The art of building a plan that can’t fail

planPayoff: An engine that prevents you failing
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This post is probably for you.

That’s if you’re trying to achieve something worthwhile in your work of life.

Usually I write for those in ‘non-sales’ who want to improve how they sell, influence the thinking of others, or develop business and their career, and in my experience 90% of these people could significantly benefit from smarter planning (if I’m honest, many seem to operate without any plan at all).

If you do this, things ahead will get better

The advice I’m about to share would help anyone embarking on a new project or business, whether you see yourself in a sales role or not.

And I’m compelled to write on this because this mismanagement of ‘personal planning’ (I’ll call it that for now since this is about creating a plan to move yourself intelligently from A to B) is unbelievably common, and easily fixed.

Eliminating major loss and frustration

So I’m frustrated for people when I see them banging their heads against the wall unnecessarily.

I’ve seen too many people invest and risk everything (their hearts, minds, savings, hopes, dreams and even relationships) in trying to make certain business ideas or projects work only to see them come crashing down for some unplanned or unthought out reason (it’s what we miss that’ll get us.) I won’t claim that all could have been avoided by smarter planning, but without a doubt, some could have had they have approached planning differently.

Whether you detest planning, love it or don’t think about it all that much, I want to encourage you to challenge and improve how you tackle things that you want to achieve. My favourite quote, “There’s a better way to do it – find it!” by Thomas Edison comes to mind once again.

So, I’ll share some of the common planning traps these people fell into and we’ll get some ideas and solutions too which you can use if you want to.

Ultimately, you’ll be better able to organise your thoughts into a quick, sharp, practical plan that can’t fail. (I’ll explain why it can’t fail too.)

The 3 major planning mistakes

So I’ll begin with the three main mistakes I see around ‘planning’ before we look at fixing them. They’re simple, but can cost you everything:

  1. Some people don’t do it enough (or at all)
  2. Some people do it too much
  3. Most people don’t do it in a way that actually works well for them

Which are you?

Most people I come across (75%?) don’t seem to do it enough on projects or outcomes that are important to them.

Of those who do, most I come across (20%?) tend to do it too much (procrastinating on rolling their sleeves up and actually getting things done, because planning is just so much easier.)

The art of planning

And the majority of both groups, in my experience, don’t seem to do it in a way that works particularly well for them. They just throw a plan together but don’t seem to realise that there’s an art to planning that goes way beyond the science of logical plans.

(In short, often they fall in love too much with the logic of their plans as they see that logic through their current lens, and then continue to manage to the plan even though it’s un-noticeably deteriorated into a very bad plan, given the changed circumstances. More on that in a bit…)

Lookout! Cliff!

(the problem with not planning enough)

As the Young Ones once said, “Lookout! Cliff!” (about 0.1% of you will relate that, but that’s ok, and it’s staying in.)

There’s a cliff edge you need to know about.

To state it simply here’s the way it works: without planning, your default journey (towards something challenging or worthwhile) usually sends you on a trajectory towards the cliff edge.

That’s the way it works.

That’s your starting point. Right or wrong, it’s healthy to begin with the assumption that it’s true. (Even if you think your passion will make you fly and soar high above any cliff edge, it’s unlikely to, and in fact I’ve often seen increased passion having people just run even faster off the cliff edge).

You start by facing the cliff edge – and by the way, it’s hidden – just on the far side of the thick dark woods there.

Your starting point is to know and believe in the cliff edge, then plan to avoid going straight off.

You need that plan.

Let me remind you of Benjamin Franklin’s point, “by failing to prepare, you are preparing to fail”.

And there’s always a cliff edge. J.R.R. Tolkien prefers to talk in terms of dragons, and he says, “It does not do to leave a dragon out of your calculations if you live near him.” And you do. You live near a cliff edge and a dragon. And they’re bang en route towards your goal.

The plan helps you avoid them.

Enjoy your trip

But that’s not all it does. The plan is your chance to define and design the journey how you want it to be. If you want the journey to be efficient, you can plan it that way.

If you want the journey to be fun, plan it that way.

If you want to do it as cost-effectively as possible, go ahead.

Brian Tracy says, “every minute spent in planning saves ten minutes in execution”. Don’t think too hard about how he arrived at these figures (I don’t want any of my readers to pop!) just consider the idea that planning well shouldn’t take long, and should provide a significant ROI saving wasted hours, days, weeks or months.

Also, I’m going to offer you a way to plan that’s particularly fast and keeps you agile.

Either create the plan or be part of someone else’s plan

Finally, if you’re still not convinced that planning is vital, consider this:

You are always part of a plan whether you choose to be or not. The only question is whose plan? Yours or someone else’s?

Right now, whose plan are you in? Whose plans are you carrying out?

Either create the plan yourself or let yourself become a part of someone else’s plan.

You might as well choose now before continuing.

The best way to plan your failure

(the problem with planning too much)

This mistake is also common, and pretty straight forward. Yet, many of the highly intelligent people I work with make this mistake. (Chew that over for as long as you need).

Many people spend too long planning, either because they have so much faith in planning that they think they’ll iron out all possible failures (these people really really hate risk) or because they’re terribly scared of actually seeing if their plans actually work.

Planning is fun for thinking types. Oh yes, they get to use their genius that they’ve earned a lot of pride in over the years. And they feel busy, like they’re making progress, which surely counts for something? And it’s nice and safe, and hard to fail at creating a plan. It suits them just perfectly.

Many people over-plan to hide.

Especially many in non-sales roles who are aware that at some point they have to engage the client in an uncomfortable conversation where they might just fail.

Unfortunately, these over-planners often over-plan their way to failure. They procrastinate so much on the execution that their plans become out of date before they even being to take step one.

And the more they plan, the more they believe their plan can’t fail, and so both they and the plan become inflexible (which we’re about to come on to.)

Peter Drucker said that “plans are only good intentions unless they immediately degenerate into hard work.” There’s a point where good enough is good enough, and George S. Patton agrees with Drucker when he says, “a good plan today is better than a perfect plan tomorrow.”

It pays to decide up front a sensible investment in your planning, then sticking to it. If you read what follows, you’ll be able to judge that sensibly.

Warning: your plan is dangerous

(misunderstanding how planning should work)


  1. you must plan if you value your outcome
  2. and you must plan enough
  3. but not too much that your planning fails you

…and here’s the big one…

Perhaps the biggest mistake made by most people when planning, is thinking that your plan is so good that it’s actually worth sticking to. “Stick to the plan!” could be your famous last words.

Let’s remember that Charles Darwin has a point, “It is not the strongest of the species that survive, nor the most intelligent, but the one most responsive to change.”

Same applies to your plan. The plan most responsive to change beats the plan that’s the ‘strongest’ and the most intelligent.

And so, to have so much faith in your plan that you honestly think you’ll bend the future if you follow it, could be dangerous.

Many who failed, followed their plan to the T, walking boldly into failure.

What they don’t tell you but really should, is that plans, just like food, have a short shelf life. They rot fast. You’re often working against the clock here (since things change fast, and your competition is often out to scupper your plans to make way for their own).

Plans become dangerous when you misunderstand the point of planning. It’s not to design a map that if you follow it will bring you success. If that map existed, we’d all get our hands on it.

The cliff, the dragon, and the punch in the mouth

The world changes around your plan. Gradually, it distances itself from your plan.

You can plan for the cliff edge, and the dragon, but you won’t always be able to plan for the inevitable punch in the mouth. And Mike Tyson warns that “everyone has a plan until they get punched in the mouth.”

Most plans fail. (Unless you’re Hannibal Smith). But ‘planning’, the act of thinking your journey through is invaluable. It gives you more reference points to sharpen later decisions. And this is precisely what many people in sales (or non-sales) miss. When unexpected things happen, they ‘wing it’, end up failing and blame something other than the fact that they didn’t plan. (Often, unfortunately (and laughably, I’m afraid), they blame the very person they were selling to all too often!)

But for the person who planned, when unexpected things happen, they’re often closer to a sensible option to progress to next. They don’t have to make so many leaps in their thinking because they already built and mentally rehearsed some bridges to their thinking. They’re simply more likely to say and do the right thing.

Plans are nothing; planning is everything

General Dwight D. Eisenhower said, “In preparing for battle I have always found that plans are useless, but planning is indispensable”.

The point of ‘personal planning’ then, that’s so often misunderstood, is not to expect that you’re about to bend your future how you want it to be. It’s to increase your chances that you can see more clearly into your future than you previously could, and to put yourself in a stronger position to be ready to bend the future when the inevitable unexpected happens.

That’s it.

That’s why you do it. You’re almost (but not quite) better off creating your plans and then tearing them up! You get the real benefit then without risking sticking to your dangerous plans.

Success could be off your plan

I’ve heard it said before that we shouldn’t manage tightly to our plans for fear of hitting our plans and missing untold opportunities. These are the opportunities that often prevent you from failing. They’re the unexpected opportunities that really propel you towards success. And they’re NOT ON YOUR PLAN!

In negotiation, despite what the guru’s tell you, the weaker negotiator is the one who is fixated on what they want at the expense of missing a much better deal that presents itself.

Ever seen one of those people who keep arguing way beyond the point at which they secretly realise they’re totally wrong?! “My plan is to win this argument!!”

How to build a plan that can’t fail

I’ve claimed that you’ll be able to build plans that can’t fail. Come on then, let’s do it. There are four things you should include in your plan that will achieve this:

1) build your plan around actions and activity that almost nothing can stop you doing. Don’t build it on outcomes or results. It’s action based. It should be all do-able. Strip out the emotion and the outcomes that depend on things out of your control. Include just the raw actions that are within your control to take (regardless of whether they work or not).

2) build your plan purely to be a launchpad to get you up in the air. Do not build a plan to take you from A to Z. Build it to take you from A to B (but sketch out high-level how A to Z could look like). Your last action once you get to point B in your plan is to plan B to C, based on your current reality.

Note that novelist Rose Tremain advises, “In the planning stage of a book, don’t plan the ending. It has to be earned by all that will go before it.” Good point.

3) mention in your plan that you will ‘fall of the horse’(multiple times, and especially at the beginning). It will happen. And plan that when you do, you will brush yourself down, stand tall, not give a damn about what others think (here’s how to do that), and get back on the horse, then update your plan from where you’re now at.

4) include your ‘quitting strategy’. Forget the advice of ‘never give in!’ (sorry Churchill, old boy). Never giving in can have people making dumb decisions where they throw good money (or time, energy and emotion) after bad. Sometimes you absolutely should quit. (Otherwise you just turn into the Monty Python Black Knight from the Holy Grail.)

What many people don’t realise is that it’s OK, no, it’s smart to quit at the right things for the right reasons. But it’s not usually smart to do it if you haven’t defined your quitting strategy up front (because your judgment becomes impaired and emotionally distorted once you’ve begun and the going inevitably gets tough).

The key is to know when it’s right to quit. So define what circumstances it makes sense to quit under, and only quit under those. You planned it. So if you quit, under those circumstances, you’re still sticking to your plan, and your plan has not failed.

A good quitting strategy completes this sentence: “I will only quit when….” and define those measurable circumstances where quitting becomes the most sensible plan, enabling you to redirect your resources towards another project (by the way, feeling 8 out of 10 on a scale counts as ‘measurable’, so long as you pick the right scale).

Your plan

The plan that can’t fail is the plan that acknowledges the current reality (you’re not just drugged up on excitement and passion), is highly action based, gets you executing imminently, contains a well-planned exit strategy, and moves you forwards in the way that you want towards your next planning point, where you just repeat.

Include those ideas in your plan, and you’ll have a plan that can’t fail.

When you have that, you feel pretty good. The art of planning in this way gives you confidence, motivation, and enough clarity to launch into what you’re doing. And once you’re flying, you learn a lot more useful things as you go which enable you to create a much more realistic and useful plan for the next phase, that’s far better than the plan you would have created from the start.

If you’d like some extra help in how to actually think your plan through, I have nine steps that you can follow quickly in almost any situation to significantly increase your chances of success. I used them (as a one man band) to land target clients of mine, including McKinsey and Company and Capgemini amongst other large consulting firms, and I’m happy to share. Just message me here.

Please share if you think others will find it useful, and if you want me to work with your team to help them plan and build the capabilities to generate more revenue for your business, please get in touch.

And if you want me to cover tips on any particular topic or question, let me know here.

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