Push Yourself – Keep Going For It

This post is inspired by my grandmother, Betty Howett. At 81 years of age, she went back to university. She’d been an entrepreneur her whole life, had businesses all across Canada, lived an amazing life, a great adventure. But when she got into her 80s, she was really curious about the religions of the world, and went back to university to study theology. I’m fortunate to have that DNA and I love to keep learning and growing. But I’ve noticed, the older I get, the harder it seems to get.

So, we’re going to talk about what you need to do to push yourself and “keep going for it”. Those are the words that my grandmother used to say – and my mother still says to me this day – “Just go for it, keep going for it, keep trying new things, keep expanding your adventure.”

How good are you at regularly stretching your personal limits? You can build your confidence as a leader by consciously choosing to do things you think you can’t do, and push yourself towards your true potential.

“We don’t stop playing because we grow old, we grow old because we stop playing.” – George Bernard Shaw

And it’s easy, as you get more established and older in life, to stop taking risks and stop stretching yourself. It’s also a sure-fire way to have your soul and your brain start to die.

Key point – Keep creating opportunities to be a novice learning from masters – to be someone in a situation where you’re very uncomfortable, probably over your head, but you’ve got an expert guide to help you figure it out and grow stronger, as a result.

You really need to work on this if:

  • In the past six months, you haven’t been uncomfortable and once thought, “How the heck am I going to make it out of this alive?” or get out of this situation intact
  • In the past 12 months, you haven’t tried something new, and then been a spectacular failure
  • A challenge makes you squeamish, you likely back down, and/or you haven’t pushed through
  • You haven’t recently felt like the least competent person in a group
  • You would love to push yourself to try something new only if someone would teach you, or there was an easy way to make it happen.

Stretch List

As we get more successful – as CEOs, executives and leaders – we often get into a comfort zone and a rut, and we don’t put ourselves back into that amateur, novice scenario. And as a result, we can grow weaker, even though we get more experienced.

The solution for this and is something called the Stretch List.

Many people will have a bucket list of cool things they want to experience in their life – the Stretch List is a similar concept that focuses on ways you’d like to stretch yourself and expand your capabilities. The key is to apply it in your work, for yourself and in your life.

Local Guides

One of the major habits that I suggest is to always find a local guide. Look, we’re not 17-year-olds anymore. We’re experienced people that have lots of great things going for us. Let’s not waste our time. Find a local expert or a local guide in whatever it happens to be.

As an example, my son Braydon and I were in London, and we wanted to learn photography. He’s really passionate about it and I wanted to learn, as well. So we found a photography teacher in London, who took us all around the city shooting pictures, teaching us the technical aspects of amazing photography. It costs us a bit of money but in four hours, we learned a ton and had a great time too.

stretch list

The Challenge

  1. Create a Stretch List – Fill out the first column on your Stretch List.
  2. Find local Guides – Fill out the ‘Local Guide’ column on your Stretch List to indicate where you would like a guide. Who would be a local guide? Now, if you don’t know a local expert, who do you know that could help you find one? Pretty well guaranteed, there’s a local expert for everything you want to do.
  3. Take a step forward – Write down the number one thing you want to do to stretch yourself, and then reach out, make a call or send an email, to find someone that you can do it with, or learn from, and get it booked.


You have to push yourself out of your comfort zone on a regular basis because that’s where the magic happens. You learn, grow, and keep your soul agile and moving ahead when you’re doing things that stretch you.

Unfortunately, as you get established and comfortable, you’re less likely to do it. What you want to do – as Liz Wiseman talks about in her book Rookie Smarts – is continually go back to that rookie mentality, and that rookie state, where there are massive amounts of learning – where you’re stretching and expanding who you are, at the core, so that you don’t become stale, stagnant, and ineffective as a leader.