Tag: work

Solve Problems Before They Happen by Developing an “Inner Sense of Captaincy”

Too often we reward people who solve problems while ignoring those who prevent them in the first place. This incentivizes creating problems. According to poet David Whyte, the key to taking initiative and being proactive is viewing yourself as the captain of your own “voyage of work.”

If we want to get away from glorifying those who run around putting out fires, we need to cultivate an organizational culture that empowers everyone to act responsibly at the first sign of smoke.

How do we make that shift?

We can start by looking at ourselves and how we consider the voyage that is our work. When do we feel fulfillment? Is it when we swoop in to save the day and everyone congratulates us? It’s worth asking why, if we think something is worth saving, we don’t put more effort into protecting it ahead of time.

In Crossing the Unknown Sea, poet David Whyte suggests that we should view our work as a lifelong journey. In particular, he frames it as a sea voyage in which the greatest rewards lie in what we learn through the process, as opposed to the destination.

Like a long sea voyage, the nature of our work is always changing. There are stormy days and sunny ones. There are days involving highs of delight and lows of disaster. All of this happens against the backdrop of events in our personal lives and the wider world with varying levels of influence.

On a voyage, you need to look after your boat. There isn’t always time to solve problems after they happen. You need to learn how to preempt them or risk a much rougher journey—or even the end of it.

Whyte refers to the practice of taking control of your voyage as “developing an inner sense of captaincy,” offering a metaphor we can all apply to our work. Developing an inner sense of captaincy is good for both us and the organizations we work in. We end up with more agency over our own lives, and our organizations waste fewer resources. Whyte’s story of how he learned this lesson highlights why that’s the case.

***

A moment of reckoning

Any life, and any life’s work, is a hidden journey, a secret code, deciphered in fits and starts. The details only given truth by the whole, and the whole dependent on the detail.

Shortly after graduating, Whyte landed a dream job working as a naturalist guide on board a ship in the Galapagos Islands. One morning, he awoke and could tell at once that the vessel had drifted from its anchorage during the night. Whyte leaped up to find the captain fast asleep and the boat close to crashing into a cliff. Taking control of it just in time, he managed to steer himself and the other passengers back to safety—right as the captain awoke. Though they were safe, he was profoundly shaken both by the near miss and the realization that their leader had failed.

At first, Whyte’s reaction to the episode was to feel a smug contempt for the captain who had “slept through not only the anchor dragging but our long, long, nighttime drift.” The captain had failed to predict the problem or notice when it started. If Whyte hadn’t awakened, everyone on the ship could have died.

But something soon changed in his perspective. Whyte knew the captain was new and far less familiar with that particular boat than himself and the other crew member. Every boat has its quirks, and experience counts for more than seniority when it comes to knowing them. He’d also felt sure the night before that they needed to put down a second anchor and knew they “should have dropped another anchor without consultation, as crews are wont to do when they do not want to argue with their captain. We should have woken too.” He writes that “this moment of reckoning under the lava cliff speaks to the many dangerous arrivals in a life of work and to the way we must continually forge our identities through our endeavors.”

Whyte’s experience contains lessons with wide applicability for those of us on dry land. The idea of having an inner sense of captaincy means understanding the overarching goals of your work and being willing to make decisions that support them, even if something isn’t strictly your job or you might not get rewarded for it, or sometimes even if you don’t have permission.

When you play the long game, you’re thinking of the whole voyage, not whether you’ll get a pat on the back today.

***

Skin in the game

It’s all too easy to buy into the view that leaders have full responsibility for everything that happens, especially disasters. Sometimes in our work, when we’re not in a leadership position, we see a potential problem or an unnoticed existing one but choose not to take action. Instead, we stick to doing whatever we’ve been told to do because that feels safer. If it’s important, surely the person in charge will deal with it. If not, that’s their problem. Anyway, there’s already more than enough to do.

Leaders give us a convenient scapegoat when things go wrong. However, when we assume all responsibility lies with them, we don’t learn from our mistakes. We don’t have “our own personal compass, a direction, a willingness to meet life unmediated by any cushioning parental presence.

At some point, things do become our problem. No leader can do everything and see everything. The more you rise within an organization, the more you need to take initiative. If a leader can’t rely on their subordinates to take action when they see a potential problem, everything will collapse.

When we’ve been repeatedly denied agency by poor leadership and seen our efforts fall flat, we may sense we lack control. Taking action no longer feels natural. However, if we view our work as a voyage that helps us change and grow, it’s obvious why we need to overcome learned helplessness. We can’t abdicate all responsibility and blame other people for what we chose to ignore in the first place (as Whyte puts it, “The captain was there in all his inherited and burdened glory and thus convenient for the blame”). By understanding how our work helps us change and grow, we develop skin in the game.

On a ship, everyone is in it together. If something goes wrong, they’re all at risk. And it may not be easy or even possible to patch up a serious problem in the middle of the sea. As a result, everyone needs to pay attention and act on anything that seems amiss. Everyone needs to take responsibility for what happens, as Whyte goes on to detail:

“No matter that the inherited world of the sea told us that the captain is the be-all and end-all of all responsibility, we had all contributed to the lapse, the inexcusable lapse. The edge is no place for apportioning blame. If we had merely touched that cliff, we would have been for the briny deep, crew and passengers alike. The undertow and the huge waves lacerating against that undercut, barnacle-encrusted fortress would have killed us all.”

Having an inner sense of captaincy means viewing ourselves as the ones in charge of our voyage of work. It means not acting as if there are certain areas where we are incapacitated, or ignoring potential problems, just because someone else has a particular title.

***

Space and support to create success

Developing an inner sense of captaincy is not about compensating for an incompetent leader—nor does it mean thinking we always know best. The better someone is at leading people, the more they create the conditions for their team to take initiative and be proactive about preventing problems. They show by example that they inhabit a state rather than a particular role. A stronger leader can mean a more independent team.

Strong leaders instill autonomy by teaching and supervising processes with the intention of eventually not needing to oversee them. Captaincy is a way of being. It is embodied in the role of captain, but it is available to everyone. For a crew to develop it, the captain needs to step back a little and encourage them to take responsibility for outcomes. They can test themselves bit by bit, building up confidence. When people feel like it’s their responsibility to contribute to overall success, not just perform specific tasks, they can respond to the unexpected without waiting for instructions. They become ever more familiar with what their organization needs to stay healthy and use second-order thinking so potential problems are more noticeable before they happen.

Whyte realized that the near-disaster had a lot to do with their previous captain, Raphael. He was too good at his job, being “preternaturally alert and omnipresent, appearing on deck at the least sign of trouble.” The crew felt comfortable, knowing they could always rely on Raphael to handle any problems. Although this worked well at the time, once he left and they were no longer in such safe hands they were unused to taking initiative. Whyte explains:

Raphael had so filled his role of captain to capacity that we ourselves had become incapacitated in one crucial area: we had given up our own inner sense of captaincy. Somewhere inside of us, we had come to the decision that ultimate responsibility lay elsewhere.

Being a good leader isn’t about making sure your team doesn’t experience failure. Rather, it’s giving everyone the space and support to create success.

***

The voyage of work

Having an inner sense of captaincy means caring about outcomes, not credit or blame. When Whyte realized that he should have dropped a second anchor the night before the near miss, he would have been doing something that ideally no one other than the crew, or even just him, would have known about. The captain and passengers would have enjoyed an untroubled night and woken none the wiser.

If we prioritize getting good outcomes, our focus shifts from solving existing problems to preventing problems from happening in the first place. We put down a second anchor so the boat doesn’t drift, rather than steering it to safety when it’s about to crash. After all, we’re on the boat too.

Another good comparison is picking up litter. The less connected to and responsible for a place we feel, the less likely we might be to pick up trash lying on the ground. In our homes, we’re almost certain to pick it up. If we’re walking along our street or in our neighborhood, it’s a little less likely. In a movie theater or bar when we know it’s someone’s job to pick up trash, we’re less likely to bother. What’s the equivalent to leaving trash on the ground in your job?

Most organizations don’t incentivize prevention because it’s invisible. Who knows what would have happened? How do you measure something that doesn’t exist? After all, problem preventers seem relaxed. They often go home on time. They take lots of time to think. We don’t know how well they would deal with conflict, because they never seem to experience any. The invisibility of the work they do to prevent problems in the first place makes it seem like their job isn’t challenging.

When we promote problem solvers, we incentivize having problems. We fail to unite everyone towards a clear goal. Because most organizations reward problem solvers, it can seem like a better idea to let things go wrong, then fix them after. That’s how you get visibility. You run from one high-level meeting to the next, reacting to one problem after another.

It’s great to have people to solve those problems but it is better not to have them in the first place. Solving problems generally requires more resources than preventing them, not to mention the toll it takes on our stress levels. As the saying goes, an ounce of prevention is worth a pound of cure.

An inner sense of captaincy on our voyage of work is good for us and for our organizations. It changes how we think about preventing problems. It becomes a part of an overall voyage, an opportunity to build courage and face fears. We become more fully ourselves and more in touch with our nature. Whyte writes that “having the powerful characteristics of captaincy or leadership of any form is almost always an outward sign of a person inhabiting their physical body and the deeper elements of their own nature.”

Mental Models for Career Changes

Career changes are some of the biggest moves we will ever make, but they don’t have to be daunting. Using mental models to make decisions we determine where we want to go and how to get there. The result is a change that aligns with the person we are, as well as the person we want to be.

We’ve all been there: you’re at a job, and you know it’s not for you anymore. You come in drained, you’re not excited on a Monday morning, and you feel like you could be using your time so much better. It’s not the people, and it’s not the organization. It’s the work. It’s become boring, unfulfilling, or redundant, and you know you want to do something different. But what?

Just deciding to change careers doesn’t get you very far because there are more areas to work in than you know about. A big change often involves some retraining. A career shift will impact your personal life. At the end of it all, you want to be happier but know there are no guarantees. How do you find a clear path forward?

No matter how ready you think you are to make a move, career changes are daunting. The stress of leaving what you’re comfortable with to venture into foreign territory stops many people from taking the first step toward something new.

It doesn’t have to be this way.

Using mental models can help you clarify the direction you want to go and plan for how to get there. They are tools that will give you more control over your career and more confidence in your decisions. When you do the work up front by examining your situation through the lens of a few mental models, you set yourself up for fewer regrets and more satisfaction down the road.

***

Get in touch with yourself

Before you can decide which change to make, you need to get in touch with yourself. No change will be the right one if it doesn’t align with what you want to get out of life.

First, do you know where you want to go? Are you moving with direction or just moving? As a mental model, velocity reminds us there is a difference between speed and direction. It’s easy to move fast without getting anywhere. We can stay busy all day without achieving our goals. Without considering our velocity, we run a huge risk of getting sidetracked by things that make us move faster (more money, a title on a business card) without that movement actually leading us where we want to end up.

As the old saying goes, we want to run to something, not from something. When you start articulating your desired direction, you give yourself clear purpose in your career. It will be easier to play the long game because you know that everything you are doing is leading somewhere you want to be.

When it comes to changing careers, there are a lot of options. Using the mental model of velocity will help you focus on and identify the best opportunities.

Once you know where you want to end up, it’s often useful to work backward to where you are now. This is known as inversion. Start at the end and carefully consider the events that get you there in reverse order.

For example, it could be something as simple as waking up happy and excited to work every day. What needs to be true in order for that to be a reality? Are you working from home, having a quiet cup of coffee as you prepare to do some creative work? Are you working on projects aligned with your values? Are you contributing to making the world a better place? Are you in an intense, collaborative team environment?

Doing an inversion exercise helps you identify the elements needed for you to achieve success. Once you identify your requirements, you can use that list to evaluate opportunities that come up.

Inversion will help you recognize critical factors, like finances or the support of your family, that will be necessary to get to where you want to go. If your dream direction requires you to learn a new skill or work at a junior level while you ramp up on the knowledge you’ll need, you might need to live off some savings in the short term. Inversion, combined with velocity, will help you create the foundation you need now to take action when the right time comes.

Finally, the last step before you start evaluating the career environment is taking stock of the skills you already have. Why do you need to do this? So you know what you can repurpose. Here, you’re using the concept of exaptation, which is part of the broader adaptation model in biology. Exaptation refers to traits that evolved for one purpose and then, through natural selection, were used for completely unrelated capabilities. For instance, feathers probably evolved for insulation. It was only much later that they turned out to be useful for flying.

History is littered with examples of technologies or tools invented for one purpose that later became the foundation for something completely different. Did you know that Play-Doh was originally created to clean coal soot off walls? And bubble wrap was originally envisioned as material for shower curtains.

Using this model is partly about getting out of the “functional fixedness” mindset. You want to look at your skills, talents, and knowledge and ask of each one: what else could this be used for?

Too often we fail to realize just how versatile the experience we’ve built up over the years is. We’re great at using forks to eat, but they can also be used to brush hair, dig in a garden, and pin things to walls. Being great at presenting the monthly status update doesn’t mean you’re good at presenting monthly status updates. Rather, it means you can articulate yourself well, parse information for a diverse audience, and build networks to get the right information. Now, what else can those skills be used for?

***

Evaluate the environment

Looking at different careers, we’re usually in a situation where the “map is not the territory.” It’s hard to know how great (or terrible) a job is until you actually do it. We often have two types of maps for the careers we wish we had: maps of the highlights, success stories, and opinions of people who love the work and maps based on how much we love the field or discipline ourselves.

The territory of the day-to-day work of these careers, however, is very different from what those two maps tell us.

In order to determine if a particular career will work for us, we need better maps. For example, the reality of being an actor isn’t just the movies and programs you see them in. It’s audition after audition, with more rejections than roles. It’s intense competition and job insecurity. Being a research scientist at a university isn’t just immersing yourself in a subject you love. It’s grant applications and teaching and navigating the bureaucracy of academia.

In order to build a more comprehensive map of your dream job, do your research on as large a sample size as possible. Talk to people doing the job you want. Talk to people who work in the organization. Talk to the ones that enjoy it. Talk to the ones who quit. Try to get an accurate picture of what the day-to-day is like.

Very few jobs are one-dimensional. They involve things like administrative tasks, networking, project management, and accountability. How much of your day will be spent doing paperwork or updating your coworkers? How much of a connection do you need to maintain with people outside the organization? How many people will you be dependent on? What are they like? And who will you be working for?

It’s not a good idea to become a writer just because you want to tell stories, open a restaurant just because you like to cook, or become a landscape designer just because you enjoy being outside. Those motivations are good places to start—because it’s equally terrible to become a lawyer just because your parents wanted you to. But you can’t stop with what you like. There isn’t a job in the world that’s pleasurable and fulfilling 100% of the time.

You give yourself a much higher chance of being satisfied with your career change if you take the time to learn as much as you can about the territory beforehand.

***

Elements of planning

You know which direction you’re heading in, and you’ve identified a great new career possibility. Now what?

Planning for change is a crucial component of switching careers. Two models, global and local maxima and activation energy, can help us identify what we need to plan.

Global and local maxima refers to the high values in a mathematical function. On a graph, it’s a wavy curve with peaks and valleys. The highest peak in a section is a local maximum. The highest peak across the entire graph is the global maximum. Activation energy comes from chemistry, and is the amount of energy needed to see a reaction through to its conclusion.

One of the things global and local maxima teaches us is that sometimes you have to go down a hill in order to climb up a new one. To move from a local maximum to a higher peak you have to go through a local minimum, a valley. Too often we just want to go higher right away, or at the very least we want to make a lateral move. We perceive going down as taking a step backward.

A common problem is when we tie our self-worth to our salary and therefore reject any opportunities that won’t pay us as much as we’re currently making. The same goes for job titles; no one wants to be a junior anything in their mid-forties. But it’s impossible to get to the next peak if we won’t walk through the valley.

If you look at your career change through the lens of global and local maxima, you will see that steps down can also be steps forward.

Activation energy is another great model to use in the planning phase because it requires you to think about the real effort required for sustained change. You need to plan not just for making a change but also for seeing it through until the new thing has time to take hold.

Do you have enough in the bank to support yourself if you need to retrain or take a pay cut? Do you have the emotional support to help you through the challenges of taking on a brand-new career?

Just like fires don’t start with one match and a giant log, you have to plan for what you need between now and your desired result. What do you need to keep that reaction going so the flame from the match leads to the log catching fire? The same kind of thinking needs to inform your planning. After you’ve taken the first step, what will you need to keep you moving in the direction you want to go?

***

After you’ve done all the work

After getting in touch with yourself, doing all your research, identifying possible paths, and planning for what you need to do to walk them to the end, it can still be hard to make a decision. You’ve uncovered so many nuances and encountered so many ideas that you feel overwhelmed. The reality is, when it comes to career change, there often is no perfect decision. You likely have more than one option, and whatever you choose, there’s going to be a lot of work involved.

One final model you can use is probabilistic thinking. In this particular situation, it can be helpful to use a Bayesian casino.

A Bayesian casino is a thought experiment where you imagine walking up to a casino game, like roulette, and quantifying how much you would bet on any particular outcome.

Let’s say when investigating your career change, you’ve narrowed it down to two options. Which one would you bet on for being the better choice one year later? And how much would you part with? If you’d bet ten dollars on black, then you probably need to take a fresh look at the research you’ve done. Maybe go talk to more people, or broaden your thinking. If you’re willing to put down thousands of dollars on red, that’s very likely the right decision for you.

It’s important in this thought experiment to fully imagine yourself making the bet. Imagine the money in your bank account. Imagine withdrawing it and physically putting it down on the table. How much you’re willing to part with regarding a particular career choice says a lot about how good that choice is likely to be for you.

Probabilistic thinking isn’t a predictor of the future. With any big career move, there are inevitably a lot of unknowns. There are no guarantees that any choice is going to be the right one. The Bayesian casino just helps you quantify your thinking based on the knowledge you have at this moment in time.

As new information comes in, return to the casino and see if your bets change.

***

Conclusion

Career changes are some of the biggest moves we will ever make, but they don’t have to be daunting. Using mental models helps us find both the direction we want to go and a path we can take to get there. The result is a change that aligns with the person we are, as well as the person we want to be.