Skip to content

Never Give Up On Something You Can’t Go A Day Without Thinking About

Wednesday 19th June 2024
Play Bigger 5th anniversary

Winston Churchill famously said, “Never give up on something you can’t go a day without thinking about.”

Although he didn’t say anything about what to do if the thing you can’t stop thinking about makes you batshit crazy?

As in, your “something” owns you. It’s in your head so much, your “something” thinks YOU, not the other way around.

Is this the difference between passionate and possessed? Is trusting this “something” how to Follow our Different?

What Churchill also doesn’t say is, what to do if 8 out of 10 ten times you share your “something”, you fail.

For 30 years?

Then what?


Well, my “something” is Category Design. And this week is the 5th anniversary of “Play Bigger”. It introduced Category Design to the world.

The book was my last-ditch effort. My hope was to help pirates, dreamers and innovators make a difference.


And, I figured the book would fail.

A 30-year .200 batting average will do that to you. I assumed, I’d end up being the weird guy drinking in the corner talking to myself about stuff most people thought was nuts, or irrelevant.

Before Play Bigger came out, most people didn’t get it. And while I was having success in my career as an entrepreneur and a CMO, most times I shared the thinking behind that success – Category Design, people’s eyes glazed over. Or they thought I was talking about nose-picking marketing or worse, “messaging”.

So, I figured Category Design would remain my secret and the secret of a handful of people who “got it”.

I tried and failed more times than I can count to leave Category Design alone. Being obsessed with something – for 30 years –- that most people think is stupid — can make you fucking “crazy”.


Then Play Bigger took off. And our podcasts, Niche Down and now Category Pirates took off.

Play Bigger made it into the top 1% of business books. Niche Down hit #1 in marketing books on Amazon. Lochhead on Marketing hit #1 on Apple’s podcast business chart and, there was the few days Follow Your Different broke the top ten on the over-all Apple charts and beat out Oprah!

If you read, listen to, got anything out of, or shared any of our work, from the bottom of my whisky stained heart, THANK YOU.


Now… here is a truth I’d like you to know.

I’d be lying if I led you to believe that Category Design is so legendary, it just became a massive viral hit. That the “product” called Category Design, was so legendary, it marketed itself. Well, I’m a lot of things, but liar is not one of them.

Some Digital Entrepreneurs, motivational “Hustle Porn Stars” and get-rich-quick “Growth Hackers” make it seem like there is a cheat to success.


I even fell for it. As I was starting off as a writer and podcaster, I thought we could hire some super ding-dong, growth hacker whiz kid to make us go viral. Then BOOM! Success.

Not so much.

Too often people who achieve success talk about it as if everything went up and to the right.

It’s almost always a lie. It takes work. Smarts. Luck. And a lot of help.


What did it really take to Category Design tip?

  • 30 years in the trenches
  • Then… 7 years, (approx. 2,555 days) of hard work
  • Legendary partners and co-Creators
  • Support from countless legendary people
  • Support from over 50 top podcasters
  • Over 50 speeches
  • A ton of PR
  • Producing over 500 of our own podcasts
  • A ton of good luck
  • A ton of readers and listeners sharing
  • And, the love and support of SAP (This is funny if you read the “10 reason not to read this book” at the start of Play Bigger)


So yes, becoming an over-night success is easy! (Coughing and saying “bullshit” at the same time).

Most importantly, please know, I know that it’s tough feeling crazy.


Feeling different.


Feeling like the world doesn’t get you. Some people find their place in the world, but many of us have to MAKE our place.

If you’re that kind of person, if you’re a person trying to make the world a different place, I believe:

The future needs you.

Please do not stop.

The future needs you.


The future needs more people working on the exponential. Creating breakthrough categories that move humanity forward.

And, if you have a “something” that makes you crazy, you might find solace, in these two musing that I often hold on to.


From Charles Bukowski:

“Some people never go crazy. What truly horrible lives they must lead.”


From Steve Jobs:

“Here’s to the crazy ones.

The misfits. The rebels. The troublemakers.

The round pegs in the square holes. The ones who see things differently.

They’re not fond of rules. And they have no respect for the status quo.

You can quote them, disagree with them, glorify or vilify them.

About the only thing you can’t do is ignore them. Because they change things. They push the human race forward.

While some may see them as the crazy ones, we see genius.

Because the people who are crazy enough to think they can change the world, are the ones who do.”

Best wishes for legendary success, bless you and…


Thank you.


Christopher Lochhead

June 2021


PS: The follow up from me (and my partners Eddie & Cole) to Play Bigger is the Category Pirates Newsletter.

If you’d like to try it free for 30 days, respond to this email with “YES” and we’ll get you on board the Category Pirate Ship ?‍☠️