I'm headed to two graduations this weekend, and that sea of caps and gowns makes me think back to my own transition from those "time-honored walls" into the real world. 

Here's a snapshot of baby Carole Ann, with my mom adjusting my silly hat and glasses; I was SO ready to close the "good student" chapter of my life and take the world by storm. But there was a hitch: I graduated with a liberal arts degree and absolutely no understanding of how to frame my skill set. (Can I get an amen?)

I'm thinking this week about David Whyte's Crossing the Unknown Sea: Work as a Pilgrimage of Identity, which I read years ago but continues to stay with me as one of my favorite books about career paths. Whyte is a poet who applies poetry to corporate life; he's even sometimes known as the Corporate Poet (you guys, there's truly a job out there for each of us). 

In his book, he examines the meaning of Rainer Maria Rilke's poem, The Swan, translated by Robert Bly, as it applies to our work identities. Swans lumber awkwardly on land, but as soon as they lower themselves into the water, they become an image of grace and belonging.

Single-track careers are a thing of the past. In the modern job economy, we want our work to be an expression of who we are and our purpose in the world. And since we contain multitudes, there is no single job that will allow us to fully express ourselves.

In today's career landscape, this is the safer path—rather than putting all of your eggs in one basket (a single role or industry), you're highly adaptable with a variety of skills to draw upon professionally...

It might seem a little foggy at first, but with a little attention and intention soon you'll see your meaningful work clearly.

A few weekends ago, I facilitated a staff retreat for a team of scientists and engineers from an innovative medical device startup. As we got to know each other over dinner, the CEO asked me: "So Carole Ann, how did you come to coaching?"

The answer is simple: It all started with a red chair.

Read more about how asking yourself "Where are the red chairs in my life?" is the key to finding your sweet spot and discovering your "thing."

One of my clients, Kelly, is on the hunt for her next position. She’s looking to pivot into something new—diving into policy in the public sector—after several years in corporate finance and operations.

Here’s the challenge: looking through job postings is like trying to drink water out of a firehose.

Culling through Indeed, sorting out job alerts, and finding the right opportunities has left Kelly feeling drained, especially on top of the full-time job that she is so ready to move on from. She’s having trouble staying motivated and positive as she looks to the future.

When embarking on a job search, we usually start with two obvious questions:

• What is the title of the role I want to step into?

• What industry do I want to work in?

We use the answers to these questions to create the framework of the search. For Kelly, that’s becoming a Policy Analyst in state government.

But here’s a different approach to a job search—one that goes far deeper than the job title and industry to bring a more purposeful lens to your search.

This year of change didn't stop me from taking stock of what's sticking with me—some things that happened in spite of the pandemic and some opportunities that came about (or had to shift) because of it. Here they are in my Annual Report for 2020.

Penney Leaderships most inspiring leads for everyone on your list.

When you develop your ability to “manage up,” you become a strategic leader—no matter your job title or where you sit in an organization.

Here’s the problem: most people have a vague understanding of what it means and why it's important.

When you manage up, you lead through influence—to impact decisions made by those with formal authority.

And in the future—when you have a position with formal authority—you won't be someone who just tells people what to do, you'll be someone that people want to follow.

A compelling cover letter doesn't start with you—it starts with them.

There are two stories about why you're applying for the job. The first story starts with you—it's your internal story.

The second story starts with them—it's the external story.

To be sure, it's important to be clear on both of these stories as you pursue a position. And they're not drastically divergent—they both stem from the same place. Both stories say the same thing, but they say it differently. The first story is about persuading yourself that this is a good move. The second story is about persuading them.

Read more to see these two stories in action and learn a subtle change in approach that will make all the difference.

Last weekend, I talked with a new client who has worked at the same company for 22 years. She told me that she feels like she’s been climbing up a mountain, and her boots are getting heavier and heavier. She hasn't felt a sense of purpose or connection to her work in a long time. And it’s exhausting.

She wanted to know: How do I start over after investing so much in my current path?

I’ve talked with so many people who, like her, visualize their work as a mountain. They chose their field and steadily scaled upward over the years. What happens, then, when you suddenly look around and think, “Oh no! I’m on the wrong mountain!”—or when your industry shifts the terrain shifts beneath your feet?

It’s daunting to think about starting all the way at the bottom again—going back to school to earn a new degree or seeking out an entry level job. It often comes with sinking regret that we’ve wasted our time or resources on a path that wasn’t the right one after all.

We need to throw out this mountain metaphor all together. Not only is it an image that keeps us trapped, it’s not true to how the world works now.

Pivoting is not making a mistake. It’s not starting over. It’s a normal part of career development.

Here are four ways to pivot into a new career path—without starting over.

Like so many leaders this year, Alex has been through the wringer. He’s the director of a small museum in northern Vermont, and even before the COVID crisis led to the closures of cultural heritage organizations, he was charged with inspiring a small team to do more with less.

When he joined a Leadership Lab session back in March, he shared some of the challenges he was facing, as well as how pandemic added layer upon layer of complexity and urgency to an already stretched role. Through his little Zoom box on the screen, I could see the heaviness of this charge weighing on his shoulders.

In that session, Alex realized: “I was ignoring the classic signs of burnout. I knew that my exhaustion ran deeper than simply shifting my schedule or delegating a project. I needed to look at my own priorities, to set new boundaries, and to redefine my purpose in order to serve my career and my community.”

As mission-driven leaders, we are taught to be martyrs to the mission—to put ourselves last, to give and give and give. But what happens when you give everything you have to the cause? You are all used up.

If we shift how we relate to our work, we can show up with energy that naturally refuels itself. We can cultivate sustainable leadership practices.

So many of us are carrying the weight of our own cloud of questions, hoping that the answers will come clear at some point. But at the end of the day, when we get a chance to finally sit down and think them through, we feel overwhelmed and exhausted. We turn on Netflix. Here’s what we can do instead.

Two years ago, when I sat down to write my personal Strategic Career Compass, I identified that one of the key ways that I feel fulfilled and successful is through maintaining something called creative tension.

Creative tension is a simple but powerful concept that was formed by Peter Senge, a professor of organizational learning at MIT's Sloan School of Management…

One of my clients recently landed a great new job, and as excited as she was about what’s to come, she came to our next coaching session weighed down with guilt and dread about leaving her current organization.

She wanted to know: How do I tell my manager that I’m leaving? How much notice do I give? How do I make this transition in a way that doesn’t put too much of a burden on my team?

It’s no wonder this was gnawing at her—she told me that her manager regularly joked that, You’re never going to leave me, right? If you do, you have to give me a year’s notice!

While it’s great to know that your boss values your contributions (to the edge of dependency?), no one wants to feel trapped in their position like this.

Here’s what I know to be true…

I have a new puppy / sidekick / coworker named Rosie. She's an adorable, quickly-growing, rescue beagle/terrier mix, and she is my first dog ever. What does having a dog have to do with leadership? As it turns out—everything.

So many of us think about finding a job as one thing: the all-in-one, full-time position where you use your skills and get your full pay.

Here's the truth: There are many different types of jobs for many different types of situations—and they are all legitimate choices.

I started sketching out job types, and created a taxonomy here…

I've seen so many mission-driven leaders dive headfirst into new jobs in a hurry. If their last day at one organization is on a Friday, they'll start the new job on Monday. And why not? They're excited to step into new challenges and the organization needed them there yesterday.

But something I've noticed during is that these rapid transitions don't give us what we truly need. Here’s why it’s essential to take time off between jobs.