‘I am 39 and feel like I have not managed to make much of my life’

Tell Me About It: ‘Some friends say that I have it all, but I feel my life is boring and unfulfilled’


I am 39 and feel like I have not managed to make much of my life. Though maybe it is not all entirely my fault. I am an only child of quite elderly parents and there was no great pressure on me to do well at school or third level as I knew that I would probably go into my father’s business. I did, learning the business and living at home. For many years, I had good holidays, a nice car and some passing relationships, but now I feel left behind – by my peers that is.

The business is doing just okay and I am not sure if it will survive any further challenges – to be honest my heart is not in it and I drag myself through days at work without much enthusiasm. It is not an environment where I might meet a partner and it has been five years now since I dated anyone.

My father died 10 years ago, and my mother and I have settled into a routine that is the same for decades (long before my father died). Some friends have commented that I have it all, every need catered for without any snide remarks from a grumpy partner, but I now feel my life is boring and unfulfilled.

I don’t have any particular skills, I’ve never done a job interview and if I leave home now, my mother would be lonely and, as she is very elderly, it does not feel safe. I know I will inherit the house and my parent’s savings, so it feels unfair to consider leaving at this late stage.

Yet, I feel that I myself will slip into inertia and even depression if I just continue to let things go as they are. I think that if I was a woman, I would have more close friends to lean on, but there really is no one I’d feel comfortable speaking to and the effort of pretending to be confident is taking its toll.

What to do?


There is something about taking on challenges and risking failure that gives life its edge and it seems that, while you have always had security, you are missing the vitality that comes from stretching yourself.

There is a clear need for self-development across all the areas of your life and your habit of taking the easy route is a block to action. Habits can form early on in life and become rigid and enduring over time. This makes them hard to break, but they can be tackled and overcome with commitment and attention.

You are 39 and probably have a good 40+ years of living to do – what do you want to use this time for and what kind of person do you want to be during this time?

Your letter suggests that the impetus to change is already in place, and the first steps are to identify your blocks and allow your own natural motivation to emerge. You feel that your working life is less than satisfactory and addressing this might begin the transformation. You may need to enrol in a course that gives you skills that allow for other career options. You are not the only 39-year-old man in this position (of wanting to change career), but you are not curtailed by the need to provide for a family so could actually do this fairly quickly. A good starting point is to engage a career adviser who will help you identify areas that you might like to work in and then work backwards to what skills/competencies you need to develop. The fear of failure and the belief that you will be discovered to be unable are both common and detrimental thought patterns that need to be acknowledged and overcome.

These thoughts and feelings undermine self-confidence and motivation and are something that all of us need to tackle in our lives, if we are to break the barriers to our self-development. The online “Aware Life-skills Course” will provide the knowledge and competencies that you will need to keep motivated during the trying times ahead. Breaking habits require continuous effort and support so it might be helpful to recruit a friend who will applaud you on your efforts, or if this is not a possibility then consider counselling or psychotherapy to bolster your determination to keep on track to change your life. You may even look at selling the business, but again seek good advice before engaging in this possibility.

Your mother will need care, and this can be provided by a mixture of options: there may be a day-care centre where she could become more involved in a community and less involved in the care of your life, (or contact Age Action Ireland for information). With this connection, she will be helped to source appropriate care when the time comes and perhaps you could oversee this without needing to be the centre of it.

You say you have not dated anyone in five years and there is a bit of “use it or lose it” about this. Either you find activities and clubs where you might meet people who are attractive to you, or you try online dating. Again, the risk here is one of rejection but this is everyone’s risk, and your lack of fulfilment may be partially related to the lack of close relationship or close friendship in your life. You have taken the first all-important step of acknowledging that your life needs changing, now follow up with determined steps in all the areas that require attention, and you will find that your confidence, motivation and engagement with life will grow.

Setbacks are normal and to be expected so take them in your stride and get back on the path when life becomes challenging, you will then build a new habit that will work in your favour, and inertia will become a thing of the past.