September 18, 2021

Rebranding Life After Hockey

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Rebranding Life After Hockey

Smart Positioning, maybe you don’t need to figure everything out the hard way.

Rebranding Life After Hockey:

Smart Positioning, maybe you don’t need to figure everything out the hard way...

What’s next for you after hockey?

Wait, what?!

If you’re anything like me, you probably didn’t know how to answer this question, or even that you were going to need to. That said, every hockey career ends before we’re ready for it to.

It’s true though, and you probably haven’t thought much about what’s next. I didn’t. I just want you to know that it’s going to be a thing. Your career will end and you’ll still have an awful lot of life left to live.

There will be pressure from your friends and family. They are going to be on your case to do something. Maybe it’s a good old fashioned 9-5 type of job, or maybe it means finding a role in broadcasting or coaching; and maybe that’s really what’s best for you.


If you like doing things on your own terms, and being in control of your own destiny, this obstacle standing in your path, isn’t really an obstacle at all. It's an opportunity to be seized.

Starting a business means building something upon your own values, perspective, and the change that you want to see in the world. It’s time you started putting that power to good use.

There’s no better investment you can make than in yourself.

So, how did we get here?

I’ve always been lucky to have a supportive network of friends and family. My family in particular has always looked out for my well-being and security, and I’m eternally grateful for that. The thing is, when you’re starting or growing a business, it’s likely that the people in your lives, especially your elders, have lived their whole lives in that 9-5 framework, so they believe that it’s the only way to live a successful life. These days however, getting a good education doesn’t guarantee you a good career. Having a good career doesn’t ensure you security, let alone a roof over your head. That system they thrived in for decades, no longer works for most people.

In fact, our parents' concept of what security looks like, is probably the least secure way to live. If you’re relying on one source of income, that someone else controls…

While, maybe you’re starting to get the idea here.

The people who build wealth these days learn how to generate multiple streams of income which they themselves control. The only problem is that entrepreneurship requires a leap of faith, and an unwavering belief in your own abilities, skills and knowledge; and that scares the shit out of most risk-averse people.

Stepping out of my comfort zone

For me personally, I realised that if I was going to grow my business I was going to need to build some new relationships with people who not only understood the types of challenges that I was facing, but also that I would need support taking risks; that the safe path, probably wasn’t going to help me grow. Fortune favours the brave, right?

My journey led me to Chris Do and the Futur. I had been learning from their content for a few years at this point, it’s invaluable for anyone working in the space where business and design intersect. Through this membership, I found myself in a very unexpected conversation with Errol Gerson.

If you haven’t heard of Errol, he’s a lovely human being with an endless library of life changing stories and advice. For example, he used to be an accountant for the band Megadeath. It’s best if you hear that story from him. His podcast episode with Chris Do is the best possible way you could spend the next hour of your life.

Leading up to this chance encounter, I had had one thing on my mind.

How could someone like me niche down?

I had been running this business for three years at this point, and while things were going really well, I was kind of stuck on how to scale and beyond my local network. I had read Blair Enns Win Without Pitching Manifesto, where chapter one, straight out of the gates, is titled

“We Will Specialize”, and goes as follows:

“We will acknowledge that it is the availability of substitutes — the legitimate alternatives to the offering of our firm — that allows the client to ask, and compel us to give our thinking away for free. If we are not seen as more expert than our competition then we will be viewed as one in a sea of many, and we will have little power in our relationships with our clients and prospects.”

Essentially, when you’re perceived as being highly specialized in one area of expertise, to the point where few if any alternatives exist, you’re free to command a premium. This might seem counterintuitive because so many people, especially creatives, are terrified that they’ll pigeon hole themselves.

Blair also went on to say that “those pigeon holes are stuffed with cash”.

So yes, thinking about niching was weighing heavily on me. I knew that I needed to do it, but I wasn’t sure how to do it in a way that suited me specifically. Blair’s partner in crime and podcasts David C. Baker, wrote in his book, The Business of Expertise:

“Without strong positioning and the opportunity that stems from effectively applied lead generation, you are stuck with whatever opportunities fall in your lap instead of making your own success. If you carve out an expertise business that fits who you are, takes advantage of your strengths, and minimizes your weaknesses, it’s more sustainable.”

He also followed up with perhaps one of my favourite quotes: “We can’t read our own label from inside the jar. We just can’t.” Which leads me back to Errol Gerson and our chance encounter.

I joined the Pro Call, with the intention of just observing. I was new to the group, not sure what to expect, and admittedly a little bit timid. As the call began, Errol came on and introduced himself quickly, and invited the first scheduled speaker. For whatever reason, that individual was nowhere to be seen, and then unexpectedly, Anneli Hansson, who was running the call, said “Hey Ken, why don’t you ask Errol a question”…

Now, I’m not one to turn down an opportunity like this, but understand, I was nervous AF.

My question was basically, how do I find my niche? I explained that I wasn’t keen on narrowing my focus in terms of industry or skill. I love the variety of helping different types of people, which is always a great opportunity to grow. To me, there’s a synergetic kind of value that comes from the continuity when the strategy creates the foundation for a brand, and you build the identity upon it, and use that identity and strategy together to form an ecosystem of touchpoints wherever people experience your brand.


Errol was quick to stop me. He said, “Ok Ken, you’ve got 30 seconds, tell me about your business and who you help, your elevator pitch, Go”.

I managed to fumble my way through something to the extent of, “I help companies express themselves from a place of clarity with smart, engaging design.” Which isn’t wrong, it’s just not terribly inspiring.

It was met with a resounding “Zzzzzzz.” He literally snored at me. I felt a bit stunned to be honest. Maybe that’s what I needed in order to be able to step outside my own mind and see the bigger picture. I was really hung up on saying the right thing, what I thought people wanted to hear, rather than just speaking straight from the heart.

Then, he asked me, “Tell me a cool story about something amazing that happened in your life”.

Here’s what I told him:

My whole life, one thing that’s always stood out was hockey. I managed to play at a decent level growing up, and while I didn’t really think much of it at the time, it opened some interesting doors for me later in life.

After university, I really wasn’t sure what I wanted to do with my life, and I had some friends that were planning to go and teach in South Korea. I didn’t know much about the country, but I decided it might be fun, so I found myself a job and hopped on a plane.

I didn’t think they would even have hockey there, but I ended up having to get my parents to ship me my gear a month in. I had found not one, not two, but three teams to play on. Where I met all kinds of awesome people from all over the world.

They even had an annual tournament called the IMJIN River Cup, where teams from other countries came to play to honour the legacy of Canadians during the Korean War who played hockey on the frozen Imjin River.

One particular year, the Tokyo Canadians team was short players, and my buddy Chris and I offered to play with them in the tournament. We ended up winning the whole damn thing.

While it was a pretty amazing experience at the time, it was also pretty awesome when they announced just last year that they would be moving that trophy to the Hockey Hall of Fame in Toronto. I somehow managed to sneak myself into the hockey hall of fame!

“Stop right there, Ken! I think we found it. I’d like to introduce you to my good friend Jack Bies. Jack helps former footballers in the UK start business”. Errols words filled me with perspective.

It made perfect sense. I mean, I finished playing competitive hockey at 20. Even the best players in the world finish their careers at 35-40. That leaves you with an awful lot of life left to live. Too much to just spend coasting off into the sunset.

So what do you do when you’re in your twenties, and you’re no longer able to do that one thing you love doing. You feel lost, stripped of purpose, and in need of direction. This is how I felt for a really long time until I found a renewed sense of purpose in business.

Suddenly, it was clear who I really needed to be talking to.

So, I started writing.

The words come to me clearly and easily. It was easy because I knew exactly who I was talking to; 25 year old me. I knew exactly what that kid needed to hear. He didn’t really fit the 9-5 mold working to build someone else’s dream, just to spend the next 40 years getting by, but rather it was to leverage his creative abilities to build something for himself, and to start doing things on his own terms. Imagine what he would have been capable of if he had heard this advice at age 20, not age 40.

Remember that elevator pitch I fumbled my way through? Now it sounds more like this:

Hi there, I’m Ken Braithwaite, and I run a strategy and design studio called cheddar, based in Toronto Canada.

We’re on a mission to rebrand life after hockey, by helping to transform former hockey players into savvy entrepreneurs.

As a former player myself, I get what it’s like to spend your entire life with a single goal in mind, only to feel lost when it gets taken away at age 25. Luckily I’ve found a renewed sense of purpose in business, and I’d like to help others like me, do the same.

A tad more compelling, right?


In my experience, we get the best out of ourselves through collaborative efforts. Some good ideas come from individual efforts, but I promise you, the very best ideas are born from conversations.

I will be forever grateful for my unexpected conversation with Errol Gerson. If you should ever find yourself with such an opportunity, get after it. Positioning yourself smartly is one of, if not the most important things you can do in business, but it’s also the hardest thing to do for yourself.

If you’re ever feeling stuck, whether it’s with something business, or maybe just figuring out what to do next, hit me up. I’m sure there’s a clear path forward, and sometimes it’s just a matter of talking it out, and taking that leap.