Successfully Happy or Happily Successful?

I recently listened to a podcast episode from The Diary of a CEO with Stephen Bartlett, featuring Kevin O'Leary - an entrepreneur known for building and investing in multiple businesses over his career and also for his role in Shark Tank US.

There’s something grounded about the way Kevin speaks - calm, direct, and confident without being forceful. He leads with honesty and speaks with the kind of clarity that comes from lived experience. Throughout the episode, they covered everything from investing and financial structure, to personal reflections on happiness and success.

One of the moments that hit hardest was when Kevin shared about his friendship with Steve Jobs. He spoke about Steve with admiration, calling him one of the most respected people in the room - someone he loved and looked up to. Yet despite Steve’s enormous success, Kevin said something that really stuck me: he never thought Steve was happy.

We often equate success with happiness. We push hard in our businesses, chase growth, scale our impact, build wealth - all in the name of reaching this goal of “success.” But what if we get there and still feel unfulfilled? What if, like Steve Jobs, the world sees our success, but internally, we don’t feel the joy we expected to find there?

This conversation brought me back to the idea that success and happiness aren’t always the same thing. In fact, I’m starting to believe that the real goal lies in learning how to hold both.

Kevin shared that happiness isn’t a destination. It’s a journey - fluid, unpredictable, and personal. That’s something I’ve really felt this year. I’ve experienced joy and sadness at the same time. I’ve felt deeply grateful and completely stretched within the same moment. Life is full of duality, and business only adds another layer to that.

The truth is, success is subjective. We each define it differently. For some, it might be building a billion-dollar company. For me? It’s being financially secure, building a business I love, and still having the presence and energy to show up for my family. It’s doing work that feels aligned and letting go of the things that don’t.

This year I have created a focus on intentionally stepping back and shutting out the noise from what doesn’t serve where I’m heading. I want to build a business and life that allows me to be successfully happy and happily successful. I know that balance isn’t always easy, but that’s the goal I’m working toward.

I can’t recommend this episode enough. It’s full of golden moments and humbling advice.

The episode is: The Diary of a CEO with Stephen Bartlett – featuring Kevin O'Leary.