A story about getting stuck in our thinking and learning to question the way we think
Self-Coaching: The Difference Between Thinking and Thinking Well wasn’t a distinction Anders had ever felt much need to make.
Thinking was part of his work.
As a creative director, Anders had spent years solving problems, developing ideas and helping other people see possibilities they hadn’t seen before.
When an idea wasn’t working, he knew what to do.
Change the angle.
Question the brief.
Look at the problem differently.
Ask what everyone might be assuming.
Put the work down and come back to it.
Invite another perspective.
Anders was good at helping other people get unstuck.
He was finding it considerably harder to do for himself.
The Saturday Morning Question
For almost a year, Anders had known that he wanted something about his working life to change.
He wasn’t unhappy.
He had helped build a successful creative agency and still cared deeply about the work.
He liked his colleagues.
He liked his clients.
He had no particular desire to walk away from any of it.
But the balance had shifted over the years.
There was more responsibility for running the agency.
More meetings.
More decisions.
More time overseeing work and less time close to the creative work that had drawn him into the profession in the first place.
At the same time, other interests had begun pulling at him.
He had been invited to give occasional talks and workshops and discovered that he loved teaching.
He enjoyed mentoring people in the agency.
There was also a personal creative project he had been talking about starting for longer than he cared to admit.
Something needed to change.
Anders just couldn’t work out what.
So on Saturday mornings, he thought about it.
When More Thinking Doesn’t Help
Anders had developed something of a ritual.
Coffee.
Notebook.
Kitchen table.
No phone.
No email.
Time to think.
He wrote possibilities across pages.
Stay exactly as things were.
Step back from some of the operational responsibilities.
Reduce his days.
Do more creative work himself.
Teach.
Mentor.
Start the project he’d been postponing.
Leave the agency altogether.
Then he considered the consequences.
Money.
His responsibilities to his fellow directors.
The team.
Clients.
What he would gain.
What he might lose.
What he would miss.
What he might regret.
Some Saturdays, Anders spent two hours thinking.
Occasionally three.
He would close the notebook feeling as though he had considered everything.
And the following Saturday he would open it and begin thinking about the same things again.
Anders didn’t have a shortage of thinking.
He had begun to wonder why none of it was getting him anywhere.
The Brief That Needed Questioning
The moment that shifted something happened at work.
One of the creative team had been struggling with a concept for a client campaign.
She showed Anders several versions.
They were different.
But not very different.
Each solved the problem in essentially the same way.
Anders listened as she explained what she had tried.
Then he looked again at the original brief.
“I think you’re trying to solve this inside a brief that needs questioning.”
They went back to the beginning.
What was the campaign actually trying to achieve?
Which constraints were real?
Which had they imposed themselves?
What were they assuming about the audience?
What would they do if one of those assumptions wasn’t true?
The conversation opened up.
So did the work.
Later that afternoon, Anders heard his own words again.
You’re trying to solve this inside a brief that needs questioning.
He had been doing exactly the same thing.
Thinking About the Thinking
That Saturday, Anders didn’t begin with:
What should I do?
He had asked himself that question enough.
Instead he wrote:
What assumptions am I bringing to this?
At first, nothing came.
Then he began writing.
If I step back from running the agency, I’m letting other people down.
He looked at the sentence.
Was that true?
Possibly.
But he had never actually asked his fellow directors.
Another:
If I’m going to continue working, I should be fully committed to the agency.
Why?
He wasn’t sure.
Then:
Teaching would mean taking time away from my real work.
That one made him stop.
Why did he think of the work he had done for years as his real work and something he increasingly wanted to explore as something else?
He kept going.
Changing my role means giving something up.
I need to know what I want the next few years to look like before I make a change.
There has to be a right decision.
Anders sat back.
For months, he had been trying to solve the problem.
He hadn’t been questioning the thinking he was using to solve it.
When Either/Or Keeps Us Stuck
Another pattern became obvious.
Much of Anders’s thinking had been organised around choices.
Stay or leave.
Agency or teaching.
Leadership or creative work.
Security or change.
Commit or step back.
He had treated his working life as though one choice had to defeat another.
So he asked:
What if this isn’t an either/or decision?
That question didn’t produce an immediate answer.
It produced possibilities.
Could he remain involved with the agency but change his responsibilities?
Could somebody else take on more of the operational work?
Could he teach without becoming a teacher?
Could he try one short course?
Could he protect time for his own creative work before deciding whether it should become anything more?
Could he change something for three months rather than deciding what the next five years should look like?
For the first time in months, Anders wasn’t trying to find the right answer.
He was exploring what else might be possible.
Self-Coaching and Thinking Well
We can spend an enormous amount of time thinking about something without necessarily thinking well about it.
We replay conversations.
Run through possibilities.
Imagine outcomes.
Construct arguments.
Make lists.
Revisit decisions.
Sometimes that thinking helps.
Sometimes it simply takes us around the same mental circuit.
Thinking well doesn’t necessarily mean thinking harder, longer or even more deeply.
Sometimes it means interrupting the way we’re thinking.
What question do I keep asking?
What am I assuming?
What have I decided is true without testing it?
Am I treating this as either/or when it doesn’t have to be?
What perspective haven’t I considered?
What could I try instead of deciding?
Self-coaching can give thinking structure and purpose.
Not by telling us what to think.
By helping us examine how we’re thinking.
When Our Thinking Needs to Change With Us
There was another thing Anders began to recognise.
Many of his assumptions hadn’t come from nowhere.
They had served him.
There had been a period when giving almost everything to building the agency was exactly what he wanted.
Taking responsibility had brought opportunities he had worked hard for.
Being deeply involved in the agency had given him work, relationships, experiences and a professional life he valued.
Anders didn’t need to decide that his previous choices had been wrong in order to want something different now.
His working life had changed.
So had he.
Yet some of the rules he was using to think about his future had been formed during an earlier version of both.
We can become loyal to ways of thinking because they once served us well.
That doesn’t mean they must serve us forever.
Sometimes changing our working life begins with recognising that our thinking needs to change with it.
From Deciding to Experimenting
Anders didn’t leave the agency.
He didn’t arrive at a five-year plan.
He didn’t finally discover the perfect answer during one of his Saturday mornings.
Instead, he had conversations.
He spoke with his fellow directors about changing some of his responsibilities.
The conversation was easier than he had imagined.
Nobody accused him of letting them down.
Together, they agreed on an arrangement they would try for three months.
Anders also accepted an invitation to teach a short series of workshops.
He protected a small amount of time each week for the creative project he had repeatedly postponed.
None of those decisions had to be permanent.
That was part of what made them possible.
Instead of trying to think his way towards certainty, Anders had created ways of learning through action.
The Difference Between Thinking and Thinking Well
A few months later, Anders was back at his kitchen table on a Saturday morning.
Coffee.
Notebook.
No phone.
The ritual hadn’t changed very much.
The question had.
He was no longer trying to work out exactly what the next several years of his working life should look like.
At the top of the page he wrote:
What am I learning from what I’m trying?
Teaching was giving him something he hadn’t realised he had been missing.
He enjoyed having more time close to creative work.
He had also discovered that there were parts of running the agency he missed more than he expected.
That was useful information too.
Anders was still thinking about his working life.
But he was no longer circling the same problem looking for the perfect answer.
He was questioning assumptions.
Changing the questions.
Testing possibilities.
Learning from what happened.
Thinking had kept Anders inside the problem.
Thinking well helped him move.
Not because he finally thought hard enough to find the right answer.
Because he learned to question the thinking that had been shaping the answers available to him.
Continue Exploring Self-Coaching
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