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Time Blocking – Give Each Hour of Your Day a Job to Do

I remember it like it was yesterday. I was sitting at the Denny’s in Ottawa, getting ready to enjoy my Grand-Slam breakfast and coffee. I had been in town visiting my mom (she was in the later part of her life, and so I often found myself travelling from Toronto to Ottawa to see her.) And being the voracious reader that I am, I always had a book with me.

On that particular morning, I was carrying around a book called “The E-Myth” by Michael Gerber. I had brought it with me on the trip, thinking at some point I’d crack it open. As I waited for my breakfast, thinking ahead to the four and-a-half hour drive back to Toronto that lay before me, I decided there was no time like the present.

By the time the server came by with my food, I was already completely absorbed in this book. I couldn’t put it down. I actually ended up saying to the server: “Do you mind if I stay here and have coffee and finish my book?” She said sure, and 90 minutes later I finished it. (And yes I left her a generous tip)

My experience with “The E-Myth” is not a unique one. It has been lauded by entrepreneurs the world over. Its main principle can be summarized like this: there’s a big difference between working in the business and working on the business.

Working in the business is all about taking care of the day-to-day. And, obviously, this is essential. Working on the business, on the other hand, is just as (if not more) important. Working on the business is all about making time to work on your future vision for the company. It’s about creating your vision and working toward its realization.

Too often, when I start to work with business owners, they are working in the business and not on the business. I always say the same thing: creating daily space for future focus is critical to your business today and you’re growing your business for tomorrow.

Many people are familiar with the concept of working in vs. working on the business. But there’s a huge gap between knowing something and actually doing it. We need to treat our brilliant brains like they are plants; we need to feed them and tend to them in order for them to grow. If we don’t do this, if we don’t invest that crucial time into expanding our mindsets, we will forever stay working in the business and not on the business.

Making Room to Create

Before we get into working on our future visions, we need to create the time and space. For me, the very first thing I needed to do was create a ‘Stop Doing at All Costs’ list. Some of the things on that list included:

1) Jumping into emails first thing in the morning.
2) Working without a plan.
3) Letting everybody and everything else grab myattention at all times – that includes texts, emails, social media, etc.
4) Saying yes to the people and projects that don’t feed my future vision.
5) Indulging in the old habits that don’t serve me.

Slowly but surely, adhering to my ‘Stop Doing At All Costs’ list gave me the space I so desperately

I created space to focus on what really mattered.

This is where a lot of people seem to get stuck. They like the idea of prioritizing focus time, but they can’t wrap their hands around where to find it in their already-crammed calendars. And they’re right. Their current calendar is crammed. But that’s where a ‘Stop Doing At All Costs’ list comes in handy. If we want to get closer to our future vision, we need to stop saying yes to things that don’t serve that vision in any way, shape or form.

I know this may sound impossible, but the truth is that we make commitments all the time. We put meetings in our calendars and, because they’re there, we show up for them. I think back to pre-pandemic times, when I used to do kickboxing classes 4-5 times a week. The class I went to was at 5:30 p.m., and the funny thing is, it was always the same 15-20 people there. Over time, as I got to know my classmates, I discovered they were a pretty high performing bunch outside the gym. I was struck by the fact that these incredibly busy people made time for this activity, and one thing they all had in common was that they put ‘kickboxing’ in their calendars. That little bit of structure and commitment feed them.

The simple fact of the matter is that when you make a commitment, even to somebody you only know as your kickboxing buddy, you show up.

It’s all about owning your calendar.

So, what does this ‘radical’ idea actually look like in practice? To answer that question, I like to lean on the advice of one of my favourite authors, Cal Newport. In his amazing book, ‘Deep Work’, he talks about a concept called ‘time blocking.’ Time blocking is the practice of assigning a job to each hour of your day. This can be challenging at first, but the results might just blow your mind. Here’s an example of how I use time blocking in my day:

‘no phone zone.’

85 percent of them will make me say, ‘what was I thinking?’ but 15 percent won’t. Plus, the sheer act of writing them down every day is like working a muscle at the gym.

At some point during the day, I will block out some time to answer emails. This may seem like a small thing, but it’s a crucial part of the time management puzzle. Before I started doing this, I would be distracted all day long. When I started restricting myself to one hour a day for checking and responding to emails, I was amazed by how focused I was able to be for the rest of the day.

Follow-through is really important here. I can’t stress that enough. If you’re reading this and thinking, ‘I’ll see if I have the time’, chances are you won’t find it. If you’re not conscious and deliberate about the way you manage your time, I can almost guarantee that your old habits will keep calling the shots.

Now, I’m by no means an expert at time blocking. It’s something I’ve been working on for a few years, and it’s still a work in progress. That being said, even in its imperfection, it’s been a total game changer for me. As I said in last month’s playbook, 80 to 90 percent of my current work and opportunities were created from time blocked periods. If I had waited until I felt fully confident starting this practice, I would probably still be struggling with the same things I was struggling with before.

Ok Shawn, I’ve Locked My Phone Up, Now What Do I Do?

So, you scheduled time into your day to work distraction free.

You turned your phone off and locked it away, or put it in another room. Now what?

I get asked that question a lot.

There is no “right” or “wrong” ways to invest your focus time, and I totally understand that it can be challenging to start.

And there is incredible power in asking great questions.

Questions are essential for lifetime growth. As children, when
we’re all growing at a rapid rate, we ask lots of questions. As we
get older, we gradually begin to think we have a lot of the
answers. For some people, their entire sense of security and self-
image depends on having all the answers – on never being wrong.
As a result, these people try to understand everything in terms of
what they know. But all growth lies in the territory of the unknown.
What we already know is in the past. What we have yet to discover
is in the future. Always make your questions bigger than your
answers, and you’ll keep drawing yourself into a bigger future with new possibilities.

Dan Sullivan, Catherine Nomura
“The Laws of Lifetime Growth”

Start Your Day Strong

Back before the pandemic, I was doing a live session at a corporate retreat with about 180 people. I
started my session by asking the following question: “When you wake up, how many of you reach for your
phone first thing?” There was a ripple of laughter, but about 90 percent of the audience put their hands

Too many of us reach for our phones before we get out of bed, before we even look over at our spouses. And when you reach for your phone before you’ve even had a chance to properly wake up, you’re effectively saying ‘I don’t want to drive the bus today.’ You start looking at all those emails and texts and meeting requests that came in overnight, and you’re letting everyone else dictate your day.

So, let’s flip that switch. How do you want to start your day every day? What is the routine you want to commit to doing that will set you up for success for the day? I had to experiment with a lot of different things, but now my mornings tend to involve some reading, some meditation, maybe a little exercise. Mostly importantly, I don’t look at my phone for the first 90 mins of the day.

Your routine might look different, and that’s okay. So long as you’re being mindful of starting your day off strong, and committing to your daily focus time, you’re going to see results – and those results will be life changing. Not just business changing. Life changing.

Own Your Schedule, Or Someone Else Will

I work with business owners and leaders who have had a tremendous amount of success, long before meeting me. Typically, when they reach out to me, it’s not because they’ve stopped seeing success. It’s because it’s challenging to take that success to the next level. In other words, the tactics that got them to where they are today won’t get them to the next level.

One of the very first things I ask clients to do is track how they spend every single minute of the day. I ask them to do this for a full week. And when I say every minute, I mean every minute. If they go on LinkedIn for eight minutes, I want to know about it. If they’re in a meeting for 63 minutes, I want to know about that too. You get the idea.

I’m sure you can also surmise that it’s not a very popular exercise. But it works. Here’s how.

Once those seven days are up, I ask my clients the following question: “Where was your thinking time?” If they stare back at me with a blank expression (which is more common than you might think) I try again: “you know, the time in your calendar specifically devoted to thinking about your future, to creating, to exploring new opportunities and ways to think?

Usually, this is followed by an awkward silence.

What I’m trying to communicate to my clients is this: if we don’t own our schedules and actually pencil in time to think, those opportunities don’t happen.

There was a time in my life when I didn’t do this. Back when I was a traveling keynote speaker, living out of suitcases and airport waiting rooms, my then-coach was always on me about my time management. I distinctly remember her asking me to look at my calendar and figure out when my next free day was.

Oh, that’s easy,” I said. “It’s in 15 days. I’ll be flying that day…

Promptly, she cut me off. “No, I want to know when is the next day you have zero plans.

I shuffled through my calendar and, horrified, realized my next totally free day was 39 days away. “Huh,

I thought. “No wonder I’m a bit burnt out.

I’ve since learned how crucial it is to give yourself time – and I mean really give yourself time – to think. I don’t know about you, but my best ideas don’t come to me in boardrooms or Zoom meetings or conference calls. They come to me in the shower, or on a walk in the park, or on vacation, or while I’m sleeping. In other words, I do my best thinking when I have nothing else to distract me.

Airplanes are a perfect example of this theory in practice (or, at least, they used to be – before they started offering in-flight Wi-Fi.) Back in the day, without the entirety of the world wide web beckoning me from my pocket, I would dream up all kinds of ideas on airplanes. Nowadays, I get the same effect on subway cars (here’s hoping the Toronto Transit Commission doesn’t introduce in-service Wi-Fi anytime soon.)

Bottom line: we need to create the conditions for our brains to get, well, creative. We live in an incredibly distracted world. Making time to think and create is an extraordinary gift we give to ourselves. But we need to actually schedule it –daily.

About five years ago, I started my journey with Strategic Coach. One of the core principles of this program is the importance of identifying each day of your week as a Focus Day, a Rest Day, or a Buffer Day. On Focus Days, you shut down all distractions and work solely on your future self or company. On Rest Days, you commit to well, resting and relaxing. Buffer Days make up probably 99 percent of the population’s every day. These are the days where you do a little bit of everything – work, social media, other distractions, etc.

Learning how to actually schedule my Focus Days, Rest Days, and Buffer Days was really challenging. It took me a long time to get into the habit, but once I did, I can honestly say it was life changing. I started by committing myself to something I called ‘Championship Monday.’ Every Monday, I would go to the local public library with only two rules in mind: 1) Turn off your phone, and 2) Work solely on ‘Future Me’ or ‘Future Company’ activities. It sounds simple, but it was extremely difficult – at first. I so clearly remember my first Champion Day. I was so excited. I went and got a large coffee, got to the library, sat down, turned my phone off, and then thought: “Now what?” Within five minutes, I was sheepishly reaching for my phone.

Luckily, I stuck with the practice, and now it’s a habit I’ve kept. More than 80 percent of the work I’m doing now got its footing on those Focus Days, my Champion Mondays.

At this point, I’m fully aware that you might be thinking: “Well, Shawn, that sounds great, but there’s no way I can schedule a full day every week just to think.” To that, I say: start with 30 minutes. Right this minute, I want you to slot 30 minutes into your calendar for thinking time. Then I want you to schedule 30 minutes at the same time tomorrow, and again for the day after, and again for the day after that. Make sure it’s always the same time (trust me on this one – it works). During that focused 30 minutes (or 60 if you’re feeling brave) I want you to turn your phone off and work on one topic or question that will bring you closer to where you want to be in the future. Whatever you do, don’t use this
time for day-to- day stuff. You can do that any other time. This 30 (or 60) minutes is just for creating your Future Self and Company.

The Power of Saying Yes & Figuring It Out

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.

We Are the Company We Keep

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?

Welcome to the first edition of ‘The Owner’s Mindset.’

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.

Are We A Good Fit?

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.

It’s Like Having Dinner With A Friend

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. 

How Answering One Question – Changed Everything

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.