How do you tend to define success? Is it an external outcome you pursue, or is it something personal you feel ‘close in’?

I’ve been preparing for our next set of Serenity Island Picnics. I’m considering how being more experimental might affect my understanding of success. I share a few of these observations in this short episode of The Gentle Rebel Podcast.

The Return to Serenity Island combines structured resources with a guided creative journey, offering a space for more experimental thinkers to explore change, personal growth, and ambition without the pressure of performance or rigid goal-setting. It appeals to those who view life as a mysterious treasure island to explore rather than a checklist of predetermined items to tick off.

I find more satisfaction in the process of writing and producing a song than in completing it. Hearing a song on the radio doesn’t give me a greater sense of success than the mini-breakthroughs and connecting the dots as it emerges.

However, I can downplay the importance of these close-in success moments. Absorbing outcome-oriented metrics can make it seem as though those don’t matter, and that true success lies in pursuing bigger goals.

In The Return to Serenity Island, we connect real-world areas with map regions to recognise micro-moments and small glimmers of ‘close-in success’ in everyday life.

A big reason I keep making videos about The Let Them Saga is what it represents. The story got a hold of me, and I’ve been unable and unwilling to ignore it. It’s been a strange experience because it is a complete departure from what I normally do. But with an experimental approach to life, pursuits can be driven by an inner compass (values, beliefs, etc.), which can lead us in directions that may seem, on the surface, unusual.

In other words, we may connect the dots and see patterns, threaded together by those intrinsic motivations. For example, I’m drawn to the Let Them story because I can see elements of it as both a symptom of and a contributor to the greater challenges we are currently facing in the world.

On Serenity Island, we use this compass to help us assess and respond to opportunities, feelings, and thorns that catch our attention as they arise. This enables us to reorient to our own definition of success and feel more confident about the path we’re on, even if it doesn’t make obvious sense to others.

For me, I feel “close in success” when I know I am acting in sync with those deeper motivators, rather than in pursuit of a quick result or the perception of growth.

I’m in awe of people who can grasp concepts quickly and understand how, why and where they fit. It seems to take unfamiliar ideas longer to snap into place for me. But when they do, it can feel like a mini-revelation. I love those aha moments.

One of my core priorities while developing The Return to Serenity Island and The Haven was the concept of seasonal return, rhythm and repetition. For many experimental people, this allows ideas to settle and dots to connect.

It’s through the familiarity of repetition that something may eventually land for us at the right time, when the conditions are right.

‘Close-in’ success can look like failure to onlookers.

On the experimental path, growth and progress often unfold in non-linear ways. They may appear as fits and starts. Trial, error, quitting, walking away, coming back, forgetting, remembering.

Popular conceptual mantras can shape our self-understanding. For example, we learn to value the ability to “always begin with the end in mind, and start with a clear understanding of your destination”. Productivity bros declare that “winners never quit and quitters never win”. Self-help influencers remind us that “the person who has a fixed purpose and backs it with the determination to see it through to the end is the one who succeeds”.

From this conceptual perspective, virtue lies in finishing what you start, even if it is no longer necessary, effective or appropriate. But for experimental people, it’s important to develop the ability to discern when it’s time to quit and how to let go sustainably.

In an experimental life, nothing is wasted. Every venture yields something to carry forward. Something old, something new, something borrowed, something blue. No, wait. That’s different.

In The Return to Serenity Island, we take time to acknowledge and appreciate our resourcefulness. We make peace with letting go and make space to focus on those sources of close-in satisfaction.

Many of us carry baggage about letting go, quitting, and changing our minds. It might have been drummed into us that stopping before the end is wasteful.

At its most extreme, an outcome-oriented framework holds that the end justifies the means. So long as you get the result, it doesn’t matter how you do it. It also holds that the end undermines the means. If things turn out unfavourably, the whole journey is seen as a waste of time.

I saw Stockport County (my team) lose to Carlisle on penalties at Wembley in the League Two playoff final in 2023.

After the match, as we walked away from the stadium, I said, “Well, that was a waste of a day.” I was joking, but part of me felt it too, because the result was disappointing. It clouded my perception of the day, especially in the immediate aftermath of that defeat.

But the day was otherwise great, full of enjoyable micro-moments.

I realise how quickly I can undermine the time I spend caring, crafting, and creating if I hand all the power to the destination. But on the flipside, I can see how easy it is to find more joy in life when I turn that on its head and give power to the joy of the ‘close-in’.

Satisfaction in small things comes from bringing real life to the landscapes we map in our imagination around Serenity Island.

If life were an island, where would you choose to hang out and explore, regardless of measurable results that may or may not follow?

What would you love to plant more of in your life? How do you want to respond to unexpected changes, opportunities, and feelings that arise? Why do the choices you make matter?

When experimental people build our lives on the foundations of questions like these, the growth we might otherwise try to force takes care of itself. When we view success up close, the path begins to unfold in unexpected, obvious, surprising, intuitive, gradual, and sudden ways.

Join us on Serenity Island to explore more. You can choose what you pay at checkout and get access to all the course materials and live events for the next 12 months.

It would be lovely to have you aboard. Head to serenityisland.me to find out more and grab your passport.