Continue the Conversation
Is success overrated?
What does success actually look like?
Is it the job title? The salary? The house? The recognition? Reaching the goals we've spent years working towards?
Or is it something much harder to measure?
Perhaps success is having the freedom to spend time doing what we love. Making a difference to somebody else's life. Living in a way that reflects our values. Or simply reaching the end of the day feeling that we've done something worthwhile.
We're surrounded by messages about what success should look like. From career milestones and financial achievements to social media highlights and the expectations we place on ourselves.
But how often do we stop to ask whether the success we're chasing is actually the success we want?
In this episode of The Third Conversation, Charlotte May, Jack Challoner and Fenella Hemus explore ambition, achievement, purpose, failure and the different ways we define a successful life.
And perhaps the most interesting question isn't whether success is overrated.
Perhaps it's whether we've been measuring it by the wrong things.
If this conversation made you reconsider what you're working towards, what matters to you or how you recognise your own achievements, here are some ways to keep exploring.
Read
The Psychology of Money — Morgan Housel
An exploration of our relationship with money, wealth and the choices we make. Particularly interesting when considering the difference between financial success and having enough to live the life we actually want.
Four Thousand Weeks — Oliver Burkeman
A thought-provoking reminder that our time is finite and that a meaningful life might not be about achieving more, but choosing what deserves our attention.
The Happiness Trap — Russ Harris
Explores how we can become caught up in the pursuit of happiness and achievement, and how living according to our values might offer a more meaningful direction.
Essentialism — Greg McKeown
An invitation to reconsider the pressure to do everything and achieve everything, and instead focus on what genuinely matters.
The Gifts of Imperfection — Brené Brown
Explores the relationship between self-worth, expectations, vulnerability and the pressure to become who we think we're supposed to be.
The Top Five Regrets of the Dying — Bronnie Ware
Reflections on the things people wish they had prioritised differently, including living authentically, maintaining relationships and making time for happiness.
Listen
How to Fail with Elizabeth Day
Conversations with people about the failures, disappointments and setbacks that shaped their lives. A reminder that the path to success is rarely straightforward, and that failure can change how we define it.
The Happiness Lab with Dr Laurie Santos
Explores the science of happiness and why some of the things we believe will make us successful or fulfilled don't always deliver what we expect.
The Diary of a CEO
Selected episodes explore ambition, achievement, burnout, purpose and the relationship between outward success and personal fulfilment.
On Being with Krista Tippett
Thoughtful conversations about meaning, purpose, identity and what it means to live a good life beyond conventional measures of achievement.
Watch
How to Gain Control of Your Free Time — Laura Vanderkam (TED)
A useful challenge to the idea that being constantly busy is a sign of success, encouraging us to think about what we choose to prioritise.
How to Make Stress Your Friend — Kelly McGonigal (TED)
Explores how our relationship with stress influences our experiences, particularly relevant when thinking about ambition, pressure and the expectations we place on ourselves.
The Happy Secret to Better Work — Shawn Achor (TEDx)
Challenges the assumption that success must come before happiness and explores how positive wellbeing can influence performance.
Why You Will Fail to Have a Great Career — Larry Smith (TEDx)
A provocative look at ambition, excuses, passion and the decisions that shape the lives and careers we pursue.
Try Something
Sometimes we become so focused on reaching the next milestone that we forget to recognise how far we've already come.
Here are a few ways to explore your own relationship with success.
Write your own definition of success.
Without mentioning your job title, salary, qualifications or possessions, how would you describe a successful life?
Look at the goals you're currently chasing.
Which ones genuinely matter to you? And which might have come from somebody else's expectations?
Create a different kind of achievement list.
Instead of recording only the big milestones, write down the small things you're proud of. A difficult conversation. A moment of courage. Helping somebody. Trying something new.
Think about what success costs.
Are there areas of your life where achieving more has meant sacrificing something else that matters?
Celebrate progress, not just outcomes.
Notice the learning, effort and persistence involved in something, even if it hasn't gone exactly as planned.
Ask somebody else what success means to them.
Try asking someone from a different generation, profession or background. You might be surprised by how differently they measure a life well lived.
And perhaps most importantly, give yourself permission to change your definition.
What felt like success at 20 might look completely different at 40, 60 or beyond.
That doesn't mean you've failed to reach your original goals.
It might simply mean you've grown.
Take a Moment to Reflect
How do I currently measure success?
Where did my definition of success come from?
Whose expectations am I trying to meet?
When have I felt most successful — and was it because of something I achieved or something I experienced?
Do I give myself enough credit for the progress I've made?
What have my failures taught me about what matters?
Have I ever achieved something I thought I wanted, only to discover it didn't feel the way I expected?
Am I pursuing goals that still reflect my values?
What am I sacrificing in the pursuit of success?
And if nobody else could see or judge my achievements, what would success look like to me?
Continue the Conversation
At the end of this episode, Charlotte, Jack and Fenella were invited to complete one sentence.
Their answers reflected different perspectives on values, doing what we love, making a positive difference and leaving a meaningful mark.
And that's what makes this question so interesting.
There isn't one definition that works for everyone.
Complete the sentence: “Success to me is…”
Living according to my values?
Doing something I love?
Making a positive difference?
Having time for the people who matter?
Finding balance?
Continuing to learn and grow?
Something else entirely?
Ask someone else how they would finish the sentence.
Then ask them whether their answer has changed over time.
Because perhaps success isn't a destination we eventually arrive at.
Perhaps it's something we continually redefine as our lives, priorities and understanding of ourselves evolve.
And perhaps the real achievement is recognising when the version of success we've been chasing no longer belongs to us.
If you'd like to share your reflections more widely, continue the conversation using #TheThirdConversation.
Because the conversations that change us rarely happen first.