"I have never had a plan of operations."

Napoleon

• The harder you think something is going to be.
• The more complex, involved, or multi-dimensional.
• The longer you think it's going to take.
• The more you have riding on the outcome.
• The more attached you are to a successful result.
• The more you get hung up with questions like "what if we don't get this right?".
• The more you care about doing this thing well.
• The more you have to invest.
• The larger the potential pay-off.
• The more you seek to be perfect first time.
• The higher the stakes.
• The more risk you perceive.
• The more certainty you want to have that this will work before you begin.

Then, the more:

• Planning you want to do before you start.
• Detail you want before you start.
• Options you want to investigate before you start.
• Fine-tuning you want to do before you start.
• Pressure you put on yourself before you start.

This is especially true where you care about the outcome in a world where everyone has the power and means to be a critic. (And if you don't care about the outcome then why are you doing this thing in the first place?)

Here's the trap. The more planning you do, the more you think you haven't done enough. But you'll never be able to map out all the steps in advance and be 100% certain that it will work out the way you expect.

Planning can be a seductive but suffocating safety blanket. It can also be a colossal waste of time and energy if you have to change your plan as you go along. It's also frustrating to be planning and not creating.

Momentum

The half-life of enthusiasm can be surprisingly short. So try to move faster. I have a bias towards fast, low-tech frictionless tools when I'm planning. I don't want to get hung up on figuring out how to make new software do what I want it to do. I want to encourage momentum, not stifle it. Momentum is important with any project but the bigger the project the more I want to keep it going.

Perfect(ionist) Planning and the Infinite Game

If like me, you're a recovering perfectionist who wants to get more clarity than the average bear on exactly where you're heading before you set off, over-planning can be doubly dangerous.

It's easy to get sucked into rabbit holes of research looking for a reassuringly definitive answer that is frustratingly always just another click away.

The part that's easy to miss is that with most things that you do there's usually the opportunity for more than one bite at the apple. Granted some things are easier to change than others (edit is such a wonderful word!) but most of the time you do get the opportunity for version 2.

Instead, we see this as a never-to-be-repeated, once-in-a-lifetime, make-or-break, must-get-it-right-at-all-costs scenario which sucks all the enjoyment out of what you're doing.

Some projects (like your website) are never completed. You might take a pause from now and again but really they evolve over time.

You're playing what Simon Sinek calls an infinite game. That realisation can be liberating enough to free you from the shackles of perfectionist over-planning.

You don't need to climb Mount Everest as often as you think

The other problem is that the more planning you do, the bigger the mountain you give yourself to climb. That can be demoralising enough in itself - so much so that you might decide that this isn't worth the effort any more. Not only are you frustrated and disappointed but not all that planning may have been necessary anyway. Then we all miss out.

Too attached

Trying to predict all the moves before you've started the journey requires a powerful crystal ball. Plans evolve and change over time. They can and should be flexible. It's easy to get so attached to your pre-determined plan that you're reluctant to change because you have so much effort invested in the script that you spent so much time crafting.

Goldilocks Planning - How much planning is just right?

• Enough to be clear about what you want to achieve. What does your destination look like?
• Enough to have a reasonable idea about the route you might take to get there.
• Enough to have clear boundaries about what you're going to do and what you're not going to do. (The obvious one here is how much are you willing to invest in this?)
• Enough to work out at least one step to get you started.

That's enough to get started. You can course-correct as you go along.

You don't need to map out all the moving parts to advance. You don't need to have all the possible pathways, diversions, actions and alternatives scripted in detail, filed away in your task manager.

At any one time, all you need to know is:

• Where are we with this right now?
• Who's responsible for what? Have they got the trust, the autonomy, and the resources to do what they've been asked to do?
• What's the next step?

You can use 80/20 here - being able to see 20% of the way forward is usually enough. For a small number of projects that you do being to plan 80% of your route is going to be worth the effort you invest in it.

What's a plan worth anyway?

"To me, ideas are worth nothing unless executed."

Derek Sivers

An idea by itself has limited value. Planning how you're going to execute an idea adds a little but not much. After all, we're unlikely to ever see your plan. Executing on the plan to make your idea reality is where the value lies.

Just Get Started

” Speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.”

Amazon Leadership Principles

So when you next have a fun idea in the shower, on the treadmill, or out for a walk, and you want to do something about it, try not to overthink it. Sometimes the back of the envelope is all the space you need to work out the first few steps. Then get started. Fast.

We’re excited to see what you come up with.