“Do not be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better. What if they are a little coarse and you may get your coat soiled or torn? What if you do fail, and get fairly rolled in the dirt once or twice? Up again, you shall never be so afraid of a tumble.”
― Ralph Waldo Emerson
When I started Extraordinary Routines, I wanted to uncover the secrets to success. I thought by probing successful artists, writers, entrepreneurs, illustrators and designers about how they live their lives, I would absorb some of their magic and that would transform my own life.
I quickly learnt that our own daily challenges or insecurities aren't fixed by simply knowing what so-and-so has for breakfast. It dawned on me that we improve not only through talking to others, but through doing.
So I decided to dive into my own pain points in life – not having a set daily routine, not being great at dating, being crippled by shyness, having a strong tendency to procrastinate – and conduct experiments to tinker and change.
Sometimes these experiments 'failed' – when I conducted a thirty-day habit experiment to find the perfect routine, I quickly resumed my own ad-hoc ways soon after. But they were always illuminating and in some small way, changed my outlook.
From attempting a digital detox, to meeting a new stranger each week for a year, to making over my dating habits, here are the lessons I've learned from years of experimenting with life.
1. Opportunities flow through people
In 2016, I quit my job as an arts journalist to go freelance. Remarkably and without actively seeking them, some of my most lucrative writing jobs and opportunities have flowed through a someone I met through my year of strangers experiment.
I wouldn’t say it’s entirely who you know that brings opportunities – but it’s certainly a large part. As entrepreneur Ben Casnocha told said to Jocelyn K Glei in an interview: “Every opportunity is attached to a person. Opportunities do not float like clouds in the sky. They’re attached to people. If you’re looking for an opportunity — including one that has a financial payoff — you’re really looking for a person.”
Read more: My year of strangers experiment
2. Test your assumptions – in dating and life
In dating, fear of rejection has often led me to pre-empt whether a date will or will not lean in for a kiss, ask me out again, or text the next day. Convinced I could read minds, I'd dutifully cut off a date or a conversation just in time to avoid being rebuffed. I'd tell myself that if it worked a certain way in the past, it was sure to happen like that again.
This occurs in everyday life, too. We make assumptions about what friends, collegues, family even strangers think of us.
Through my dating habit experiment, I learnt that my premonitions were sometimes wrong; I also learnt not to fear rejection. The response might sting, but it could also delight. After all, you don't know what someone else is thinking.
Stop letting previous experiences determine current situations and put yourself out there as if each new interaction and experience is new, because it is.
3. Uncertainty is where the magic is
In my digital detox experiment, I became intimate with the uncomfortable nature of uncertainty. What we are doing when we compulsively reach for our phone in moments of awkwardness or boredom is escaping uncertainty.
Artist, writer and filmmaker Miranda July acknowledges that some of our best ideas come to us when we felt a bit lost, but we are losing the art of being okay with not knowing.
“All those little moments when you are like, ‘Uh, what do I do next? Who am I? – you now look at your phone and refresh, refresh. It is a big problem for me, it is like someone just took away the livelihood, so I have to work really, really hard to protect this thing.”
Read more: Living comfortably in uncertainty
4. There's nothing wrong with downtime
During my 30-day habit experiment, I slipped up. But it led to the creation of what is now my favourite habit: the sabit. It's a sabbath from your habits and means that for one day each week, you can have a break from your routine.
There's this pressure to fill our days from morning to night – to seize each day – but learning to be comfortable with doing nothing, and free from being enslaved by a to-do list, was the most important takeaway for me.
In order for creativity to really flourish, we need a break. We need to give ourselves time to breathe. There is a place for doing nothing in our day, and we don't need to taint it by telling ourselves we should be doing more, or we should be doing things differently.
When I interview people about their daily routines, one of the most common things I hear is how difficult it is to do nothing. People complain that they don’t know what to do when they have nothing to do. Myself included. But we really need to get better at that. We need to get better at enjoying the time we have available to us, instead of mindlessly trying to fill it for the sake of being "productive."
We all have creative slumps. We miss deadlines. No one sticks to their routine all the time. And I think that’s far more interesting.
Read more: Habit experiment Part One
5. There's no ideal daily routine
The perfect schedule doesn't equate to living a perfect life. There is no such thing.
As psychologist and Buddhist teacher Tara Brach quotes in one of her meditations:
“If you can start the day without caffeine or pep pills. If you can be cheerful while ignoring aches and pains. If you can resist complaining and boring people with your troubles. If you can eat the same food every day and be thankful for it. If you can take criticism and blame without resentment. If you can face the world without lies and deceit. If you can relax without liquor. If you can sleep without the aid of drugs… Then you are probably a dog.”
We needn't strive to follow another person's idealised routine in the hope of attaining their version of success. All we can do is experiment with what works for us.
Read more: Habit experiment Part Two