Personal Inflection Points: Shift the Trajectory

Bill Tobin, Faculty

When I was growing up on the East Coast in South Philadelphia, people around me had “jobs,” not “careers.” Most workers were men and had blue-collar manual labor or service jobs. My own path ended up being quite different.

My father was a longshoreman (as was his father and uncles on his side): a dock worker who started out loading and unloading ships from ports around the globe and who retired fifty years later as a logistics manager directing container traffic for the port. My mother’s eight brothers also worked the docks or drove trucks, but they also each had a building trade.

I was introduced to engineering when a few professors brought computer parts to one of our high school guidance classes. I was immediately hooked: Not only could I take things apart, but I could learn to put them back together! As an undergrad at Drexel University I was not much for theory, but I thrived in the labs where I could build things and make them usefully work. After graduation I was recruited to Intel just as the x86 architecture was catching on.

I was not satisfied just to be the first in my family to graduate from college, so I continued to study at Stanford while working full-time. I dropped out of my master’s program a few years later when my second child was born and I was on my second digital video startup company; there were no classes to help me with the things we were inventing, even if I had the time. I made some money and lost some money in the five startups I was involved in during the 1990s (two went public, and one was bought by Sun Microsystems); I now work with investment teams and those at their portfolio companies in more of a “fund-of-funds” model, rather than the serial basis of my earlier years.

My own career path is definitely not a straight line, reflecting the fact that today’s world is much different. People now have the luxury of thinking about purpose and passions; at the same time, workers of all types also compete more heavily in a global market. In order to succeed in the long run, we are better served by bringing innovation and design to how we approach our invaluable careers. In my early years I did not have the advantage of a structure or blueprint for how to approach career planning—I hope that readers will benefit from what I have learned in my own voyage traversing almost three decades.

Characters Welcome (And Expected…)

USA Network uses the “Characters Welcome” slogan as their tagline to distinguish their lineage of strong, relatable, unique characters in their original programming (“Monk,” Michael and Fiona in “Burn Notice,” Shawn and Gus in “Psych”); these “characters” have unusual personalities and behave in distinctive or interesting ways. In the Kauffman Fellows Program (KFP), we use the recruiting and selection process similarly to unearth exceptional candidates for each new class of Fellows.

We look for entrepreneurial spirits with deep domain expertise, leadership potential, and an appetite for risk, ambiguity, and the unstructured environments that the innovation ecosystem requires. Those are just table stakes, however, as integrity, humility, empathy, service orientation, and a sense of gratitude are all emotional components that distinguish outstanding finalists from the pool of extremely capable nominees.

Once the program begins, we focus on both the industry mechanics (“what” we do: diligence, term sheets, fiduciary responsibility, etc.) and the leadership skills (“how” we do it: style, emotional intelligence, personal brand, etc.) to differentiate Fellows in the increasingly aggressive and unforgiving global market. This approach increases awareness and enhances empathy, leading to greater trust and influence. The focus on “how” in addition to “what” gives our Fellows the ability to “perform in the storm.”

“Character” development is a central mission of the KFP: the building of a Fellow’s capacity to effectively respond. As we support increased response-ability, or the Fellow’s ability to choose her response,1 the original “character” authentically remains and is enriched and refined over time. This behavioral fitness and agility should lead to more successful collaborations and better overall returns in the long run, through “out-behaving” the competition.

Using my own experience and the Kauffman Fellows Program as examples, in this article I examine how a person’s distinctive “character” might play out over time, and in particular, how to design a career and make that design a reality.

Career as Journey

When I started my product development career in the early 1980s, I thought that my future work would still have me tinkering in the lab. My original view was more of a fixed destination (similar job, only bigger and better) rather than the journey that it became—I certainly never imagined that thirty years later I would be on my third career. In my first startup, though, one of founders took me under his wing; through his introductions to the marketing team and the OEM2 salesperson, I discovered the business side of running a company.

In order to successfully transition my career (not once, but twice), I had to shift my worldview from the deterministic, fixed outlook of being a lifelong product designer to a more open, learning mindset (for more, see Carol Dweck’s MindSet3). My “frame of mind” and how I looked at the world informed and shifted my “state of mind” and what I “saw” was possible.

My first transition from product development to IP licensing was a big risk in my early 30s, as I was a capable designer with a solid history; I still remember the sound of the door closing behind me as I left my data books in the lab. The company also took a chance, gambling that my transition to business as a licensing manager would be successful. It paid off for both of us, and the experience I gained in that position coupled with the development of skills to process my human experience allowed me to shift careers again a decade later.

Once on the business side, I adapted and grew over many roles, from licensing to product manage ment and then to CTO and CEO executive roles. I was always learning (not unlike constantly absorbing multitudes of new, cutting-edge technologies as an engineer) and I strive to continue that practice today. I noticed that more opportunities opened up when I did not have a fixed idea of how best to create and add value.

After participating in the founding and growth of five startups, I took my next career leap and traded my serial executive role for my current role as a team-development specialist with a portfolio of consulting and investment clients. Twenty years of product development and direct business management provided the foundation for the past fifteen years of helping others develop their business cultures and more effectively manage the human dynamic in the workplace.

These experiences and transitions taught me that while I started with my base “character,” I needed to have an open mind as I engaged the journey that is my career. As faculty and mentor to Kauffman Fellows, I focus on helping others take a more proactive approach to developing their career plan and executing upon that plan. In the next section, I consider how to project oneself forward to explore how we can participate in a future that has not yet emerged.

Inflection Points

In geometry and calculus, an inflection point is the position on a curve that begins a significant positive (or negative) run; in business, inflection points are infrequent events that result in a significant change in the current developmental course of a person, company, or even an industry. Andy Grove, Intel’s cofounder, described a strategic inflection point as “an event that changes the way we think and act.”4 The competitive marketplace and a person’s place in it are dynamic and constantly evolving. In the midst of dramatic change and upheaval, one cannot always distinguish the actual turning points that delineate the “new normal.”

The second half of the 20th century was dominated by technological innovation; business-model innovation emerged only in the late 1990s but has led the way since then. Culture—the human operating system—is composed of the standard practices that reflect “what people do when no one else is looking.” Going forward, cultural innovation will be a competitive advantage and will distinguish the leaders, companies, and markets that thrive and flourish.

Some of the market evolutions that I have participated in were the move from analog audio-video systems to all-digital ones (doing that in professional film and broadcast applications before bringing that revolution to the desktop and then consumer markets) and the move from client-server computing to early internet-based web businesses in digital printing. Likewise, I had to map personal inflection points alongside my professional ones.

During my transition from product development to business, I found myself on my second child and second startup; my life (and my time) had to be reconfigured. Classes on engineering gave way to a more eclectic mix of finance, law, and leadership sessions. If I had not had the explicit agreement of the executive team and pre-developed customer skills, I might still be drifting along on my previous engineering career trajectory. Instead, the trades that I made allowed me to take on P&L responsibility and start new businesses. A decade later, I parlayed my earlier leadership training and consulting experience into a new trajectory doing individual and team coaching.

The foundation for realizing the life you want is to notice, create, and seize coming market and personal inflection points—instead of waiting for them to happen to you. Investing in career design is an important component in inventing a future that needs you.


Matt Mochary, Class 2
Author, “Jumping into the River,” Kauffman Fellows Report 2 (2011): 60–66.

The biggest inflection point of my career likely occurred when I “gave up.” I was a new Kauffman Fellow at Spectrum Equity Investors. I didn’t have a single day of experience in the industry, and I was surrounded by four other Associates, all of whom had several years under their belt with top-notch investment firms. They seemed to know exactly how to source deals and were doing it every day. I, on the other hand, didn’t have a clue and no one was teaching me.

So, eventually, I gave up. I told myself: If I can’t find a deal, at least I can make myself useful in some way to the senior partner who hired me, Brion Applegate. But the only thing that I could think of to do was get him coffee. Literally—I did it every day.

A year later, Brion signed a term sheet for the largest deal the firm had ever done by a factor of five. He needed a lackey to accompany him on the deal. Of all the Associates, he had had the most contact with me, from the daily exchange of a coffee cup and a hello. He told me to join him. A few weeks into the process, once the terms were baked, he tired of the execution minutia and asked me to “finish” the deal, a $1.2 billion buyout. I did, and was made Partner a year later.

From this I learned that “being in the room” is the most important thing I can do; what I do in that room matters little. Getting the coffee is a worthy task. Because in that room is where the information flows, the decisions are made, and the most important relationships are built.

Matt runs Mochary Capital, his family office, as well as the Mochary Foundation, which trains ex-convicts to get and keep jobs. He was formerly the CEO of Fortune Data Center Development Group, the Cofounder and Chairman of Totality (now Verizon Business), and a Partner at Spectrum Equity Investors. He co-directed Favela Rising, a feature-length documentary that won the Tribeca Film Festival. He holds a BA from Yale and an MBA from Northwestern Kellogg.


Design Versus Drift

All three of my careers required deliberate forethought, planning, preparation, and execution.5 It is extremely unlikely that I would be where I am today if I had merely gone with the flow of the marketplace. In the 1950s, choosing to follow market drift was much like floating down a lazy summer stream on a raft while holding a cocktail. These days, it is more like riding the Class IV rapids resulting from the melting snowpack above the Yosemite Valley—I definitely want my life jacket and helmet firmly in place.

Russell Redenbaugh from Kairos Capital was a valuable teacher for me back in the early 1990s; he taught the concept of “reading the world”6 to anticipate and effectively deal with the rapidly changing marketplace. Reading the world involved paying attention to the “weak signals”—rather than just the loud noises made in the mainstream. By listening to and integrating what may today seem like marginal practices, leaders can participate and help shape what will be core in the coming future.

Using what Russell referred to as “Forces at Work,”7 attending to nacent emerging trends can help us as leaders create criteria to assess and filter the overload of information we receive every day, and inform an active decision about where to focus our limited attention span. These forces create dramatic market-made changes that act upon us as business leaders rather than those that we get a say in; as the market’s volumes, complexities, and velocities have increased, so has its global footprint—leaving behind those whose choices left them obsolete and dispensable, victims of the drift.

Taking this more active role allows us as leaders to become the designers of our futures, not only for maximum impact and satisfaction, but also to be able to continuously adapt to new situations. Career inflection points can be deliberately created (as I did when I shifted my focus from product to business to human capital, and as Fellows do as they traverse their careers)—by preparing and executing only those actions that will directly impact your career trajectory. These key actions include the sequencing, progression, and development of skills and abilities as well as the offers you can make (and that others will accept) in the markets you have chosen.


Keith Lenden, Class 16

In 2007, I was two years into building and running a Series A startup biotech company in a jack-of-all-trades business development job reporting to the CEO. It was the job I had always dreamed about…and I was miserable.

With the guidance of a professional coach, I identified two themes that explained my feelings. First, the extrinsic measures of my success (title, status, wealth) which had led me to that role were out of sync with the intrinsic measures (professional creativity, balance) I had come to value more and more over time. Second, while the CEO and I had worked together famously at first, recent challenges had uncovered major differences in our values. With the help of my coach, I shared how I was feeling and offered suggestions on how we could improve our relationship. He fired me three months later.

This was a pretty traumatic experience. There I was being vulnerable and trying to make things better, and this was how I got rewarded—what gives? Honestly, though, looking back I now realize that was the point when I stopped making choices based on how others would view me and started focusing on how I would feel about myself. Six years later, I have since started two biotech companies (Receptos and Abide Therapeutics). Currently, I am building a new investment platform to address the capital efficiency and incentive alignment challenges faced by all biotech entrepreneurs and investors, an idea that started as my KFP field project. Who knows what’s next.

Keith is a cofounder of FallLine BioVentures, a strategically focused and financed, early-stage, novel biotechnology product funding and development platform. He has cofounded two biotech companies and was previously VP of Product and Business Development at Maxygen and head of business development at Genteric and Acologix. Keith started his career in biotechnology at LEK Consulting. He earned an MBA from UC Berkeley and engineering degrees from Dartmouth College.


Frameworks and Criteria for Design

There are several different frameworks to consider when building out a “going forward” career design. In that process, one must also consider the time horizons required to develop the expertise that the market will value in the future (à la Wayne Gretzky’s “skating to where the puck will be…”8).

First, consider what motivates people. Dan Pink’s book Drive9 outlines what he calls “Motivation 3.0” (1.0 being “mere survival,” and 2.0 being the old “carrot and stick”). He asserts (and I agree) that people today are looking for more than just extrinsic, material rewards; people will expend more daily discretionary effort in the pursuit of intrinsic motivations such as a meaningful purpose, masterful skill development, and choice in the execution of their work. Zappos CEO Tony Hsieh called this “a path to purpose, passion and profits.”10

Being motivated begins with having a calling that is larger than oneself: each person’s work should matter and make a difference in the world.11 It is useful to ask, “What causes resonate for me? Do they compel me to act?” Beyond the present and near-term future, consider the legacy you aspire to leave behind. Non-profits are a great place to practice before fully committing; they are always short on resources and can test a person’s new skills in development.

Mastery is where challenge meets skill: a person’s work must be compelling, but not impossible; one may always make progress over time, but will never reach perfection. If a person aims too low, boredom quickly sets in, but if what one must do is greater than what one can do, it creates anxiety.12 When as business leaders we consider this aspect, we must go beyond what we enjoy doing, are good at, or even excel at—and consider what we are uniquely qualified to deliver to the market.

Lastly, autonomy is about choice: as a business leader, what environment are you playing in? Can you choose your teams, task, the time you do it, and technique for getting it done?

Pink calls the resulting passion, engagement, and “flow” states provided by this trio (motivation, mastery, and autonomy) the “Oxygen of the Soul.”13 How do we leverage a person’s existing skills and future learnings to ignite these passions? What is the “highest point of contribution”—where an individual’s passion meets their talent and at the same time fills a clear market need (see Greg McKeown’s “The Disciplined Pursuit of Less”14)?

Next, evaluate the time horizons needed to develop excellence in the chosen career. Popularized by Malcolm Gladwell in his book, Outliers: The Story of Success,15 the “10,000-Hour Rule” was based on a study by Anders Ericsson16 which finds that greatness requires enormous time investments and that expert performers acquire superior execution through extended deliberate practice: focused, high concentration practice beyond the person’s normal comfort zone.

Gladwell uses examples of the Beatles’ musical talents being honed in the basements of Hamburg and Bill Gates’s computer savvy starting with real-time programming on a time-shared computer in the eighth grade; medicine, music, chess, and sports all can provide similar examples of the development of such virtuosity and expertise. According to his theory, individuals must find something they genuinely enjoy doing and have some skill at, and that the market has a need for; as they keep learning by consistently investing time and practice, a decade later some advanced-level expertise will emerge.

ccording to Jim Kouzes, the co-author of The Leadership Challenge,17 their research on 1.3 million leaders around the world for over thirty years18 indicates that humans assess themselves as “good” at something after five years and truly feel “competent” after ten years—somewhat consistent with the 10,000 hours identified by Gladwell. In my own history, my college co-op experience allowed me to hit the ground running as a designer when I graduated; I had similar ramp-up periods on the business and consulting sides, where I kept my “day job” while practicing and volunteering my new and developing abilities.

Once a leader has considered what inspires and stimulates her and has ideas about how the future may unfold, it is time to design her roadmap and define the interim steps necessary on the way from novice to journeyman to expert. Put another way, those of us who have followed this path now know what energizes us and what we are pursuing, and it is time to think about the best way forward.

Development Timelines and Planning

When approaching development and career planning, there are several things to consider. First, where do you want to be later in your career? How far out can you see? The further the better—not to set a destination per se, but to set a course and a trajectory. Each person is likely to adjust and change that destination as they learn and gain experience, and as market demands and opportunities shift. Looking two or three decades out is great (though most people cannot), but even a ten-year horizon is better than simply floating along with the drift of the market.

After looking out as far as possible, work that vision back to the present. Your vision for the ten-years-out point can be telescoped back to a five-year scenario, then two years, and then a single year. Once you envision how your future will emerge over time, turn to planning: What needs to be done today, next quarter, and over the next year to prepare and practice for what lies ahead five and ten years from now? Focusing efforts in a concentrated fashion will help move those plans along to fruition.

My last transition into consulting and coaching was approached from this perspective; at forty, I looked at what might be possible for a shift by age fifty. I determined what skills, abilities, and experiences I would need to be able to make a difference in an executive’s and her team’s effectiveness while also making a good wage. I then was able to work my way back to what classes and pro bono consulting work I should focus on initially, build upon a few years out, and on forward. In less than three years—a third of the way through the execution of my plan—I was recruited into the PwC consulting practice from my business development role. I have spent the time since then continuing to execute the plan (on the development side) while continuing to build my practice at Strayer.

In the Program, Fellows create development plans over the two-year fellowship with guidance from their mentors and program coaches. A one-year snapshot (broken out by quarters) looks at what the Fellow wants and needs to learn, what activities and tasks need to be addressed, what network(s) need to be developed, and what support structures are needed to make these things happen. Goals, objectives, actions, metrics (a defined way—not necessarily numerical—to know if the Fellow has achieved a certain objective), and timelines are all considered and designed as part of a larger picture of where the Fellow is headed in the medium- to longer-term of their career.

With the longer view that this process affords, it is possible to consider priorities and the sequence for learning, to build scenarios for moving forward, and to use the framework to assess progress and make decisions on how to proceed in the future. Revisiting these plans quarterly and revising them at least yearly establishes a cadence for ongoing success.

For you as a business leader, the key here is to determine your own personal values, how they are authentically reflected through the prism of your character, and how they are then aligned with your role, your partners, the market you play in, and the ecosystem that affords you greater freedom to operate.

Field Project: Shift the Trajectory

Going forward at Kauffman Fellows, we have shifted to a “project-centric” approach to the program. Field project ideas are explored with potential Fellows beginning with the selection process—we are still screening for “characters,” but we want to interact around “what you would create” given the opportunity. The project is something that you “get to do” instead of something you “have to do”; we want Fellows to wake up in the morning looking forward to contributing what they can each day.

In the midst of the first KFP module, we ask the new Fellows to articulate their vision or ambition for being in the program along with their goals and what would be enabled via accomplishment of those goals. They visualize a rough sketch of what they aim to create while in the program, along with the bigger picture of where they are headed. Their project then can encapsulate the formation of their inflection point and create the foundation for others in the future, deliberately shifting an already well-established trajectory.

One of the central tenets of KFP is that of acceleration: through structured exposure to essential venture mechanics, best practices, and networks, a Fellow can compress what normally would be a three- to five-year initiation process into two years. Having field project goals, milestones, objectives, and actions as part of ongoing development plans reminds Fellows to work on their project daily, compiling hundreds if not more than a thousand hours over the two years. The keys to that execution and accumulation are alignment and focus.

When building a brand, a company’s leaders consider how to differentiate their brand from others in the marketplace; we inspire our Fellows with similar questions like the following. What is your competitive edge and how are you perceived in the marketplace? What are you uniquely qualified to do? A holistic approach to brand design includes who you are, what you value, what skills and experience you have, how you present yourself, and where you do all that. We consider those same components when evaluating our field projects, to ensure that each Fellow has good alignment with who he is. To continue that alignment, his choice of emerging investment topic should also be of interest to other Fellows as well as to his firm and other firms, and should be for the benefit of the society and the wider investment ecosystem. This alignment will keep a Fellow’s passion lit through the tough spots as well as creating support for the research process.

The beauty of articulating a research thesis in orientation and then working on it daily is that the field project goal (along with the other items in the Fellow’s development plan) provides a set of criteria to make strategic decisions on where to allocate and spend time. This “One Decision that Makes 1,000”19 provides incredible focus and the ability to steadily make progress from beginning virtuosity in the chosen arena. Sticking to those criteria and decisions supports the outstanding “characters” who begin the Kauffman Fellows Program to develop and move their careers forward more quickly.

Based on the ideas presented in this article, the program has been re-architected to include design thinking along with ongoing cohort discussions and clinics. New Fellows will develop, evolve, and refine their projects and how they pitch them in the spirit of experimentation (“Fail Fast, Succeed Faster”20) that has been a hallmark of the program. Taking a cross-functional approach and taking their ideas to implementation will help them develop their own process of innovation. In this, we see ourselves on the cutting edge of this question: How can each of us simultaneously access and contribute to society’s insights, opportunities, and resources?

The field project can be a seminal event in our Fellows’ early investment careers and a significant brand-building experience. Their unique storytelling will set the stage for what offers they are making to the market, who they want to work with, and why.

Going Forward

The opening premise of this article was to provoke how we as business leaders think about our careers and suggest using design to help us include our passions and purpose toward greater satisfaction and fulfillment in life. Having explored how one man’s journey might allow others to build their own maps and models to do the same, I look forward to future issues of the Kauffman Fellows Report where I can read other Fellows’ accounts of how their field projects created career inflection points and what opportunities resulted.

Bill TobinBill Tobin

Bill is a partner at the Strayer Consulting Group, an organization development firm specializing in building strong teams. SCG has worked with hundreds of startups and has been an advisor to dozens of venture groups. At CVE, Bill oversees the Kauffman Fellows’ curriculum, assuring that their experience in each module is challenging and grounded in the realities of the venture industry. Bill brings 25 years of consulting and executive experience to his work, including the founding of multiple startups as an executive and board member. He has an engineering degree from Drexel University and has completed post-graduate studies at Stanford and the University of California. He is active in a variety of organizations that support early-stage entrepreneurs.


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2 Covey, Stephen R., The Seven Habits of Highly Effective People: Powerful Lessons in Personal Change (New York: Free Press, 2004).

3 Original equipment manufacturer.

4 Dweck, Carol, MindSet: The New Psychology of Success (New York: Random House, 2006),.

5 Recep Ozdag, “ONS Recap: ‘Changing the Way We Think and Act,’Wired Ethernet, 18 April 2013, para. 1.

6 For more detail, read my blog, Worst Kept Secrets.

7 The four forces he cited were the rising importance of technology, the spread of democracy, changing global demographics, and regulatory and other political policy changes (see Russell Redenbaugh’s blog, Reading the World.

8 Natalia Davis and Russell Redenbaugh, “Value: Know It, See It, Design For It,” interview at the IIT Institute of Design’s Strategy Conference, May 2006, Chicago

9 This quote is commonly attributed to Gretzky and seems to originate from advice from his father, to “skate where the puck’s going, not where it’s been,” according to Roy MacGregor, “Fortune Smiled Upon Us,” in Total Gretzky: The Magic, The Legend, The Numbers, ed. Steve Dryden (Toronto: McClelland & Stewart, 1999), p. 19.

10 Daniel H. Pink, Drive: The Surprising Truth about What Motivates Us (New York: Riverhead Books, 2009). Find it on Amazon.

11 Tony Hsieh, Delivering Happiness: A Path to Profits, Passion, and Purpose (New York: Hachette Book Group, 2010).

12 See Greg McKeown, “What Will You Create to Make the World Awesome?,” Harvard Business Review Blog Network, 26 March 2013.

13 This is where a manager or coach can be of help: to notice and help you adapt to your skill level, enhance performance, identify gaps, and provide techniques to steer clear of tedium or apprehension.

14 His words borrow from the quote, “Freedom is the oxygen of the soul,” which is popularly attributed to Moshe Dayan (e.g., BrainyQuote.com).

15 Greg McKeown, “The Disciplined Pursuit of Less,” Harvard Business Review Blog Network, 8 August 2012.

16 Malcolm Gladwell, Outliers: The Story of Success (New York: Little, Brown, 2008). Find it on Amazon.

17 Anders K. Ericsson, Michael J. Prietula, and Edward T. Cokely, “The Making of an Expert,” Harvard Business Review (July–August 2007).

18 James M. Kouzes and Barry Z. Posner, The Leadership Challenge (4th ed., San Francisco: Wiley & Sons, 2007), Find it on Amazon.

19 Jim Kouzes and Barry Posner, “Our Authors’ Research,” available from The Leadership Challenge website, para. 1.

20 Greg McKeown, “The One Decision that Makes 1,000,” (blog post, 4 October 2012). Originally published as “If I Read One More Platitude-Filled Mission Statement, I’ll Scream,” Harvard Business Review Blog Network, 4 October 2012.

21 Anders Melin, “Fail Fast, Succeed Faster,” Forbes, 16 October 2012.

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KFR Volume 5 Cover