What leaders regret ... and how you can avoid these

Edith Piaff’s stirring Non, Je ne regrette rien always prompts me to question whether I have any regrets — and more importantly how I am living my life to eliminate, or at least minimise, regrets in the future. Is this a leadership question? Well yes, it is, and for two main reasons. Firstly, because your life as a leader touches other people, and you want to look back and see the positive impact you have had. Secondly, your life as a leader often creates extraordinary demands on your time. Everyone seems to want a piece of you and/or your time. And then it becomes hard to make the time for who and what really matters.

There is a natural tension for a leader between the difference you want to make and the life you want to life — and this can lead to regrets in the future if not managed wisely.

The most common regrets people have when at the end of their life include: working too much, thinking too little, and not focusing enough on what ultimately matters. You may already be worried about these leadership challenges. What practical steps can you take to avoid these pitfalls? Here are three ideas that can help you avoid having the most common regrets: 

1. Make non-negotiable commitments to your family

What will matter at the end of your life is how you fulfilled your responsibilities and loved those close to you. Yet, it’s easy to get carried away by work and make excuses for your absence from the lives of your family as ultimately being for their good (I know. I’ve said it.) While this can be true to a point, the thing to watch out for is when long hours and hard work ‘for the family’ is merely a self-justification for your own inability to prioritise effectively and choose wisely. Failure here can lead to profound regret later.

Establish very clear boundaries you will not cross. For example, one busy CEO told me that she has a very clear understanding with the Board with regard to how often she must be home for dinner and home for weekends with her family. Non-negotiable. And those boundaries are established in advance.

Rabbi Lord Jonathan Sacks tells a story from a time working on a documentary on the state of family life in Britain. He took Britain’s then leading expert on child care to a Jewish primary school on a Friday morning.

“There she saw the children enacting in advance what they would see that evening around the family table. There were the five-year-old ‘mother and father’ blessing the five-year-old children with the five-year-old ‘grandparents’ looking on. She was fascinated by this whole institution, and asked the children what they most enjoyed about the Sabbath. One five year old boy turned to her and said, ‘It’s the only night of the week when daddy doesn’t have to rush off.’ As we walked away from the school … she turned to me and said, ‘Chief Rabbi, that Sabbath of yours is saving their parents’ marriages.’”

Whether you celebrate a day of rest, eat dinner as a family, or make a point of being home for your children’s birthdays, having non-negotiable commitments to your family and friends who matter most will help you avoid the common regret of not being present enough in the lives of those you love.

2. Build reflection into your schedule as seriously as you book meetings (seriously)

In an always-on society, how can you sit quietly thinking when your to-do list is crying out for attention? 

Bronnie Ware, a palliative care nurse and author of Top 5 regrets of the dying, is convinced that meditation is crucial to avoiding regret later in life. She says: “I think if you can develop compassion for yourself, you’re not going to have regrets. Rather than judging yourself for something you did or didn’t do and having regrets about it, you can actually look back on it later with compassion for who you once were. I think in our busy lives, without meditation, it’s very easy to be ruled by your busy mind, by fear and others’ expectations. I think once you do connect with that part of yourself with a regular practice, there comes a time when your heart speaks too loudly for you to ignore.”

Many busy leaders are ‘ruled by a busy mind’. When are the times this is not the case for you? It’s almost certainly somewhere not at your desk and in a different environment. Try building reflection into your schedule the same way you fit meetings into it. When you have a short break, take a walk without your phone. Try writing reflectively every day — even if only for five minutes — not on a computer. Spending some time truly by yourself is the surest way to retreat from the expectations of others and to think clearly about your own priorities, goals, and purpose.

3. Focus on what ultimately matters — not just to you, but to life itself

Spend time cultivating an appreciation of beauty, goodness, and truth — seeking out beautiful sculptures in art galleries and goodness in creative communities. Doing so expands your senses and your horizons and is a great source of growth and development as a human being.

Reinhold Niebuhr said: “Nothing that is worth doing can be achieved in our lifetime; therefore we must be saved by hope. Nothing which is true or beautiful or good makes complete sense in any immediate context of history; therefore we must be saved by faith. Nothing we do, however virtuous, can be accomplished alone; therefore we must be saved by love.”

Many leaders want to leave a legacy, and do something of significance. You will find the power for this comes from enduring values such as beauty goodness and truth. Discovering these in art, for example, will help you foster them in the world around you.

Make “appointments” with goodness, beauty, and truth. Feed your spirit and avoid the common regret of paying too much attention to fleeting concerns.

The most common regrets people have at the end of their life include: working too much, thinking too little, and not focusing enough on what ultimately matters

How do you balance the tension between the demands for success today and significance tomorrow? What are you doing to create a life with no regrets?

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