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.

Shawn Shepheard is an executive coach, business strategist and keynote speaker. He loves coaching business owners, or people that act like owners, and provides them with clarity, focus and accountability that leads them to new opportunities, income and more time off.

To inquire about his group coaching programs, executive retreats, and keynote speaking, please visit shawnshepheard.com

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