Recently, I met a 70 year old former engineer, who by all accounts was in great shape for his age. I remember thinking I’d like to look that good at 70. He had been a mechanical engineer for more than forty years and recently left the industry he enjoyed to retire. These days, he tells me travel and leisure take up a good portion of his time. We struck up a conversation about length of work, working on what you love and why he left. This gave me great perspective on work, the future of the work we do, and how long I might continue to be an IT Guy in an industry filled with younger folks.

The big question that seems to be on my mind is when do you stop? When you’re an IT Guy who works on his own or a freelancer that started a company from a great idea, you know that you can’t last forever. I even sat down with my sister a couple weeks ago and she asked me if I would take a 9 to 5 job. She thought that, in these uncertain times, the stress of what I do would be too much to handle. This is the kind of thing that stays top-of-mind when it keeps coming up in conversation.

I know why the conversation goes that way too. I’m 38 and not getting any younger. Probably a few years from a mid-life crisis, but my twenties have come and gone. Sure, I’d like to still be in my late teens, but I wouldn’t like to take back many of the struggles. The sad fact too, is that ageism in the technology field is a reality. So, as an IT Guy pushing 40, I’ve recently had a number of chances to stop and ponder the possibilities of what my future holds.

And that future is very much the present for my recently acquainted 70 year engineer. He talked about his love for traveling and he recent difficulties elsewhere, but I was struck by how alert and lucid he was. Sure, I guess I shouldn’t be thinking a 70 year-old should be senile. But, the thought did creep in to my mind. I asked him how he liked working with clients. His response was that it was often the client’s mistakes that caused the issues, but they were commonly unwilling to accept it. These kinds of struggles caused him great difficulties reconciling his love for the work, and the struggles with the people.

Then, I asked the question that I can say I’ve wanted to ask someone in his position for a good long time. I asked “How do you reconcile you love for the work and the fact that you’ve left it?” I really didn’t want this question to be taken the wrong way, and thankfully he understood what I was asking. His answer surprised me. He missed it. He seemed like person wishing he could go back and keep doing what he loved. I even asked at one point if he could go back, and he hesitated while saying something that amounted to a no.

In these moments I often feel a rush of thoughts that bounce between the ideas of why those in Okinawa, Japan have such a high life span and how important it is to keep experiencing flow in our lives. We live in this society that has ended the legislated and end to retirement at the age of 65 (In Ontario the law was eliminated Dec. 12, 2006). Canada is also a country of people getting older (on average). Do we know how many of the 70+ year olds are high functioning capable people in my country? I’m not sure that we do.

My question is this then: when do I see myself stopping? Should there be a line in the sand that says, ok I’m done doing this work and I’m going to ride off into a retirement sunset? This question I can’t answer with any great certainty because it’s not a choice I need to make right now – but it’s one I often wish I had the direct answer to. I do wish that I would be able to continue what I do, as long as I can.

Now, let me turn this discussion to you. If you have also pondered this question – when do you see yourself stopping work? Will that be a day you look forward to?