"Work" in Retirement

“Never get so busy making a living that you forget to make a life.”

— Dolly Parton

Welcome to my inaugural “B-sides” post since I split this Substack into two parts. Today, I am answering a friend’s question about my “work.”

Steve - I would love to know more about your "work." I know you are retired, but it seems like you do some consulting and mentoring. How do you decide what and who to be involved with? How much do you do? How much can you do before it interferes with your other goals and how do you handle that..?

To answer this question, it’s probably easiest to describe first my choice of “who” to be involved with. In general, I haven’t really done much in the way of lead generation, so all the “work” I have done has been largely referred to by friends. I am grateful to these friends for involving me in their current projects. This is a picture of me and a friend at an event for one of these past consulting gigs, when we took the opportunity to snap a photo with Anne Chow, former CEO for AT&T Business.

To describe “what” types of “work” to be involved with, I’ll limit this answer to paid consulting gigs, as opposed to the things I do either for free or associated with investment activities. I have done three types of paid consulting:

• Interim exec roles. This type of work took advantage of my availability in retirement to quickly fill a role, even if not permanent. It provided the companies with a way to quickly provide leadership and ongoing mentoring for groups while new executives roles were being specified and recruited for. I found that filling these roles required a scheduling commitment for me more like a regular job because of the need to sit in a set of recurring executive staff, departmental, and project meetings to fulfill the needs of the roles, on top of the 1:1 coaching for team members or leads.
  
  Also, even when holding down the fort in the interim, the roles required a different psychological mindset than a regular job, knowing that any forward progress could likely get “undone” by a new permanent executive (justifiably) wanting to carve out their own initiatives. Because of the time commitment while engaged, I am not really looking to do more or these in retirement. At the same time, it’s also not clear they’d easily come my way anymore! In the cases where I performed these roles, I had “inside” contacts within the companies, and the number of people I know well who would request this of me in the future is likely very finite!
  

• Projects.  Finite projects can be fun in retirement. They tend to be more “hands on” and as such are distant from the constant juggling of a startup tech exec. These projects can take advantage of my experience across a range of functions, as well as my ability to take on “bursty” work that doesn’t provide a consistent stream of hours (income).
  
  For some color, one of these I did in the past was to lead a company’s participation as a launch partner with Google on their announcement of some new conversational AI capabilities. There were a set of deadlines that needed to be made for a launch announcement but so much of the progress relied on Google’s development milestones as well as the pilot customers’ abilities to implement and deploy their applications. And when there was work to do, there was a lot. There was technical work to ensure that demos worked well and to support customers in their implementation. On top of that was a lot of evangelism with potential partners to help bring the solution to market.
  
  I’ve also done other types of projects associated with product specification, pricing and packaging, content development, and training. After so many years, as a Dilbert pointy-haired boss (PHB), these projects have offered an ability to engage at a different level . I also think that the client companies benefit from my past experience of being a tough reviewer of these types of deliverables myself, so there has been very little need to iterate a lot on the work I have done.
  

• Executive coaching. These engagements likely best utilize my experience as a startup tech exec, without requiring the time commitment of being an interim exec.  These gigs take advantage of having someone that knows how the game is played.  I have been the recipient of a lot of coaching and I have now done a bunch, too. This work primarily involves helping executives identify their “blind spots” as well as to help keep them accountable to development plans we create together. Depending on the client, this can be fulfilling work. The work can also be hard because executives generally have successes behind them that can serve to reinforce less-than-helpful behaviors. I have been guilty of falling victim to this negative reinforcement myself!

While these types of consulting are not mutually exclusive, I have found it most enjoyable to “pick a lane” for any point in time.  I mentioned how interim exec work worked best for me when not working on other things because of the schedule commitment. 

When doing project work, it’s actually OK to have multiple clients simultaneously. At one point earlier in retirement, I allowed myself to take on too many of these to the point where it was impacting my health and psyche again. I spent much of 2023 ramping down my overall activity levels across the board to basically nothing. It was actually good timing because we dealt with a number of close deaths with family and friends at the beginning of 2024, and clearing the decks before then gave me the opportunity to further reset. (I am actually writing this post in October 2024 from Los Angeles for a memorial service of another cherished friend.)

At this point in time, I am in the executive coaching lane. This may change in the future, but I am having a good time now.

To be more concrete on “how much”, I estimate I am probably working most weeks at between 10-25 percent capacity right now.  I am not currently putting out any vibes to the universe that I am seeking more “work” for now, largely because I decided I wanted the headspace to more intentionally take my retirement journey. This is where the Dolly Parton quote above comes in!

I hope this answers the question! If anyone else has questions for me to write about, don’t hesitate to put them in the chat!