“Stay Relevant, My Friends…” (B-Day Edition)

Bill Tobin
11 min readMay 14, 2017

I must admit that I am far from being the “Most Interesting Man in the World”, but one thing that I can claim is that I have been successfully navigating the vagaries of a 30-plus year career to date… Enclosed is some current thinking that I have been using myself in my journey (as well as with a few clients more recently).

A few weeks back, I started saying the new words that show up every year around this time: the age I am about to become on that next birthday. This year is no different; I am, as of today, 56. It took the first few times of saying it to get over the shock… 56, 56, 56…; holy crap, somehow I got old more quickly than I expected. I guess that this is the time of life when still being fairly immature can work in my favor. Earlier this week, I started thinking that perhaps I would count down towards zero instead and see how far I can get: welcome to the new 54 edition… Make sure that you remember this next year when I roll under to 53…

Anyway, back to the core of this post. You might think that the paragraph above is purely a self-indulgent (which it is) aside (which it is not): I am in the midst of my third career here in my mid-50s. Over that professional time arc, I think that I took a more structured design approach to staying relevant as I got older, my interests shifted and so did what the market valued. Why and how did I make those shifts? What were the considerations at each stage?

My first career as an engineer was almost serendipity. I had wanted to be a recording engineer since the 8th grade when Bowie released “Young Americans” in 1975. I was reading the liner notes one day when I saw that it was recorded at Sigma Sound Studios in Center City Philly; once I pressed my nose against the windows there and peered in, I was hooked. In junior year of high school, however, a few professors from nearby Drexel University came by one of my classes with various parts from a mainframe computer that they were working on there; a new possibility opened up: I could design the mixing boards that the sound engineers used rather than moving the knobs myself (this will become relevant again later in the story). I was able to abstract myself from my love of music with a more highly valued outcome: I would learn to take things apart AND put them back together. Magically, it could help alleviate the immense amounts of shit that I regularly received from my less-mechanically-minded father (who didn’t bother to take things apart) and my mother’s eight brothers (who all knew a trade and were able to build things almost from scratch) for my propensity toward taking things apart (toy cars, clocks, small electronics, etc.) and either not putting them back together at all or winding up with a few extra parts without a home when I did.

Upon graduating as an electrical engineer from Drexel with a few years of relevant coop experience, I chose to come to the Valley and join Intel from among the few dozen offers that I received. Over the next decade, I moved from Intel to Ampex, but still as a designer; I went from making chips to building digital audio and video systems with those same chips. The next few jobs built on the same base: RasterOps brought digital A/V to the desktop (ROPS helped enable the Avid film editing system and was became the model for critical parts of Apple’s QuickTime framework) and 3DO brought it to the consumer via a gaming system and a set top box (cable modems being the main surviving technology from those early STBs). As I joined 3DO, I noticed that the kids that we were hiring out of school were smarter, better trained, and were equipped with better tools than me: time to plan for my first transition.

So what is the framework that I use to approach these shifts? First comes passion: I am easily bored, so if I don’t have a meaningful connection to my work, I will be a short timer. I had a number of those sorts of jobs during college: parking lot manager, print delivery, fry cook at Burger King, maintenance at the exotic plant nursery; they all lasted 9 months at best. The jobs in the previous paragraph touched my love of computers, electronics, music, and movies. How was I to continue that path while pivoting to something different that would allow me to make room for those smart, well-trained designers that were coming available?

When I was still a lab-rat engineer, I would have been eternally happy spending the rest of my career geeking out with imaging cards and writing code, but it was around that time that the founder of RasterOps brought me out of the lab and introduced me to the OEM sales guy and the marketing folks: What? There are people out here? This was the first clue…

Second clue… Back before I joined 3DO, I spent a year part-time and then good part of the following year consulting instead of working for a company (after being fired from my previous job; another story for another time); I was doing fairly well and was making upwards of $15k per month (real money in 1992). The earlier introduction to sales and marketing coupled with having to deal with cash flow, billings, etc. in consulting helped me see the value of the business side of things. I used that as a trade when I set up a “Tour of Duty”-style compact upon agreeing to join 3DO: “I’ll give you my video and systems expertise for a year or two and then I’d like to make the transition to the commercial side or running a business; can we do that?” We both kept our sides of the bargain and I even stayed a year longer than I might have because my loyalty for their having kept the promise and for facilitating my transition from engineering to business. But even that journey was not so smooth nor as linear as a sentence might make it seem…

Joseph Campbell was the first person to encourage me (and the rest of the universe) to “follow my bliss”: “If you do follow your bliss you put yourself on a kind of track that has been there all the while, waiting for you, and the life that you ought to be living is the one you are living. Follow your bliss and don’t be afraid, and the universe will open doors for you where there were only walls.” I was fortunate to find his classic series of interviews with the PBS journalist Bill Moyers, the “Power of Myth”, in the in the late 80s and early 90s. But what happens if we only follow our bliss, our passion in life? Passion by itself (even with market demand) is pretty much a non-starter (even if you are able to hire someone to implement your good ideas), but who cares what you are interested in if you are not any good at it? Bottom line, passion is necessary, but not sufficient; we need it to fuel our motivation during the inevitable pressures of the marketplace.

Once I’ve settled in on a current area that I can be passionate about, the next vector to consider is skill. Just because I might be able to get a promise to be able to interview for a business position at 3DO, did I have any skills that would qualify me to attain or keep one of those positions? Right; I didn’t think so. Passion was not going to help me push through those walls when presented, but I did have 18- to 24-months to prepare. After some soul searching, speaking with others who made similar shifts, and interacting with our execs at 3DO and led me to see that finance and law were the largest gaps between me and commercial role. I got two great external finance mentors while also learning from his right hand man; I also developed a relationship with our general counsel, who taught me contracts while I was still working on MPEG video and the DVDs that we needed to deliver it. While I was far from fully commercial compliant, I understood enough about balance sheets, income statements and cash flow to be moderately literate; I also knew enough about contracts to know the high-impact variables that made a technology licensing deal attractive and profitable or a dog. Thus became a decade or so journey in the commercial realm: first as a licensing manager, then as a product manager, market and business development managers, CTO and CEO of various startups over the next 8 years before going back to consulting at PwC in 2001.

The last important vector to consider in this mix is market value. Being passionate and skillful is not enough: if the market does not currently value what you have to offer, you may simply be an artist waiting to be discovered. Nothing wrong with that (in fact, thank you very much), but do it as a skillful choice rather than being confused when people don’t accept your offer and rain dollars in your direction. Another thing to consider: you are not “selling out” if your artisan craft has commercial allure, only make sure that your values are being honored and your are being fairly compensated. As I’ve spoken to countless folks who are in the midst of evolving their evolutionary career arc, I’ve had the “artist” and “sell-out” conversations with the idealists many times.

BTW, I can’t claim that I have been perfect in these pursuits myself; there were times that I have had to trade off one of the “3 Overlapping Circles” (Passion, Skill and Market Value) during my career; usually my interests expand or migrate to new areas or the company that I happen to be working for or with do the same. Since I’ve been consulting over the past 15 years, this has happened much less (and even more-so since going independent in 2008); I am blessed with lot of choice in that my projects are shorter term and I am able to refer out those that don’t truly resonate with me (see the end of my Working a “Retired Lifestyle” post).

Recently, I was surprised when the “mercenary” (skill plus market value without the passion) conversation emerged with a new potential client; it is the first time that I have actually encouraged someone to follow that route… He is a fairly senior executive at a company being acquired by a larger rival, has two middle-schoolers at home, a wife that cares for those kids and a long, stressful commute. In his early 40s, he’d love to follow his emerging desire to do more in the community… I recommended that he continue to bank as much excess cash as he can through the merger process, see if he gets a package (to leave OR stay) and, if he doesn’t, to decide whether to trade off the commute for a bit less cash taking a job more in his own backyard. He can serve the passion side now by working with local non-profits in low intensity (time-wise), but high impact projects, something that he has already started to explore. Again, actively trading the influence of the 3 Circles by design rather than happenstance can lead to greater satisfaction in all areas of your life.

My second major career transition happened in my early 40s after serving a variety of roles in startups (designer, product manager, CTO, CEO) when I realized that my risk profile had changed post the dot com bust: I had two kids who I needed to put through high-school and college and my retirement was in a bit of a shambles… The bigger issue by far was that I was deathly afraid of being disposable by the time I turned 50; I had started to see people half a generation older falling by the wayside and settling for jobs that were way less attractive (and lucrative) then the careers they had spent decades laboring over. I’ll save that journey story for another post, but needless to say, I had a six-month black cloud over me as I went through a long stretch of existential despair about my working future. I found this period pretty painful, but it definitely solidified my practice of planning to stay relevant over the next few decades.

The approach is inexact and always needs to be risk-adjusted for the VUCA (volatile, uncertain, complex, ambiguous) would that we live in… Questions to consider start with:

  1. Where is the market headed? Not like, tomorrow, but in the next five to ten years; we need to follow the advice that “The Great One”, Wayne Gretzky, gave us years ago: “Skate to where the puck is going to be, not where it has been.” When we have a sense of where the market will open up and other places where opportunities might shut down, we can test our theories with others: what do investors, technologists and other players in the ecosystem have to say about our visions for the future?
  2. Next we have to consider where we fit into the new marketplace and our highest and best use in that evolving market. What do we care about and how might our style, experiences and preferred ways of working play to our competitive advantage?
  3. Once we have some sense of where the puck is headed and how we might fit into, new questions emerge: What skills do I need to have to make valuable offers in that new world? Which ones do I have? Do they need sharpening? What gaps do I have? Which are highest impact (translates to value later) areas to focus on? Where can I get trained and/or mentored with those that have gone before me, intern at places that are beginning to deploy in these new areas? Where can I partner up with others that have the skills where my gaps are too large?

After we consider all of these factors, we can work multiple paths in parallel: we continue to monitor our assumptions about how the market development will roll out and check the signals that confirm our speculations on how things will play out. Secondly, we can begin to acquire the skills we need for that new future and start hanging out with folks who can be force multipliers in those domains. Lastly, we can be looking for places to practice in advance of making a move: where can we become advisors, board members, consultants, etc. to practice our new skills while we keep our current roles?

With the advent of autonomous vehicles (drones and driverless cars, trucks, etc.), artificial intelligence, machine learning, breakthrough medical advances and other emerging technologies, the design practices that have enabled me to viably enter the third third of my career might be even more important and useful for those early in their early careers and the others that are still preparing to enter the job market in the coming years.

As is my custom, I’ll now turn it over to you:

  • What insights or learning show up for you? How have you approached your career path to date? What might you differently going forward?
  • What Qs do you have? What would you like to hear more about?
  • What new or different actions will you take tomorrow?

Bye for now…

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