A few years ago, I met this entrepreneur from Boston named Kevin Cassidy. As you might recall if you caught the most recent edition of The Owner’s Mindset, Kevin is the founder and owner of Cassidy Corp., a leading commercial asphalt paving company in Haverhill, Massachusetts.

Kevin and I met when we were both participating in a program for business owners. We quickly bonded over our shared love of hockey, entrepreneurship, and learning.

About two years later, my wife and I decided to travel to Boston to see my beloved Bruins in action with Kevin, who has season tickets. A couple weeks before the trip, Kevin and I got to talking about the power of LinkedIn. He asked for some of my advice on using the platform, and I gladly shared what I knew. During that conversation, we decided it might be good for me to come in and talk to his senior team while I was in town for the hockey trip. I was happy to do it.

Fast forward a couple weeks, and my wife and I are having a lovely dinner on our first night in Boston. She asks me what I’m doing tomorrow and I tell her about my one-hour presentation with some paving executives. She looks at me and says: “What do you know about paving?” Huh. My answer, of course, is: “Well, absolutely nothing.”

At that time in my career, most of my experience was with corporate audiences. As I sat in that restaurant across from my wife, I started to feel a bit queasy. ‘Oh my god’, I thought. ‘I’m so not prepared for this.’ Back at our hotel, I found myself staring at the clothes in my suitcase and thinking: I don’t even know what to wear.

The next morning, Kevin came to pick me up at the hotel to bring me to his office. I had decided on jeans and a golf shirt, the first time I’d ever worn such a thing for a presentation (now, good luck getting me to wear anything else.)I had no idea if I looked the part of someone who could confidently speak to a room of paving professionals. But Kevin had confidence in me, and this made me feel more relaxed. I can do this, I thought. I can figure this out.

So, we arrived at the office, and we went into the boardroom. As Kevin’s executive team filed into the room and he started his introduction, I thought to myself: ‘I’m not going to be doing myself any favours by pretending I understand what these people do all day.’

And so, I started my presentation by stating the following: “I’m going to be honest; I know nothing about the paving industry. But I do know about putting more money in your pockets, and for the next hour I’m going to share some easy strategies that will help you do just that.”

One guy in the room responded by shouting: “Yeah! Bring it!” I let out a breath I didn’t know I’d been holding in.

The session went really well. We had some great, honest conversations, and we all went out for lunch after. It was a great day, followed by two more great days in Boston with my wife, in which we caught the hockey game (The B’s won), explored the city and had a fantastic time.

About a week later, after my wife and I had returned home to Toronto, I received an email from Kevin in which he introduced me to a friend of his; a man named Jim Kaloutas, founder and president of one of New England’s leading commercial painting, industrial flooring and fireproofing companies. (You may remember Jim from another recent edition of The Owner’s Mindset.)

In the email, Kevin said something like this: “Shawn, this is Jim. He’s one of the smartest, nicest guys I’ve ever known. Jim, this is Shawn. He knows what he’s talking about. I think smart, good people should get to know each other.”

And that’s how I met my next all-star client, and now great friend and mentor.

The funny thing is, more than half my clients are now business owners in the construction field – guys like Jim and Kevin. Would I ever have imagined that? Absolutely not. But that’s the power of saying yes, and figuring out the rest later. This essential idea lies at the centre of my three main takeaways from this whole experience:

1)     “All growth lies in the territory of the unknown.” These immortal words from Dan Sullivan ring true, but we don’t always follow their wisdom. We talk about the importance of taking chances, we post quotes on social media, but do we actually follow through in our actions? So many people spend most of their lives staying comfortable, doing what they know, even if it’s for a job that doesn’t make them feel alive. Life is too short to stay too comfortable. Say yes to the things that scare you.

2)     Change up your environment. Most people only ever hang out with the same people from the same industry, and guess what that leads to? The same kind of thinking. It’s so important to immerse yourself in different points of view. One of the greatest (and most unexpected) gifts I’ve received in the last 18 months came from going virtual with my previously in-person ‘Socials With Shawn’ series. In these meetings, I’ve been able to get together with business leaders from all around the world, spanning so many different industries. We’ve learned together, laughed together, and experienced some real light bulb moments – all from sharing that special space once a week. This isn’t anything revolutionary. It’s common knowledge that changing our environment can lead to new ideas and growth opportunities, but does everyone actually do it on a regular basis? Ask yourself these questions: who are the people you hang out with every day? Are they the same people you’ve been hanging out with for years? How could you switch this up?

3)     A little less conversation, a little more action. All the best lessons are in the doing, not in the talking about the doing. Next time you feel a little uncertain about something you really want to do, try saying yes – and then figuring it out later. So often, when I ask people what it is they want, the answer is ‘I don’t know. I haven’t figured that out yet.’ The thing is, the vision doesn’t come first; the courage does. So, have the courage to do things differently. Have the courage to say yes.

Looking back on that fateful trip to Boston, I am so glad I said yes. I am so glad I got a little uncomfortable, because it led to so much joy and new opportunity in my life; a life with ‘perfect fit clients’ like Kevin and Jim. I can’t wait to see what happens the next time I decide to say yes.

A few years ago, in my former life as a travelling keynote speaker, I was invited to speak at the semi-annual sales retreat of a major global company. I was told they were struggling to come up with new ideas, and they needed someone to help them shake things up.

When I arrived a few days into the week long retreat, I decided to sit down with the National Sales Director and ask him a few questions before diving in.

First up, I asked: “Are you noticing that the same issues tend to come up at this event year after year?”

He said yes, about 80 percent of the problems discussed at the retreat were the same ones they’d been tackling for years.

My next question was: “Do you have a lot of turnover, or is it always the same people in this same room twice a year?”

He told me it was pretty much the same people, and yes, they always came to this same resort.

“So,” I said. “Just to summarize: you bring the same people, with the same problems, to the same room, every single year? Twice? And you’re wondering why you can’t come up with anything new?”

For a few beats, he just stared at me. Then, he broke into laughter.

“Damn, you’re good”, he said. “I guess I’ve never thought of it that way.”

I assured him this was totally normal, that we all get stuck in our habits. We’ve all had that experience of realizing we may be in need of a fresh pair of eyes.

Take my friend Kevin Cassidy, for example. Kevin runs Cassidy Paving Corp, a leading commercial asphalt paving company in Massachusetts. When Kevin first reached out to me, it was to ask if I’d be interested in providing coaching and training to his team. I was definitely interested, but before going any further, I needed to make sure he understood something that I considered to be kind of important.

“Kevin, I don’t know a damn thing about the paving business,” I told him.

To my surprise, Kevin replied: “Good.”

“I have a lot of paving experts in my life. I don’t need another one,” he went on to say. “What I don’t have is a good coach, or somebody with your fresh perspective.”

Huh, I thought. Isn’t that interesting?

Looking at these two stories, I’m reminded of the famous quote from Albert Einstein:

“We cannot solve our problems with the same thinking that we used to create them.”

Over the years, I’ve seen many professionals, spanning many different industries, following the exact opposite of Einstein’s advice (and let’s be honest, he was a pretty smart guy.) Bankers hang out with other bankers. Pharmaceutical representatives hang out with other pharmaceutical representatives. Insurance brokers hang out with… well, you get the idea.

The thing is, there is tremendous power in mixing and matching different groups of people – particularly when those people have great leadership skills. The exchange of ideas that can occur in these unique circumstances is extremely powerful. What might be considered a breakthrough idea in one industry is just standard practice in another industry.  

Creating these special environments is what I do best.

When you bring together world-class leaders from a variety of industries, magic happens – but only if you have the right people in the room. These are people who are honest and open-minded, who have growth mindsets, who don’t hide behind bureaucracy. They have a willingness to learn, to not take themselves too seriously, and they are genuinely interested in helping one another. In other words, it’s a ‘No B.S. Zone’ when these kinds of people get together.

I am currently hosting the Leadership Advantage Olympic Games, during which the magic described above was on full display. As part of this unique event, 22 professionals from around the globe were invited to participate in a series of challenges aimed at helping them grow as leaders.

These folks came from all different industries, but they had a few things in common: they’re all people for whom I have a ton of respect, and they’re all doing amazing things out in the world. Not to mention they all play at the ‘Olympian’ level – that is to say, they give it their all and play full out. In other words, they’re the only kind of people I work with.

The idea behind this event was simple: if you want to be the best, you need to hang out with the best. Meaningful change happens one conversation at a time, and it involves people with different experiences and perspectives than your own. That’s what the Leadership Advantage Olympic Games were all about: having real conversations, having fun, learning lots, and then taking action.

This same spirit will drive my upcoming invite-only group program for world-class leaders. Once a month, these superstars will come together from across a wide range of industries to learn and share ideas. They will leave each one of those sessions with insights they can bring back to their businesses.

When we compare this model to one in which the same 20 people are brought to the same room year after year, it’s pretty obvious which ones works better.

So, my question to you is this: what’s your plan to play like an Olympian? How can you up-level your game, and who do you need on your team to get you there?

In this new series, you’ll be introduced to some of my all-star clients, as they share their story on the journey as a business owner.

First up is Kevin Cassidy, President and Founder of Cassidy Corp., a leading commercial asphalt paving company in Haverhill, Massachusetts.

Kevin is an entrepreneur at heart, having started his first company when he was just a teenager. Today, he oversees one of the largest driveway and parking lot paving companies in New England, all while maintaining his reputation as an amazing employer who truly cares about his employees.

Shawn: Kevin, we first met at Strategic Coach a few years ago. As I seem to recall, we bonded over a love of beer, the Bruins, and entrepreneurship. I want to start off our conversation today by going back to one of the questions we tackled that night – one of my favourite questions, really. Where did you get the entrepreneurial bug?

Kevin: You know, I imagine it probably came from growing up with not many means or material things, and just wanting more. I was raised by a single mom, and I had two younger brothers. It was wild. We had a lot of love, but not a lot of money.

Shawn: Fast forward to high school, when you started your first business. What was that about?

Kevin: The want for money! I had a job at a local hardware store, and I noticed that people were always looking to get landscaping work done – picking up weeds, cleaning up yards, that kind of thing. The typical stuff people do in high school for extra pocket money. From there, it just got bigger and bigger, to the point where I had eight employees by the time I graduated.

Shawn: Help me fill in some blanks here. How did you go from working in a hardware store to being self-employed?

Kevin: I bought a truck – before I had a license – and I paid somebody who had a license to drive me around. We would go around and mow lawns, and I made some okay money – a lot better than what I was making at my minimum wage job, anyway.

Shawn: And then what happened, in terms of your decision to bring on more people? Did you get to a point where you had too much work that you couldn’t do it on your own?

Kevin: Yeah, it was pretty much just a necessity thing. I reached out to one of my classmates in high school and asked if he wanted to work a couple days a week mowing lawns with me. Then I asked a second classmate, and a third, and a fourth, and so on. Just grabbing bodies. Pretty soon we even had a name – ‘Groundmasters Lawn Maintenance.’ 

Shawn: I didn’t know that, amazing. I imagine it didn’t take long before you went from cutting the grass yourself to managing the team. Tell me about that.

Kevin: The Company just kept growing. It got to the point where it became a fulltime job just to go out and look at the work and bid the work, and so that’s what I started to focus on. It forced me to change my mindset in terms of the role I had to play in the company.

Shawn: Looking back to when you started out, just cutting grass on your own, did you imagine the company growing as much as it did?

Kevin: No. I just thought it was a good way to get paid.

Shawn: And then you sold the company, is that right?

Kevin: That’s right. It was 2007. By then, the company had 15-20 employees, and honestly, I was starting to get a little bored. I’d been doing it for five or six years out of high school. It was around then that I heard about this guy in my neighbourhood who paved driveways – including my mother’s. I found out he paved four driveways on my street in one day, at four grand a piece. That’s 16k in one day!

Shawn: You were inspired.

Kevin: Oh yeah. I couldn’t stop thinking about it. Then, that spring, I couldn’t find anyone to fix my curb, which had been broken by the snowplough in the winter. So, I bought a machine to fix it myself. It wasn’t long after that I started working with asphalt. I thought, there might be a real business here. So, I sold my landscaping company. 

Shawn: And that was the birth of Cassidy Corp?

Kevin: Yes it was.

Shawn: Did you know a lot about the paving business back then?

Kevin: Not a thing.

Shawn: So, how did you get there?

Kevin: Sheer stupidity.

Shawn: Well, in that case, I wish I was as stupid as you, my friend.

Kevin: Honestly, I was young and dumb. When you’re young, you don’t even think twice. You’re just like, ‘screw it; I’ll give it a try.’

Shawn: Tell me about your first year in business. What was that like?

Kevin: Oh, I got a hardcore education the first few years. Really got my ass handed to me. I quickly learned how much of a capital intensive process it all was. There’s a lot of equipment involved. To make matters even more challenging, it was the start of the 2008 recession. It was a few years of losing money before we were able to turn the tide. Definitely a painful time. Looking back, though, I’m lucky I kept my head down. Too stupid to do anything other than just keep plowing through.

Shawn: Were there days when you didn’t want to do it anymore?

Kevin: Oh yeah. The struggle was real, no doubt about it. You’re barely making money, it’s not easy work, and it’s tough to see the light at the end of the tunnel.

Shawn: Did your friends and family think you were crazy?

Kevin: Definitely, whether or not they admitted it. I remember one of my best friend’s dads, a guy who was very successful in real estate, asking me if I had rocks in my head.

Shawn: I don’t think we talk enough about the real struggles of those early days; the losing money and the doubtful voices of those around you. But that’s where the lessons are. It takes courage to keep going through all that. So, what was the turning point?

Kevin: It was slow. I can’t put my finger on the exact year that things started to turn around, but it would have happened around the time that I learned about the importance of human capital. I started to get talented people, and that’s when things started to fall into place. Looking back, I can think of a couple key hires that made a huge difference.

Shawn: It seems you’ve always placed a lot of importance on finding good people – would you say that’s true?

Kevin: Most of my success in my 15 years in business has happened in the last three or four years, and it’s all thanks to my team. There’s some stuff that goes on day-to-day that I don’t even know about, and honestly, I think that’s the real turning point.When you can let go of things and admit there are people on your team who are more talented at doing certain things than you are, that’s when real growth happens, because that’s when you can focus on what you need to do: growing the company.

Shawn: What is the key to hiring a great employee?

Kevin: To me, it’s all about how you show up. I’d much rather have someone on my team with a great attitude but less in the way of skills; everything else, we can work out. That’s why, when I see talent, I grab it. It’s also important to remember that it’s not the end of the world if it doesn’t work out. If it works out 8 out of 10 times, you’re doing awesome.

Shawn: So, what’s the world look like right now for Cassidy Corp? In 2021, what kind of shape are you in?

Kevin: We’ve got about 40 employees, and we do about 10 million a year on municipal work, state/federal government work, commercial work, and residential work. I’d say most of our work is at the municipal level, currently.

Shawn: And talk to me about your company culture. I know that’s really important to you. What kinds of opportunities do you strive to create for your employees?

Kevin: The bottom line is that we’re people helping people. That goes for me, my employees, and our customers. At the end of the day, I’d rather lose money on a job and have our people be successful than anything else. It’s people over profit, all the way. Too many times, that’s a tagline for companies and they’re full of shit. But we try to live and breathe that.

Shawn: You care about people. You know their families. You provide a really good wage and benefits. There are a lot of things you do that other companies don’t.

Kevin: There are a lot of guys in this business who are really greedy. My thinking is: at the end of the day, if there’s a million or two lessin the bank, does that really matter? No. Did we take care of our people? Did we treat them the way we want to be treated? That’s what it comes down to.

Shawn: I’d love to hear a little more about some of the challenges you may have faced around growing the business over the years. We’ve all heard the saying, ‘what got you here won’t get you there.’ It’s a cliché, but it’s a cliché for a reason. So, tell me, what have been some of the biggest challenges for you in terms of getting to the next level?

Kevin: In the first five or six years of Cassidy Corp, we were making between 500,000 and 1.3 million. It really felt like we were stuck in that million dollar run. At that point, I started investing more in people, and more in myself. I joined some entrepreneurship organizations in Boston, I joined the Strategic Coach program, and I started doing more professional development overall. From that point on, we grew to 2.3 million, to 2.6 million, to 4 million, and it just kept going up year after year. 

Shawn: And you attribute that to your own commitment to self growth, and the growth of your employees?

Kevin: It was strictly because we developed people. I also developed myself, and came to understand what my blind spots were. I realized where I needed to be focusing my attention to help the company grow. As much as I love to be in a Caterpillar – digging in the dirt is every big kid’s dream, right? – my energies are best put toward developing scalable business ideas. Opening my eyes to that – and actually following through with it – was huge. I used to be convinced I was the best person in the world at grading parking lots and driveways. Now we’ve got four guys who do it better than me.

Shawn: I want to rewind to about a year ago, when you reached out to me and said, ‘Hey, I might need some help here.’ What was going through your mind at that point, and what’s changed since then?

Kevin: Well, it was the start of the pandemic, and I felt like I had climbed into my procrastination bed and pulled the sheets over my head. I wasn’t pushing myself enough out of my comfort zone. I knew you from Strategic Coach, and so I reached out to see if we might be able to work together. You proceeded to beat me over the head with all that ‘focus time’ stuff – which turned out to be the very thing I needed to do in order to move the needle.  

Shawn: As you know well by now, investing in ‘focus time’ is all about committing to  an hour a day, 4-5 days a week, reflecting on the big things that will help grow your company. When we first started working together, did you find it difficult to invest in that time? Even just to turn your phone off for an hour?

Kevin: Oh, it was extremely painful. My phone vibrates 60 or 70 times a day, and it’s really hard to just turn it off. But once you’re there, it’s a good spot to be. Everybody wants to have the 1-year plan, the 3-year plan, all of those plans for their business put in place. But in order to do that, you need to be willing to go through some of that pain, and for me, that meant turning off my phone. It really helped me get into the zone.

Shawn: Tell me, what would you say to new entrepreneurs or business owners? Now that you’ve gone through the battleground, you’ve had struggles and successes, what are two or three tips you might share with the owner of a company who wants to grow?

Kevin: First things first, the struggle is real. Success doesn’t happen overnight. It’s a long, long process, and even when you think you’re at the top, you’re not. Secondly, don’t judge yourself against anyone else. There’s always going to be somebody with more, somebody who got there faster. But at the end of the day, it’s irrelevant. The race is only with yourself. Lastly, as cliché as it sounds, I’d say it’s not how many times you fail, but how many times you get back up. It’s easy to throw in the towel. There are times I wish I still just had the one crew, and we were just doing driveways. Those were simple times, without real problems. But with those perceived “problems” has come a lot more profit.

Shawn: Last question. I want to know you’re deeper “why” for the work you do. I know your family means a lot to you, and you love getting to spend more time with them. So, how do your goals and your love of your family fit into all this?

Kevin: Being an entrepreneur, you get that freedom to do what you want when you want. Even if that isn’t the case 100 percent of the time, 60 percent of the time is still a really good place to be. Having the freedom to come and go, and to spend more time with my family, that’sone of my biggest driving factors.

I want to tell you about two wildly different phone calls, each of them having taken place within the last three weeks.

Phone call No. 1 was from a major multi-national corporation. They were interested in having me do a presentation within the scope of their global leadership initiative, a program they had been running for about two years. On paper, it sounded fantastic.

 I started off the meeting with the leader of the initiative by asking with: “Before we talk about me being involved, can I ask you a few questions?”

1)     What does success look like in the program you are running?

2)     How do you measure success?

3)     If this program is a success, how are people acting differently?

The reason I ask these questions (or a variation of them) at the onset of any potential client relationship is two-fold: I want to get a sense of where they are with respect to their vision, and I want to be able to measure their progress. I have no interest in one-off gigs with any follow-up or behavioural change.

This time, there was silence on the other end of the line (or, rather, the other end of the Zoom call.) After a moment, she said: “Those are really good questions.”

“Thank you,” I replied, and waited, patiently.

As the call progressed, it became clear that these were not questions the company had considered before, or at least, they weren’t prepared to answer them. At the end of the call, I was told they would need to check on the budget before anything else could happen. In that moment, I knew in my heart that I would not be proceeding with this client.

I knew this for two reasons:

1)     They weren’t serious. If they had indeed been running this program successfully for two years, these types of questions should already have been on their radar. 

2)     They weren’t being honest. I had seen their quarterly earnings (anyone could.) I knew there was money in the budget. In other words: don’t lie to me.

So I responded with thanks, but not interested.

Phone call No. 2 was from someone I’d never met before, a gentleman who owned a small family business. He started off the call by telling me he knew one of my other clients. Someone who he has a great respect for, both personally and professionally.

“If you work with him on that level, I want you on my team,” he said.

“Well,” I replied. “Can I ask you some questions first?”

In the conversation that followed, this individual was extremely honest about some of his biggest challenges and struggles, as well as his goals and dreams. He also shared that he couldn’t do this alone, that he needed help, and he wanted to know: when could we start working together?

I suggested we slow down for a minute, schedule another call to really iron out his goals, and then decide from there if we were a good fit. In the meantime, I recommended he reach out to that special client of mine and for his honest feedback on working with me.

This gentleman was floored.

“Wow,” he said, with a chuckle. “I had my credit card ready to go.”

Reflecting on these two phone calls, it’s clear which one came from “my kind of person” – the kind of person I’m meant to serve. This small business owner was honest with me from the very start. Unlike the first caller, he wasn’t playing any games. There was no swimming upstream on my part, no exhausting myself trying to convince someone who wasn’t going to come around to my way of thinking, anyway. I vowed to stop doing that kind of thing years ago, and I have no plans to go back.

Nowadays, when people ask me who my “ideal client” is, I don’t think about target markets or industries. I think about the characteristics of the people I love working with, who love working with me. These people:

1)     …have a bias for action. There are people who talk and people who do. These people do both.

2)     …have the courage to ask for help. They know they can’t do everything on their own, and they aren’t afraid to say so.

3)     …continually invest in themselves. They invest in their future vision, be it via coaching or other programs.

4)     …have a vision for the future. They might not be totally clear on how to realize that vision, but the vision is there.

5)     …have a growth mindset. These individuals are either business owners or they act like business owners.

6)     …don’t take themselves too seriously. They like to have fun and know how to laugh at themselves.

My ideal client is someone who embodies these six characteristics, and these two phone calls were a great reminder of this. One call hit all six. The other hit zero. I think it’s obvious which is which.

These calls also served as an excellent reminder of why I work on an invite- and referral-only basis. I have found that a lot of consultants are worried about going “too narrow” in terms of the services they provide and the clientele they choose to serve, but in my experience, it’s been the best decision I ever could have made for my business.

Think about it this way: would you rather go to a big, brand-name hotel with 600 rooms, where you’re one of 600 anonymous guests? Or would you rather go to a small, intimate, boutique hotel or bed & breakfast where they know your name, they care about you, and they make sure you know it? I like to see myself as a boutique hotel. Interested in making a reservation? Give me a call and we’ll talk.

In my previous life as a traveling keynote speaker and corporate trainer, I found myself at a major international conference for a large corporate client on the west coast. In front of hundreds of industry leaders from across North America, I got up on stage and presented.

Following the evening’s events, the client was kind enough to invite me out for dinner with their whole team – about 30 people in all. We planned to meet in the lobby of the hotel at 6 o’clock and then walk over to a nearby Japanese restaurant for sushi.

At 5:45, I was down in the lobby – I’m eager, what can I say? – And was the first one there. A few minutes later, a gentleman entered the lobby, came over to me, and introduced himself. As we waited for the others to join us, we talked about everything under the sun – everything except business. We really hit it off, and decided to walk over to the restaurant together so we could continue our conversation.

At the restaurant, we sat down side-by-side. It was only then that it occurred to me to ask him what he did for the company.

“Oh,” he said. “I’m the president.”

I had to laugh. I’d had no idea.

We continued chatting over dinner. About halfway through the evening, the two gentlemen sitting across from us started to pepper me with a variety of business-related questions. They wanted to know my thoughts on their company’s marketing strategies and distribution plans, and a variety of other subjects.

“Look,” I said. “As much as I’d love to answer your questions, I don’t work for the company. I think you’d be better off asking them to this gentleman on my left.”

I gestured to the president of the company, who laughed and said: “Actually, Shawn, I’d love to know what you think. What would you do if you were me?”

Half jokingly, I replied: “well, I’ll give you this one for free, but then I’ll have to start billing you.”

Then, I went off. I started with the three things I’d do immediately if I were president of the company. I went on to list all the decisions they had made (or hadn’t made) that I found questionable. I didn’t hold back. I spoke the same way I would share if I speaking to a close friend; honestly, passionately, with plenty of colorful language, and with their best interests in mind. In other words, it was a ‘No BS Zone.’

When I was finished, the president nodded, smiled, and thanked me. Eventually, we went back to talking about other things. I figured that would be that.

About a week later, when I was back in Toronto, I got a call from the person at that same company that books all my speaking engagements. My contact explained that the president wanted me to come back to the west coast and speak to his senior management team at a cocktail party. He said he wanted the Shawn he saw at the sushi restaurant, she relayed; the open, passionate, no-holds-barred Shawn, the one with all the great ideas.

“Obviously,” she said. “You made a big impression.”

I considered this for a moment, and then asked her to communicate my fee to the president – about 12 times what I typically charged for speaking gigs.

“Really?” she said.

“Yes,” I said, not skipping a beat. “It’s a senior executive team. If they take action on only one insight it be exceptionally well invested money”

She called back 10 minutes later and said the president didn’t even hesitate before saying the words: “send an invoice.” 

So, I went out there and delivered what was asked of me. I was 100 percent Shawn, bringing forth all the honesty and passion that I often felt the need to temper during my regular speaking gigs.

I’d say that about half the people in the room loved it. The other half? Meh. Now, looking back, I know the latter half simply weren’t my people, and that that’s perfectly fine. At the time, however, I took this as evidence that I needed to continue playing by their rules.

On the plane ride home, I reflected on how cool it was to be able to just be myself – and make good money doing it. But I saw it as a one-off; something too good to be true – let alone sustainable. Time to get back to the boardroom, I thought with a sigh. Being 100 percent Shawn was too much of a gamble; I didn’t want to risk offending anyone again. 

The sad truth is that it took me about six years to learn that the best way to serve my clients is to be 100 percent myself.

Oscar Wilde said it best: “Be yourself. Everyone else is taken.”

When I chose to embrace this philosophy, the right clients for me started showing up. These were business owners who had the courage to ask for help, who possessed growth mindsets, and who were honest with themselves and everyone else around them. My kind of people.

In the last 14 months, I (like many people) have had to rethink how I do business. While this process has definitely been challenging at times, it has also woken me up to the fact that being my true self is the greatest gift I can give to my clients – and to myself. The world doesn’t need more yes people, people who insist on playing politics and covering their own butts however they can – and I certainly don’t need to be one.

What I thought was a one-off experience, I’m proud to say, has turned into 100 percent of what I do. I am now 100 percent Shawn, all the time. He isn’t for everybody – and I wouldn’t have it any other way. 

I want to take a moment and look back 14 months ago, when the pandemic (I know it seems like it has been longer than that).

Two weeks into the lock down, I received a phone call from one of my biggest retainer clients. It went something like this: “Shawn, we love you, and this has nothing to do with your work, but we need to halt everything right now.”

This was devastating not only because I hated the thought of losing this particular client, but because I had been receiving phone calls just like this one for two weeks. A lot of my business was in person, and suddenly, “in person” was on hold – indefinitely. And so, it seemed like, overnight, I had lost about 85 percent of my business.

With this latest blow, I felt utterly crushed. In that moment, there was no internal pep talk. No inspirational quotes floating above my head, ready for the plucking. No reminding myself that this was a “learning opportunity.”

I want to be really clear here: it sucked!

I remember walking downstairs and having lunch with my wife. As we sat across from each other over our grilled cheese sandwiches and tomato soup, I decided that the time for wallowing was officially over. That’s when I asked my wonderful wife for a favor. “Can you call me out if I start complaining and playing the ‘ain’t it awful’ card?” I asked her. “Gladly”, she said.

I went back up to my office, and launched into “figuring it out” mode – still wearing my soft pants.

Only one problem…..

I had no idea how to figure this one out.

The irony of my situation wasn’t lost on me. Helping people through their hardest days at work is what I do for a living. And now here I was, the one in need of help, with no clue where to start.

So, I took a page from Who Wants To Be A Millionaire, and I phoned a friend. Not just any friend, mind you. I called someone I have a lot of respect for, personally and professionally, and I asked him what he thought about my predicament. His response, though I didn’t know it right away, would change everything.

He said: “Shawn, the next little while is going to be full of unknowns, and it’s going to be tough financially, regardless of what you do – whether you spend your time complaining or whether you try something new.” Then he said:

“Just focus on serving the clients that you absolutely love, and go from there.”

When we got off the phone, I thought about my friend’s advice – and thought some more. “Couldn’t he have been a little more specific?” whispered my inner voice. I decided to start by taking out a pen and paper and writing down a list of those clients I absolutely love; the clients I’d love to have over to my house for dinner; the clients whose company I simply and truly enjoy. When I was finished, I looked over each name on my list and thought: “how can I serve them today?”

And I did that every day.

Some days, I’d pick one or two names on the list; other days, three or four. I would do something as simple as record a voice message or a goofy selfie video, saying something along the lines of: “Hey, I know what you and your team are going through – here’s a tip.” Nothing major. But I just kept focusing on them.

And guess what happened?

They started calling me.

Before I knew it, I was being inundated with “thank yous” and requests to share my videos more widely. I started to ask myself: how else can I create and serve? “Wait a minute”, I thought, “Why don’t I get everyone in the same room – virtually?”

And that was when I decided to bring my pre-pandemic “Socials with Shawn” series to the wonderful world of Zoom.

In the old days, “Socials with Shawn” was an in-person event that brought together my best clients and their friends. There was music, and food, and coaching, and fun. I had no idea how such an event would translate to the online world, but I was willing to give it a shot. So, I created a Zoom account, set a date for the following Monday evening, invited those clients from my list, and hit “send.”

Then, I stared at my computer screen. Would anyone even be interested?

As it turned out, the answer was yes. That same day, much to my surprise, the RSVPs starting rolling in. “Oh”, I thought, “I guess I’d better come up with something!” 

As someone without much prior experience in online hosting platforms, I called one of my Zoom-savviest friends. I explained my situation, confessed that I was afraid of hitting the wrong buttons and screwing the whole thing up, and she generously offered to serve as my backstage manager for the event on Monday. Phew.

Over that weekend, I solidified my vision for the inaugural virtual edition of “Socials with Shawn.” I had a pretty good feeling that what people were largely looking for was a nice distraction from all the craziness swirling around them at the moment. They wanted an opportunity to connect with other business leaders and talk about what they were going through, but they also wanted to have some fun. So, that was my goals I put together some exercises and activities for the big event (which, at that time, I viewed as a one-and-done affair.)

On Monday evening, five minutes before the event started, I logged in with my backstage manager and waited. There was nobody in the waiting room, just the two of us. Two minutes passed, and I started to get queasy. “This is so embarrassing,” I said to my friend. “I’m so sorry to have wasted your time.” She shook her head and said: “Just wait.”

Then, someone showed up. Then another. And then another. And all of the sudden, there were 14 people in the Zoom room. Fourteen people from three different countries. The 90 minutes flew by, as we reconnected over laughs, shared experiences, and tips and tools for the workplace. 

At the end of the event, someone said: “This was great, thank you. When’s the next one?”

For a brief moment, I was speechless. I hadn’t even considered doing a second event. “Well, when would you like it to be?” I asked. Everyone agreed on the following Monday, and every Monday after that.

And so, for the next 12 weeks, that’s what we did. Every week, the numbers got bigger. A few people even reached out and asked if I’d be willing to come and host socials with their teams.

What began as an experiment has become so much greater than I ever could have imagined. By taking a risk and dipping my toe into the virtual landscape – despite having no idea what was beneath the water – I realized just how much potential lay before me; potential I didn’t even know existed 14 months ago.

Before the pandemic, I was used to going to clients’ houses, presenting in their boardrooms, playing by their rules. And as much as I loved that, in a way, it kept my horizons from expanding. I was always working with the same people, around the same tables, repeating the same patterns. Having to move away from in-person interactions forced me to re-think everything. It forced me to think about how I could play host instead; how I could both provide the content and create the connections that so many of my clients were longing for.

Now, I’m in the habit of welcoming all these wonderful people – and their wonderful friends – to my house (cue ‘Welcome to My House’ by Flo Rida.) I’m getting to live my dream of having my favourite clients over for dinner on a regular basis – with some small adjustments (namely, the actual dinner part.) And my online offerings are only continuing to grow. This summer, I’ll be launching my ‘Strategic Focus Program’ online, bringing together world-class leaders for meaningful conversations, contact building, and awesome resources.

None of this would have been possible if I hadn’t first gotten really uncomfortable. I’ve come to learn that, sometimes, a comfortable job or pay check can actually be a barrier to fresh thinking and creative ideas. We can get a little bit lazy, without something to shake us up every once in a while. I know I certainly did. I needed a wake-up call, and I got one – big time.

My next step, a crucial step, was asking myself that one essential question:

 “How can I serve and create for the people I love and respect?” I’m so glad I asked.

Every spring, I take part in an event called ‘Actionable Conversations Summit.’ It’s a three-day summit that brings our community together of business leaders, coaches, and consultants from around the world together. We share best practices, we learn what each other are going through, and we laugh – a lot. I look forward to it every year.

This year, things were a little different. Because of the pandemic, we had to meet over Zoom. Like many people heading into the online version of a formerly in-person event for the first time, I wasn’t sure what to expect. To my surprise and delight, I ended up having some absolutely phenomenal one-on-one conversations with people from across the globe. It was a wonderful experience.

Immediately following the summit, I went into a nine-day intensive with Rich Litvin, an incredible business coach whose event sells out every year. Unlike ‘Actionable Conversations’, I had never been to Rich Litvin’s intensive. Each day of the event offered four hours of connection, in which I got to meet 249 other coaches from around the world. Throughout those nine days, I built great bonds with people I might never have met otherwise – all from the comfort of my home office.

All the while, I have continued to host ‘Socials with Shawn’ – a virtual version of my formerly in-person event series. Each month, I bring my all star team of global leaders together over conversation, laughter, and resource sharing.

So, why am I telling you all this?

Here’s the thing: over the last 14 months of this pandemic, I have connected with more new people than I have in the past five years. While being locked up at home, I have benefited from so many meaningful conversations with people I didn’t know a year ago. By becoming an active participant in my own growth during these unprecedented times, and seeking out those amazing opportunities for conversation and connection, I have discovered so many new ways of thinking and doing business that I never would have thought about 14 months ago.

Unfortunately, a lot of organizations have completely wasted this opportunity. They have stayed within their same four walls, having the same conversations with the same people around the same table. The only difference is that they’ve been doing it online instead of in-person. Well, I hate to break it to you, guys, but you know that boring meeting everybody hated when it was in the boardroom? It’s doubly brutal on Zoom.

I think there’s a big gap between companies that are looking to make connections and learn new things, and those that are content to put up their walls and stay in their bubbles – and the gap is expanding.

The organizations that are thriving are the ones that are looking to create new opportunities for growth, the ones that are open and honest and brave. Those that are struggling are the ones that are closed-minded and unwilling to adapt.

So, the real question is: which kind of organization are you?

Every January – when there isn’t a pandemic going on – I run a two-day event in San Diego called the ‘Strategic Focus Program.’

This is a very special event in which business owners and growth minded leaders, have the opportunity to invest in their future vision by planning for the coming year – both personally and professionally. It’s a chance to get away from the office and benefit from a new environment.

Without fail, that environment is the Lafayette Hotel in San Diego’s bustling North Park neighbourhood.

The Lafayette is a tiny boutique hotel that has been around for generations. It’s got a fantastic retro vibe and some of the most stellar customer service I have ever experienced.

From the moment you check into the Lafayette, you are treated like an old friend. The last time I was there, in January 2020, I was greeted at reception after a five-hour flight with a warm “it’s great to have you back.”

This small gesture alone went a long way, but as is always my experience with the Lafayette, it didn’t end there. Later on, when I needed some photocopies made for the event, I called down to the front desk to inquire about local printing shops. Without skipping a beat, the woman on the other end of line said she would be happy to complete them right then and there. “Are you sure?” I responded. I needed about fifty colour copies made. It seemed like a lot to ask. “We would be happy to do those for you” was her reply. Twenty minutes later, a knock on my hotel room door yielded fifty beautiful, laser-printed photocopies – on the house.

I shouldn’t have been surprised when, a few days after my return to Toronto, I received a beautiful hand-written card from the Lafayette in the mail. It said: “Thank you for staying with us and bringing your smiles. We love having you here every year.”

The Strategic Focus Program is not, by any means, a massive event. At most, we’re a group of 12 people. That is to say, we’re not some corporate event bringing in hundreds of customers. And yet, the Lafayette makes us feel special, year after year; a prime example of Maya Angelou’s words come to life:

“People will forget what you said. People will forget what you did. But people will never forget how you made them feel.”

Maya Angelou

It goes without saying that I do not consider any other hotel every time I’m in San Diego. Simply put, the Lafayette creates such a unique and unforgettable experience for me and my clients that I don’t need to look elsewhere.

So, my question to business owners is: how can you create a unique, genuine experience that your clients can’t help but share? How can you serve your clients beyond the product that you’re offering? How can you show them that you actually care?

Which brings me to Jay Culbert of Kaloutas, a commercial painting, industrial flooring and fireproofing company in Peabody, Massachusetts. Jay is a man who takes these questions to heart. He’s also one of the nicest guys I’ve ever met.

Every two months, Jay hosts a virtual event called ‘Facility Rock Stars with Jay.’ He brings together his clients – facility managers from various industries – and opens up the floor for them to discuss the biggest problems they’re facing. It’s an opportunity for them to connect, problem solve, and build relationships.

There is no infomercial at the end of the event, no flashy plug for Jay’s business. After one of his first events, an attendee reached out to Jay and said: “I was waiting for the Kaloutas commercial and it never came.” Another said: “That was fantastic, and so needed in our industry. We often feel alone. Do you mind if I invite more people next time?”

Jay is a perfect example of how to show your clients that you care. And guess what happens when you show your clients you care? They can’t help but talk about you, just like I can’t help but talk about the Lafayette. We are wired to want to share great experiences, our focus should be on creating more of them for our clients.

So, how are you creating a great experience for your clients?

“Shawn, you have Type 1 diabetes, you will need to take daily insulin injections for the rest of your life, and it will shorten your life expectancy.”

Sitting in my doctor’s office in Ottawa, hearing these words for the first time, I was speechless. I was 30 years old, engaged to be married, and working as the head of business development for a major international company. In short, life was going pretty well. And suddenly, there was this.

The rest of the news came hard and fast. Within a matter of minutes, I knew this diagnosis was going to change my life forever.

What I didn’t know in that moment was that it was also a gift.

As I would soon come to learn, this diagnosis was presenting me with the invaluable opportunity to re-evaluate what I wanted out of my time on this Earth. As I left the doctor’s office that day, the iconic words of Mary Oliver rang in my head: “Tell me, what is it you plan to do with your one wild and precious life?”

My burning desire to answer this question is what steered me to the Life Wheel, a powerful self-coaching tool that divides your life into eight spokes:

·        Health

·        Career

·        Income

·        Friends

·        Family

·        Contribution

·        Recreation/Fun

·        Relationships

The Life Wheel explores each of these spokes in detail, and asks the question: What would a ‘perfect 10’ in each of these areas of your life look like?

One Saturday afternoon I headed to the public library and invested a few hours into creating my future vision.

I spent the next two-and-a-half hours reflecting on each of the eight spokes, and carefully writing out my answers. When I was finished, as I stood back and looked at my work, I thought: I can do this. This is doable. I can create my future on my own terms. I can live by design and not by default.

In the words of Peter Drucker: “The best way to predict your future is to create it.” And from that moment on, that’s what I decided to do.

I left my successful job in Ottawa, moved back to Toronto to be with my fiancée (now wife), and started creating the life that we wanted to live. Did I know, back then, exactly what the future would look like? Absolutely not! What I did have was a greater vision for my life, and the attitude I needed to make that vision a reality. 

In the years since making that fateful decision, I’ve been asked: “Shawn, isn’t it a risk to be self-employed?” : “Shawn, where does your positive attitude come from?” and “Shawn, you are so lucky to not have to deal with corporate BS”

We live into the stories we tell ourselves.

The truth is, I have more than just my diagnosis to thank for instilling in me the desire to live each day to the fullest. I have been extremely fortunate to know some incredibly inspiring people over the course of my life.

One of those people was my mother – or, as she was affectionately known by family and friends ‘Momsy.’

If she was down to her last $5, my mom was the type of person who would give it to her kids. She was always thinking of others. She loved having fun and putting a smile on other people’s faces.

In the later years of her life, I watched, heartbroken, as my mother slowly slipped away due to Huntington’s disease. The same disease that took the life all of her siblings. The same disease each one of my siblings has a 50-50 chance of developing.

Like so many who are faced with this kind of loss – along with the understanding that they may fall victim to the same fate – I realized I had two options. I could feel sorry for myself, or I could recognize that each day is a gift. I chose the latter – or should I say, I choose the latter, over and over and over again. It isn’t always easy. But whenever I need a little inspiration, I think of Momsy, who passed away in 2007, but is with me every day.

Another person who had a major impact on my life outlook was my friend Tarek.

Every Tuesday, for years, Tarek and I would get together to play pickup hockey with a group of friends. Tarek was the kind of guy who would always find a way to make you laugh – but never at another person’s expense. After each game, he would channel his inner sports reporter and type up a hilarious recap of everything that went down on the ice. He called it “The Chesswood Howler”, named after the arena where we played. It was a highlight of everyone’s week, every week.

There are lots of other things I could tell you about Tarek, but one of my favourites is that he always wore these bright green hockey pants. While everyone else was sporting the default black, Tarek showed up like he was on the Minnesota Wild. 

One day, seemingly out of the blue, Tarek was diagnosed with Stage 4 cancer. ‘Devastating’ doesn’t quite capture how it felt to hear this news. When he knew the end was coming, Tarek wanted to have one last outing with each of his friends. He and I went out for lunch, where we ate ribs and laughed together one last time. As we sat there, he looked straight into my eyes and said: “Shepheard, don’t ever change who you are and what you do. Promise me that. I learnt this lesson too late in life.”

Tarek passed away three month later. .. I think of him every time I am challenged to stay true to myself in this short and precious life – then, and every time I don my bright green hockey pants, purchased in honour of our dear friend.

There is one more person who comes to mind when I think of major influences on the way I live my life. Her name was Chelsea.

I met Chelsea when I was speaking at some business leadership events across North America. She was involved in the organizing of these events, and we got to know each very well. As our friendship grew, I learned more and more about her amazing story. Chelsea grew up in North Dakota, and her family didn’t have much. In spite of that, she always maintained this wonderful, go-getter attitude, and she started her own company in her mid-twenties. To say that we clicked would be an understatement.

One year, Chelsea invited my wife and me to come visit her and her husband at their home on the beach in Florida. The entire trip, Chelsea went to all lengths to ensure our time together was special. There was nothing she wouldn’t do to put a smile on your face. She was always thinking of others.

About eight months after that magical vacation, Chelsea was diagnosed with Stage 4 cancer. As she was undergoing chemotherapy, we would text back and forth. One day, she sent me a message saying she was thinking of starting her own foundation. She explained that she wanted to provide goodie bags to people in her same position, containing everything you might want or need during those long stretches at the hospital; things like lip balm for when your lips get dry, or oatmeal for when you get hungry. I knew Chelsea was an incredible person. But here she was, living with Stage 4 cancer and undergoing chemotherapy herself, and all she could do was think about everyone around her.

Chelsea started that foundation in her last couple months of life. Today, The Foye Belle Foundations is still going strong (foyebelle.org) Chelsea’s legacy will live on long after her 34 years, not only through the amazing work being done by her foundation, but simply in the way she made the people around her feel. I can’t think of anything more worthy of emulation.

So, these are the three individuals I think of every time someone asks me why live the way I do. Each in their own unique way, they taught me – and continue to teach me – of the importance of living every day as though it was your last. Hey, it’s a cliché for a reason.

In my work, I meet people all the time who are in careers they don’t like; who are living lives that don’t nourish or fulfill them. They have never asked themselves the big questions: What is my vision for the future? What do I really want out of my time on this Earth? What would a ‘perfect 10’ look like in every aspect of my life?

There is a cost to avoiding these questions. Without taking the time to sit down and reflect on what you really want, you risk staying in that same miserable job for years, continuing to buy into the lie that this is ‘just how it is.’ The number of people who believe this lie is, quite frankly, heartbreaking.  

My goal, of course, is not for people to simply up and quit their jobs. My goal is for them to dream a little, to give themselves a chance to live the life they want. If I have learned anything from Momsy, and Tarek, and Chelsea, it’s that life is simply too short and too precious to do anything less.

If I need a daily reminder of how precious life is, I just need to glance down to the insulin pump that is attached to me that I literally can’t live without.

I can’t determine what it is you want from this life. Only you can know that. What I can do is help get you there – once you know what “there” is.

“Our work, our relationships, and our lives succeed or fail one conversation at a time”

Susan Scott author of Fierce Conversations

Often, prospective clients will reach out to me with questions like: ‘Hey, can you do the closing keynote at XYZ conference?’ or ‘Hey, can you work with my sales team? They’re stuck on this one problem.’

Don’t get me wrong: I’m always honoured that they would even think of me, but before I make a decision about whether or not to take on a client; I need to have some questions answered first. So, I schedule a call, and these are a few of the questions I ask:

1)     What would wild success look like – one month, three months, and six months – after this action? 

2)     In the event of wild success, how are you and your team acting differently?

3)     How will you measure everyone’s progress towards that vision?

Usually, after I ask these questions, there’s a bit of an awkward silence, followed by something along the lines of: ‘those are really good questions.’

Sometimes people don’t necessarily want to answer these questions, but the way they answer them plays a key role in my decision to move forward, or not.

The thing is, I don’t want to just take a gig just to get a gig. I want to be as a person who is just as invested in a client’s business results as they are. I don’t just want to be your guest speaker – I want to be your partner. 

Learning Alone Doesn’t Create Change

Ideas Are Only Valuable When Applied

Learning + Behaviour Change = New Business Outcomes

My Three Step Process:

Step 1: I provide context– or what some might call the ‘topic’ or ‘framework’ of the event. For the purposes of this example, let’s say the context is “Innovation in Challenging Times.”

Step 2:  I facilitate expert conversations – I have participants talk to each other (I know, crazy, right?) The bottom line here is that I’m not the expert in the room – at least not when it comes to the inner workings of this particular company. I don’t know what it’s like to work there every day. So, I provide the context, and then I have them talk to one another and exchange ideas.

Step 3: I help develop a 30-day action plan (with follow-up!) – Using the ideas that were generated during the expert conversations, we develop a plan that will work for them and their organization. I use a tool called the ‘Habit Builder’, in which we identify the behaviours that need to be addressed to reach their goals, and then track those behaviours for every person in the room for 30 days.

This process has been a total game-changer. It takes a one-off presentation and turns it into an interactive, 30-day experience with measureable results.

I’ve tried it with groups small and large – most recently, as part of a keynote with more than 300 people in 18 different countries. After the event, I got a call from the executive director of the organization, who said it was the most beneficial keynote they’ve ever had.

So, if you’re interested in creating real, lasting, measurable change within your organization, give me a call. If all you’re looking for is someone to come in and help you check off the “hire a speaker” box, I’m not interested.