Turns Out It's Long and Winding

The phrase “career path” is an interesting one. It implies accessibility, a straight-line approach, just out there waiting for all of us. Has it, in fact, always been elusive? Certainly there is no question that it has been billed as real, perhaps by our belief in the power of planning, or by corporations who held on to the concept. Whatever the truth, this concept has become a bit unclear, and rather than any kind of straightforward road ahead, is now more of a long and winding one, frequently fading away in the distance.

In a recent blog, The Trade Cycle (August 2026), SmarterWisdom told the story of LaDonna Glass and her journey from college coursework toward becoming a youth therapist who chose instead to train as an electrician. Her career path had appeared mapped; she’d gained a place in a four-year college program, but she ignored the straight-line direction and improvised, taking a turn toward a guaranteed, decent income after two years, instead. She pre-empted a possible dead end that might have stymied her financial well-being and followed her own read on success.

At 23, perhaps this kind of side-step is easier?

So what about professional changes that 35, 45, or 55-year-olds might want or need to make? Can they side-step as readily? Do they have the prerequisite skills to do so? And will their mid- or later-career changes be respected and understood by prospective employers?

We know one client, let’s call him Max, in his early 50s, with an MBA from a reputable graduate program. He’s held stable positions as a CFO, a CEO, and led his own start-ups. Now, as AI reshapes the professional area he works in, he needs to be nimble and quick-footed. However hard he tries, and however well he improvises, he doesn’t get that next role. Where can he get the help he needs? How does he translate 25 years of experience into a different vocabulary — a presentation and focus that speaks to his ability to succeed in a new environment?

Members of Gen Z (born 1997–2012) may well be more equipped for this shift in how we access work. The messages reaching them are full of the gig economy, flexibility, and the relative ease of building a life away from where they grew up. Millennials and Gen X-ers, probably less so. All of them may see that the career path isn’t straight or mapped out — the lack of stability is becoming predictable, which doesn’t make it any smoother to accept. But Max’s story raises a sharper question underneath the generational one: Is this a game only the young are allowed to play? Some may admire the way more mature people can pivot seemingly on a dime. Others, especially those in positions of power in the work world, may be suspicious of these movers, reading reinvention as instability rather than skill.

That suspicion is really the crux of this apparent need for directional changes. The deeper issue, however, isn’t whether people can keep changing paths — it’s whether those in the power seats are willing to respect the steps people have made to get there, and the growth they remain charged to continue.

For Max, and for people like him, the question becomes less about strategy and more about identity. Who am I? What can I offer? What stories can I tell, what examples can I give, that show a prospective employer I’ll bring them the success and results they want, and need? It was easier, once, to manage a career when you could point to a straight line of expertise in one industry. Now Max has to be a much better manager of his own search — and that search runs through identity before it runs through strategy.

What does this long, winding road mean for coaches and consultants — how do we help clients manage a trajectory that no longer has a fixed shape? It places a greater emphasis on self-knowledge: as an individual, a team member, a leader. It places weight on flexibility within a skillset. It means helping clients convey how their intrinsic make-up and what makes them tick, presents them as right for the job. Awareness of their inner life and motivation, and the ability to integrate it fully into the presentation of their professional persona, become a vital component of seeking a new role on this brand-new journey.

Perhaps one key to easing this obvious tension is inviting the wisdom of elders more fully into the picture. If the resolution to this topsy-turvy world lies in knowing ourselves and truly leveraging our strengths, then this may be a real opening for mentorship — for older job seekers to share hard-won wisdom with younger companies and their less experienced teams, and, just as importantly, for those companies to learn to see that wisdom as an asset rather than a liability.

ADDITIONAL BLOGS THAT COULD BE OF INTEREST

Words of Wisdom

Turns Out It's Long and Winding

The Fragility of Reputation

Reputation plays an important role in our lives and has a particularly impactful significance in our success at work. How others think of us affects how they relate to us. Yet the flood of information coming in from channels makes it particularly tricky to manage one’s professional reputation today.

The Trade Cycle

A headline in the New York Times recently caught my eye: Mom, Dad, I Want to Be a Welder. Callie Holtermann’s bright and interesting piece (July 13, 2026) told the story of LaDonna Glass, aged 23, who had wanted to be a youth therapist and left college after one year to join a trainee electrical engineer program. Ms. Glass was loving it — snaking conduits between electrical boxes, installing wall sockets, learning on the job, and enjoying not only feeling useful but knowing that if she joined the union, she might earn close to $90K a year as an IBEW electrician.

Getting Out Front — Why the Higher You Climb, the More You Need to Look Outward

A few weeks ago, on June 22, British Prime Minister Sir Keir Starmer announced his resignation—less than two years after winning a landslide election. What struck many observers wasn’t the fall itself, but the speed of it, and the degree to which Starmer appeared, in his final weeks, to have lost the thread of connection to his own party, his voters, and the shifting political ground beneath him. In his own words: “The question my party is asking now is whether I am best placed to lead us into the next general election. I have heard the answer….”

He heard the answer — but perhaps too late.

Definitely Not the Pits

30 years after TV phenom ER captured the attention of viewing audiences, one of its stars is once again fighting for patients’ lives in a new screen venue. ER featured a fresh-faced Noah Wyle as a newly-minted doctor in an urban Chicago hospital emergency room; within its worn facilities he gamely faced a daily deluge of the city’s citizens, victims of violence, carelessness, poverty and bad luck.

But ER also featured hospital politics and budget concerns and storylines related to staff life, issues such as career concerns, family conflicts or romantic entanglements. This go-around Wyle is back in the emergency room in Pittsburgh as a veteran medic: several decades older and, possibly, wiser.

Love, Grief and Loss at Work

In my work with non-profit leaders I know that we can never spend too much time on mission—since it is truly at the core of everything we do and need to pay attention to. I find that most of our conversations can either flow from mission, or mission-related matters, or we quickly pause and ask the question: how does this relate to the mission? Leading a mission-driven entity is a great honor, frequently the perfect place to develop both our focus on being a servant leader and also understanding more deeply our purpose and the purpose of our colleagues. We are, however, unless we lead a faith-based organization, neither preachers nor counselors: we are chief executive officers with the success of our organization as our core goal.

So what do we do with emotion, feelings and human connections? And can we, should we, and how might we, truly and successfully harness and incorporate the relational aspect of our lives and the experiences of those whom we serve into the ethos of our place of work, both organically and generatively?

Predictions: Not for the Faint of Heart

With constant change, upheaval and churn all around us, we yearn to know that we might predict our way to a future that seems calmer and clearer. Any new year brings resolutions for improvement and very quickly resolutions morph into predictions as to how things might look. Predictability is super seductive at these times, providing that much longed for sense that we have our bearings, know pretty well what is going on around us and can leverage those insights to plot out a trajectory to our future. As 2025 gave way to the early days of 2026, however, many of SmarterWisdom’s clients are not feeling as if they possess the prerequisites to do so. As a result, many don’t feel confident predicting a future based on their own insights.

Reflective Leadership: Takes Time, Well Worth It

A recent snow day all across New England has made me think deeply about how I might have squandered those days when I was a head of school. Partly because I lived on campus, it was easy to pop down to my office and do the organizing and paperwork that I rarely had time for. Fellow staff members were often around and would pop in and our conversations were longer because we had the time, and I could always get a lovely brunch over in the dining room. Not a bad way to spend such an irregular day, and truly nothing lost and absolutely something always gained. But…might I have found a way to use these fairly rare days differently, not to catch up or get ahead, but rather to commit an act of truly generative leadership: to reflect, ponder and learn more deeply about what I was doing well and where, perhaps, I might improve.

Coaching an Insecure Leader

SmarterWisdom has written a lot over the years about the foundational needs for a leader to become better at what they do: self-awareness, a growth mindset, the willingness to take feedback, holding themselves and others accountable, building and practicing trust of their team, treating people with respect and listening well, just to name a few. What about those insecure, or less confident leaders who lack these skills and who in fact might have a list of opposite traits which impede their own growth and the growth of their organization? We work with all kinds of leaders and for sure it is those that lack confidence in themselves, knowingly or not, that present with a tough challenge, even for SmarterWisdom!

So how do we partner effectively with these types? And is it possible that they may overcome some of their tendencies towards insecurity, and, as needed, develop more self-awareness that might set them on a path towards further growth?

Under Pressure in 2025

As we begin 2026, SmarterWisdom is taking its annual look back on the year just past. We have enjoyed, over these past 6 years of our work together, gaining new insight and cementing prior relevant learnings as we check our rearview mirror. Looking at the culture and context we have lived through and noting the qualities of a specific year adds to our wisdom and propels us forward. At this late December/early January time, we have noticed many references to a good-riddance-to-2025 sentiment in our readings and social media accounts. To us, it conjures a throughline for 2025 that combines fragile wishful thinking about the future, with the necessity to keep an eagle eye on the past to ensure it stays in that rear view!

The Winner Takes It All

As readers of Words of Wisdom have surely observed, I like win-win arrangements. At their core, they are self-managing, since everyone needed to make the solution work is also invested in reaping its benefits. The solution itself has built-in motivation, since everyone involved is motivated to make them succeed! Really solid win/wins are self-fueling, so they don’t need continual monitoring, pressure applied from the outside or a pipeline of external energy to keep them running for quite a while. These are the reasons why I love the concept so much!

Go Team!!!!!!!

I was running a team-building workshop recently. During a short break I was considering how it was going and what I might like to adjust in my facilitation or the agenda. I was reflecting on the strength of this team of eight talented leaders and how fortunate the school was to have them in their individual roles; in addition it was clear that there was significant potential present for them to soar as a high-performing team and take the organization to the next step. Something was irking me though: was it the pride they had in their ability to disagree? The belief some of them expressed in how they could all speak their opinions honestly? Somehow too perfect perhaps? And then it hit me: this seemed to be a group of people who might be confusing family values with deeper, and more necessary, work values, perhaps leaning into dysfunction rather than high function?

This raises the question: should a senior leadership team ever be like a family?

For Better

Staying optimistic, looking on the bright side, holding on to hope: these are all wonderful mindsets, and I expect you have experienced, as have I, how elusive they are to hold on to in trying times. Some days, it seems as if there is more bad news than good, and it comes at us relentlessly, and from countless sources. My friends and colleagues tell me that they have simply stopped looking at the news. While I don’t do that, I can understand it. Avoidance---and the genuine phenomenon of contagion---make it not an unreasonable response. Upon further reflection, I have realized that I’ve been influenced by the idea of a stop -staring-at-the-problem strategy, and am even willing to consider denial which, as a bonus, results in almost immediate gratification!

The Resonant Leader

Richard Boyatzis and Annie McKee coined the term, resonant leadership, or at least made it more widely known, in their book, Resonant Leadership: Renewing Yourself and Connecting With Others Through Mindfulness, Hope and Compassion [Harvard Business Press, 2005]. They had collaborated with Daniel Goleman, a leading proponent of emotional intelligence, on their volume Primal Leadership a few years earlier. The trio defined resonant leadership as a concept or approach that leaders could embrace, and in doing so they would become stronger and more adept in their strategic work with colleagues and teams. Adopting this approach would create a strong culture where working together, towards common goals, leads to high level success.

Be the Change...

Most of us know that, in the vast percentage of major enterprise transformation efforts, stockholders, the Board, the CEO and senior management care about the desired organizational change succeeding. Lower-level employees know, in particular, that their boss (if the boss is on the right side of the issue as assessed by those in the layers above her/him/them) cares, as well. They know all these people care because, (1) they hear them trumpeting about it all the time and (2) they know (and don't need to be told this part) that in most cases, these change promoters have a lot of skin (read $$$’s) in this game of change.

In fact, many employees are well aware that their superiors and the board members above them, care about the success of the organizational change that is afoot. But what about those who are not typically in the know when an organization merging with another, shifts its focus or is taken over by another firm? And what is the impact of organizational change on employees?

Tapping Into Function

SmarterWisdom has written a lot about teams. We believe in their good work and we see the immense advantages of highly functional teams. In a recent workshop with a large independent school that I led, I decided, with the head, to use Patrick Lencioni’s seminal work on teams: The Five Dysfunctions of a Team, as my primary reference. I read this excellent short book several years ago after another school client recommended it to me. (Her school hired The Table Group, Lencioni’s firm, to work with them on team-building and so she had excellent first-hand knowledge.) The book is a great read, and I highly recommend it. It has stood the test of time, since its publication in 2002.

People Managing People

Many responsibilities fall under the job title manager. For an array of reasons, the demands on those holding this position have expanded considerably in recent years. As a result, managers are telling us that performing their job well is getting tougher. This is a trend that deserves serious attention.

The bottom line is that good employee management is a key lever in producing good employee performance. But in recent years expectations for the people in charge have escalated and the degree of difficulty for achieving effective people management has increased. It is only through an understanding of the components of this enhanced demand that effective strategies for preparing and supporting managers in our organizations can be generated.

Artful Discovery

I recently returned from a lovely vacation to New Mexico. I have travelled there before many times and it is always a trip that never fails to bring me some renewal, relaxation and learning.

A few aspects of this visit helped me think more deeply about organizational culture, customer service and relationships. Any chance I get to reflect in these areas typically rewards me with deeper knowledge.

I Just Need To Take This

Imagine the scene: you are happily sharing a meal with friends or family (whom perhaps you have not seen in a while) when suddenly one of the participants jumps up with their phone in hand, mumbling, “Sorry, I just have to take this?” Another possible situation: you are about to begin a group or team meeting at the office (perhaps it was a tough one to schedule) and as your colleagues arrive, several of them immediately place their phones right in front of them—some devices facing up, some down. In any variation of this theme, when a phone rings or vibrates, the owner not only moves quickly to answer the call, they frequently begin the conversation before they have left the scene.

What is Worth Learning?

Learning is at the center of my universe. I believe deeply in the value of education, and I wake up in the morning excited to learn what’s happened during my sleeping hours. I regularly absorb curated sources: blogs, on-line publications of all sorts, podcasts; you name it, I take it in. I’m a learning junkie. So, even questioning the value of learning tears at my heart.

But I have many coaching and organizational clients who want my advice on learning and development issues. Individuals seek my input on whether or not, for example, they should go back to school to further their careers. Organizations too are often looking for counsel on training curricula and employee development programs. As discomfiting as it may feel to question a value I hold so personally dear, in my professional role I want to assess the benefit of all kinds of learning in today’s work world.

Learning on the Job

Recently as I was collecting my thoughts in preparation for our quinquennial Words of Wisdom, I realized how important to us at SmarterWisdom the concept of learning on the job is. It is kind of core to our work that the people we work with want to get better, learn more and be good and helpful mentors to their team members. Creating a feedback-feedforward culture means that you are harnessing the idea of a growth mindset, and that what you expect of others is important to you too. So how might learning on the job become an integral value in your workplace and a robust part of your culture? Might there be additional ways for you to promote it?

Five Years of [Smarter] Wisdom

It’s extremely hard to believe that 5 years have passed since we founded SmarterWisdom Consulting. As we celebrate our quinquennial, we have been discussing whether or not we became any wiser over the time period. And by “we” we are certainly referring to Jane and Marcie! We thought the best way to assess our possible increased sageness was through taking a close look at the now 72 posts, our Words of Wisdom, that have appeared online since our founding, and in doing so, understand more about how our work together has continued to place us on a path of learning.

The BHAG Revisited

When Jim Collins’ book Good to Great was published back in 2001 the term “BHAG” was on the lips of every leadership consultant or CEO. Going for that Big Hairy Audacious Goal was what you needed to be doing if you wanted to drive success through clear vision and direction. Fast forward to 2024, and we are now suggesting something a bit different. No one is saying that you shouldn’t have a big stretch goal, but we’ve learned a few things about getting to the top of a large mountain on a different planet. Specifically, both research and experience tell us to start small.

Dealing With Dilemmas

When I was a head of school, it was quite common for members of my Board of Trustees, usually at an annual conversation about how things were going, to ask me: “What keeps you up at night?” When I moved into my current role as a leadership coach/thought partner, I found that I too began to use this question quite consistently. What are those nagging thoughts that re-visit us, usually as we try to drop off to sleep, or in those hateful hours when we simply cannot get back to our desired rest.

The quandaries that show up in our minds at these times, and others, are frequently puzzles where all possible solutions offer some kind of downside. In addition, they are issues that simply won’t go away, neither night nor day and in fact, we are driven to find a way forward. The word dilemma comes from the Greek word dilēmma, and the combination of the words di- meaning "twice" and lēmma meaning "premise" seems to scream interminable difficulty! In fact, the word dilemma was originally a technical term in logic that referred to a type of argument where a choice had to be made between two equally unfavorable options.

Back to the Future: Building Competitive Advantage

Over 20 years ago I co-authored a book focused on how organizations could re-envision diversity as a competitive advantage. Fast forward to 2024 and I realize I did not anticipate how the DEI effort would look in 2024. The need, when my colleagues and I penned the book, for an enlightened perspective on the value-add of equity in the workplace (not to mention the ethical impetus to address this issue) seemed both clear and compelling, as it well remains. As I look back and gaze forward with some hope that the competitive advantage might still emerge, with focus and intentionality, I plan to hold on to that brighter outlook from two decades ago. Because I envisioned that the dominos in the workplace were lined up neatly and the first ones were falling, I anticipated that the next stage of the initiative would pick up momentum and make major inroads through the tangle of debris wrought by lack of systemic efforts and change during the centuries of racism, sexism and homophobia that had interwoven irrevocably within our country. In my mental model of achieving equity at work, at least in recent decades and during the Civil Rights movement, the arrow of social justice had been launched, and it seemed as if our aim was true and our intended bulls-eye was within reach. In retrospect, and sadly, I was naive and lacked accurate foresight.

Deliberately Growing Up

Those of you who read our posts regularly know that we at SmarterWisdom are quite obsessed by several general approaches to leadership development. Themes and thoughts about self-awareness, intentional thinking and action, growth mindset and (Marcie’s favorite) letting the structure do the heavy lifting, are just a few that run through our writings, just as they percolate through our thinking. Many of these approaches that we care about help to form the framework of our work with the individuals and teams with whom we spend our time. Many of them even come together and align to create a structure that we can overtly share with people in an explicit form.

Which One?

Deciding on your dessert at a lovely evening out with friends can be hard. Is it the lemon mousse with white and dark chocolate? The strawberry shortcake? Tarte Tatin? Blackberry or peach sorbet? OK, you might make a choice you regret, or it just may not arrive and look or taste as you expected, but seriously this is not a complex decision: you won’t let anyone down, you can’t really make a bad decision here. Your dessert decision is simply a matter of choice, your choice alone. According to some scientific research, adults make around 35,000 conscious decisions every day, while others estimate that number to be as high as 350,000. Deciding on the initial path to take ,and the nature of the decision, whether it be a simple choice of sweet, or more, is definitely a huge part of our lives as leaders.

Some Leaders Are Born Women

Examples of women, who are at the height of their careers and those on the fast track to getting there, offer support for the notion that indeed other women should be following this path. From Beyoncé to Oprah to Taylor Swift, women entertainers are taking names and taking charge. No longer simply the pretty faces of success, these women are smart business people who followed their insight and their guts as they saw inside their industry and ensured that they reinvented what it could be for themselves. Oprah became a mega-performer and international figure; Beyoncé became a Harvard Business School case study and Taylor Swift has not shied away from taking on the behemoths of the music industry, from Spotify to Live Nation. Each has stuck her neck out to go a different way, straying from the path most taken, and carved out the way that brought her the time, clout and, yes, financial reward, she was seeking. They are each reinventing what it means to be living their own high-powered career by redefining what that is, and by taking on established power as they do so. By seeking to control the narrative and be in control of their actions and approach, their courage and smarts are setting the bar high and at a new level for all.

Hijacked!

I work with many school leaders. These leaders tend to be open-minded, consensus-oriented people and the schools they lead believe in the benefit of creating forums for discussion with and among employees. The idea that open discussion will nurture an engaged group of workers is a good one, especially during current times when employment engagement is at an all-time low. Freedom to ask questions of others, especially those who supervise programs and departments, in a group setting, encourages trust, develops leaders and allows group process that generates ideas that in turn can solve problems. Arguably, the existence of a place to speak up, to use your voice to improve the place you work, is vital to a successful organization of any kind.

The Existence of the Soul

Recently with my friend and colleague Julie Faulstich, of Stonycreek Strategy, I led a group of senior women administrators from independent schools in a yearlong seminar called: Female Leadership, Finding your Authentic Authority. We enjoyed deep and wide-ranging conversations; we unraveled dilemmas and we discussed the potential isolation of perhaps being the only one in the role of dean, assistant head, or division head, that is a middle manager and reporting to the head of school. Being in the middle in any kind of organization, is not always easy and the work these middle managers do frequently goes unnoticed—and yet without that work, the organization would suffer. So here’s SmarterWisdom’s tribute to the ones in the middle—to their very existence, and, even more perhaps: to our paying more attention to what they do and how important it is.

Career success, Team-building, Flexibility, Leadership, managing new ideasJane MouldingOctober 9, 2026Covid-19, Flexibility, Time-of-change, Partnership