8 Passages for Uncertain Career Journeys

CPAD JournalMy friend and former career adviser Helen Harkness was asked to edit a special edition of a journal for career development professionals in 2010. She invited me to submit an article/essay, which was accepted. The theme of the special edition was Mid Life Career Crisis: How chaos theory and positive psychology can help.

The edition was published and distributed in February 2011, although the cover unfortunately and mistakenly notes “Spring 2010.” I also was displeased with the production formatting of my article, “Passages for Uncertain Career Journeys,” in that the production editor suppressed most of my paragraph breaks. Therefore I’ve converted the text to HTML with my intended formatting, shown below.

I sat back in my chair, content with yet another recitation of my life’s achievements. Looking across the desk and out the window, past the placement specialist who specialized in placing ex-military junior officers at leading corporations, I hoped this would be the last of these interviews. I gazed across the nondescript suburban office complex toward downtown Houston. Was this the landscape of my future?

“So let me get this straight.” Glancing up from his notes, the specialist brought me back to the present.

“You didn’t really know what you wanted to do coming out of high school. You went to the Air Force Academy because it was the best college offer you got, not because you really wanted to go there. You didn’t know what you wanted to study, so you majored in Humanities because you made better grades in those courses. Your eyes were too bad for pilot training, so after graduation you went to navigator training because you were told that was your best opportunity. You gave up a graduate school slot because you decided to get out of the Air Force, and now you’re looking for a civilian job. But you can’t really say what you want to do.”

“Other than,” he glared at me as though I were a defendant under cross-examination, “you’re just looking for ‘the best opportunity available.’ Did I get that right, Mr. Stockdale?”

I didn’t appreciate it at the time, but I had entered the turbulent waters of my first uncharted career passage. I had left a secure, predictable, but unfulfilling work life where my responsibilities were simply to follow orders. I didn’t know where I wanted to go or what I wanted to do. I just wanted to find an employer who wanted me. Then I’d prove myself and adjust, just as I had adapted to life at the Air Force Academy and in the Air Force. And that’s what I did, for awhile.

Two months after that interview in 1982, I got a job in program management at a defense electronics company in the Dallas area. After seventeen years (which included a divorce, midlife crisis, and multiple attempts to find another job), the company moved our business unit out of state. Rather than relocate, I accepted a severance package. Six months later, I found a similar job with another defense electronics company. I lasted a year before I remembered how much I didn’t enjoy that kind of work. Then I attempted to begin an Internet venture; three months later I admitted failure. For the next two years I worked part-time for a nonprofit organization while I tried and failed to develop a consulting business. Then I became the full-time chief executive of the nonprofit and felt, finally, that I had found my place, my career home. Four years later I resigned when it became apparent that the trustees did not share my vision for the organization. I taught one course as an adjunct professor at a private university. For a year I produced virtually no income. I moved to Santa Fe to fall back, re-group, and start over. Two years later, I’m still re-grouping while enrolled in an Educational Psychology graduate program. I’m doing what I want to do.

My ‘expertise’ is obviously not in realizing a successful career. I have, however, survived a series of career passages that, of course, are unique to me. But it’s possible that some of my experiences and learned lessons can serve to instruct, motivate and even inspire some of your clients. Therefore I offer these eight passages that have helped me navigate my own career journeys — from my own self-exploration and discoveries, to the potentially paralyzing fears and anxieties of the unknown, to the zigs and zags of good and bad decisions, and through the unexpected and unpredictable circumstances that have brought me to my current, self-selected, present position.

Passage 1

I lived with the terrible knowledge that one day I would be an old man, still waiting for my real life to start. — Pat Conroy (1)

Before your clients come to you, they’ve probably already experienced some kind of triggering event or catalyzing moment, possibly resulting from factors that have been accumulating over time. My moment came when I read this passage from Pat Conroy’s novel, The Prince of Tides. Conroy, through his fictional character, expressed an inner feeling that had resided in me for several years, but I didn’t have the courage, awareness or vocabulary to articulate it myself. For almost twenty years, this statement has served as a touchstone for me to measure my progress against, as well as a consistent source of motivation and encouragement for me to live my real life.

Of course, this specific quote may not mean much to your clients. They may have different quotes, anecdotes or experiences that serve a similar purpose for them. If so, encourage them to keep those memories handy. And if any of your clients have not verbalized that trigger or event, ask them to articulate it in whatever way they’ll find most meaningful. Because at some point during their own explorations into uncertainty, they’ll need to remember why they chose to embark on this journey, and why they don’t want to turn back.

Passage 2

The self explorer, whether he wants to or not, becomes an explorer of everything else. — Elias Canetti (2)

Like me, your clients may have difficulty in answering the question, “What do you want to do?” Of course, if they can admit that to you (and themselves), then they’ve already taken the first step in acknowledging that they need to undertake a process of internal examination, exploration, and discovery.

Psychological assessments and inventories can provide indispensable insights to individuals seeking to better understand themselves. I considered myself to be more self-aware and introspective than most. But I realized how much more of my “self” I needed to explore when I became familiar with instruments such as the Strong-Campbell Interest Inventory, the California Psychological Inventory, the Myers-Briggs Type Indicator, the 16PF Development Profile, and the Holland codes indicated by the Self-Directed Search. Integrating the results of these tools with my own life experiences, I gained insight and understanding that I don’t believe would’ve been possible otherwise.

For example, my Myers-Briggs results highlighted two items that I found immediately relevant and helpful. My type (E/INTJ) indicated that I did not exhibit a clear preference on the Extraversion-Introversion scale. This ambiguity can result in internal tensions in terms of whether or not I want to work alone or with other people; how willing I am to assert myself in a leadership role; and how willing I am to socialize, network, develop contacts, etc. I also understood how my type results define the boundaries of my temperament preferences, or “comfort zone.” I realized that my strong preferences toward the iNtuitive, Thinking, and Judging scales revealed potential deficiencies on the other ends of the scales. In other words, to expand my “comfort zone” with a strong iNtuitive preference, I could benefit by paying more attention to the cold hard Sensing facts of a situation; with a strong Judging preference, I needed to exercise more Perceiving spontaneity.

I think it’s important for clients to understand three things regarding their strengths as indicated by assessment instruments. First, clients need to build on their strengths; these are what most differentiate them from others and most likely feed into their interests, motivations, etc. Second, clients should not take their own strengths and natural abilities for granted; just because something comes easy to them, they should not assume that “it’s no big deal, everybody does that — don’t they?” Third, the cautionary adage about “too much of a good thing” holds true in terms of strengths; they can lead to problems, especially with respect to very strong Myers-Briggs preferences.

The results from these types of instruments may strengthen your clients’ sense of self-awareness, motivations, and expectations. These instruments can also, within limits, help clients gain understanding and appreciation for others in terms of similarities shared, or differences evidenced. So as clients utilize these instruments to explore themselves, they may also find them useful in exploring their relationships with others.

Passage 3

By midlife, most of us are accomplished fugitives from ourselves. — John Gardner (3)

One of the possible outcomes of self-exploration resulting from career uncertainties is the realization that a sizeable gap may exist between one’s long-held self-perceptions, and what one discovers from these explorations. “Where did the old me go? How did I end up here? Who am I really?” As part of the career development process, your clients will each have to reconcile this gap; what do I want to be true, and what will I have to do to make it so?

This gap between self-perception and reality is lyrically reflected by John, bar friend to Billy Joel’s “Piano Man”: Well I’m sure that I could be a movie star, if I could get out of this place. John cannot make his self-perception (movie star) become true because he can’t, or won’t, initiate the prerequisite (to get out of this place). Like Marlon Brando’s Terry in On the Waterfront (“I coulda been a contender”), Joel’s John has made himself a fugitive from his hopes, dreams, and possibly needs.

Sometimes we simply choose to say “no” to opportunities to escape this place. I said “no” twice.

From the day I graduated from the Air Force Academy and entered active duty, I wanted to return to the Academy and teach. I applied for a program in which the Air Force would send me to graduate school in preparation for a faculty position. I was accepted into the program, but I had to wait three years until my graduate school slot opened. Rather than wait, I decided to resign my commission when my duty commitment was over, which led me to that placement specialist’s office in Houston.

While working for a defense contractor in 1987, I was offered my dream job — a position I had lobbied top management to create in then-West Germany. But I turned it down because my wife wouldn’t consider moving. That, on top of other previous issues, resulted in a steady deterioration of my marriage, uncertainty and dissatisfaction with my employer, and a full-blown, no holds barred mid-life crisis. After three years of therapy, I had to accept that the marriage could not be maintained and I initiated a divorce.

Your clients would do well to realize that their occupational conflicts are inseparably interrelated with other realms of their lives such as marriage, family, friends, and social involvements. It’s difficult to compartmentalize career concerns without affecting or being influenced by other aspects of one’s life. If clients aren’t consciously aware of their own attitudes, behaviors, and relationships — across all aspects of their lives — the gap between self-perception and reality may grow; they may find they are fugitives from themselves in more than one respect.

Passage 4

The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man. — George Bernard Shaw (4)

Whose sets of expectations are your clients trying to fulfill — theirs, or someone else’s? It’s become a theatrical cliché, and predictable plot conflict, to portray a doting parent trying to re-live past glories or live unrealized dreams through a child. Or the parents who expect to feed their own egos through the accomplishments of “my daughter, the doctor.” For a variety of reasons and circumstances, some children grow up with a desire to please their parents, or accept without question that they should follow in a parent’s footsteps.

A few years ago, I participated in a Career Day activity at a high school near Dallas. My assignment was to conduct mock hiring interviews to give the soon-to-graduate seniors an opportunity to practice their interviewing skills. I remember one young man whose résumé was filled with references to band, drama club, and several service organizations. I was surprised when he informed me of his college plans to major in accounting. Nothing on his résumé mentioned accounting, math, or business — all of his interests and accomplishments related to creative, social, or service activities. I asked him about his interest in accounting and he replied, “Well, my dad’s an accountant so I thought it would be good for me, too.” I asked him about his other interests — music, drama, his volunteering experiences. He explained, matter-of-factly, that he did enjoy all those things, but he didn’t see how he could make a living at them. On the other hand, he expected he could make a living as an accountant.

That’s a responsible, practical attitude for a high school senior. That’s conventional wisdom. That’s playing to the script, dancing to the beat, and coloring within the lines. I wonder, however, how many of these prudent 18-year olds will become career development clients over the next 20-30 years because they willingly, if unwittingly, appropriated someone else’s aspirations as their own.

Passage 5

There is no coming to consciousness without pain. — Carl Jung (5)

The term “growing pains” is not just a metaphor. Real growth can result in real pains and aches. The aphorism that nothing grows in nature without shedding is worth remembering in this context. The changes that one pursues in order to reconcile the differences between self-perceptions and actual life; the changes that result from self-explorations and recognition of personality, temperament, and attitudinal preferences; the changes that will propel one to correct back to “real life” — these changes will not be realized without some degree of anxiety, stress, discomfort, and even pain. Author Barbara Winter asks, “What would you do if you weren’t afraid?” (6) Every client should confront that question, as well as the implications of their own personal answers.

Rather than expose themselves to these emotional challenges, some clients may deny the need for significant change. They may rationalize that they just need to do a better job of adjusting or adapting to their circumstances. They may try to wish the change away or passively bequeath responsibility to Fate or Destiny: Things aren’t really that bad. I can make it until things get better. They may well become worried and fearful when contemplating what a major change might mean. As Helen Harkness has written, for them change isn’t possible until the pain of their actual present becomes greater than the fear of their imagined future. (7)

Jung also acknowledged the role that emotion, more so than reason, plays in initiating action: “There can be no transforming of darkness into light and of apathy into movement without emotion.” (8) Your clients were probably motivated to begin their journey of self discovery by their own versions of my waiting for my real life to start moment. As they actually venture out into the uncharted and uncertain waters of taking real action, they need to remember that triggering moment and the emotions that accompanied it. At this critical decision point in their career passage, when they either launch into the unknown or return to the intolerable comfort of living as fugitives from themselves, they will likely need the memory of that initial emotional charge to fuel their advance and deny their retreat.

Passage 6

If you are distressed by anything external, the pain is not due to the thing itself, but to your own estimate of it; and this you have the power to revoke at any moment. — Marcus Aurelius (8)

Emotional courage from a catalytic trigger may get your clients to embark on their journey into the unknown and uncertain, but of course that won’t be the last challenge they’ll have to confront. They can expect disappointment, failure, doubt, anxiety, and perhaps every emotion in their vocabulary. How they navigate around and through the myriad obstacles that can host these potential emotional crises is crucial to their willingness, motivation, and confidence to continue the journey. Events such as an ambivalent interview, a rejection letter from an editor, or a disappointing networking contact can become simple setbacks easily forgotten, or journey-ending crises, depending on how the client responds to them.

The growing field of Positive Psychology has much to say in this regard. As explained in the PBS series “This Emotional Life,” psychologists differentiate between rumination in which individuals tend to obsess or fixate over an event or a situation, vs. re-appraisal, whereby the event or situation can be evaluated from multiple perspectives or contexts. In other words, our emotions do not have to be held captive to emotional triggers, crises, and disappointments; we can control or re-appraise the degree to which those outside events affect our inside responses. Psychologist James Gross at Stanford University offers this finding in simple, unambiguous terms: “There is an important role for thinking in emotions. If you can change the way you think, you can change the way you feel.” Narrator Daniel Gilbert, talking about a class in forgiveness offered by Stanford professor Fred Luskin, explains that Luskin “provides exercises to help the students see that they can’t control what happened to them, but they can control how they think about it.” (9)

Channeling the spirit of Marcus Aurelius, the appropriately nautical aphorism reminds us that, “We cannot command the wind, but we can adjust our sails.”

Passage 7

The voyage of the best ship is a zigzag line of a hundred tacks. See the line from a sufficient distance, and it straightens itself to the average tendency. Your genuine action will explain itself, and will explain your other genuine actions. Your conformity explains nothing. — Ralph Waldo Emerson (10)

One of the standard mantras of career counselors and advisors is for clients to set goals and work religiously toward those goals to ensure a successful career. I’ve known people who were able to follow this formula to very successful and fulfilling careers. High school friends knew they wanted to become farmers, veterinarians, doctors, teachers, coaches, business owners, and that’s what they did. Classmates from the Air Force Academy became pilots, test pilots, airline pilots, space shuttle commanders, and even four-star generals. They set a course early and took off, into their own individual wild blue yonders.

This approach becomes problematic, however, for people like me, and perhaps some of  your clients, who have trouble answering that pesky “what do you want to do” question. That’s not to say that the principle of goal-setting can’t be applied by someone who is uncertain or conflicted — it just requires that the goal be defined a little more broadly and a little more flexibly. This quote from Emerson’s essay “Self-Reliance” serves as a reminder that point-to-point, direct line courses are great if possible, but during the course of any career there are going to be times when the job-related winds, currents, and other factors beyond the individual’s control preclude a point-to-point course. It takes effort, and confidence, to steer in a direction that you know is off the point-to-point course and will eventually require a compensating correction. But as Emerson points out, careful, deliberate, and accurate tacking will get you to your destination; what’s important isn’t the track of the tacks, but the course of the “average tendency” such that the ship (your career) arrives in its intended port.

Applying the navigation metaphor to careers, even if your clients can’t articulate precisely what they want to do, they can probably determine a general direction where their interests might lie. And they can certainly avoid heading in what they know to be a wrong direction. This or that particular job might not be a for-the-rest-of-my-life job, but it might serve as a “tack” that positions one to gain necessary experience, establish a well-connected contact, or learn lessons that will prove valuable when initiating “course corrections” in the future.

Passage 8

Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backwards ten years later. Again, you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life. — Steve Jobs (11)

This concluding passage comes from the 2005 commencement address at Stanford University. Steve Jobs’ metaphor of looking backwards to “connect the dots” provides a nice bookend to Emerson’s “zigzag tacking” metaphor. Effective navigating includes not just looking forward, but regularly taking a “present position” to assess where you are relative to your intended course. By connecting these present positions, or dots, you establish and visualize your track. If you extend this track, you can project where you will be when the time comes for your next present position update. If that projection (or “dead reckoning position,” in navigational terms) shows you off course, you can initiate a turn (or tack) back to course. In other words, it’s a good idea to regularly stop and determine where you are, where you’ve been, and if you’re “on course” for where you want to go. The longer you delay correcting back to course, the further off track you’ll wander, which means you’ll have to make a more severe correction to reach your destination.

The second part of this quote is about trust. Although Jobs allows this trust to be allocated in “your gut, destiny, life, karma, whatever,” for the benefit of your clients I would specify that they need to develop trust in themselves and their own intuitions, decision-making judgments, etc. Throughout this career process — from the earliest dissatisfactions and frustrations to the fears and pains of life-altering decisions to the challenges and struggles inherent in major course corrections — there is no sure-fire, can’t lose, guarantee for success. At various points along the way, your clients will have to make decisions that result in actions. Knowledge, awareness, and understanding are necessary but not sufficient — each one of them will have to act, to do. And every decision made and every action taken will involve some degree of risk. As your clients develop confidence and trust in themselves, that trust will inform their abilities to judge risk and empower their determination to act.

Perhaps I should conclude with a disclaimer: DO NOT TRY THIS AT HOME. I hope that’s not necessary. I doubt anyone will read my story and be so inspired to proclaim: Yeah, that’s how I want to do it! I have zigged and zagged through at least a dozen different jobs with six different employers in five completely different fields. At every decision point I’ve encountered or created, my choices could rightfully be judged as irresponsible, not practical, and against conventional wisdom. They deviated from the script, didn’t conform to the beat, and strayed way outside of the lines. But each choice represented a tack, a career course correction that, in hindsight and with sufficient distance, reveals my authentic “average tendency.” These course corrections document the trail of a former fugitive returning, not to a safe harbor, but to the openness of an uncharted, but navigable, sea of possibilities.

After four decades, I’ve come to understand and internalize the poster I had on my wall through high school: A ship in the harbor is safe; but that is not what ships are built for. (12)


  1. Conroy, Pat. (1987). The Prince of Tides, New York, New York, Bantam Books.
  2. Canetti, Elias. (2005). The Secret Heart Of The Clock: Notes, Aphorisms, Fragments 1973-1985. New York, NY. Farrar, Straus and Giroux.
  3. Gardner, John. (1990). Personal Renewal. Delivered to McKinsey & Company, Phoenix, AZ. http://www.pbs.org/johngardner/sections/writings_speech_1.html
  4. Shaw, George Bernard. (1922). Man and Superman, A Comedy and a Philosophy. New York, NY. Brentano’s.
  5. Jung, Carl. (1928). Contributions to Analytical Psychology. New York, New York. Harcourt Brace.
  6. Winter, Barbara J. (2009). Making a Living Without a Job. New York. Bantam Books.
  7. Harkness, Helen. (2005). Capitalizing on Career Chaos: Bringing Creativity and Purpose to Your Work and Life. Mountain View, CA. Davies-Black Publishing.
  8. Jung, Carl. (1953). Psychological Reflections: An Anthology of the Writings of C. G. Jung. New York. Pantheon Books.
  9. “This Emotional Life.” http://www.pbs.org/thisemotionallife/home
  10. Emerson, Ralph Waldo. (1838, 1974). Essay on Self-Reliance. The American Tradition in Literature. Fourth Edition. New York, NY. Grosset & Dunlap.
  11. Jobs, Steve. (2005) Commencement Address, Stanford, CA. http://news.stanford.edu/news/2005/june15/jobs-061505.html
  12. Shedd, John A. (1928). Salt from My Attic. Portland, ME. Mosher Press.