Aaron McHugh | Prioritizing People and Building Relationships

On this week’s episode of Franchise Freedom, we speak with special guest, Aaron McHugh. Aaron is a writer, podcaster, adventurer, and the author of the best-selling book, Fire Your Boss: Discover Work You Love Without Quitting Your Job. He is also mastering the art of living a sustainable work-life balance that constantly interweaves rhythms of play and adventure.

In work, Aaron has covered the spectrum, from humble beginnings selling office supplies door-to-door to ringing the opening day trading bell at the London Stock Exchange. In play, he is an adventurer, Ironman triathlete, and mountaineer, is learning to surf, and recently accomplished a lifelong dream of mountain biking the entire Colorado Trail, from Durango to Denver.

We speak about Aaron’s entrepreneurial journey, as well as:

  • Prioritizing people and building relationships
  • His book, Fire Your Boss, and learning to lead yourself from the inside out
  • His podcast, Work Life Play, and restoring wonder to our lives and our work
  • His advice for those considering entrepreneurship
  • And more

Listen now…

Mentioned in this episode:


Giuseppe Grammatico: Welcome to the Franchise Freedom Podcast. I’m your host, Giuseppe Grammatico, your franchise guide, and today we have a very special guest. We have Aaron McHugh. Aaron is a writer, podcaster, adventurer and author of the best selling book, Fire Your Boss: Discover Work You Love Without Quitting Your Job.

He’s mastering the art of living a sustainable work-life balance that constantly interweaves rhythms of play and adventure. In work, he’s covered the spectrum from ringing in the opening day trading bell at the London Stock Exchange to humble beginnings of selling office supplies door to door. In play, he’s an adventurer. He’s an Iron Man triathlete, mountaineer and is learning to surf just like myself. So I would like to know about that. Recently accomplished a life dream of mountain biking the entire Colorado Trail from Durango to Denver. Wow. Awesome. Aaron, welcome to the show.

Aaron McHugh: Yeah, thanks, Giuseppe. It’s nice to meet a fellow learner in the surfing community.

Giuseppe: Yes, yes. And learner is key. I, really quick, I was out there with my son. My son’s 12 years old. We’re out there. I get complimented. I bought this used board. I think it was a nine footer. Got complimented. Saw the way I surfed. And I said, Well, if I knew how to surf with this type of board, we’d be all set. So he had a, we had a good laugh out there. So it’s funny, I have the nicest board out there and the worst surfer. So we all got a laugh out of that, and I was probably hurting for a week after that.

But that’s a whole nother story. It’s a whole nother show. But yeah, I wanted to welcome you to the show. Just to kick it off, if you could fill in the audience, as we discussed before the show, our audience is aspiring entrepreneurs or people looking to make that switch and not sure if it’s the right fit for them. And then we also have current business owners, both franchise and not, that are looking to expand their investments and work on their exit strategies. If you could just fill everyone listening in on your background, how did you get started? And what does that journey look like?

Aaron’s Entrepreneurial Journey

Aaron: Yeah, I’ve always been in business, but very accidentally. I had a friend of mine that, you know, 25 years ago, invited me for coffee and said, I think you’d be great in sales. He was a manager in a radio station, so selling 62nd radio commercials. And I told him all the reasons why I couldn’t because I couldn’t lie, cheat and steal. And that was my perception of what a salesperson was like.

And he said, Great, you’re hired. I can’t teach people not to do those things. So I hire people with integrity, and that’s what you just professed that you have. So that really started a business career in a very accidental way. And what I discovered early on in, yeah, just kind of that door to door work of bars and liquor stores and homebuilders and, you know, Home Depot grand openings, was just this fascination with, I’ve always loved people and found that what was really liberating was that in the context of business, that ideas were a way to be, differentiate yourself.

And, you know, things like work ethic and all these things that just kind of, for whatever reason, I didn’t grow up a lot around a lot of business people, I didn’t have a lot of context. And so I just became really fascinated with it. And then this idea of entrepreneurship, I became really kind of intoxicated with early on like in early 90s. They call it now the dot bomb era, but it was kind of the, you know, beginnings of the internet.

There were companies getting funded, you know, in college dorm rooms for something that stood up over the weekend. I was reading magazines like Fast Company and Wired and thought I was destined to be one of them. So I found myself moving into technology. You know, renting hotel rooms with a colleague and us writing, I would loosely call it a business plan today, but that’s what we thought it was. You know, printing t-shirts and logos and, you know, trying to be on the cover of the next Wired.

And so really, I would just say that my career has been in and out of these categories of entrepreneurship, intrapreneurship, inside organizations, and then freelancer, I guess is what I would kind of call that. Also where I’m just out actually, more in like a professional services, selling my time, my attention, my interests, my wisdom that I have to offer. And really just kind of finding that this is more of a dance for me. It’s never been a clear black and white where I belong. And I’ve just found that it’s more in the spirit of innovation and in the spirit of curiosity that’s always fueled my career.

Giuseppe: Yeah, yeah, that is a great story. I, you know, entrepreneurship is on everyone’s mind. or not on everyone’s mind, but it’s been on a lot of people’s and they don’t really understand exactly what it is. There’s a lot of, you know, assumptions that if you’re an entrepreneur, all entrepreneurs are wealthy or all entrepreneurs are doing that for one reason or another. Maybe they’re just doing it for money. And it’s interesting, having this show and listening to people’s perspectives and, but at the end of the day, you had mentioned your beginnings in sales.

And, you know, the biggest thing, and I’ve had a few shows today alone, and we talked about just one thing that has not changed, technology has helped in so many different ways with email, text messages, LinkedIn, and I feel, you know the trend and I feel the way I’m, you know, treated, you know, from salesmen kind of from the outside contacting me to gain my business, I feel like the relationship part, in many cases, kind of gets dropped. I’m getting a two-page message from LinkedIn and I don’t want to embarrass anyone, sometimes I want to repost them.

And I have never met the person before and he’s pitching me on his grand social media marketing program that’s going to generate 20 leads a day and I don’t even know, I don’t know this person from the next guy on LinkedIn. And I just feel the relationship part. People have felt like to be efficient, let’s go right into it and let’s, the relationship isn’t important. And I truly feel that when we do business with people that we have a relationship with.

There’s a million marketing people, there’s a million people that do the same service as the next guy, but who do you have that relationship, who do you feel comfortable with? So I don’t know if you, you know, I go off on this just because it’s been a very, very common theme. I know that’s kind of in a different direction but while it’s on my mind, because if I don’t bring it up now I’ll forget. But I just wanted to get your perspective, your thoughts on that since it’s been, you know, a recurring theme.

Relationships are Primary

Aaron: Yeah, Giuseppe, I agree with you and for your listeners, whether again, you’re an entrepreneur today or you’re considering, regardless of where you find yourself, I’ve found in my, whatever 20-plus year career, that bottom line that relationships are primary. What’s really important is I find that as soon as we prioritize products, services, and solutions over people, then most astute people can smell that a mile away.

And I’ve always chosen to. and I had a friend of mine early, early on, take me to coffee after I took the sales job. And he said, you know, just so you know, people will smell it. If you need to make your quota, if you’re trying to close a deal, whatever it was and he said you should just leave. If you’re there in panic and worry or you’re there making this person an object that you need to tackle or some conquest you need to achieve, that will actually not work for you long-term.

So I’ve always chosen what I would just call is as I played the long game. There’s a short game and there’s lots of tactics and strategies that people use, especially in our modern technology era. And there’s also a long game. And I think that the long game is more serving at a human level, and actually, ultimately more serving at a business level to achieve predictable and reliable and consistent results versus just temporary spikes that may be hollow and not actually sustainable.

Giuseppe: Right. Yeah. And to your point, you’re right, people can sense that. And it is about the long game. It’s about the relationship. And that relationship’s an investment, right? That trust is formed and that relationship, in many cases, is priceless because that individual may continue to do business with you. And even if they don’t do business with you, they can be just a wealth of referrals and just a great sounding board for what you do. So I’ve come across that where people have maybe just not moved forward and, you know, and what we do is we help people figure out if business ownership is right for them.

And we, you know, we do a lot of work in between to find a few franchises that match what they’re looking for but it’s not the right fit for everyone. So absolutely, the long game is key and you can’t be leading with that product or service. Absolutely, definitely comes across no matter how much you try to hide and no matter how long you’ve been in sales. So some great advice there. You know, a mutual friend of ours, Paul Edwards, that had put us in touch and thought we’d be great on the show and we’ve had a conversation before this show.

And I love the title of your book, and that was kind of the one thing that stood out. So what is that, Fire Your Boss: Discover Work You Love Without Quitting Your Job. I want to, I’d like to talk a lot more about that book because that definitely caught my interest. You know, I like what you had to say in the book. So can you talk a little bit about what the book is about, who the book is for?

Upgrade Your Personal Operating System

Aaron: Yes. The book is really for, there’s so many books in the market today about tactics, strategies, how to make a career decision, when to stay, when to go, when to become an entrepreneur or not. And what I found is that before you get to all that, that in my career, there were parts of my operating system that needed attention, that needed renovation, and that needed an upgrade. And what I’m referring to is my inner leadership, learning to lead myself as a human, as an entrepreneur, as an executive, as a dad, a husband, father, whatever it may be. A friend.

And what I discovered along the way was, there was recurring themes in my career that showed up every place that worked. And in the beginning, whether regardless of the format or the structure, and what I mean by that is didn’t matter what the role was, didn’t matter what the industry was, didn’t matter if I was, you know, had an entrepreneurial hustle or not or if I was a contractor or whatever the format, and then I’d have these themes just keep reoccurring. And what I found is that my own issues were following me everywhere I went.

Now, along the way, I didn’t realize that because I really had projected and outsourced my happiness and my contentment and my inspiration and my passion on other people and in other circumstances. So Fire Your Boss is really foundationally about upgrading your operating system, about learning to lead yourself from the inside out regardless of circumstances so that you can thrive, so that you can have with joy, passion, meaning and purpose, bring that to whatever situation you find yourself in.

And so as you and I talked offline, this isn’t about whether you are or you aren’t an entrepreneur, this is about learning to lead yourself so that you can, whatever you’re investing your energies in, then you can maximize the return on those efforts, versus us being in our own way and us having hang-ups that we just drag from one place to the other, that then limit our ability to have the greatest impact in the world that we can.

Giuseppe: Very well put. You know, someone reads the book, you know, your book, and they need a little bit advice, do you, is that something that you offer additional services for? Can they get additional information on your website? How would that work if they do have questions or want to dive in a little bit deeper?

Aaron: Yeah, all things aaronmchugh.com. That’s MCHUGH or you can type in Work Life Play, which is my company brand. And you’ll find everything from, I do do some coaching. I do a lot of work with clients, existing clients and executive teams today. I do some private coaching in addition to that. And then all of my blogs and podcasts and writings and guides and all those are all in one place. So my body of work I started in 2011 and fast forward today, I’m still at it.

Giuseppe: Sounds great. And talk to us about your podcast. You know, who’s on the show? If people listening in want to, you know, gain some additional information, is there a link for the podcast on the website as well?

Aaron: Yeah, there sure is. So knocking on the door around 200 episodes. Started the podcast in 2012. And the guest list is everything from, you know, big names that you would recognize from, you know, Seth Godin marketing thought leader to, you know, to guys who climb mountains like Conrad Anker, you know, on the Northface Climbing Team to people that I just find interesting that are up to. One of the guys I interviewed recently was a guy named Alister Humphreys out of the UK. And he became National Geographic Explorer Adventurer of the year a number of years ago.

But what made him famous wasn’t the fact that he had rode across the Atlantic or bicycled, you know, 47,000 miles across the globe, but because he rediscovered adventures out of his front door and framed these as micro-adventures, about learning to be curious with whatever’s outside your front door. So, so much of what I curate on the podcast and my other work is about just restoring wonder in the life that we live, in the work that we do, about doing work that we love, about living well with the people that we’re entrusted to care for, and about learning to play and adventure in everyday life.

Giuseppe: I like that because I feel many of us are, you kind of feel stuck and you feel there’s no hope. So stuck in a job you know going from one job to the next just unfulfilled, unhappy. So this is crucial. And, you know, a book like this is definitely a game-changer and just perspective, mindset, you know, the way you’re thinking of things. So we appreciate you writing such a nicely well-written book like this. So what’s, you know, one thing we like to ask everyone is kind of what’s new and or what’s exciting in your world right now? You know, whether it’s a future project, things you’re working on that you’d like to share with the audience.

Dispel the Groundhog Day Effect

Aaron: Yeah, just recently, just for my own sake of play, you know, in the world that we’re living in right now, it can feel intense, right? And, yeah, like high stakes. I don’t know, with presidential elections to global pandemics. And, you know, there’s a lot going on the world and I find, for me, wilderness is always a great escape living in Colorado.

So I find it’s really helpful for me to get out with my fly rod and go scare up some trout in a local river, to I just finished a couple-year project of a backpacking route through Rocky Mountain National Park that finishes near a town called Winter Park. That’s a ski resort area. And it’s a high route, they call it, so it’s like 70% off-trail like, map and compass, and just finding your way through these high ridgelines and passes. So I just find stuff like that is really helpful for me to get out of my daily life.

And sometimes the hamster wheel or the Groundhog Day effect of my life and really just gives me an opportunity to have perspective back on what’s happening in my real life really builds a lot more gratitude for me. And to me, it doesn’t require that it has to be those kinds of things. But what happens, I find for so many people, especially driven people in business and entrepreneurship, it’s so easy to tend to everyone else in our life and in our companies and our responsibilities and actually deprioritize the care of ourself.

And I find that this author, Greg McEwen, wrote in his book Essentialism about protecting the asset, when we begin to protect and prioritize ourselves as the asset of the story, then we can actually begin to maximize the impact that we make in the world. So that’s been exciting me lately. And then on a kind of work impact with leadership teams. I’ve been doing a lot in the world of, they call it agile methodologies, or agile transformations.

And really, what that comes down to is how do you eat an elephant one bite at a time, you know, is, but how do you do that at a business level? How do you reinvent organizations that are not top-down and hierarchical, but are actually more like a bunch of small seal teams that are actually at work all advancing the operative together? So I find it super fascinating and really kind of on the cutting edge of what the world of work is gonna, is becoming.

Giuseppe: Interesting. What was the name of that book you had just mentioned?

Aaron: Essentialism.

Giuseppe: Essentialism.

Aaron: The Disciplined Pursuit of Less is the subtitle.

Giuseppe: That’s very interesting. And the reason I asked and bring that up was, I worked with a coach a few years back and he publishes a lot of free info. And the one takeaway that really stuck with me, we’re no longer working together, but he had said, when setting up your calendar, and this is so basic, you know, it sounds like common sense, but it’s been a life-changer for me. So whatever, if you’re an employee, entrepreneur, it doesn’t make a difference.

If you get your calendar, so Google Calendar, I share that. I’m married, share that with my wife, we have the kids’ activities and things like that. So what do I do? I schedule the podcast and the meetings and this and that, and then if there’s time, you know, who’s taken a soccer practice? You know, if we’re going to dinner tonight?

Are we not? So he’s like, you know, we’re all doing it backwards. And I go What do you mean? He goes you start out the week with a clean slate. You know, what’s important to you? What are the things that really matter? And I’m not saying business is not important, but he said, Put down, you have to work out Monday to Friday minimum, you know, whether it’s 20 minutes to an hour. So he made me block from seven to 8 am, we’re on Eastern time, you know, working out.

And he’s like, at bare minimum, if you did that and one additional thing, date night with your significant other, put that on the calendar once a week. It could be, you know, we’re not in New Jersey, we’re not allowed to eat in restaurants and outdoor dining and it’s very, very hot outside right now. So it’s been a lot of takeout here and there. So have the date night. Doesn’t have to be anything fancy. That alone, and he talks about so much more, is a gamechanger. Because you start to lose sight of everything. It’s all about work, work, work.

And then finally things are going well, and it’s 20 years later, you’re like, wait, I missed out on so much. You know, things happen so fast. Kids grow up. So that book just triggered that thought in that coaching session we went through. It was an hour that truly changed the way I thought about how I schedule my time. And truth be told, do I work out every day? No. It’s on my calendar and I need to do a better job and I admit that. But it was just a game-changer. So I really have to, I got to check this book out. It definitely piqued my interest there. So

Aaron: Yeah, and you’ll find, one thing that your listeners might find helpful as well on my website, there’s a keep going guide. And its subtitle is learning how to pace yourself. Just a free download you can pull and it’s on this same idea. How do we actually learn to pace ourselves and go the distance?

And what that practices you just mentioned about being more strategic. And what I find often happens for most of us is that there’s two ways life can go, and this is inclusive of our health to our relationships to our career, is we either are co-creating and architecting a life and work and relationships we want to have, fitness we want to have, or life is happening to us.

Most people, life happens to them. They allow that. But the perception is, well, look at how much life just happened to me so how could I ever turn this around? And that’s where this work here we’re talking about can make a big difference. So back to, you know, do I get on the path of entrepreneurship? Or how do I maximize my impact of entrepreneurship that I’m already in? Or do I stay where I’m at?

All those are great questions. And these questions that we’re asking are actually deeper questions that will travel with you, regardless of the circumstances that you find yourself in. So how do we have sustainable practices in our health and fitness? So those are the great questions. You know, but those are things you have to settle and you have to, unfortunately, things just don’t align naturally on their own. We have to have strategy for how we bring it to life in our real life.

Giuseppe: Right. Yeah. So we will put on the website and all the information on the show notes. So you have all that information. So Aaron, you know, there is a lot of people given the pandemic and what’s going on, they are kind of in limbo. They don’t know if their jobs will come back. I have, I work with people, I’m friends, family members that have jobs and but they are currently working from home but they are required, we’re requiring them to go back to work. You know, for example, to Philadelphia, to New York City, big major cities where they may not feel comfortable. You know, you can’t really drive into New York City.

If you’re familiar with the area here, you have to take a bus or a train. They’re kind of in between what to do. They’ve had, they’ve thought about entrepreneurship, you know, they aren’t sure if it’s the right fit. A lot of times they’re doing that research before even speaking with me. And we definitely take a deep dive and figure that part out. But, you know, they’re reading a lot of blogs, and they’re listening to podcasts.

And sometimes it just becomes, as in my case, when my journey started, you know, just over 15 years ago, becomes overwhelming to the point where I have all this information. What the heck do I even do with it now? So any kind of parting of advice, and maybe if it’s not advice, some, you know, key questions that you can leave the audience within figuring out or putting some things in perspective.

Know Why You’re Doing What You’re Doing

Aaron: Yeah, I think it’s a great question. And, like you said, it’s rubber meets the road real-life stuff is I think the challenge that we’re all faced with right now is because the world is full of so much uncertainty right now that I think it does add a layer of dis ease, like unease to it. So these big questions of do I go down the path of entrepreneurship or not, they’re by themselves, when the world was as it was six months ago, they’re kind of big questions already.

Well, then when you add the complexity of the world that we’re living in, then it all of a sudden becomes, can feel maybe even more challenging. And it really does activate in us these places of fear and worry and uncertainty and anxiety.

And then for some, maybe it’s just exhilaration of like, you know, I have a savings account, I have some time and some choice. And that’s great if you’re in that place. What I would really encourage you is that no matter what that route you choose to go or you are exploring, and irregardless of how uncertain the world is right now, it’s really, really, really important to know why you’re doing what you’re doing.

Because if we act out of fear, worry, anxiety and of course correction, well, six months down the road or 12 or 18 months down the road when the world’s maybe back to some semblance of some version of more predictability, maybe some more stability, hopefully, then you’re still going to have to revisit that question. Why am I doing this? And so right now if it’s why am I doing it, well it’s so that I don’t have to do this other thing, that is an okay answer but that’s actually not a sustainable reason to get out of bed for the next five years or 10 years.

And so I think where people can get their wires crossed is during points of tension. I won’t call them crisis, but let’s just say crux moments in your life, when we are not thoughtful about what’s the deeper reason why am I wanting to be an entrepreneur? Is it because the current place I work and the person that I’m working for is just impossible? Well, that’s probably not the best reason. So I’m sure there’s another reason of like, maybe, hey, it’s freedom of choice of schedule.

Maybe it’s really want to author something that you’re in charge of and stewarding. Maybe it’s because it’s a crescendo moment for you and all of your life is built up to this moment of choice and it’s less of a leap and it’s more of a migration from a path you’ve already been on. But I just think that a really, I know, the more aware and conscious you can be about those difficult questions, then the more you can set yourself up for success for whatever you choose to do next.

Giuseppe: Yes, I cannot agree more and very well said. The only thing I would add to it when you’re thinking about these questions, I’ll just, this is just an add-on to what you just said, I would recommend maybe doing this on the weekend, maybe if you work Monday to Friday, because I know sometimes I try to make some difficult decisions to try to figure something out and you’re doing it, you know, there’s a million things going on during the week. There’s school, there’s stresses, get a good night’s sleep. Maybe, you know, take a mini-vacation, long weekend, and really give it some thought when you’re in a calm state.

Not when something bad just happened or you just found out you may lose your job and you’re just, as you mentioned, you’re kind of thinking or acting in a state of panic, not thinking clearly, adrenaline’s pumping. So I always recommend making these decisions, sometimes when I do calls with individuals looking at franchise ownership or asking them some of these difficult questions, I’ll tell them these are the questions, if you’re not ready to answer them, no problem.

Think about it over the weekend and we’ll touch base Tuesday the following week. And it’s night and day because they, you know, during the week with everything going on, there’s just too much distraction, too many things going on. So that’s my additional two pieces or one piece of advice, I should say. So that’s awesome. I, this is some really good advice. There’s, it sounds like there’s a ton of information on the website.

Anything else, I think we had mentioned before, but anything else? I know we were going in different directions but this is all extremely helpful and we like to change up the shows a little bit, to not talk about the exact same thing every time and from, you know, from people in different industries. So this is, you know, I took a lot away from this interview. Anything else you’d like to leave the audience with? Obviously, check out the book, go to Aaron’s website. Anything else that we maybe didn’t touch on today?

Aaron: Yeah, just love just to close out with, for you, our friends listening, I hope and pray that the wind will be at your back and not at your face. And I pray that the hills that you’re climbing that you’ll be able to do it with a friend, someone that can walk it with you, a mentor, whoever it may be. And yeah, good on you for tuning in for great wisdom from Giuseppe and what he’s curating here. So it’s been an honor. Thanks for having me.

Giuseppe: Yeah, thank you. This has been a great interview. As I mentioned, learned a lot. Check out the show notes for all the site links. And Aaron, once again, I wanted to thank you for being on the show.

Aaron: Yeah, thanks. Keep going.