Rita McGrath presents some thought-provoking questions in her book about transient advantages and continuous self-disruption, experimentation, and individual & corp. development. She says if you answer "no" to any of these questions that you better think hard about how to become more transient.

If my current employer let me go, it would be relatively easy to find a similar role in another organization for equivalent compensation.
If I lost my job today, I am well prepared and know immediately what I would do next.
I've worked in some meaningful capacity (employment, consulting, volunteering, partnering) with at least five different organizations within the last two years.
I've learned a meaningful new skill that I didn't have before in the last two years, whether it is work related or not.
Ive attended a course or training program within the last two years, either in person or virtually
I could name, off the top of my head, at least ten people who would be good leads for new opportunities.
I actively engage with at least two professional or personal networks.
I have enough resources (savings or other) that I could take the time to retrain, work for a small salary, or volunteer in order to get access to a new opportunity.
I can make income from a variety of activities, not just my salary.
I am able to relocate or travel to find new opportunities.