallagher: All right. This is a very, very good question, by the way, and this could have gone a number of ways. I tried to give you have a fairly diverse one, wherever the conversation wants to head in the next hour and a half or so. All right, so here are my 10, they’re in this order but this does not have any particular relevance to the order here. So here’s the 10: global citizen, designer of lifestyles, former corporate American, workout nut, adventurer, writer, speaker, boyfriend, threw that in for my girlfriend, Civil War nerd, and questioner. 


Billy: I do like that your girlfriend’s Instagram is @complexwomanguide. 


Brian Gallagher: She’s completely jacking my style. She liked it and stole it. And it’s super cute.


Billy: That’s wonderful. I’m curious here because she’s Italian, correct? So did you meet her during your travels here because you’ve been able to free up your life a bit? 


Brian Gallagher: No, I met her when I was in New York before I left for my travels. I met her on Instagram. I just haphazardly shot a DM across the Atlantic and it connected and we started chatting, I went over to meet her like two months later, and we’ve been together ever since. This July will be three years since I sent her that first DM.


Billy: Oh, that’s a great story. I love that. Seeing as you reached across the globe virtually here to find your girlfriend, let’s talk about this idea of being a global citizen. So, that’s one of the roles that you’re most looking forward to in the second half of life. Talk about what is that, a global citizen?


Brian Gallagher: I mean, not in the extreme sense, like I’m talking about like Albert Einstein was looking at like renouncing his citizenship. I haven’t gone that far yet. But I do like the idea of just being able to pick up and go anywhere that I want to go at any given time for any amount of time pending any visa, you know, like Europe, for instance, I have to go for three months and then I have to leave for three months unless I get a longer term visa. I like being able to do that and it just gives me a level of flexibility and adventure that nothing else has before and I want to keep that up as long as I can. That is one of the three that I’m looking forward to in the second half of my life. 


Billy: Yeah, and you also have speaker here. So, talk about that. I’ve followed you for a while here on Instagram and I don’t know what sort of speaking you have done yet. So tell us more about your speaking gigs. 


Brian Gallagher: I’ve only done two at this point. They were a few years back. I haven’t done any in a while but I put that there in a manifestation sense. I want to do that and I love — I actually love speaking. When I first started my corporate roles, I did not. I was very shy, I didn’t feel like getting up in front anybody —


Brian: Most people don’t. 


Brian Gallagher: — and I don’t know if that was because, yeah, I don’t know if it was because of the shit I was talking about, I couldn’t care less about so I didn’t really have an interest in like learning it deeply enough to be able to share with others, but then when I got into opening the fitness studio, I did what I considered like four or five mini presentations to 15 or 20 people per day, four or five per day, for years. Me and my partner figured it out. We each taught over 3,000 classes. I got so used to speaking in front of people that, now, it does not bother me and I have a message that I want to share. I have a pretty aggressive goal for myself and it’s to help a thousand people leave the corporate world behind and go live life on their terms and whatever that life is for them. It doesn’t mean that they have to go travel around the world and work from wherever they want. I want to help them live the life they want to live but I want them to do that outside of the bounds of a corporate job if they don’t like it, which majority of the people that you talk to tend to not like what they’re doing. 


Billy: Well, and that kind of brings up this point here, you put questioner and I noticed that on a lot of your Instagram posts, you put, “Question everything,” at the bottom of that. So, where does that come from, “Question everything”? What makes you a questioner in general?


Brian Gallagher: I never like to just blindly do what everyone else does. And part of the reason that I write that is because the first half of my life, I did that. I went to college, I got a corporate job, I stayed there, I planned on getting married, having a house, having two cars, having all this nice stuff, and then after a while, I was like, hold up, I mean, this is not really what I want. This is not contributing to my happiness. And then I started to question everything. But if I had done that earlier, maybe it would have had led me on a different path. I have no regrets with the path I chose because it got me to where I am now but I don’t know what would have become if I had started doing what I wanted to do when I was 20 years old instead of 34. Fourteen years of doing something that you love, I mean, that’s a lot of time to get really good at something. And I didn’t do that and I would encourage others to kind of explore what it is they enjoy, because I think of it, the example I think of for myself is that I chose finance as a school major not because I liked it, shit, I didn’t even know what the hell it was or what I was going to do with it, but it was because it had the potential to make me the most money. And I wish I would have thought more about something that I liked or followed a path that I liked without this fear of like, “You gotta chase the money, you gotta chase the money,” like I wanted to go into physical therapy because I love working out, I love helping people do that stuff, but all I kept hearing was, “Yeah, you’re gonna be taping ankles for the rest of your life.” Yeah, maybe, but it’s a job that I love and like there’s more of a curiosity behind it and that encourages you to dig deeper into something. There might be something that you really enjoy out of that and you could be the guy that does it and everybody comes to you for this or you write this book or you discover this thing or whatever it is. But I know for one thing, if I’m a finance guy, I’m not going to discover anything because I have no interest to learn about it outside of what I have to do within the confines of my job. So that’s why I want to question everything, why I’m doing something, why I’m not doing something. That’s the reason behind it. 


Billy: It sounds like you got caught up in the checklist that Dr. Yolanda Holloway and Tiffany Byrd talked about in episode 43, I believe it was, and we talked about trash the checklist, and, again, if you’re not listening to the Trash the Checklist podcast, what are you doing with your life? You need to check it out. That’s a fantastic podcast for everybody to listen to. But I think it’s important for us to dive a little bit deeper into questioning the checklist, which you have done and you’re on this pursuit now to be a speaker and a global citizen and to help at least a thousand people leave their corporate jobs. So let’s do this. We’re going to take a quick break and then when we come back, we’re going to continue talking to Brian Gallagher. 


Thank you for listening to the mindful midlife crisis.



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If you’re listening somewhere safe and quiet, close your eyes and slowly inhale for four, three, two, one. Hold for seven, six, five, four, three, two, one. Slowly exhale for eight, seven, six, five, four, three, two, one. Let’s do that one more time. Inhale for four, three, two, one. Hold for seven, six, five, four, three, two, one. Slowly exhale for eight, seven, six, five, four, three, two, one. Go ahead and open your eyes. You feel better? We certainly hope so. And now back to the show.


Billy: Welcome back to The Mindful Midlife Crisis. We are here with global citizen Brian Gallagher. He is a former corporate American who left that life and is now doing his own thing. He is trying to help people leave that corporate life. You can follow him at @simplemanguide on Instagram. So, Brian, just kind of tell us a story here about leaving that nine-to-five grind. 


Brian Gallagher: I got let go, let’s start there. That’s the easiest way to get into that. But it was not out of nowhere. I was — it was out of nowhere to be let go but I had already been working on my exit for probably six to eight months at this point. My last day was — it’s coming up on eight years in 10 days, February 20th was the day that I got let go. But back in probably a year before, my business partner, Ryan, had approached me. He used to work with me at this bank that I got let go from and he had since left but he asked me if I wanted to have lunch with him and we were in Rink Bar in Rockefeller Center and he’s like, “Look, I got this idea for a fitness studio. Here it is. Are you interested in working on it?” I was like, “Yes. 1,000 percent yes.” I was like this is it, this is my way out. So in the background, we were working on that, talking to investors, creating a business plan, everything in PowerPoint like a good little investment banker would do, that’s exactly what we did. And then we finally started to teach classes because we were like, “We’re gonna open this fitness studio and we haven’t taught a single class yet. How is that gonna work?” So we rented some equipment, we rented a space, we started teaching classes. We did that for about eight months before that February date where I got let go. We had actually signed a lease for the studio on Valentine’s Day, six days before I got let go so my plan was to leave, I was waiting for my bonus check to hit. If anyone’s familiar how the pay structure works in investment banking, half your compensation comes in one check three months after the year ends. So I was waiting for that check to hit. In the meantime, my firm was planning to let me go and they did and they gave me severance, they gave me a bonus, and then I left and then I was off to the races. We had decided that one of us was going to have to leave their job anyway to get the studio up and running because we signed the lease on February 14th, we were going to start hosting classes on April 1st when the lease like officially started so we had six weeks to get the studio ready. I was the one that was going to leave. So March 3rd was my quit date, or my escape date, as I was calling it, but they let me go 10 days before which seemed shocking at first but I got to tell you the hardest part was sitting in that meeting and holding back my smile from them telling me that they were going to pay me and all this stuff and I was like, “Man, if you guys had any idea what I was about to do 10 days from now.” So it worked out pretty well. But, prior to that, things started to like go off in my head, like I’m not happy doing this, what kind of work am I doing? I’m dicking around in PowerPoint, all day every day in Excel, and my work is not really exciting me anymore. I have no intellectual curiosity to go out and learn more about it and like do the things that you would do if you were involved in something that you were interested in. It was kind of like I can’t wait to get out of here. I was so dreading the five days a week to live the two that were mine, but when you’re in banking, those two were not really yours. You might have off, you might not, so it was really like savoring any free time that I had and try not to think of work but the environment was so stressful and so fast paced and everybody wanted the work they assigned to you two days ago, it was kind of crazy. Now, they paid me very well. I mean, I got paid very well for that. But after a while, once I had my debts paid off and I had a pretty comfortable savings cushion, and then this whole idea of like minimalism hit me. When I went on a trip to Kilimanjaro in 2012, I had the best three weeks of my life with just a backpack, some clothes, and the essential foods that I needed to survive and hike and the water I needed. And it was like I came back and I was like, “Well, I have so many things that I don’t care about or I don’t need or I don’t use,” and I went on a complete spree and got rid of everything in my apartment, to the fact that like people were like, “Wow, did you just move in here?” I was like, “No, I’ve been here for eight years. I just get rid of everything.” So then I was like I don’t need all these things, I don’t need all this money, and if I don’t need all this money, I don’t need to give away all my time in exchange for it. So then I was like, well, I don’t even need this job. And then I started to like I really got disconnected from it. I was like, I went on like a path of least resistance, which is probably 50 percent of the reason I ended up getting let go anyway. It was like I wasn’t sticking my head out for new projects, I wasn’t like, “Hey, I’m willing to work.” It was like somebody gave me work, I hid under my desk, I did it so nobody could find me, and then I would just kind of wait around for somebody else to kind of find me and I was not taking initiative, I was not going out and seeking new projects or new growth opportunities or any of that shit. So the time finally came where it was like I wanted to leave, they wanted me out of there because I wasn’t going to continue to climb the levels here, and it all kind of worked out in everybody’s favor. Everybody kind of got what they wanted. So, it was a long time coming. I was in corporate for 11 years. I worked two jobs in that period. I was in accounting at Johnson and Johnson. Hated it. I knew within the first two months, it was like this is not for me, but I stuck it out for two years to graduate this program I was a part of and then, almost immediately after I graduated, I found this investment banking job and I left and then I stayed in this banking job for nine years then went to the fitness studio. But the corporate grind was, everything about it just started to kind of make me kind of sick of it after a while, like in New York, I was like, “I can’t wait to wear — I get to wear suits every day at work, I can’t wait to go dress up nice,” and then, at the end, I was like, “Oh, my God, I’m never wearing a tie ever in my life again.” I have not worn a tie since and that’s like my one thing I refuse to wear because of what it represents to me. I’m like, first of all, it’s a stupid, useless piece of clothing. It was like I had to wear one every day and it was like the final thing of like making me feel like a prisoner, it was like just tying that not every day was like, “No, this is suffocating. I’m never wearing this again,” and I haven’t.


Brian: Good for you. 


Billy: So I am not a fan of the follow your passion ideology. I think it’s very short sighted. Do you feel like you had to go through that nine-to-five time in your life in order for you to get to the point where you are now? 


Brian Gallagher: Yes and no, and I want to back up. The follow your passion advice, I don’t think is bad, I think it’s not complete. I have passions, like I have a passion to like go and find cool places to work out. It would really be difficult to make a living at that but that’s what I love to do. Now, if I could do other things with that, like follow your passion and then team it up with your skills and then maybe if you have some other experience you can kind of mix in, follow your passion is not bad, in my opinion, it’s incomplete. To answer your second question, like, yes, I did need all of that experience to do what I’m doing now. Did I need it to follow my passion and go more into fitness? No, absolutely not, but I couldn’t have graduated college or not even gone to college and be like, “I’m gonna be a coach.” I don’t have anything to teach, I don’t have any experience, I don’t have any skills, I have no knowledge. The stuff that I’ve learned and the things that I’ve done in my 11 years in the corporate and how I use those to get out of corporate and do what I’m doing now I feel is something that is useful for other people to hear, to see, to know that they can do the same thing. I’m not special. I didn’t come from a wealthy family. I didn’t inherit a shitload of money, like I came out of school with $40,000 in debt and I had to figure out how to pay it out. Now, fortunately, for me, I had a well-paying job and I was able to pay it off quicker than average, but I also lived in a very expensive area too so it wasn’t like you can’t just say like I just made a shitload of money. I kept my expenses purposely low after I kind of figured out what I wanted to do. So I lived in a two-bedroom with a roommate. I didn’t go on super fancy trips all the time. I didn’t go to the hottest restaurants in New York all the time. I didn’t buy a car in New York. That was one of the things that some of my friends were doing, they were like buying cars. Once they got like a bonus check, they’re like, “I think I’m gonna get a car.” I’m like, “For what?” I didn’t see the point in any of it. But then what I’ve realized, like what I could do with the excess money that I was able to save from not spending on this, I don’t like to say stupid shit, it was stupid to me, but I like to say distracting shit, like taking me away from what I really wanted to do, like, yeah, if you want a nice car, cool, if you don’t mind giving all of your time away at a corporate job, have at it. Like I’m not here to judge anybody. You do what you want to do. But, for me, that just didn’t make any sense. I don’t really care. I’d rather — in New York City, I was just reading about this today, I worked at a WeWork that was three miles away from my apartment and fuck if I was ever going to drive to that, I’d rather run. It was 20 minutes to run. It would have taken me 45 to drive. I’m like, “What am I? Nuts?” like no way, I’ll run, it’s just so much better, like it made me a better person doing that for six months than anything else I’ve done when I was in New York, Just kind of thinking about what I was doing with my money and what I wanted my money to do for me, it just helped me make the decision that much quicker. And what I’ve been able to do now that I’ve done that is condensed that timeframe and take all those things that took me years to figure out and years to do, now I can help somebody figure it out much quicker, like what took me five years, I can walk somebody through all the stuff that I did and I can walk them through it in 45 days and they can be ready to leave their job. Now, not going to be able to leave their job in 45 days, that is very variable, like depending on where you’re starting. But we can get a plan together in a few weeks like to what you’re going to do. 


Billy: So you alluded to the tie not wanting to wear that again and when you look back on your nine-to-five grind and when you talk to other people, what are a few things that come up as far as things they never like to do again, where they can get that time back? 


Brian Gallagher: Meetings is a huge one. I mean, just the amount of time that they had to spend doing bureaucratic work with other people that almost seems unnecessary and like I’ve had people mentioned, “Man, some of the stuff I do, I wonder if it just didn’t get done, would anybody notice? Is it even worthwhile doing?” I just had a call with somebody yesterday who was trying to figure out what their plan is. They’re unsure whether or not they’re going to be forced back into the office. And I think, I mean, given the situation now, I think a lot of people are going to be dealing with this too, especially if people have moved out of the major city areas that they were living in to avoid expenses and all that, to avoid congestion, and, now, if offices are saying, “Yeah, we want you to come back in,” like the commute, that’s a huge waste of time for a lot of people. I mean, especially if you’re driving. Talk about more of a waste of time. I mean, my first corporate job, I drove an hour each way and that’s two hours a day that is just completely wasted. I mean, now, at least, you can like listen to a podcast, it’s not completely wasted and you can actually take steps to move you in a different direction, but when I was out of college 20 years ago, I mean, I hate even saying that, 20 years ago, I feel so old, but there wasn’t podcasts. It was like books on tape were just coming out, it’s like you could start to do that stuff. But a commute is just a complete waste of time now, especially because we know that we can all work from home. It has worked for everyone, it had to work for everyone for two years, and like if you’re in a corporate job now and you don’t want to go back to the office, I mean, you should just dig your heels in and not go back, or go find something else that’s remote. I mean, there are plenty of opportunities now that I think are going to be remote, unless you are like dying to get back into the office. Which some people are. I mean, that’s totally fine, it’s whatever you like to do, if you love the interaction with people and you like that corporate environment. I just hated it so it’s like it wasn’t for me. If you’re one of those people and you like the idea of working remotely, stand your ground, because it’s clear that it works for people. And, I mean, yeah, I’m trying to think if there’s anything else that I missed in that about like the corporate stuff that people want to avoid. I mean, there’s bosses and toxic environments, I mean, all this usual stuff, like we know these things, especially those that have dealt with those environments and worked at corporate jobs and maybe know how they’re like. I mean, making it a successful time for you in a corporate job doesn’t always mean how well you do your work, it’s how well you can play the game and play with other people and play other people off one another and do that kind of stuff and kiss your boss’s ass. I mean, all the stuff that — I don’t know, I just don’t have time for it anymore. I just don’t want to do that. And I want to help people who feel the same. If you don’t want to do this anymore, there are options, let’s talk. 


Billy: My brother-in-law works for a large corporation, I was staying with my sister for a month, e’s working remotely now and he absolutely loves it, because if he doesn’t have a meeting, he’ll go for a walk and get some fresh air and that’s time that he gets back from never having to commute. And if you live in Minnesota, December to February is not a fun time to be on the road at all because if it’s a snowstorm, that instantly just doubled your commute, anywhere you want to go, at least. And by the time you get home, you’re so frazzled from that drive because you’ve been white knuckling it the whole time that not only are you exhausted from a work day but you’re also exhausted from that commute, what do you have left to give to your family or even to yourself? That really is a time suck and so I’m transitioning into this and, truth be told, Brian and I are actually having a half-hour sit down here to talk about what potential opportunities there are for me out there here as I make this transition. So I’m greatly looking forward to having that conversation with you, Brian. So you kind of talked about this already but how has the increased demand for working remotely shifted the way you’re now working with clients? And is it more of a goal to liberate them from corporate America or is it a goal to help them transition into something that allows them more time?


Brian Gallagher: I’m looking at this through my lens but I have to focus to not do that for helping other people. I want to help other people do what it is they want to do, whether that’s leave corporate America or find a more flexible situation for themselves, like not working in corporate America is not going to be an option. A lot of people are very risk averse and the emotional toll that the drive to have to eat what you kill, as you will, as you work for yourself, I mean, that is a tough toll and it takes a lot out on people and if people are not in a situation where they can take those risks, part of the thing I help them do is put them in a situation where they can take those risks, but if they are not willing to do that, that’s fine. We can work on a plan to get you in a more flexible situation that fits what you want. Again, the goal of this program, I know, I talk about getting you out of corporate America because that’s what I did and that’s what I feel a lot of people would like to do if they can understand that it is an option. 


Billy: I was going to say, what do you got against corporate America, man?


Brian Gallagher: I have nothing against it. I have everything against the idea of one staying in a job that they hate because they feel stuck and they’re unaware of options. I have everything against that. Corporate America, it’s good and bad, especially, I mean, if I’m talking about it from my own experience, good and bad. It keeps you trapped. It’s usually work that is not something that people have a strong desire to do. I mean, Billy, you hit on this earlier, like it’s not their passion but, I mean, again, follow your passion is incomplete advice. I’ve yet to find someone who is passionate about accounting, passionate about SaaS, you know what I mean? No one’s passionate about this shit, it’s just what they do because they can make money that way and it’s an easier way to make money than taking on the risks and going on and working for yourself and trying something else. I want to help people understand that they can try something else but if they don’t want to try something else, I want to help them figure out what fits best for them. And if that’s working them through like how to tell their boss they only want to work remote, fine, and we can hatch a plan for that. But if you’re sitting at your job thinking, “Man, there has to be something else I can do because this sucks,” then corporate America sucks for you and you should figure out a way to get out. I do say like leave your corporate job and I do that to inspire people and help people figure out that there are options if they want to leave. And from my experience, a lot of people want to leave.


Billy: Well, we’re seeing — they’re calling it the great resignation but I actually was doing some research on this and the numbers aren’t as high as they’ve been made out to be, that it’s not as great of a resignation as that name seems to make it be. I am seeing though more and more teachers and educators flee just because of the demands that have been put on them, especially now during the pandemic. I have resigned from my job and I know that, as I’ve been looking for jobs in the past, I’m not doing this anymore but when I’ve looked for jobs in the past, I would look for jobs with the same title, like I was looking for English teacher, I was looking for dean of students positions because I thought, “Well, I’m unhappy at my job here so I’ll just get another job doing the same thing somewhere else,” but that might not be the solution so what’s the danger in going at it with that approach? 


Brian Gallagher: I think the danger is that the same deep down gut feeling that you don’t want to be there will eventually emerge again. So, yes, you might have a shitty boss and you might avoid that in another company but I’m pretty sure that the shitty boss is not the only thing that you hate about your job. Again, the only caveat here is like if you have a gut feeling that you don’t like corporate America and you’re staying because you feel that there are no other options. If you have a shitty boss at one company, cool, you may go to another company and find a great boss. But that same feeling is not going to go away. You’re just going from one kind of prison to another prison and you’ll find that same feeling will reemerge, from my experience and from what I hear from others also. It’s like, I mean, you’re doing the same thing and expecting to feel different about corporate America in general and it’s just not — the structures are pretty much the same across any company you’re going to go to but with a couple variables being different. You might have better teammates, you might have a different role, you might have a better boss, you might have better things that you’re working on or more upward mobility, like one of those things might be better in the new position you go to, but, ultimately, if you don’t want to be there, that one thing that’s better is not going to turn the whole situation around for you and I think, after a while, you’re going to find yourself with the same feeling that, “This isn’t what I want,” and will want to leave and try something again. And the mistake which seems to be common is that, “Let me just go get another corporate job,” and they end up running into the same feelings again. Now, not saying that job hopping is bad. I mean, it seems to be that most people can expect a pretty significant pay raise with job hopping and I’m all for that, if that’s what you want to do if you have a desire to stay in corporate America. 


Billy: Well, let’s do this. We’re going to take a quick break and then when we come back, we’re going to talk to Brian about what a coaching session with him would actually look like in case what he’s talking about in terms of leaving your corporate job has piqued your interest any. 


Thank you for listening to the mindful midlife crisis


Thanks for listening to The Mindful Midlife Crisis. We will do our best to put out new content every Wednesday to help get you over the midweek hump. If you’d like to contact us or if you have suggestions about what you’d like us to discuss, feel free to email us at or follow us on Instagram at @mindful_midlife_crisis. Check out the show notes for links to the articles and resources we reference throughout the show. Oh, and don’t forget to show yourself some love every now and then too. And now back to the show.


Billy: Welcome back to The Mindful Midlife Crisis. We are here with Brian Gallagher. He is a global citizen, former corporate American trying to help people leave the nine-to-five grind. You can follow him at @simplemanguide on Instagram. Brian, we want to dive in a little bit deeper here because you and I are going to do a coaching session in a little bit. So you’re going to break down what we’re going to look at here. So, one of the things that you continually stress, which I think is extremely responsible of you, is that if someone wants to escape the nine-to-five grind, one of the first things that they need to do is sit down and really take a look at what they’re financially responsible for before just saying, “Fuck it, I’m out. I’m not coming back.” So what does that conversation look like with you? And I know that you’re a spreadsheet guy, which is so near and dear to my heart because I too love, love a good spreadsheet so this is a match made in heaven right here. So, talk a little bit about what that process looks like. 


Brian Gallagher: The main problems that people — or I should say the main issues that people need to solve when considering the option to leave the job: usually money, “What the hell am I gonna do for work?” Those are the two main things. Now, as we dig deeper, within those two main things, then we start to figure and find the fears that are holding them back but the fears most frequently will relate to one of those two things. Now, there’s other things in there too like societal pressures or family pressures or all their friends are doing certain things or all the people that they went to high school with all have kids and they’re all climbing the corporate ladder and they’re comparing themselves to other people, like all that stuff comes in too and that’s within those fear buckets, but, really, the main things that we’re focusing on are how are they going to pay for their transition, assuming that if you leave your job you are going to have zero income, and for what period of time can you afford to do that. How long can you afford to do that? And then, on top of that, or I guess additionally is going to be what are you going to do for work? What are you going to do for income when that transition fund runs out? And, most of the times, you can start to formulate that escape plan with respect to what you’re going to do for work while you’re still in your job. So, it doesn’t have to be, “Okay, I’m gonna quit my job at the end of the year, I do nothing to plan for it from now until December 31st,” and then January 1st, it’s like, “Oh, shit, what am I gonna do for work?” and now we start that process, like not the smartest way to do it, not the most efficient way to do it. You can do those things in parallel paths. So, first thing would be to figure out the finances. What are you spending? What are you earning? What do you have saved? Do you have any debt? And figuring out a plan to maximize your income, your savings while minimizing your spending and figuring out a way to sock away the most amount of money possible without making you completely miserable and holing you up in your apartment for a year. So there are things I’ll walk them through to get to that point. And that’s different for everybody. Some people will come to me and say, “I’m 25 years old, I have my $30,000 of student loans,” or other people will come to me and say, “I’m 37, I have $300,000 in the bank.” Like, okay, those are wildly different situations to be in and really take different methodology to help either one of those. One is a lot closer and one can get there, it’s just going to take a lot more work and a lot more time and a lot more discipline. And putting together that plan to help them —


Billy: He really does.


Brian Gallagher: — figure out what to do while they are getting to their savings goal is part of what I do and using me as accountability is another big thing. And just creating that customized, I like to think of it as like — and I, personally, you guys can tell me if you agree with this, I, personally, you get daunted by big goals at first but if we take that big goal and we break it down into one or two things that you’re going to do every day for the next 100 days or 150 days, it takes a lot of that anxiety out of it. It’s like, “Okay, I just have to wake up today and I have to do this and I have to wake up tomorrow and I have to do this. And then in six months, I’ll have this,” like you can think about it with anything, like you want to write a book or you want to start a blog or you want to create your new job. It’s almost, with anything, you can take this approach and make something way more palatable than it was when you just think of it as like, “Shit, how the fuck am I gonna write a 300-page book?” Well, you’re going to write it one page at a time, just like anybody else would. And looking at it that way makes it a lot more palatable. And the goal is to help them see that and to help them realize that. They’re like, “Hey, it’s just a ton of little steps that you’re gonna take one at a time and we will get you where you wanna go.” It’s the same process with creating what they’re going to do for work. So it’s taking that what are your passions advice and just adding some stuff to it. What are your passions? What are you good at? We go back and look at all of your jobs. What are you good at? What have you learned in all those jobs? You’ve learned something from every one of your jobs. My first job, I served lunch meat at the tiny little grocer but I learned that I can connect with people pretty quickly in those 90-second interactions. Like you learn something, it doesn’t matter what it is. And I was 14 years old cutting domestic ham and American cheese for people but I figured that out. I look back and I’m like I can have pretty nice conversations with people over that little minute thing that we were doing there. So helping people realize that and figuring out what it is they’re good at, what it is they’re interested in, and then what are the experiences they had, if any, that they’ve overcome or that they’ve gone through that other people would look at and be like, “Wow, I would like to do that,” or, “How did you do that?” or what do your friends ask you for for free all the time, like thinking about all these things that you may not think of and helping them take steps towards what could be their next role. And that’s part of what makes this seem like it’s a lot more palatable and a lot more doable. And if you first think of it, like so somebody coming out of a corporate job who makes $100,000 a year, they’re like, “Well, shit, I gotta come out of here and make $100,000 a year,” like, yeah, you can think of it that way but you can think of it also like, “Okay, I’m gonna do this and I’m gonna offer it to these people and I’m going to make $1,000,” or, “I’m going to make $2,000,” or, “I’m gonna make $500,” and then just doing that one step at a time and starting off slow and realizing that everyone starts at zero and working your way up from there. It’s a process, just like everything else. You just have to find what it is that you want to do and then we put together a plan to help you do it and to help you execute it. So I found that solving those two problems for most people alleviates a lot of their fears and anxieties with making a move that can be as daunting as this, like when I got let go, I called my girlfriend and my mom and my mom went into panic mode. She’s like, “Oh, my God, are you okay? Let me see if I know someone.” I’m like, “Mom, mom, mom, it’s okay. It’s okay.” And I feel like everyone else is going to have the same reaction if you tell them they need to quit their job or you tell them that you got fired or you tell them that you’re leaving your job, people are like, “How are you gonna pay your rent?” I guess my dad says to me too, like, “How are you gonna pay your rent?” I’m like, “Dad, I didn’t just decide to quit and not have anything else in the hopper,” you know what I mean? So just helping people alleviate those fears and anxieties that I think like a lot of people put on them, parents included. Gotta love them but, shit, man, they know how to really drum up some weary and anxiety.


Billy: So it sounds like a lot of people come to you then with fears and apprehensions. How much of your conversations are reality checks, where you’re like, “Oh, no, no, no, no, you’re coming in a little too hot with these expectations. Let’s dial it back and let’s take it — we really need to step back and start at level one here and you’re at level eight”? 


Brian Gallagher: I don’t run in that situation much. Most of the people that I run into are on the other end of that. Super fearful, going to run out of money, have already started to kind of pare down because they can see the writing on the wall or they know that they want to do something else, like most of the people that I deal with, you get a feeling a long way out. I haven’t run into too many people where it’s like, “Shit, I’m making $100,000 a year, I’m leveraged up to the gills with my car and my house and all this stuff and now I just got fired,” like it’s very rarely that. It’s mostly people that are like, “I know that I don’t wanna do this. I don’t know what I wanna do and I need help.” 99 percent of the people that I talk to are that. So, it’s way more pushing people past their fears than slowing people down and bringing them back to Earth. It’s very rarely that. Very rarely. 


Billy: So you and I are similar in a lot of ways. One, we’re both in Mexico right now. Two, if people could see, we’re both wearing white V-neck shirts right now —


Brian Gallagher: White V-necks.


Billy: Yep, yep, yep.


Brian Gallagher: This is pretty much all I wear.


Brian: Same headphones.


Billy: And we both love spreadsheets, right? We also are two guys who have never been married, we don’t have children, and I like this idea of coaching and helping people live their best lives, that sort of thing. The one thing that I’ve always struggled with, though, is impostor syndrome so I’m wondering, how do you have conversations with people who will say to you, “Well, Brian, you just don’t get it, man. I have a family”? How do you navigate those conversations when they come up?


Brian Gallagher: The process is still the same. I don’t care if you have zero kids or you have five, you still have to do the same thing. Now, it might be harder to do those things but you’re still going to have to do the same things. I mean, it comes down to saving yourself enough of a transition fund to make sure you can leave an income and go create one for yourself. That doesn’t change. I mean, yes, I might not understand the nuances of trying to get three kids to get on board with your savings plan, I might not understand the nuances of that, but, regardless, you’re still going to have to do the same thing. I’ll leave the parenting stuff to you but I’ll tell you that the money stuff is going to be exactly the same. It’s rare that I run into that. I’ve had clients that have had kids, I’ve had clients that have had no kids, I’ve had clients that are 25, I’ve had clients that are 53. I hit a wide swath of people, which is not really what I expected. I was like I’m going out with a very direct message, “You are a single guy, you feel a little disenfranchised with the path that you’re on, you’re starting to dislike your corporate job, you wanna do something, anything to get out of it, and I wanna help you,” and I’ve come across people who are 30 who run their own business who want to go back into corporate because they started a business doing something they love but they realize that all the other administrative and management shit they have to do to keep that business running, they’d rather just go back and do the work they love for somebody else, so that’s fine. I mean, again, I know my message is leave your corporate job but that’s the main fear and thing that I see people wanting to do but I still think the message, “Doing what you want to do,” resonates with a lot of people. And I’ve had people that are 53 and have kids and want to go to another job but want to have something that’s a little more flexible. So I really do get a bunch of different things. Even with the very direct and very pointed message that I have, I still think the idea of being able to do what you want to do hits home for a lot of people. And whether that’s like, like I said, your dream life doesn’t have to be what mine is, “Hey, I’m gonna go work in Mexico for months so I’m just gonna book a flight,” like that’s not for everybody. That’s definitely not for everybody. Some people would want to do that but some people definitely do not want to do that and they like the house that they purchased with all their furniture and amenities and they like their neighborhood stuff and they like the area they live and they like their car and they like their comforts. That’s fine. That’s totally fine. And that’s why the message that I like to push forward is I want to help you live your dream life, not mine, and I still think the process is the same to get you there. 


Billy: So you talked about fear and you talked about not sure if they’re going to be able to afford this transition, what are some other self-limiting beliefs that you hear from your clients and how do you help them navigate those? 


Brian Gallagher: Things like what am I going to offer? What do I have to offer? What’s special about what I do? And, sometimes, it’s as simple as like you can do the corporate work you’re doing now just on your own, which allows you that flexibility to do it from where you want, you set the schedule, you set the details. Giving people ideas that they may not have thought about, this I find to be a big one. If you worked in corporate for a really long time, it’s very difficult for your mind to expand beyond what is available within the corporate realm. Now, there are so many other things you can do outside of that but when you are literally in that environment, living, breathing, eating that corporate environment for 2, 5, 10, 15 years, your automatic instinct is like, “Okay, I can just go do this, the same skill I’m doing now, I can just go freelance and do it for somebody else.” I’m like, yeah, but let’s dig into like what else you — what do you like? What else can you do? What things have you overcome? What experience do you have? It’s kind of opening people’s eyes and letting them see that there is life outside of just living within that corporate realm. Whether you are an employee for somebody else or you are a contractor and you are setting the terms on your own, there are things you can do beyond that. There are tons of solopreneurs, Billy, like me and you and Brian, like us guys who are doing things who need help, like I have a client now who we just finished, she is going to help people with copywriting. I mean, what’s the first thing you do if you’re running a business? You need to have a website, she’s like, “I’ve been in copywriting for 10 years,” I’m like, okay, let’s work with this. There’s so many things you can do here. You can teach people how to do it, you can write a course for them to learn how to do it, you can do it for them and you can charge them three times as much as you would for a course, you can coach them through it. I mean, there are so many options that you just have to explore what your skills are, what you like, and what you want out of your daily life, and helping people expand beyond that corporate realm that they get stuck in if they’ve been trapped by it for a number of years. That’s probably one of the biggest ones that I found. Everyone’s like, “Yeah, I can just go do this and freelance, I’ve talked to this person.” I’m like, hold up a second, let’s explore some other things here. Maybe there’s something else. Maybe there’s not, but it’s worth exploring, especially if you’re in this phase where you’re going to make a transition, why not turn over a couple more rocks, you know what I mean? And see if there’s some other things that you can chase or you can pursue. 


Billy: I feel like you are a series of stoplights where people drive up to them and then you make them stop and you’re like, “Hold on, let’s think about this. Okay, green light, now, bring it into the next intersection here, we’re gonna stop,” and then you green light it after that. I like that approach that you have there because it makes people slow down and reflect, but it allows them to continue with the flow of things even if they get more apprehensive, like I know that when I’m driving, I get anxious if it’s a long line of traffic but as I get closer to where I am, I can feel, “Okay, I’m almost there. I could see, I’m getting over the hill, I know that that means we’re on the other side of this jam right here,” and so I imagine that’s one of the best parts of what you do is helping people get to the other side like that. What are some things that you really enjoy about your job and where are you off to next? 


Brian Gallagher: I really love being able to see the light bulb going off in people’s heads, like figuring out what they want to do is definitely attainable if they just stop and think about it. I love that red light analogy, Billy, like, yes, I want people to slow down, stop, think, and question everything. Question why they’re going to go right and run to another corporate job. Why is that? So thinking about those things and helping people stop, slow down, and think, that’s one of the biggest things I love about what I do is seeing that light bulb go off in someone’s head and one of my favorites was one of my first clients, he wanted to live somewhere else. He wanted to live in Italy and Croatia, where I have some experience and where I’ve loved and I fell in love with that part of the world, if I was living exactly what I want to do and if my girlfriend was on board, I would do three months Italy, three months Croatia, three months Italy, three months Croatia for the rest of my life. It’s just so beautiful over there. I love it. But one of the lightbulb moments we had with him was like, “Okay, here’s what I want you to do. Go into Airbnb, find me three cities that you wanna live in within that region and then go find me three places that you can stay in,” and he did that and he came back and he’s like, “I never thought to go check and do that.” I’m like, “You see how simple it is?” Just making people stop and think and simple exercises, having somebody go tool around on Airbnb for an hour, it opened their eyes to a whole new world of possibilities. So just that one simple little exercise was just eye opening for him and I loved that. Seeing the light bulb go off in people’s heads is the favorite part of what I do and seeing the direct impact that you can have on somebody else’s life with what you help them do.


Billy: Hey, everybody, this is Billy. Unfortunately, our interview with Brian Gallagher got cut short due to a faulty internet connection while we were in Mexico but we hope you enjoyed that conversation. There wasn’t much left. Brian was talking about where he’s going next and he is actually on his way to Amsterdam to be with his girlfriend, the complexwomanguide, because she just got a new job there. Congratulations to her. And thank you to Brian, the Simple Man Guide. You can follow him there on Instagram. We really appreciated him sharing his insights on how to break free from the nine-to-five grind. It’s certainly something that’s on my mind as I navigate my new path in life so I really appreciated that conversation. I also really appreciated the one-on-one conversation that I had with him. He really spoke to the importance of me finding clarity in what it is that I want to do so that is something that I’m still trying to figure out and working really hard and I’ll tell you that the guests that we’ve had this season have absolutely helped me find some clarity and some direction as to where I’m going next during this mindful midlife crisis that I’m having. So, once again, we hope you enjoyed the show. Thank you again to Brian Gallagher, at @simplemanguide. For Brian Gallagher, for Brian on the Bass, this is Billy, thank you for listening to The Mindful Midlife Crisis. May you feel happy, healthy, and loved. Take care, friends.


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