by Niall Doherty

I find myself with about two hours to write and edit this post, starting from scratch. I was tipping away on another post all week, but I’ve realized that it’s nowhere near ready for publication just yet.

So I need to publish something else for you fine folks. I was lying in bed this morning, scratching my head, no idea what to write about, trying to come up with something that would be worthy of your time and attention.

And then I remembered a friend of mine from college.

He had to prepare and deliver a presentation in front of his class. Except he completely neglected to do the prepare part. So when the time came, he got up there in front of everyone and gave a presentation on winging it. He spoke, from the height of experience, about what to do when you’ve completely neglected to prepare for such a presentation. He embraced the uncertainty and rolled with it, turned his fear and doubt into fuel for brilliance (as Jonathan Fields would say).

My friend’s presentation was unique and unexpected. It was fun. And as I recall, he came away with a pretty good grade.

So I’m going to wing it here, too. I feel I’ve learned quite a lot about the subject in the past year or so. Via four different areas:

Improv Comedy

Right before I left New Orleans last year I took an eight week course in improv comedy (run by these legendary people). At the end of the course, myself and my fellow-improv-newbie classmates performed a live show in front of about fifty people.

And it was brilliant.

The whole improv experience taught me a lot about trust. By the end of the course, I was stepping out on stage with a teammate, neither of us having any clue what was about to happen, yet we’d somehow end up pulling a humorous scene out of the ether. We’d allow ourselves to freefall. Everything that was said or done on stage was considered a gift, and we graciously accepted and built upon each one.

The worst scenes were those in which we stepped on stage with a firm idea of what was going to happen. We’d already have a character in mind or a punch line at the ready. The scene would then come across robotic and rehearsed. There was less flow, less spontaneity. No trust, no freefall, no magic.


If you work for yourself, you know all about winging it.

I have no idea how much money I’ll earn next month. It might be a lot, or it might be nothing. I don’t know exactly what kind of work I’ll be doing, what projects I’ll be working on, or who my clients will be.

I’m almost a year deep in self-employment now and I still have lots to learn. But I find myself developing an ever-stronger belief in myself. I don’t know exactly how everything will turn out, but something tells me that it’s all going to be okay.

As Jacob Sokol says, security comes not from having things, but from the ability to handle things. And my ability to handle things is improving every day thanks to this foray into self-employment.


As you may know, these past couple of weeks I’ve been working on my flirting skills. I’ve made myself approach and try flirt with at least five attractive women every day since I arrived in Amsterdam.

The best interactions I’ve had have been those where I go in with no hidden agenda. I just try to have fun and share that experience with the other person. I let myself say whatever pops into my head, be as open and playful as I can be.

It’s much like that freefall concept in improv. You don’t think too much. You let yourself be in that creative space and say whatever comes to mind. You trust yourself completely, and let the real you shine through, free from all the usual, crippling thought filters.

After a while, you begin to realize that it’s not so much what you say, but the confidence with which you say it and how self-assured you come across in spite of the uncertainty. And then you find yourself spending several hours in the company of two hot Malaysian girls you just met on a Wednesday evening in Leidseplein.


My recent travel adventures have also helped develop my ability to wing it.

That hitchhiking adventure through Spain and France back in August really stretched me. I didn’t know where I was going to sleep from one night to the next. I didn’t know who I’d be spending my time with. I didn’t know if I’d be able to meet my writing and work deadlines from the road. I didn’t know if I’d ever make it to my destination.

Likewise, I arrived here in Amsterdam two weeks ago with no map, no friends, no accommodation arranged. All I had was a positive attitude and a willingness to take action.

It all worked out great in the end, and I learned to trust myself a little bit more.

So that’s me and winging it. I believe it’s an important skill to develop (one that may even help you write and edit a blog post in less than two hours). There’s only one way to work on it though: you have to keep putting yourself in uncertain situations. Start small, then ramp it up as you grow more confident. In time you’ll become comfortable with the discomfort and the not knowing. That’s when you’ll thrive.

I’ll leave you with a quote I heard from the aforementioned Jonathan Fields when he spoke at The World Domination Summit back in June:

Anything that’s worth doing, you will not have complete information about before you do it. The only way that you can actually have a lot of information is if either you’ve done it before, or someone else has done it before. At which point, that thing that you’re trying to create instead becomes something that you are trying to recreate.

Is that what you’re here to do?

P.S. I’ll be posting my October site progress report this weekend, for email subscribers only. Make sure you’re on the list by signing up below, and I’ll tell you all about the traffic explosion I saw earlier this week.