Carlie and I presented at a forum of about 50 business leaders and entrepreneurs on using context for business strategy and decision-making. We asked the group the question what would make you feel successful? Encouraging them to consider that before setting the strategy for their organisations.
We’re expecting vague responses that we could tease out into thought-provoking potential, but what we got back was very specific financial and organisational development goals. The surprising thing was that most of the entrepreneurs had replaced their own personal success with that of the organisations they lead.
“So what’s the big deal?”, you may ask. The work we do is there to empower us to live the life we want to live not the other way around.
Success. It’s a word that gets thrown around all the time in the business world. But here’s the thing—have you ever really stopped to define what success means for you? Not your industry, not your competitors, not your LinkedIn connections—but you, personally.
A lot of business leaders chase success without ever questioning whether the finish line they’re sprinting toward is one they even want to cross. That’s why we see high-achievers who have all the external markers of success—money, status, influence—but still feel unfulfilled.
The Trap of “Success” as a Moving Target
Patrick Lencioni, often talks about the difference between being rewarded and being fulfilled. He warns against chasing status or wealth without aligning it to something deeper: “Success is not about climbing the corporate ladder, but about finding meaning in your work.”
If success always feels like something you’ll reach when you hit the next milestone, it’s time to pause and redefine it on your terms. That approach just doesn’t allow the space to connect with what’s really important to ourselves as a person. It might sound good. I’m telling it to somebody else but it will be hollow and meaningless.
Michael Singer, author of The Untethered Soul, would tell you that real success comes from inner freedom. He challenges us to stop clinging to external validation and start asking ourselves: What do I actually want?
A Simple Activity to Explore What Would Make You Feel Successful
If you’re feeling stuck, try this:
- Imagine your perfect day five years from now. What are you doing? Who are you with? Forget about ‘how’, focus on perfect.
- Write down three things that make you feel deeply satisfied. Not “things that look good on paper,” but moments when you feel truly alive. Imagine what if you could do them more regularly.
- Identify what you can eliminate. What activities, obligations, or pressures are keeping you from that vision of success?
- Set a “Success Rule.” Define success in one sentence. For example: “Success means having control over my time while working on projects that inspire me.”
Own Your Version of Success
Greg McKeown, author of Essentialism, says “If you don’t prioritise your life, someone else will.” Instead of adding more, he suggests subtracting the noise and focusing only on what truly moves the needle for you.
In a recent family conversation, our daughters astounded us by telling us that they were living their best lives at the moment and if they died tomorrow they wouldn’t have any regrets. That’s about as close to my version of success as I could imagine.
Success is personal. It’s not about ticking off boxes on someone else’s checklist—it’s about knowing what actually matters to you and designing your life around that. So, take a step back, strip away the noise, and ask yourself: What would truly make me feel successful?
The answer might just change everything.
Darren Clark