Planning As A Toxic Trait

I have done the thing I always tell people not to do. Which doesn’t really narrow it down, it is forever easier to see clearly the solutions for others than it is for yourself. But what I am referring to in this instance is thinking too far ahead.

I love to plan. I have often spent a weekend researching and building an itinerary and shortlisting restaurants for a trip I ultimately will never go on. I like to structure a weekend of activities weeks in advance. I like to write out the contents pages of books that I never work on. I like to outline product ideas and potential business models in spreadsheets with scary figures next to them.

“What’s bad about that?” is the obvious question. Surely this is a trait to be nurtured, surely it helps you get stuff done, makes you more organised, helps you set great goals. You would think that, I’ve always thought that. But actually, it has the opposite effect.

It means that I get anxious about the structured weekend actually being as good as I want it to be (and about other people enjoying it). It means that I stamp the life out of the tiny flickering book idea before it’s had a chance to catch light. It means I get overwhelmed and panicky about the business ideas, means I blow them up like a balloon full of expectations, blow so much that they burst before I’ve put a work on a page. 

In all these scenarios what the planning actually leads to is paralysis. I have built ideas up to be so big that I don’t know where to start with them. They are a great monolith and I am simply running around the outside of it, scrabbling against it’s sides, unable to find a foothold. When what I needed was a pebble I could start to roll down a hill.

It is not the planning itself that is the problem, it’s when the planning is happening. And here is where I circle back to what I said at the beginning. The conversation I’ve most frequently had with clients over the last few years is to start at the beginning. I hear them worrying about the future what ifs, how will it ever work, stressing about figuring out the nuts and bolts. I can see them, clear as day, clawing at the monolith. And I can also see that if they walk up the hill a little way they’ll be able to get a run up.

So often we start thinking about step 6 of the process, and it feels impossible because it is impossible – it’s impossible because we haven’t done steps 1-5 yet. Once we’ve done them, step 6 is nothing but another foothold to grasp.

Yet here I am, starting at step 6. Starting at the middle instead of the beginning. 

As you may have read, this was the month I started to burn down what Simple & Season was before. I knew I need to clear out the existing business model in order to properly develop one that was a better fit for my life and the tone I want my work to take. So with the building in flames I turned and set about trying to build the new one – but I was stuck. And I couldn’t work out why I was stuck until I realised – I was trying to start the building before I’d made a blueprint, gathered the materials, dug the foundations.

I was trying to come up with the number one most ideal signature business model for total longevity before I’d worked out what I even want. Before I’d acknowledged restrictions I put on myself about what I think offerings “have” to be. Before thinking about what I have capacity for.

And what all of that did was stamp out the creativity and curiosity and bring in pressure and stress and guilt. That isn’t the place I wanted to be working from anymore. So I had to wind it back, even further than I thought. 

“I just need to come up with one standalone offering” I said. “I don’t need to come up with three excellent perfectly staggered offerings, I just need to start with one thing”. And that’s true and it gave me relief and it is what I’ll do - but it’s step three, not step one. Step one is “what do you want? Where are you going? What are the non-negotiables? Where is the energy leading?”. Step two is explore.

We want to skip to the good bit. Or maybe it’s not the good bit, just the comfortable bit. The bit where we have the illusion of certainty, where we have a plan and we’re executing it and everythingisfine. But you end up puzzling at another monolith. It takes a bit longer to turn around and walk up the hill, it feels like you’re going backwards to turn your back on the monolith. But once you’re at the top it all looks easier. And maybe you’ll even find a pebble up there, maybe you’ll start it rolling, and maybe you’ll find yourself somewhere better than you’d imagined.

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6 Month Check In - The Year Of “More”