Top 5 Regrets of the Dying

Top 5 Regrets of the Dying

With a subject line like that you could be forgiven for thinking that this would be a morbid or depressing subject. However, I ‘discovered’ the Top 5 Regrets of the Dying a few years back and I find them inspirational.

In this episode I walk through each regret and put my own perspective on them and share some views from the work I do with families.

In summary the top 5 regrets are listed below;

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.


If what I speak about in this episode resonates with you and you want to explore your own purpose or passion and the role your family business can play in it, please get in touch. I can help.

My email address is

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Top 5 regrets of the dying – A Family Business Perspective


With a title like that there is a danger that this post could be viewed as quite morbid, but please read on, the aim of this is to inspire and provoke some thoughts rather than depress.

For those familiar with the ‘Top 5 regrets of the dying’ hopefully this will be a useful reminder, for those unfamiliar with them, please allow me to introduce you to them.

Bronnie Ware spent many years as a palliative care nurse and in 2009 she wrote an article called Regrets of the Dying. Bronnie grew close to those that she cared for and had honest discussions with them about life, death and regret. She documented these regrets as a way of highlighting that when we are faced with our own mortality and we are reflecting on our lives, looking back rather than forward, there are many things that we wish we could have told our younger selves.  

You can learn more about the book that followed here.

In summary the top 5 regrets are listed below;


  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.


I am going to discuss each of these regrets in the context of family business, drawing on my own experience as a human being, but also as a family business adviser and what we can learn from the regrets of others in the hope that we can avoid these in our own lives.

I wish I had the courage to live a life true to myself, not the life others expected of me

This was the most common regret and it is really easy to see how this can be present within a family business.

Remember the scene in Lion King where Rafiki presents Simba to the Pride Lands, at that point the life expected of him was laid out before him. There were no discussions, no choices, the path to him becoming King was set.

This is obviously an extreme example and there are only so many career choices for lions to follow, but the fact that Simba, simply by being the first born, had his choices, responsibilities and expectations dictated to him is not an unfamiliar scenario within a family business.

There is often an expectation, either sub-consciously inferred or explicitly stated that the eldest child will take on the role of MD, with their choices, responsibilities and expectations dictated from birth.

I often hear parents say that there is no pressure on the next generation to join the family business, that there is a place if it’s needed but certainly no pressure and whilst this might not be explicit or intentional, when I then speak to the next generation they tell me that there is still an unspoken, unaddressed pressure to join or contribute to the business.

To be clear, I am not suggesting that the next generation should not join, run or own the business if that is what they want to do and are suited for. However, I am suggesting that this should be a choice that is discussed and explored fully.

These discussions should be on a regular basis, in an appropriate environment. If the choice is to join, own or run the family business, what can be done to make this as smooth as possible with the best interests of all in mind. If the decision is to pursue a career outside of the family business how can the business or family wealth be utilised to enable the best opportunity outside of the business?

This may seem a simple solution, but for me it is for us all to be honest about what we want to do with our lives, if we don’t know we can spend some time exploring that. If today was our last, what would we have not done? Who did we not get to be?

This may take time and will possibly change over time as our lives change but the clarity and direction that this can provide (I speak from personal experience) can be liberating and energising.

I wish I hadn’t worked so hard

OK, I’ll admit it, I am as guilty of this as the next person. If I am honest with myself, I spend too much time working instead of taking time out to do other stuff.

If you have your own business you may be in the same position, what you do is something you feel passionate about, it is something you at least enjoy doing, if not love doing.

So, why shouldn’t we do it more?

My learnings from this is that it is all about balance, working 24 / 7 to the detriment of your health, relationships and overall wellbeing is clearly not good for anyone but finding a range of activities to do that leave you fulfilled and doesn’t neglect your health or happiness is surely a good thing.

Time is our most valuable resource and one that cannot be replaced. Our businesses should be able to act as an ‘enabler’ to allow us to spend our time well. For many of us that is why we went into business in the first place.

Finding that balance between working ‘too hard’ and working hard enough to achieve this can be tough, but I am a firm believer that it is balance here that can be transformational.

Finding time to spend with friends and family, on creative outlets beyond our businesses, on our physical and mental health should become a virtuous circle. Having the discipline to do this can be tough, but I would argue that the discipline now is better than the pain of regret later on. Remember, we can’t get that time back.

Being accepting of a ‘balanced’ lifestyle may also be part of any conversations around succession and the role of the next generation within the business.

I have come across senior generation in the business who feel that the next generation have it too easy, and that they should need to work at least as hard as they had to in order to enjoy the benefits of working in or owning the family business.

Contrast this with the view from the next generation that they don’t want the business to be as all-consuming as they have seen in the generations before them.

This can be a source of tension in the relationship between generations and have a negative impact on the business as a result.

Listening to and understanding each other’s perspective here is an important step. If there are contrasting views on lifestyle and perhaps disagreements on what is needed in order to be effective within the business, appreciate that you are both right, it is an opinion and it is not so easy to convince the other party that they need to change their view.

That doesn’t mean it can’t be overcome and often a balance (that word again!) can be found that works for everyone. 

I wish I had the courage to express my feelings

I’m scared, I’m sorry, I’m not happy, I’m really excited about this, I’m angry, I love you.

Easy to write here, easy to read but much harder to say.


Is it because we have to be vulnerable to say these things? Is it because we are worried about what people will think of us after we have said these things? Is it because we can’t control people’s reactions to us saying how we feel, or we’ve already decided how people will react and therefore there isn’t any point saying it?

These are legitimate concerns, but it is important to me to remember that all I really have control over is what I say and how I say it. How people react to that is out of my control and influenced by more than simply the words that leave my mouth. 

Given the stress and strain that many of us find ourselves under given the current situation being able to express how we feel is more important than ever. 

The danger in not expressing how we feel is that we bottle this up and that is not a good thing, there is also a danger that we end up avoiding critical conversations and backing ourselves into a corner on an important issue. 

If you are finding it hard to speak to your family given the intertwining of business and family and you are feeling isolated having friends that you can call on for support is priceless. However, this can also be a difficult group to express how you really feel as they may not be able to relate to your circumstances and also may not be objective in their views as they will naturally be ‘on your side’. 

A possible solution here could be to join or establish an accountability group. I have been a member of one for a few years and the value of having people I can be absolutely honest with, about anything and everything has been huge in my own life. 

Being able to be honest with people, with zero judgement and have them relate as they are in similar situations has been a game changer for me, my accountability group have challenged me and (as the name would suggest) held me accountable to what I said I would achieve.

I have been able to express my feelings to them in way that is different to speaking to my partner or my parents, if you can find an accountability group I would recommend them highly.

I wish I had stayed in touch with my friends

Again, I am guilty of this one, too many times I have called, text or met up (when we are allowed!) with friends and said “it’s been too long” and then as we head off home, we say “let’s not leave it so long next time”

I mean, it’s December now and it feels like only yesterday that I was in January saying I would be better at staying in touch with people.

It has not been a deliberate act, more a reflection of how busy our lives are and how easy it is to fall into this trap. 

Without looking like I am criticising social media, I think it seems much easier to stay in touch with people simply by looking at their status updates on social media. 

Platforms like Facebook, Twitter and Instagram provide us with a window into the lives of our friends, however they are windows through which our friends are asking us to look, where they control what we see. 

Far better, in my view, is to pick up the phone, meet up (if we are able to) and simply ask “how are you?”

And then to be present and to listen to their response. 

I don’t want to come across all preachy here as I am guilty of this myself and my goal for 2021 is to ensure that I am here for my friends, I will listen to them when I ask “how are you?” and I will reach out to them irrespective of whether I have seen a recent Facebook post or Instagram picture.

I wish I had let myself be happier

I am particularly interested in this one. I find the language used fascinating. It isn’t I wish I had been happier, it is I wish I had let myself be happier.

For me this places the emphasis on us letting ourselves be happier, it suggests that we are far more in control of our happiness than some would have you believe. 

It also suggests that those interviewed during this process had a moment in their own lives where they realised they could have let themselves be happier. It suggests that they had a moment where they had a better understanding of what happiness meant for them, what was important to them and I can only imagine the regret of thinking “I wish….” I spent some time understanding what makes me happy and I am focussed on getting more of that in my life. I’ll admit this has been really tricky this year, but what I have been able to do simply by being more aware of what makes me happy is, when circumstances won’t allow, what qualities or characteristics does a certain thing bring to me and how can I replicate that. 

A simple example is, I love travel, I love discovering new places and new cultures and it is this sense of discovery that I value from the ability to travel. Given that this has not been possible this year I have focussed my travel locally and understanding more about what is right here on my doorstep. This has been an enjoyable way to spend weekends with my family, and goes some way to replace the quality of ‘discovery’ that I get satisfaction from.  

I have prattled on about this in the past and I don’t want to bang on too much about this, but your success as both an individual and as a family is not defined by your ability to pass a business from one generation to the next. 

Far too much of the literature and rhetoric on family business seems focussed on passing a single legal entity from one generation to the next. For me this discussion needs to be expanded to incorporate our own definition of success and what role our businesses can play in achieving that success. 

You are in control of what you define as success but it may require some work to understand what it is that you want more of in your life. Once you have done this you will have the clarity around what your business needs to do for you in order to achieve what you want to. 

Mindfulness helps me here, alongside gratitude exercises. This may sound a bit ‘woo woo’ but taking time in becoming more self aware and understanding ourselves better, again makes us better able to a life true to ourselves and not what others expect of us.

Life is not a rehearsal and so taking time to understand what it is important to us, what brings us fulfilment and happiness, as defined by us not what others expect of us, has to be a good thing and I would encourage anyone and everyone to explore this. I am able to help, just get in touch. 

Final thoughts

Life is short, life is precious, and we only get one shot at it


A challenging question, but one to think about is ‘if today was my last on this mortal coil, what didn’t I get to do? Who didn’t I get to become? Who do I wish I’d spent more time with?


This isn’t intended to be a depressing thought, more an inspirational one. We don’t know when our last day is, but hopefully today isn’t that day and so we have time to do something about this


I went through this process late last year learning more about a coaching technique that I now use with the individuals I work with and it became the catalyst for a lot of change in my own life, including me setting up my own consultancy business.


I spent a week with a great group of people where we spent time reflecting and learning about ourselves, what motivated us and what was really important to us, including that question above and it has left me determined to ensure I make the best of my life. The festive period can be a very useful time for reflection and for us to think about this stuff.


So, together why don’t we make a deal with each other that we will turn those top five regrets into the following affirmations:


  1. I will have the courage to live a life true to myself, not the life others expect of me.
  2. I’m glad I realised I don’t have to work so hard.
  3. I had the courage to express my feelings.
  4. I stayed in touch with my friends.
  5. I let myself be happier.


I wish you all a very happy festive period and look forward to speaking with you more in 2021