Stuck, frustrated, discouraged? Ask a better question

Updated to Habits, Productivity on January 3, 2023.

I was in a car the other day with a radiologist and a neurosurgeon talking about hypertension. 

This conversation is actually not as unusual as it might sound. I volunteer for a local society that does trail clearing in a popular hiking and mountain bike park and many of the volunteers happen to be recently retired doctors. 

Back in the car, one of the doctors happened to mention that recently his medical partner, who is in his early 60’s, had a mild stroke. As we wound our way further up the dirt road to our work site my education continued. 

I learned that strokes are the second biggest cause of mortality worldwide and the third most common cause of disability. The scary statistics get worse. As you age your chance of a stroke doubles every 10 years after 55

There’s a checklist of health conditions that make you more susceptible to a stroke, like obesity, high cholesterol, and diabetes. But the biggest culprit – six times out of ten – is hypertension or high blood pressure. In my books, that’s worth paying attention to.

What’s interesting is that stress, in itself, is not the direct cause of high blood pressure. It’s what we do when under stress that leads to nasty results. We eat too much, drink too much, and move too little. Basically, we deal with stress by making unhealthy choices.

For me, stress starts with worry.

Ngoc Son Temple, Hoan Kiem Lake, Hanoi, Vietnam

I’ve had a lot of worries

There is a world of problems you can worry about – take your pick. You can worry that Ukraine will be pummeled into a tiny province of rubble, or that we’ve passed the tipping point with global warming, or the tiny spot on your chin is cancer. 

Or not.

“I’ve had a lot of worries,” quipped Mark Twain “most of which never happened.” Our mind loves a good worry. Like a dog chewing a bone, we want to turn our worry around, looking from all angles, poking and prodding until it swells up into something bigger than it really is.

I used to worry incessantly before every keynote speech. I’d worry I’d miss my flight or wasn’t prepared enough, or I would be greeted by the “audience from hell.” Trust me, when you have 60 minutes to educate, entertain, inspire, motivate, and get laughs from an audience you’ve never met before, any sane person would invent a long list of worries.

It was at one of those events when a fellow speaker opened an exit door for my worries. He suggested that audiences don’t want you to fail – in fact, they want you to succeed. “They want to see you having fun—enjoying yourself. That way,” he explained, “they can enjoy the ride with you.”

When I accepted the long list of what I could never control – my flights, the audience, the speaker before me going overtime – I was free to focus on what I could control.

Enjoying the moment. 

What your life will have been

In her book, Comfortable with Uncertainty, Buddhist nun Pema Chödrön tells the story of delighting in the preciousness of every single moment.

A woman is running from lions. She runs and she runs, and the lions are getting closer. She comes to the edge of a cliff. She sees a vine there, so she climbs down and holds onto it. Then she looks down and sees that there are lions below her as well. At the same time, she notices a little mouse gnawing away at the vine to which she is clinging. She also sees a beautiful little bunch of strawberries emerging from a nearby clump of grass. She looks up, she looks down, and she looks a the mouse. Then she picks a strawberry, pops it in her mouth, and enjoys it thoroughly.

Learning what to focus on, and what to ignore, seems to be the ultimate secret to living a healthy, stress-free life. “Whatever compelled your attention from moment to moment,” writes Oliver Burkeman in Four Thousand Weeks (a must-read for anyone over 50), “is simply what your life will have been.”

So, what are you focussing on?

What to focus on

You can learn a lot when you’re the dumbest one in a car full of doctors. I learned that strokes are a silent pandemic. And that hypertension is the leading cause of that pandemic. And I learned the leading cause of hypertension is stress. 

I was also reminded that stress is a choice.

We all have lions and tigers in our life. Maybe even a mouse or two gnawing away at something we value. Meanwhile, we have the moment.

Choosing what to focus on (and what not to) might just be the healthiest choice you can make.

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Photo of eggs by Nik on Unsplash
Photo of Ngoc Son Temple by author
Photo of tigers by author

Working at home, late at night, after putting in a full day at his job at DuPont, Earl Tupper was about to have a breakthrough that would change his world forever and launch an international company. Modeled after an over-turned paint can lid, Tupper used early forms of Polyethylene to create a simple, re-sealable lid that could be used for hundreds of shapes of containers.

His invention?


The original Tupperware parties

Not only did that simple invention launch a thriving company that now reaches over 100 countries, it introduced multi-level marketing to the world of selling.

And it started by asking a better question.

When Tupper asked himself how he could adapt the sealing properties of a can of paint to other containers he unlocked a whole new world of thinking.

Just like it did for George de Mestral (Velro), Spencer Silver (post-it notes), and Jacques Brandenberger (cellophane).

Let’s look at why questions are so critical to good thinking.

Our brain loves questions

The average adult brain weights in at about 1.3 kg (3 lbs), or about 2% of your body weight – not much. On the other hand, it chews through about 20% of your body’s energy – it’s a voracious engine that needs to be fed.

To save fuel it takes short-cuts.

Not sure what to make for dinner? Cook up stir fry, again.

Thinking about going to the gym? Put it off till tomorrow, again.

Need to make that sales call? Check your email, instead.

Still feeling the bruise from last night’s argument? Assume it’s his/her fault, like always.

Need I go on?

We all do it – take the path of least resistance. It’s easier, it’s faster, and, heck even more rewarding – in the short term.

And as you know, dear reader, once you think something is true, you can’t help notice evidence that proves you’re right.

The trick is to trick the brain.

Ask a better question

When you ask a better question you trick your thinking into exploring a new path. Instead of “Why is she is always….”, you venture down “What can I learn from this about me?”, or “What does she need right now from me?”

Usually it’s not that important if your question is the right one – as long as it prompts new thinking and new behaviour.

That’s what I did when I envisioned BOSS.

Why I created the Business Of Speaking School

Over past six years I’ve experimented with hosting conferences, bootcamps, one-day retreats, webinars, podcasts and other ways of teaching people the business of speaking. All methods worked – some were riskier (unless you’ve rented a hotel conference room and paid for catering, you’ll never know) and more work than others.

I wanted an anchor program – one I could be proud to offer every year – that wouldn’t be a huge risk to launch.

So I asked a better question.

Rather that asking how I could host a bigger conference, or how could I enrol more people in my bootcamps I asked this question:

“What could I invent that was good for both me and the students?”

You see, all the previous program designs were convenient for the students (just come to the conference, just sign up for the webinar, just listen to the podcast), but they left me exhausted.

The answer that emerged was a hybrid model combining recorded and live lessons with a community forum. That’s BOSS (the Business Of Speaking School). Every week, for 8 weeks, students learn from pre-recorded curriculum, we have a live 90 minute call with me and visiting expert faculty, plus we use a private Facebook group for daily conversation and answering questions.


It’s super convenient for the students (this year we have students from 8 countries) and convenient for me: no hotel room to rent, no catering, transportation, or crazy logistics. The profit is more predictable and I can put more energy and time into curriculum and helping the students.

What about you? Have you got an itch that needs scratching?

Start with an itch

To challenge your assumptions with a better question, start with an itch – what frustrates you over and over?

Maybe you’re putting in too many hours at work, procrastinating about speaking up to your boss, or skipping the gym. The trick is to recognize the frustration as being worthy of improving and then to narrow the question to one point.

If you want to enjoy better health, it might not help to tackle long work hours, children in hockey, and your spotty history of commitments. Instead, choose one area to improve (like how you spend the first hour after waking) and then form the better question you need to break through your story.

When I wanted more exercise when traveling I asked what can I do in just 15 minutes. The result (which I’ve used consistently for over 5 years) was my 15 minute hotel room workout.

Got an itch? Ask a better question – you might be surprised at what you invent.