Here I am packing my suitcase and getting ready to participate in a couple of conferences coming up at the end of the month. I will be participating on a panel, discussing the emerging trends of SDN — the virtualization of the network, at CP’s Cloud Evolution Conference. Then I will be heading to the NSCA Pivot-to-Profit Conference for a presentation on successful models of integrators that have pivoted from selling products to becoming cloud resellers. In addition, I will explore models of integrators that have chosen a different path and are building their own competitive cloud solutions. Both conferences will be very interesting and I am looking forward to attending. When you move toward the end of your career conferences are great ways to stay connected.

But one of the most important parts of the conferences is meeting up with friends, industry acquaintances, even my former competitors. However, it has been six months since I handed over the keys and said goodbye to the company that I sold at the end of 2016. I have always been very collaborative but there were a few times I held a little back based on the audience at the table. Not anymore. I am free from my 256-employee company and $156M revenue goal that challenged me to think differently every year. Don’t get me wrong: I miss the people, the families and the challenges.

But freedom has another side to it. The question is, “free to do what?”

When I left I was excited to be setting sail to an unknown future. I was told by those who went before me that it takes about six months of time being free to really figure out your course. Well now I am here and the time sure did sail by.

I am still a little unsure of where I am navigating to, although my sails are down. I have been focusing on what I love to do and that is to share my 35 years of experience helping others accelerate their business. Today my role and influence has changed. My identity has been reborn into something less relevant to many in the industry.

On the panels I moderate or participate in I am asked to provide a brief introduction and that is also very different for me. I present myself now as a consultant, past business owner, a board member and even a grandfather, which is the best job that I have ever had. My grandchildren even call me “Skipper.”

So as you face the last quarter of your life and ponder your next steps of retirement you may want to consider:

  • Spend more time upfront exploring things you want to do before setting sail. Still allow some time to separate from the past.
  • Prepare for a soft launch and continue to stay connected by attending conferences, peer groups and joining industry associations. 
  • Explore the world of philanthropy by being involved in non-profit work. Get involved in CompTIA and impact the industry.
  • Share your experience as a mentor or a consultant.
  • Be prepared like any good skipper for the change of identity. 
  • Set your course for what you like to do and be sure of why you want to do it.
  • Chart your course with some milestones and stay on course.
  • Don’t underestimate your value based on your past experiences.
  • Be prepared to navigate some stormy seas; it’s normal.
  • Make sure your first mate is fully in the boat with you and not a stowaway.
  • Have fun and live your passion.

Good luck Skipper in your new voyage as you navigate the “Sea of Change.” I wish you a strong wind beneath your sails and I hope to see you out on the sea.

If you would like to share more about my voyage in to retirement and transitioning out of my own company please connect with on LinkedIn or contact me at Until then, bon voyage.