My position: Plan seriously. But never confuse the plan with the point. The people I admire most know what they are trying to achieve, prepare properly, and when reality destroys the route they expected to take, they recover quickly enough to find another one.
I have worked with some very good sales leaders over the years.
They all seem to have one thing in common.
They don’t worship the sales process.
Of course they know it. They prepare. They understand the customer, the stakeholders, the numbers, the product and what needs to happen.
But their actual plan is much simpler:
Close the deal.
Customer says no?
Okay.
Why?
Price?
Timing?
Product?
Budget?
Wrong stakeholder?
What can we change?
What else can we offer?
Who else can we speak to?
They keep pressing until either the deal closes, another opportunity appears, or everyone finally agrees there is nothing sensible left to do.
Then they walk.
Not because the process said Step 5 was complete.
Because the objective is no longer worth pursuing.
I have also worked with the opposite.
We followed Steps 1 to 5.
We did everything we were supposed to do.
Customer still said no.
Better luck next time.
Technically, nobody did anything wrong.
And yet somehow that answer has always bothered me.
Because sometimes:
I followed the plan
becomes another way of saying:
Don’t blame me for the outcome.
The plan is not the point
I am not anti-planning.
Quite the opposite.
Good preparation matters.
If you create problems because you couldn’t be bothered to think ahead, then run around calling yourself adaptable when everything catches fire, you are not agile.
You are just poorly prepared.
But a plan is ultimately still a prediction.
It is what we think should happen based on what we know today.
Reality does not owe us compliance.
The customer changes their mind.
The market crashes.
Your company restructures.
Someone gets sick.
A relationship changes.
An opportunity disappears.
Another one appears from somewhere you were not even looking.
Then what?
This is where some people are unusually good.
They don’t necessarily have some brilliant Plan B sitting inside a drawer.
A lot of the time, they don’t have a Plan B at all.
They are simply better at making one when Plan A dies.
They know roughly where they are going.
Then they wing the rest when they have to.
“Winging it” does not mean anyhow whack
I like the phrase because that is genuinely how it looks sometimes.
The best people can appear as though they are making everything up along the way.
Maybe they are.
But there is a difference between intelligent improvisation and bullshit.
The people I respect usually understand enough to know what can move and what cannot.
A good sales leader may change the price, structure, timing or proposition.
But I have also watched the good ones say:
Fuck it. Walk away.
When the customer becomes unreasonable.
When colleagues are being bullied.
When closing the deal means promising something the organisation should never promise.
They would rather lose the commission.
Miss the target.
Take the bad month.
Because the deal was never the highest thing in the hierarchy.
People mattered too.
Reputation mattered.
Principles mattered.
That taught me something.
The plan can be flexible. Your principles don’t have to be.
Some people spend too long arguing with reality
I don’t think great reactors are necessarily calmer people.
I’m definitely not.
When something goes badly, my first reaction is usually some version of:
sigh.
If it is bad enough, I can get angry.
Usually at myself.
Maybe two or three minutes.
Then eventually:
Okay.
Shit happened.
What now?
I used to run a startup.
I ate fuck-ups for breakfast, lunch and dinner.
After enough years of that, problems become familiar.
The useful part is that I learnt not to spend too long being shocked that something went wrong.
Of course something went wrong.
Things go wrong.
The difference is how long you surrender your agency to it.
Some people spend five minutes angry.
Some spend five months explaining why this wasn’t supposed to happen.
They blame.
They defend the original assumptions.
They wait for reality to return to the version they prepared for.
Meanwhile somebody else has already accepted the new reality and started moving.
My life certainly did not follow the plan
I used to imagine my career as a straight line.
Study.
Start somewhere respectable.
Work hard.
Get promoted.
Earn more.
Keep climbing.
Very neat.
Life had other ideas.
Family circumstances knocked me off my original starting point.
I tried things.
Took opportunities.
Hustled.
Built.
Failed.
Started again.
Eventually my career moved up.
Then came back-to-back retrenchments.
My wealth followed roughly the same pattern.
Up.
Down.
Up again.
Nothing was straight.
But the general direction kept moving forward.
Ten steps forward and nine steps back?
Still one step forward.
Then, after leaving a work environment I no longer believed had much future for me, another plan broke.
I expected the career break to be temporary.
Very temporary.
The job market disagreed.
Suddenly I was spending much more time at home with my son.
For a brief moment, I wondered whether I was going backwards.
Then something unexpected happened.
I enjoyed it.
A lot.
I started seeing my time differently.
I helped my wife think more seriously about her own career.
I spent time with my son.
I had autonomy.
I started building things again.
Thinking.
Writing.
Living slightly differently.
I still knew I would eventually go back out and earn.
But the route had changed.
And somewhere during that period I realised something else.
For years I thought my objective was money.
Make more.
Build wealth.
Become financially strong.
Then I got some of it.
And realised money itself didn’t fulfil me very much.
So why did I want it so badly?
Protection.
Then another question.
Protect what?
Eventually the answer became obvious.
Me. And the family I never had before but chose to build now.
Once I understood that, many of my old plans suddenly became much less sacred.
Sometimes the plan fails because you misunderstood the point
This may be the biggest thing I have learnt.
Sometimes reality doesn’t merely force you to find another route.
Sometimes reality reveals that you were heading towards the wrong destination in the first place.
I thought the objective was career.
Then money.
Then perhaps status.
But those were layers.
Useful ones.
Important ones.
Still not the deepest thing.
The deeper point was building enough capability, security and freedom to protect the people I care about and live in a way that feels like mine.
That means sometimes the route changes.
Sometimes the destination changes too.
People change.
Priorities change.
We discover things about ourselves embarrassingly late.
Maybe that is fine.
You do not need to know everything before you start moving.
A failed plan is information
A plan can fail.
A company can fail.
A deal can fail.
An investment can fail.
A career move can fail.
I have had enough of those.
Maybe the combination wasn’t right.
Wrong timing.
Wrong people.
Wrong environment.
Wrong assumptions.
Maybe I screwed something up.
Fine.
Learn.
Adjust.
Try again.
Maybe the exact same idea works beautifully five years later under different conditions.
Who knows?
But sitting there feeling sorry for myself because life didn’t follow the script achieves absolutely nothing.
Take a break if needed.
Change direction if needed.
But eventually:
Move.
Keep moving. But keep checking.
Moving for the sake of moving can be stupid too.
You can spend ten years running very hard in the wrong direction.
That is why I still plan.
My wife and I roughly know the family we are trying to build.
We roughly know what kind of retirement we want.
We have ideas about our children’s future.
We have financial plans.
Career plans.
Plenty of plans.
Then everyday life happens.
Two careers.
Young children.
No perfect support system.
Some days we are not executing a grand strategy.
We are just surviving Tuesday.
So we move.
Every now and then, we look up.
Still going roughly where we want?
Yes?
Continue.
No?
Adjust.
Something changed?
Okay.
Adjust again.
That, increasingly, is what planning looks like to me.
Not drawing the perfect line from here to there.
Pick a direction. Move. Look up. Correct. Continue.
The people I admire recover faster
Maybe that is the actual difference.
Not intelligence.
Not courage.
Not even planning ability.
Recovery.
When reality punches through the plan, how long before you become useful again?
How long before:
This wasn’t supposed to happen.
becomes:
Okay. What now?
The phenomenal people I have met plan.
Some plan exceptionally well.
But they are not emotionally dependent on reality behaving itself.
They don’t worship the map.
They don’t use the process as an alibi.
They know enough to improvise intelligently.
They protect the things that actually matter.
And when the route disappears, they find another one.
Sometimes that new road takes them slightly off-course.
Sometimes it changes everything.
Sometimes years later they realise the detour took them somewhere better than the original plan ever could.
So plan.
Plan properly.
Prepare.
Think ahead.
Know what you are doing.
Then hold all of it lightly enough that when life inevitably says:
No.
you can sigh for a minute, accept it, and ask the only useful question left.
Okay. What now?