Stop Planning Your Life
There is a certain relief in being unprepared and yet arriving at your destination with grace. It feels rebellious — as if you have defied the very fabric of nature, as if you have vaulted over your mental barriers rather than inching around them. The best stories, after all, involve a bit of unplanned shenanigans.
There is nothing wrong or inappropriate about being organised. Certain things reward planning — investments, insurance, your career, your overall wellbeing. But you shouldn't place too much emphasis on planning your experiences. The very word experience implies that you go out there and feel your way through whatever you are engaging in.
Like all good things, striking the right balance between the two makes life sweeter. For anything with long-term reward, plan deliberately — structure your life so you get to enjoy the fruits of today's labour. But say you're going out on a date with someone. Pick a handful of good restaurants and give her the choice. Choose the ones that nudge you both out of your comfort zone. She will love the spontaneity, and besides, you will have a great story to share.
These stories become the bedrock of everything great that follows. Plan experiences, but don't choreograph every last detail. Have a sense of how to arrive, what to avoid — but take her on a ride where you're both wearing the hat of an explorer. It brings out the best in you. While you are living an experience, you are also uncovering yourself, without a rigid structure holding you in place.
And this applies to everything in life where there's no long-term consequence. Especially your conversations. Don't rehearse everything in your head — what to say, how to say it, what the counter-argument might be. Forget that. Have some direction, but trust your gut to find the flow. It's perfectly fine to come across as an emotional person. It is always better to be disliked for who you are than admired for a performance.
An organised structure has its place, but it never breeds spontaneity. It compels you to plan everything in meticulous detail — including how you feel and what you ought to feel. But the best moments of life are felt, not engineered. So cultivate a sense of direction, and then follow your heart. Live a life full of stories worth telling your grandchildren.