You’ve built several startups, launched a podcast and made a career out of helping people become the best versions of themselves. How did you get there and what did that take?
I’m skeptical that we can take credit for any of our achievements in life – we are all the receivers of mountains of unseen help, from genetic pre-dispositions to the love we received and the ideas we were exposed to. It’s an illusion to believe that any achievement, be it a startup or creative project is ever a solo effort.
With that said, I think that I was fortunate enough in my early 20’s to glimpse what corporate life might hold; what terrified me the most was the sense that I could see exactly how my life would unfold for the next 5, 10, 15 years.
And so I intentionally set out to go in the complete opposite direction and cultivate a relationship with uncertainty.
I would make a note of anything that I felt afraid of… surfing big waves, solo travel in the middle east, starting a company… and then did my best to I throw myself towards these fears. I didn’t want to become someone who was afraid of fear itself.
What major obstacles or failures have you faced on your journey? How did you overcome them? Or how did they set you up for later success?
Not properly taking care of myself.
During the startup accelerator program Techstars working on Maptia, we burnt the candle at both ends and it didn’t get us anywhere. We were pulled in lots of different directions and didn’t stay true to our reasons for starting our company in the first place.
But this taught me to try to manage my energy levels over my time and the value of taking a step back to ensure that I’m working on the stuff that matters.
(For more, here are 10 things we learnt during our 5 year adventure)
Who are/were your heroes? Who helped you get where you are today?
In terms of who helped me to get to where I am today, three people come to mind:
First, my economics tutor Matteo once said to me that he believed that I was capable of anything that I set my mind to. I took this literally and attempted a very ambitious dissertation project (which ended up being published in Forbes).
Finally, Michael King my mentor and meditation teacher who has been coaching me for the last 18 months has shared so many gems of wisdom with me that I’ve lost count. I feel grateful to have him in my corner!
How do you decide what things are important to you in life as well as how and when you will work on them?
There are three key habits that help with this:
- Journaling and Monthly Reviews – At the end of each month I have a series of questions that I will ask myself as well as checking in on my values and how I spent my time (here’s my annual review template)
- My decision making spreadsheet – this is where I keep tabs on all of the open threads of project ideas, learning goals, adventure plans and ways to give back.
- Meditating on decisions – To complement the left-brain spreadsheet decision-making process, I will often drop a question in at the end of my meditations and do my best to pay attention to what arises. I’ve found that my intuition usually leads me in the right direction if I can sufficiently quieten my monkey mind!
How do you try and balance all the things you want to (and must) do without letting them all overwhelm you?
This question brings up the question of balancing ambition and appreciation, which is something I’ve thought about a lot recently.
Speaking as someone who graduated hoping to ‘make a big old ding in the universe’, this is something I’ve wrestled with for a while, recently feeling mistrusting of my own ambitious tendencies.
I was however somewhat surprised to find a compelling answer lurking in a five-thousand-year-old yogic text: ‘The Bhagavad Gita’.
At the crux of this epic tale, the wise Krishna advises our protagonist warrior Arjuna to separate his ambitious drive into noble ‘aspirations’ and ‘grasping’ or clinging to specific outcomes — which inevitably lead to suffering or ‘dukkha’.
The more I thought about this, the more sense it made and I’ve loosely adapted the idea as a surfing analogy (because, well that’s just how my brain works) so please bear with me…
Much like jazz improv, the craft of surfing well emerges from responding and improvising as each new section of the wave reveals itself, perhaps racing ahead of a fast section or pulling into the tube if a steep section appears.
As a surfer, you might have a noble intention (e.g. getting barrelled) but if you were to pull in on every single wave you will likely end up wiping out 99 times out of 100.
Therefore, an aspiration of ‘getting barrelled’ must be ‘held loosely’, since your wave will tend to have its own ideas. The great art of both surfing and life is knowing how to read the unique shape of the wave and then join the dance.
So to sum up, I do my best to let go of my attachment to the outcomes of any projects that I embark on (and also make lists… lots and lots of lists!)
What are your favourite ways to eliminate daily distractions and focus on doing what matters?
Three cornerstone habits*:
- Training my attentional capacity (through ‘Dharana‘ meditation)
- Morning pages and planning my mornings in 30 min chunks
- 5 daily Pomodoros (with handstands or breathwork during the 5 min breaks)
(*aiming never to miss any of these twice in a row)
What advice would you give to your 18-year-old self? What advice should they ignore?
My main advice which is very in line with The Art of Living would be to “Be an absolute learning machine“. Love the learning process. You don’t need to know all the answers before you begin… and you absolutely can learn everything you need along the way (you may even learn to love the questions themselves as the poet Rilke put it).
But I would preface that with all advice is contextual. The best advice you can give would be in the form of questions for my 18-year old self to ponder (ideally during some form of long-term travel!)
(I also wrote this list of 100 things I believe when I turned 10,000 days old)
What 3 books would you recommend to your 18-year-old self and why?
At that age, I had a lot of questions about my path in life and a hunger for devouring books by the shelf load. Here are three that I wish I’d discovered earlier:
- The Art of Learning by Josh Waitzkin;
- The Great Work of Your Life by Stephen Cope; and
- Atomic Habits by James Clear
What do you love most about the work that you’re doing and life that you’re living right now?
I get to go surfing almost every day and spend my days following my curiosity – through podcast conversations, writing and teaching workshops.
I feel most alive when I’m in these flow states and feel beyond fortunate for the opportunity to wake up here and work on projects that stoke my curiosity.
What are the biggest changes you’ve noticed in yourself over the last 10 years?
Honestly… navigating grief has changed me more than anything else that has happened in the last 10 years of my life.
I wouldn’t wish loss or heartbreak on anyone, but it does have the capacity to change you and give you a dose of perspective as to what really matters in the end.
If you could have a gigantic billboard anywhere with anything on it what would it say and why?
“If you feel like you’re falling, dive.”