Are you Chasing the Wrong Success?

If you’re like most owners, you wake up thinking of your to-do list or all the places you have to be today. Your day continues in much the same way. You run from job to job, meeting to meeting, and at night you probably fall asleep with work on your mind. But is this living?

Now I’m no Dalai Lama, but I’m pretty sure that mastering your to-do list is not why you were put on this earth. It’s probably not the example you want to set for your kids, and I don’t think it what you dreamed success would look like either.

Now I’m no Dalai Lama, but I’m pretty sure that mastering your to-do list is not why you were put on this earth.


Here’s a simple thought experiment for you: of everything you worried about or daily crisis you handled last year, which of them do you still remember?

Not very many right? And this is the question that keeps me honest. It’s the reminder that most of what we do or the things we worry about don’t really matter. We waste a lot of time focusing on things that aren’t important in the long run.


I have a personal example that brought this idea home for me. Several years ago, we were living on a boat in the Caribbean. One evening we were anchored off a beautiful little village on the island of Grenada, and I had a pen and paper in hand. I was trying to develop a schedule that would help me organise and stay on top of the endless list of boat maintenance jobs that were starting to overwhelm me.

As the sun set and the colours changed, I had an epiphany: we were sailing together for two years and I wanted to be able to say we had made the most of our time together. Our goal was to explore and experience the wonders of the world, together as a family. My goal was not to be able to say “man, I really nailed that maintenance list”.

At that moment, my definition of success became clear and with it, how I needed to prioritise my time and my days. It changed what I thought about when I woke up and what I reflected on at the end of each night.

Sure I still needed to maintain the boat and to do the things that kept us afloat but I now no longer let that dictate my focus or experience of where I was, what I was doing and most importantly, why.


You’ll have heard of Simon Sinek’s “Start with Why” concept. Well, this is as true at an individual level as it is at an organisational level. It’s an approach I discovered anchored off that beach in Grenada, and it’s one that continues to serve me well today in business.

As so I ask you the important questions:

  1. Why do you get up in the morning?

  2. What’s your definition of success? Not just what you read on a poster but the complete holistic definition of success?

  3. Are you waking up thinking of the main game or just today’s calendar and to-do list?

The questions are easy, but in truth, the answers are often hard. Not because they’re missing but because for most of us, they are buried so deep, we’ve forgotten them. The great news is that it’s never too late to start asking the right questions. There’s always time to reconnect with your purpose.

If you need a little help, I find coaching an invaluable tool to redefine and reconnect with my “Why”. If you don’t have a coach…well, you should. If athletes need a coach, then why not you too. A little time with an independent person is sometimes all you need to reconnect with your definition of success and ensure you’re spending time on the things that really matter.