When is an IT Executive Really Ready to Retire?

I recently retired. After almost 35 years of work, the last seven years as CIO of Water Street Healthcare Partners, I decided that I was “done.”  It was a great run, and by and large, I enjoyed it. But I felt that I was ready to retire since there are many other things I want to do with my time.

But it raised the question of what "done" really means in terms of one's career. Indulge me in a story, since that is what retired people do, tell stories:

Years ago, when I was a CIO, a developer came into my office and was excited to report that he was "done" with a project. I said, "Great! I've got the next big thing for you to do!" He said, "Well, I'm 'done' except for the final documentation, deployment to Production, and fixing any Day One issues. So, I'm not ready for the next thing quite yet."  I said that I had understood that he was "done" so when he was "done-done" he should come back and see me again.  A few days later he came into my office, smiled, and said he was "done-done" now, and for me, a distinction born!

Retirement Criteria

I knew I was "done," but I started thinking about whether I was "done-done." And how would I know?  Here are the criteria I came up with to help me answer these questions:

The first three are most likely symptomatic that you just need a vacation, or maybe a new job. But you are probably not ready to be done-done.

The next two are a little more nuanced. It is great that you want to start spending more time pursuing a beloved hobby or traveling with your spouse/significant other. Those may indicate that you are ready to be done-done, or they could mean that you have other interests you are passionate about that are outside of work.

Spending time with my wife easily put me over the top of "done-ness." For work though, the final five criteria really differentiate done-done from done. For me, they come down to self-motivation, staying engaged, giving back, and having other things that are more important to do AND being able to do them.

Additional Considerations

Before jumping too quickly from being done to being done-done, remember that being done-done quickly becomes irreversible. If you "flunk retirement" in the first few months you still may have the chance to go back to working if you so desire, but after a year or two, it is not likely that you will be able to pick up where you left off.

I can't assess these criteria for you, but I can for me. I am done-done, except for the "stay sharp" and "give back" categories. So I have joined a corporate board, I am an investor in a couple of ventures, and I continue to mentor some promising professionals. Even writing this article is an example of staying sharp! Since it is hard to go from full-speed to no-speed, I will continue doing these things as long as they don’t get in the way of the other things I want to do.

So, does that mean I am done or done-done? I believe that I am done-done, but check in with me in a few months and I'll let you know for sure.