About Boldness and Caution

About Boldness and Caution

About Boldness and Caution

Extolling the virtues of ‘chronic unease’, the recently identified disease that keeps even the most successful of entrepreneurs awake, Pilita Clark in the Financial Times suggests that too much boldness can be a Bad Thing and Caution is really the Name of the Game. Ms Clark has a point but not an overwhelmingly good one. Chronic Unease brings with it ulcers, cancer and mental derangement. That is why so many top people drink to excess. Near oblivion negates unease. It must be added that drinking to excess also brings with it ulcers, cancer and mental derangement.

If, like me, you have been through the gamut of moods on the BOLD-WARY continuum you will know that the amount of control you have over many of these forms of self-presentation is strictly limited. I once spent two years in a job I hated, for which I was not equipped and without help of any sort from my boss or peers. Every day as I drove to work I stopped my car some way from the office and made a great resolve and effort to go the final mile. My mood may have reflected the quality of my work and my willingness to learn but it was still a horrifying experience.

Perhaps what I have described is not Chronic Unease, but Failure Panic. I still think it’s in the ballpark of CU. At that point of my career I felt like Churchill must have felt in his ‘gardening years’ when out of office. He built a wall. I tried to build a knowledge of management communications and personal engagement that founded my Mentoring, Coaching and Training business twenty years later. Meanwhile I had built a company of modest size but which sold for twenty-five times earnings. Was that achieved by boldness or by caution?

Certainly by some boldness but even more importantly by being aware of how bold I was being.

Looking back, I can see that I was more often correctly bold than cautious about the company decisions I made but more often wrongly bold – to the point of incaution – about the way I dealt with my bosses. The company was, to me, what we were all about. I loved it like a baby, possibly too much. Manipulating It or its clients never crossed my mind. The effort and dedication I put into it, often at the expense of my family, was my ‘boldness’ contribution to its success. If I thought one of my bosses was not showing the same dedication I told him so (they were all ‘him’ in those days).

This was daft, of course. The company was a bit dependent on me but not all that much. Companies generally outlive people. I was more dependent on my bosses than I was willing to admit. It is odd to reflect now that I seemed to respect the company more than I respected many of them. Not all my bosses were bad. In fact, I probably had a better quota of good, helpful bosses than most people. But It’s the bad ones you remember, isn’t it? Anyway, they’re the ones you have to handle and I did a poor job of it.

You have to woo a boss, especially the atrocious ones. Pander to their insecurity as expressed by their need for adulation but work into your sycophancy the things you want approved, especially those that you need to have forgiven. For it is the best rule that you do not seek permission, rather that you need forgiveness. A little practice and you become adept at how close run your decisions can be to unacceptable and yet still pardoned. Caution must always be laced with boldness.

To grow a business is a different matter altogether. Here you need your BOLD to the fore. Frighten your colleagues with your crazy ideas, push some of them, even the weird ones, to the point where they demonstrate how failure is a great lesson not a sin. Bezos, Jobs, Musk, Gates, Page and Brin all did this to effect. They weren’t lucky winners, they were bold innovators. They had courage.

And it is at courage that boldness and caution meet, for courage is persistence, different from the others but essential as a partner to them. Unlike boldness and caution, courage is not wild or manipulative. It is plain, straightforward determination. Courage never gives up, never surrenders. When sweat is turning to blood, courage goes on, stumbling sometimes, falling even, but always getting up. Courage doesn’t shout, nor does it whisper. It perseveres.

And by doing that it activates boldness and caution. Together they are a trinity of sorts.

They are the flag bearers of the innovative.

They are the harbingers of the future.

Good morning
John Bittleston
Your Daily Paradox scribe is going to be travelling in the next few weeks. His prolific outpourings may be somewhat reduced as a result. Bear with us, please. We shall as always have you in mind.