Just Wing It

Gareth I. Jones
4 min readJul 19, 2022


We often think of people who wing it as being chancers and blaggers, but maybe they’re a more realistic bunch than the planners.

Photo by D Santiagø on Unsplash

There’s so much value and trust put into having a plan. We think that people without a plan are unfit leaders and clueless wanderers.

The wonderful Four Thousand Weeks by Oliver Burkeman smacked me in the face when he wrote about a plan being nothing more than an idea. We often think that a plan is a sacred thing, but it is just an idea that we all agree to.

Plans very rarely survive their first encounter with reality, this doesn’t mean that we need to write a new plan. The idea changes, but our goal remains. Whether that is the destination that we are heading to when our train is cancelled (again) or the mission that we are undertaking through our business or professional career.

It’s much more important to have a direction than a set list of actions in sequential order*.

If you’re aiming to get to a destination then the how can be adapted if things change. Equally, the destination might change if you gain new information along the way or if new opportunities come up.

You need to be nimble to respond to those opportunities that come your way, many of which you could never predict on day one.


There’s another aspect to this, in that after the event we want people to think we knew all along how it would work out. We might even believe that to be true.

Post-rationalisation is the tendency that we have to create a narrative that fits what was actually a fairly chaotic and unpredictable time.

We like people to think we had a plan all along, and that everything ran smoothly, when the truth was anything but.

The opportunities that come up at unexpected times are part of the joy, it’s ok to not know what they are at the beginning.

You might believe that the spontaneity and randomness was anticipated, but there’s an extra level of candour in telling the story of that being out of our control.


This is even more important when it comes to serendipity and unexpected opportunity.

We have to leave an opportunity space where we can have these serendipitous encounters and where our plan can be allowed to be hijacked.

This can be the plan, and your actions and attitude can increase the likelihood that those serendipitous events occur.

I talked a lot more about this back in Loving Problems, Breaking Up With Ideas and how what we believe to be true at the start might need to change as we learn new things from our customers, market and product.

The risk is the sunk cost fallacy preventing us from breaking upwith the old idea which won’t take us into the future.

These serendipitous moments can either be welcomed for their insight or hated for inconveniently smashing up our perfectly crafted plan. But we can’t hide from serendipity in fear of our plan being wrong.

What this means for business planning

When we’re writing our plans there are two things that are more important than saying exactly what we will do: how we make decisions and how we take action. These are then both driven by the why behind what we do.

The why might be a theory of change, or it might be a mission or mantra or north star — whatever works for you.

The how we take action might change as you create new products and services, and as you learn more about your market. The howyou make decisions will change as your team changes, as your governance develops and as you grow to be responsible to more stakeholders than just you and your co-founder.

Planning is important, it has its place, but we can attribute too much value to it. Planning allows us to ensure that everyone is on the same page and that there is consensus on issues that may not be articulated. This is crucial in a team filled with excitement at the start, but nothing is sacred, and everyone needs to be ready to accept when predictions are wrong.

* Of course, it goes without saying that if you’re building a house there’s no point in telling the window fitters and roofers to come down on day one because you have a “vision” for what the house will look like. Some complicated activities with many stakeholders playing different roles require more intricate planning. This is especially highlighted when you’re being asked to prove that you know what you’re doing to an external partner such as a funder or client. But these plans will not go by the letter — I’ll talk more about this in a future post.



Gareth I. Jones

Founder of TownSq, focused on building communities of entrepreneurs, supporting startups and B Corps - businesses that are better for the planet.