How to stay stuck in the wrong career

A three-point plan

We like to think that the key to a successful career change is knowing what we want to do next, then using that knowledge to guide our actions. But studying people in the throes of the career change process (as opposed to afterward, when hindsight is always 20/20) led me to a startling conclusion: change actually happens the other way around. Doing comes first, knowing second.

Why? Because changing careers means redefining our working identity. Career change follows a first-act-and-then-think sequence because who we are and what we do are tightly connected, the result of years of action; to change that connection, we must also resort to action — exactly what the conventional wisdom cautions us against.

Conventional career change methods — Susan’s ‘logical’ CV progression, Harris’s networking, and Gary’s planning — are all part of what I call the ‘plan and implement’ model of change. It goes like this: first, determine with as much clarity and certainty as possible what you really want to do. Next, use that knowledge to identify jobs or fields in which your passions can be coupled with your skills and experience. Seek advice from the people who know you best and from professionals in tune with the market. Then simply implement the resulting action steps. Change is seen as a one-shot deal: the plan-and-implement approach cautions us against making a move before we know exactly where we are going.

It all sounds reasonable, and it is a reassuring way to proceed. Yet my research suggests that proceeding this way will lead to the most disastrous of results, which is to say no result. So if your deepest desire is to remain indefinitely in a career that grates on your nerves or stifles your self-expression, simply adhere to that conventional wisdom, presented below as a foolproof, three-point plan.

Know thyself

Like Gary McCarthy, most of us are taught to begin a career change with a quest for self-knowledge. Knowing, in theory, comes from self-reflection, in solitary introspection or with the help of standardized questionnaires and certified professionals. Learning whether we are introverted or extroverted, whether we prefer to work in a structured and methodical environment or in chaos, whether we place greater value on impact or income helps us avoid jobs that will again prove unsatisfying. Having reached an understanding of his or her temperament, needs, competencies, core values, and priorities, a person can go out and find a job or organization that matches.

Gary did all these things. Armed with his test results, he researched promising companies and industries and networked with a lot of people to get leads and referrals. He made two lists of possibilities: ‘conformist’ and ‘non-conformist’. But what happened from there, and what consumed 90% of the year he spent looking for a new career, is what the conventional models leave out — a lot of trial and error.

Gary started with several rounds of talking with traditional companies and headhunters. Next, he tried to turn a passion or a hobby into a career: he and his wife wrote a business plan for a wine-tour business. The financials were not great, so they dropped it. Next, he pursued his true fantasy career: Gary got certified as a scuba instructor and looked into the purchase of a dive operation. He soon learned, though, that his dream job was unlikely to hold his interest over the long term (and thus was not worth the economic sacrifice). So he went back to the headhunters and traditional companies, only to reconfirm that he did not want what they had to offer. Next, he identified entrepreneurs he admired and looked for ways to get his foot in their doors. He explored freelancing, trying to get short-term projects in exciting young companies. But a precise match did not materialize.

Certainly the common practice of looking back over our careers and identifying what we liked and disliked, what we found satisfying and not satisfying, can be a useful tool. But too often this practice is rooted in the profound misconception that it is possible to discover one’s ‘true self’, when the reality is that none of us has such an essence. Intense introspection also poses the danger that a potential career changer will get stuck in the realm of daydreams. Either the fantasy never finds a match in a real-world, paycheck-producing job or, unlike Gary, we remain emotionally attached to a fantasy career that we do not realize we have outgrown.

We learn who we have become — in practice, not in theory — by testing fantasy and reality, not by ‘looking inside’. Knowing oneself is crucial, but it is usually the outcome of — and not a first input to — the reinvention process. Worse, starting out by trying to identify one’s true self often causes paralysis. While we wait for the flash of blinding insight, opportunities pass us by. To launch ourselves anew, we need to get out of our heads. We need to act.

Consult trusted advisers

If you accept the conventional wisdom that career change begins with self-knowledge and proceeds through an objective scrutiny of the available choices, who should you turn to for guidance? Conventional wisdom has it that you should look to those who know you best and those who know the market. Friends and family — with whom you share a long history — can offer insight into your true nature, and they have your best interests at heart; professionals add a dose of pragmatism, keeping you grounded in the realities of the marketplace.

In times of change and uncertainty, we naturally take comfort in our enduring connections with friends and family. But when it comes to reinventing ourselves, the people who know us best are the ones most likely to hinder rather than help us. They may wish to be supportive, but they tend to reinforce — or even desperately try to preserve — the old identities we are trying to shed. Early in his career, Gary discovered that his close circle would not be much help. “I wanted to do something different but was shocked to realize that people were already pigeonholing me,” he says. “I tried to brainstorm with friends and family about what other things I might do. All the ideas that came back were a version of ‘Well, you could get a middle management job in a finance department of a company.’ Or ‘You could become a trainee in a management program.’” John Alexander, an investment banker hoping to make a go of fiction writing, reports that he had often discussed his career predicament with his friends and family. “They would tend to say, ‘I can see why writing might be interesting, but you’ve got a very good job, and do you really want to jeopardize that?’”

Mentors and close co-workers, though well meaning, can also unwittingly hold us back. Take Harris Roberts, the health care company director who wanted to assume a general management role. The people around him, who were invested in his staying put, only mirrored his normal doubts about moving outside his comfort zone. His mentors cared about him and held the power to make his desired change a reality. But they made a fence, not a gateway, blocking the moves that would lead to career change. By talking only to people who inhabited his immediate professional world, people whose ideas for him didn’t go beyond the four walls, Harris seriously limited himself. Not only did he lack outside market information, but these coworkers could no more let go of their outdated image of a junior Harris than he himself could.

Headhunters and outplacers, today’s career change professionals, can keep us tethered to the past just as effectively. We assume, rightly, that they have the market perspective we lack — but we forget that they are in the business of facilitating incremental moves along an established trajectory. At midcareer, however, many people are no longer looking to ‘leverage past experience in a different setting’. They want to invent their own jobs and escape the shackles of corporate convention, in some cases to do something completely different. What Susan Fontaine, the management consultant, experienced is typical: “I found headhunters unhelpful, basically. I would say, ‘Here are my skills; what else might I do?’ And they kept saying, ‘Why don’t you move to Andersen?’ or, ‘Why don’t you try Bain?’ All they could suggest was exactly the same thing. I kept saying,‘ I’m quite clear I don’t want to do that, and if I did want to do that, I would not come to you. I can do that on my own.’”

So if self-assessment, the advice of close ones, and the counsel of change professionals won’t do it, then where can we find support for our reinvention? To make a true break with the past, we need to see ourselves in a new light. We need guides who have been there and can understand where we are going. Reaching outside our normal circles to new people, networks, and professional communities is the best way to both break frame and get psychological sustenance.

Think big

We like to think that we can leap directly from a desire for change to a single decision that will complete our reinvention — the conventional wisdom would say you shouldn’t fool yourself with small, superficial adjustments. But trying to tackle the big changes too quickly can be counterproductive. Just as starting the transition by looking for one’s true self can cause paralysis rather than progress, trying to make one big move once and for all can prevent real change.

When Susan Fontaine decided to leave her consulting career, it was with good reason. A single mother of two, she was finding the travel and other demands on her personal life increasingly intolerable. She quit her job and resolved to spend some time exploring her options. That resolve vanished, however, when financial pressure coincided with a flattering offer to join the management team of a former client. She accepted the new position only to discover that its demands would be very similar to those of the position she had left. “I thought, ‘What have I done?’” she later told me. “I had had the opportunity to leave all that!” By hoping to solve all her problems in one fell swoop, Susan made a change that amounted to no change at all. Two weeks into the new job, she resigned.

As much as we might want to avoid endless procrastination, premature closure is not the answer. It takes time to discover what we truly want to change and to identify the deeply grooved habits and assumptions that are holding us back. The lesson of Susan’s story is that trying to make a single bold move can bring us back to square one all too quickly. A longer, less linear transition process may leave us feeling that we are wasting time. But as we will see below, taking smaller steps can allow a richer, more grounded redefinition of our working identity to emerge.

Three success stories

Although they floundered, victims of conventional wisdom, Gary McCarthy, Harris Roberts, and Susan Fontaine eventually moved on to a different — and more successful — approach. Gary is now at a media company he admires, working as an internal venture capitalist, a role that allows him to use his skill set in consulting and finance but grants him great creative latitude and total ownership of his results. Harris is president and COO of a growing medical device company and very much involved in setting the strategic direction of his new firm. Susan is working with non-profits, bringing her strategy expertise to this sector and loving her work.

None of them followed a straight and narrow route. Gary dabbled in wine tours and flirted with buying a scuba diving operation before settling on what his wife called a more normal path. Harris had his prized general management role snatched from under him a second time as the result of a corporate restructuring. He considered leaving for a biotech start-up but realized that he simply did not have the appetite for such a risky move. Susan set up temporarily as a freelance consultant, landing traditional consulting projects to pay the bills and using her discretionary time to explore a more varied portfolio of assignments.

Their experience is typical. Nearly everyone who tries to figure out a next career takes a long time to find the one that is truly right. Most career transitions take about three years. It is rarely a linear path: we take two steps forward and one step back, and where we end up often surprises us.

Working identity

Once we start questioning not just whether we are in the right job or organization today but also what we thought we wanted for the future, the job search methods we have all been taught fail us. But that doesn’t mean we must resign ourselves to a random process governed by factors outside our control — life crisis that forces us to reprioritize, an unexpected job offer. There is an alternative method that works according to a different logic than the plan-and-implement approach. Gary, Harris, and Susan, as well as many other successful career changers I have observed, shared this method, which I call the ‘test and learn’ model of change. During times of transition — when our possible selves are shifting wildly — the only way to create change is by putting our possible identities into practice, working and crafting them until they are sufficiently grounded in experience to guide more decisive steps.

The test-and-learn approach recognizes that the only way to counter uncertainty and resist the pull of the familiar is to make alternative futures more vivid, more tangible, and more doable. We acquired our old identities in practice. Likewise, we redefine them, in practice, by crafting experiments, shifting connections, and making sense of the changes we are going through. These three common practices lie at the heart of the most disparate of career changes, lending logic to what can look like chance occurrences and disorderly behavior.

Crafting experiments

By far the biggest mistake people make when trying to change careers is delaying the first step until they have settled on a destination. This error is undermining because the only way we figure out what we really want to do is by giving it a try. Understandably, most people are reluctant to leap into the unknown. We must test our fantasies — otherwise, they remain just that. I discovered that most people create new working identities on the side at first, by getting involved in extracurricular ventures and weekend projects.

Crafting experiments refers to the practice of creating these side projects. Their great advantage is that we can try out new professional roles on a limited scale without compromising our current jobs or having to leap into new positions too quickly. In almost every instance of successful change that I have observed, the person had already been deeply engaged in the new career for quite some time.

There are many ways to set up experiments that work. Newly resolved to explore a range of possibilities, Susan took freelancing assignments in her old line of work and did pro bono work for charities as her lifeline to get her through this difficult period. Through that work, she began to develop contacts that led to paid charity consulting. Gradually, she became immersed in nonprofits, a sector she had never expected to find a career in. And she found herself enjoying freelancing. Today, she is working with the largest UK consulting firm that specializes in charities, and she has this to say: “All I hope is that I never again make the mistake of jumping before giving myself the chance to explore what I really want to do.”

Other people use temporary assignments, outside contracts, advisory work, and moonlighting to get experience or build skills in new industries. Thanks to a temporary stint at the helm of his division, Harris got over his fear, which had silently plagued him for years, that he lacked the finance and cross-functional background necessary to be a good general manager. This concrete experience, more than any amount of self-reflection, helped him envision himself as a general manager. Taking courses or picking up training and credentials in a new area is still another way of experimenting. For many of the people in my study, an executive program, sabbatical, or extended vacation improved their capacity to move in a new direction. These breaks are powerful because they force us to step back from the daily routine while engaging us with new people and activities.

Shifting connections

Consider how common it is for employees to say of their companies, ‘There is no one here I want to be like’. At mid-career, our desire for change is rarely about only the work we do; it is perhaps more importantly about changing our working relationships so they are more satisfying and inspiring. Shifting connections refers to the practice of finding people who can help us see and grow into our new selves. For most successful career changers I have observed, a guiding figure or new professional community helped to light the way and cushion the eventual leap.

Finding a new job always requires networking outside our usual circles. We get ideas and job leads by branching out. Gary, for example, used his alumni and company networks quite successfully. It was an ex-employee of his company — someone he didn’t know personally — who got him the temporary project at his current company. But what clinched his decision, what made this job different from all the other conformist roles he had considered, was the opportunity to work for a role model he had long admired and from whom he could learn the ropes.

Seeking refuge in close working relationships is natural in times of change and uncertainty. But Harris made a classic mistake in turning to an old mentor, Alfred, who was too invested in Harris remaining the unsure protégé to give him room to grow. Harris’s way out of this ‘co-dependent’ relationship came via a person he had met casually at a professional conference. Gerry, the company founder who later hired Harris as his COO, initially approached Harris for regulatory advice. Eventually, they developed an informal consulting relationship. In Gerry, Harris found a person who believed in his potential as a general manager and offered a different kind of close, interdependent working relationship: “It was such a contrast to my relationship with Alfred,” Harris says. “It’s not as paternal. Gerry knows things I need to learn — things that re late to creative financing, ways to raise money — but he also needs to learn from me. He doesn’t know how to run a company, and I do. He’s looking to me to teach him what’s necessary to develop an organization, to build a foundation. I think I can learn a lot from Gerry, but it’s a more mature and more professional relationship than I had with Alfred.”

To make a break with the past, we must venture into unknown networks — and not just for job leads. Often it is strangers who are best equipped to help us see who we are becoming.

Making sense

In the middle of the confusion about which way to go, many of us hope for one event that will clarify everything, that will transform our stumbling moves into a coherent trajectory. Julio Gonzales, a doctor trying to leave the practice of medicine, put it like this: “I was waiting for an epiphany — I wake up in the middle of the night and the Angel of Mercy tells me this is what I should do.” The third working identity practice, making sense, refers to creating our own triggers for change: infusing events — the momentous and the mundane — with special meaning and weaving them into a story about who we are becoming.

Every person who has changed careers has a story about the moment of truth. For John Alexander, the would-be author I’ve mentioned, the moment of truth came when, on a whim, he visited an astrologer. To his surprise, the first thing she said to him was, “I’m glad I haven’t been you for the last two or three years. You have been undergoing a painful internal tug-of-war between two opposing factions. One side wants stability, economic well-being, and social status, and the other craves artistic expression, maybe as a writer or an impresario. You may wish to believe that there can be reconciliation between these two. I tell you, there cannot be.” Another career changer, a woman who had grown increasingly frustrated as an executive in a high-tech start-up, said, “One day my husband just asked me, ‘Are you happy? If you are, that’s great. But you don’t look happy.’ His question prompted me to reconsider what I was doing.”

It would be easy to believe from such accounts that career changes have their geneses in such moments. But the moment of insight is an effect, not a cause, of change. Across my many interviews, a striking discovery was that such moments tended to occur late in the transition process, only after much trial and tribulation. Rather than catalyzing change, defining moments helped people make sense of changes that had long been unfolding.

Trigger events don’t just jolt us out of our habitual routines, they are the necessary pegs on which to hang our reinvention stories. Arranging life events into a coherent story is one of the subtlest, yet most demanding, challenges of career reinvention. To reinvent oneself is to rework one’s story. At the start of a career transition, when all we have is a laundry list of diffuse ideas, it unsettles us that we have no story. It disturbs us to find so many different options appealing, and we worry that the same self who once chose what we no longer want to do might again make a bad choice. Without a story that explains why we must change, the external audience to whom we are selling our reinvention remains dubious, and we, too, feel unsettled and uncertain.

Good stories develop in the telling and retelling, by being put into the public sphere even before they are fully formed. Instead of being embarrassed about having visited an astrologer, for example, John told everyone his story and even wrote about it in a newspaper column. The closer he got to finding his creative outlet, the more the episode made sense and the less often his story elicited the ‘Why would you want to do that?’ reaction. By making public declarations about what we seek and about the common thread that binds our old and new selves, we clarify our intentions and improve our ability to enlist others’ support.

The road now taken

Most of us know what we are trying to escape: the lockstep of a narrowly defined career, inauthentic or unstimulating work, numbing corporate politics, a lack of time for life outside of work. Finding an alternative that truly fits, like finding one’s mission in life, cannot be accomplished overnight. It takes time, perseverance, and hard work. But effort isn’t enough; a sound method and the skill to put it into practice are also required.

The idea of working one’s identity flies in the face of everything we have always been told about choosing careers. It asks us to devote the greater part of our time and energy to action rather than reflection, to doing instead of planning. It tells us to give up the search for a ten-point plan and to accept instead a crooked path. But what appears to be a mysterious, road-to-Damascus process is actually a learning-by-doing practice that any of us can adopt. We start by taking action.

Read the original article on Harvard Business Review.