Cautious boldness

We use maxims, aphorisms and proverbs all the time. Short, pithy sayings that we think wise and helpful.

My parents taught me ‘Waste not, want not’ and ‘Every penny counts’. The Scouts gave me the motto ‘Be prepared’. Nowadays we warn children about ‘stranger danger’. Signs and ads say ‘Don’t drink and drive’. Short sayings are remembered, and often keep us right.

A few years back I coined my own to improve my golf game: ‘Cautious boldness’. Those two words have helped me win trophies. With golf, it’s sometimes best to play safe. Perhaps there are deep bushes alongside a fairway – time for caution. But you can’t be cautious all the time. If you’re on the green, putting from only a few metres, you must be bold. ‘Never up, never in’ is the right thought, because, obviously, no putt has ever been holed which didn’t reach the hole. So, I realised being cautious all the time was no good, and being bold all the time was no good. Therefore cautious boldness became my maxim – sometimes one, sometimes the other. Winning depended on knowing which was right in each situation.

That seemingly contradictory mix, cautious boldness, is also relevant to living life wisely and well. I’ll illustrate how it could apply in four contexts. The first two concern important life-directing issues. The other two are more down-to-earth, but perhaps will make you think and smile.


Like many I suffered the teenage angst of wondering ‘Does she like me?’ and ‘Will she laugh if I ask her out?’ But I worked my way through my inner turmoil, occasionally holding back wrongly and occasionally pushing forward wrongly. Sometimes too much caution. Sometimes too much boldness. (It was all better in my early 20s when I met Alison…)

Getting the caution/boldness balance right is important too in long-term relationships. Let’s imagine Colin and Christine. Colin is struggling with depression. He feels his life is useless; he can’t see a good future. The last thing he needs, at that moment, is Christine telling him to pull himself together, to brighten up and be positive. Colin can’t handle that. Christine needs to take a more cautious, gentle, reassuring approach.[1]

A few years earlier Christine had her own struggle, albeit of a very different kind. She excelled in her administrative role for a large firm, and was often called on to supervise new colleagues. She had a gift for bringing out the best in them. One day the managing director asked Christine if she’d consider being appointed department head. Christine’s head spun, and sensibly asked for a day or two to decide. At home Colin listened as she poured out a catalogue of doubts and fears about her abilities. Wisely, Colin let Christine get it all out of her system, and then carefully but positively drew out from her an equal catalogue of abilities and strengths she knew she had. He followed that with encouragement, helping her believe this was a deserved promotion, and one good for her and for her firm. She took the job, and never regretted it.

There are times to exercise caution and times to offer boldness.

Career / work

In my journalism years I had two types of colleagues. One group were ‘journeymen’ (they were all men at that time). The news editor could send them to a meeting, where they’d take shorthand notes and write an accurate report of what had happened. Or they might interview someone making news, and write an acceptable story. But that’s all they did. They didn’t spot news opportunities. They never wrote in an exciting, captivating style. They just went about things in their quiet and cautious way year after year.

Some were different. They could do the routine stuff, but they had eyes and ears to discover news. Maybe it was something a politician let slip. Maybe they picked up on gossip about a sports star. They followed up on their leads, and often had a front page story in the next edition. They showed initiative and talent, and moved on fast in their careers.

I’ve seen the same distinction in other places where I’ve worked. One type of worker is slow and dependable, another type creative and pushing forward. Each has their strengths. But most of us can have both strengths. There is wisdom in moving between times of caution (working carefully and steadily) and times of boldness (offering new ideas, striving for advancement). Those with only an abundance of caution may come to regret the tedium of doing the same thing constantly. Those with overmuch boldness may find themselves promoted beyond their competence (aka, promoted to the point of incompetence).

Caution at times and boldness at times – when rightly judged – has much to commend it.


My friend Keith, a policeman, was an examiner for motorbike riders attempting to pass an advanced test. He’d been my examiner, and we’d remained friends afterwards. ‘You wouldn’t believe,’ he told me one day, ‘how many flagrantly break the speed limit while taking their test.’ Keith eventually realised they never rode within the speed limit, so it didn’t occur to them to ride differently during the test. ‘And speeding is a definite failure,’ he said.

Interestingly, though, just as you can fail an advanced test for going too fast, you can also fail it for going too slow. I’ve taken both car and motorcycle advanced tests, and, thankfully, remembered the formula for getting the speed right: ‘make good progress’. In other words, don’t go too slow because then you’re a hazard, and don’t go too fast because then you’re a danger. So, in a 30 mph area, I should aim to drive or ride very close to 30, but not more than 30. That’s good progress.

Not everyone makes good (and safe) progress. We’ve likely all moaned about a slow driver on a standard (single lane each way) road, with tight bends, oblivious that there’s a queue of 20 cars behind with frustrated drivers because there’s next to no chance of a safe overtake. It’s little better on a busy motorway. The slow driver cruises along at 40 or 50 mph in the middle lane, causing a blockage and hazard as cars jostle to move into the outside lane to get past. (In the UK, going past another car on its nearside isn’t allowed.)

Of course I’ve seen many dangerous attempts to overtake on narrow roads, and plenty times, when I’ve been driving on a motorway at the speed limit of 70 mph, a car has roared past me doing at least 90 if not 100 mph. Is it a sin to pray there’s a police speed trap just ahead? If so, I have sinned.

People die trying to overtake someone who’s dawdling along at a dangerously slow speed. And people die because they’re driving far too fast, killing not only themselves but possibly others too. There are times to be cautious and times to be bold. Lives depend on judging which is appropriate.

Practical tasks

I have no memory of my father doing DIY jobs around the house. He worked, played golf and did gardening. He didn’t repair or maintain things. So, when I left home aged 16, I’d no idea how to look after a property.

I learned fast when, with family help, I bought a near 100-year old tenement flat in Edinburgh. It was affordable for two reasons: 1) It was very small, just two rooms; 2) it had never been modernised – it had an old range, electric wiring hung loose, there was no bathroom, and so on. There was plenty to fix. I couldn’t take on a complete renovation of the place. That would involve new walls, new electrics, new plumbing, which would require experts. But there were innumerable small jobs.

I got hold of a DIY book, read the relevant sections, and did my best. Much was trial and error, but I soon learned how to drill holes, use wall plugs, and hang towel rails or shelves. I replastered a section of wall – not perfect but acceptable. I stripped about seven layers of wallpaper away, including varnished wallcoverings which may have dated from the flat’s construction. After a while I was quite good at DIY.

It was several years before I had a car, and the first was not at all in good condition. I set about treating the rust with metal brush, fiberglass, filler, hardener and careful, gentle rubbing to get the surface perfectly smooth. Eventually I resprayed the whole car. In the engine area I put in new spark plugs, adjusted the tappets and fitted a new clutch. The sills on the underside of the car were rusted through, so I welded fresh metal in place. I had to do something about the car’s poor braking, so bought new brake shoes, fitted them, and, thankfully, the car stopped when it was meant to.

As the years went on, I did less DIY work. For three reasons:

  • I simply didn’t have time. My real work was all-consuming.
  • We had enough money to pay mechanics, plumbers, electricians. They did things better and in a fraction of the time I would have taken.
  • I realised the limits of my skills, and that I’d probably overstepped those limits in the past. There were no disasters, but there might have been. It was time to be more realistic about what I could do and what it was best I didn’t do.

But I’d learned that with a lot of courage and a bit of skill I could do many practical things. There was no mystery about most of them; nothing about which to be frightened – and a lot of money could be saved. But, the wisdom of the years taught me about my limits, and when it was best (and sometimes legally required) to bring in professionals.

Times for boldness and times for caution.

Two last things.

First, I don’t believe for a minute that DIY is a ‘man thing’. While working in America, a colleague mentioned his wife was visiting her parents for a few days, so he’d be on his own. ‘But,’ he said, ‘I won’t be idle. She’s left me a long Honey Do list’. I had to ask what a Honey Do list was, the answer being ‘Honey, I want you to do this and do that’ – a long list of jobs his wife wanted done while she was away. (Go online, type in Honey Do, and you’ll find templates for a Honey Do list, plus innumerable posters or cartoons related to it – my favourite is of a skeleton on a bench with the caption ‘Waiting on that honey-do-list to be done’.)

I’m happy to report that my wife, Alison, is very capable with DIY – mending our shower, unblocking sinks, laying carpet, painting, wall-papering, sharpening tools, repairing appliances. She’s about to replace a tap washer (which she’s done before). But, like me, she’s well aware of her limits.

Second, I’ll tell the story of when we literally pushed our personal boundaries.

Alison and I lived in that tenement flat after we were married. We modernised most of it, but of course it was still very small. When Alison was pregnant, we knew a baby came with baggage, and we’d need another chest of drawers to store baby things. Except, we didn’t have anywhere for another chest of drawers. There never was a lot of wall space, and every inch had something against it already. Except the back wall of a deep cupboard. We measured its width, bought a chest of drawers an inch or two smaller, and thought ‘problem solved’. It wasn’t solved. We’d only measured the back wall, and the doorway into the cupboard was narrower, even with the door removed. We could carry the chest of drawers into the cupboard by turning it sideways, but then it had to be straightened, and at an angle it was wider than the cupboard, so that didn’t work. So, we took the chest of drawers out again, thought hard, thought some more, and then we knew what to do.

First we took out the drawers and then dismantled the ‘carcass’. Off came the top, sides and back panel, leaving us with the equivalent of a modern ‘flat pack’. We took all the parts into the cupboard, and reassembled the chest of drawers facing in the correct direction. Alison was at the far end of the cupboard to screw the back panel into place. She did her job perfectly. But, of course, Alison was now completely blocked in behind the chest of drawers. However, we had a plan. I’d lift the chest of drawers as high as I could, spread my legs as wide as I could, and Alison would crawl out underneath the chest and underneath me, and then I’d lower the chest in place. At any time that plan was at the far edge of boldness because the chest of drawers was not light and the space for Alison to crawl through was small. At this time there was another complication. Alison was now fully nine months pregnant. But we had to try. I spread my feet to each side of the cupboard, lifted up the chest of drawers, Alison crawled, and all was well. Our son was born two days later.

(When we eventually left the tenement flat, the chest of drawers was dismantled again to get it out of the cupboard, then later rebuilt, and used in four other homes for over 20 years.)  

I tell that story hoping only to amuse. But perhaps it has some lessons. We were thoughtless in our purchase, but bold with our idea for how we could fit the chest of drawers into the cupboard, and then actually quite cautious/careful about how we did it. But I would urge: be bold about what you do, but super cautious when someone is nine months pregnant.


[1] During my own time of deep depression, Alison had the wisdom not to scold me for feeling so low, and not to offer trite solutions. But, when I was at my worst during the darkest hours of the night, I’d feel her hand take mine gently and just hold on. It was all I could cope with, but also all I needed.