Lessons in Navigating Career Lostness

How to recalibrate your inner compass and rediscover your professional fire

Quick announcment! I’m thrilled and, dare I say, delighted to share that Applications for the Spring 2025 Downshift Decelerator are now open!

This will be our third cohort where, over seven weeks (including a 4-day retreat) we take a group of ambitious professionals who are navigating career transitions through a journey of transformation in their relationship with work. Unpack your attachments to success, reconnect with what lights you up, and rewrite the next chapter of your career to be more energizing, intentional, and aligned. Sound intriguing? You can find all the details by clicking the button below.

Space is limited to 20 participants. Applications are due on February 27th (early bird until February 14th). I’ll be one of the lead facilitators for this cohort. If you have any questions, just hit reply!

For years, I lived a dream career.

I felt deeply inspired by the work I was doing in the field of community building. I was obsessed with the topic of community, endlessly curious about how humans connect, how I could create containers to facilitate that connection, and how it could become a pillar in the world of business.

For 15 years I leaned hard into that passion and was rewarded with great success and fluidity. I led community teams, cofounded and led a business to acquisition, published a book, and established myself as a leader in the field. To this day, I’ve never interviewed for a role, I just rode the wave.

Then came the reckoning. I don’t know when it happened exactly. Sometime after the acquisition. One day the passion was just gone. I lost my spark. My creative tank was empty. It was like I took a wrong turn somewhere but just blindly kept sprinting until I looked around and realized I was helplessly lost.¹

Something needed to change but I had no idea what. This path had taken me so far. It was all I knew. The idea of changing course was terrifying.

I see this happen to a lot of ambitious people: the life they worked so hard to build just stops making sense one day. Burnout, disillusionment, restlessness—whatever form it takes, the message is the same: Something isn’t working.

This isn’t just about career pivots or finding a new job. It’s much deeper. There’s a gaping void between who you are inside and how you’ve been moving through the world.

I thought in this moment, as we open up applications for the Spring ‘25 Downshift Decelerator, it would be a good opportunity to share some of the core lessons I’ve learned so far about navigating career lostness.

I’ve spent the last three years navigating my career and life transition and the last year coaching and supporting dozens of other ambitious professionals in navigating their own transitions. Here’s some of what I’ve learned so far…

I.

It’s scary to take this leap

People will live their whole lives sensing this deep misalignment, but never stopping to take a real look at it.

The reasons are fairly logical and common:

• It’s hard to change course when you have momentum

• The sunk cost fallacy of your career, worrying about having wasted your time

• Worry about what friends and family will think if you make a change

• Community and societal pressures to do things a certain way

• The discomfort of being with your emotions

• The fear of what you’ll find if you look inward

• A sense of obligation to earn for your loved ones

• It’s just easier to stay the course (until it isn’t)

So we push it off. “Next year”. “After I hit this next milestone”. “When things feel more secure.”

Making this change tasks risk. It requires a leap of faith. You have to lose sight of the shore and be willing to float in the abyss.

II.

Ambitious people have similar inner stories around success

Once you’ve taken the leap, the first step is to take a peek inside.

Ambitious people tend to suffer in similar ways. Of course, we all have different flavors, but there are clear themes.

Some of the common stories I’ve seen in myself and others:

• “I feel like I’m wasting time if I’m not working.”

• “If I don’t leave a legacy, my life will have been a waste of time.”

• “My self-worth is dependent on my most recent success or failure.”

• “I constantly feel like everything is urgent, and I’m always in a rush.”

• “I see other people who seem to have it all figured out, and judge myself for feeling so lost.”

• "I’m worried that if I’m not successful, I’ll end up broke and struggling financially.”

These are just some of the stories that lead us to chase success, push through exhaustion, and tell ourselves the struggle is worth it.

The first step is to just become aware of these stories and how they’ve been influencing how you show up in the world. For me, the moment I realized a deeply-held belief that “I am not enough”, and that I needed to be successful in order to be enough, everything started to change.

I’d tell you to try to recognize these stories without judgment but I know from experience how hard that is. “Being gentle” with myself hasn’t come easily. My first response is usually judgment and self-criticism.

If you don’t feel gentle right away, that’s okay. Let yourself feel whatever there is to feel as you surface these stories. There may be shame, guilt, anger, sadness… the full spectrum. These emotions won’t hurt you. It’s the refusal to feel those emotions that’s been causing you suffering.

The gentleness and compassion will come in time, I promise.

III.

Slow is fast, even when it feels really fucking slow

Ambitious people are always running. There’s always another goal, another milestone, another problem to solve. The brain is constantly scanning for what’s next.

At Downshift, we talk a lot about slowing down. Some assume that means doing less—stopping, opting out. That’s terrifying for ambitious people who have long stayed busy in order to avoid all that arises when we’re still, and who tie their self-worth to being productive.

Slowing down isn’t about inactivity. Slowing down means coming into contact with reality—not the imagined future, not the past, but this moment.

It’s from this place of presence that we can start to clean up—to notice where we’re stuck in old patterns, where we’re repeating inherited fears, and where we’re making choices that aren’t truly ours.

It’s not about doing nothing. Trust me, you’ll be doing a whole lot. It just won’t be external doing. It won’t be doing for the perception of achievement or success.

You’ll be doing work on yourself, to reduce your suffering and, as a result, the suffering of the lives of others. I can’t think of anything more productive.

IV.

Alignment happens when your inner truth matches your outer choices

Burnout isn’t just about working too much. It’s a symptom of misalignment. It’s the result of spending years ignoring your heart and soul.

Most of us shape our careers based on fear—fear of rejection, insecurity, conflict. That fear leads us to say yes when we want to say hell no and say no when we want to say oh fuck yes. It leads us to pursue paths that feel “safe” instead of true.

The challenge is, we’re social creatures. We crave belonging. And to some degree, we need to adapt to be included in the spaces we share. That’s natural. But these contortions take a toll. Over time, if the gap between our inner truth and our outer life becomes too big, we lose sight of who we are.

The work is to close that gap—to recalibrate our inner compass until our outer decisions reflect who we truly are.

V.

Being lost is part of the process

When I first stepped down from my company I treated transition like a problem to solve.

I jumped straight into action—testing out new skills, exploring different career paths, taking courses—believing that if I just experimented enough, I’d figure out my next move.

Transformation doesn’t work that way. As William Bridges would say in his book Transitions, I rushed into my “new beginning” without fully acknowledging what was ending.

Before we can move forward, we have to make space for what’s ending and sit in the uncertainty that follows. That uncomfortable, in-between space—the neutral zone, the abyss—isn’t a problem to solve. It’s where change and realignment happens.

Sitting in lostness can feel excruciating for ambitious types who are so used to doing. But when you’re lost in the jungle, you don’t just keep sprinting. You stop, and get your bearings.

This may be the first time in your life that you’re asked to do less, to slow down. Working with the parts of you that crave productivity and busyness will be a regular part of your journey.

Many of my coaching clients come to me thinking that my job is to help them get out of the jungle as quickly as possible. My true job, at least at first, is to support them in staying in it.

VI.

We tend to ignore our bodies and rely too much on our minds

For most of my life, I’ve led with logic. Every decision has been a process of weighing the pros-and-cons, an endless intellectual exercise. I used to roll my eyes at phrases like “listen to your body.”

But it’s real. And it’s been a game changer.

This is common for ambitious professionals. We tend to be head-types, using our intellect to move through the world. But our bodies hold immense wisdom, constantly signaling what feels aligned and what doesn’t. It took practice, but I started tuning in—paying attention to tension, warmth, constriction, movement, etc.—and I learned these sensations weren’t random. They were guiding me.

Fear shows up as tightness in the chest, a knot in the stomach, a fiery wave of energy across my shoulders, and a busy mind.

Alignment feels like expansion, warmth, openness, flow, and a quiet mind.

Try it out:

Think about a decision you’re sitting with at this moment. As the thoughts arise, turn your attention instead toward your body.

Set a timer for 10 minutes to give you the real space you need to be with your body (the temptation will arise to just move back to your thoughts quickly).

Close your eyes and, one at a time, bring each potential path into your awareness. With each one, notice what you feel. What sensations, feelings, images, energy movements arise? Where do you notice expansion? Where do you notice contraction?

What does your body have to teach you?

Tip: If you’re having trouble feeling into it, take a few deep breaths into the part of your body where you notice subtle sensations, inviting it to expand.

VII.

There’s no map

Transition is a complex process. There isn’t one perfect path out there waiting for you. On the contrary, the options are limitless.

Again, imagine yourself standing in a dense jungle—there’s no horizon in sight, just towering trees and thick brush. Wouldn’t a map feel nice? The urge to find a clear, paved road is strong.

But transitions don’t work like that. We don’t get a full plan—we get a direction. We use our intuition to figure out the next step to take. Then we take it and see what new insight is revealed.

Eventually, the landscape shifts. The path becomes clearer. The trees may become less dense and we can catch glimpses of a new horizon. But we don’t start with a destination—we start with a feeling, a pull.

VIII.

Transition is a team sport

For the first year of my transition, I tried to figure it out by myself. I sat in uncertainty, paralyzed—afraid of taking the wrong step.

It wasn’t until support started arriving—through coaches, therapists, retreats, friends, and communities—that things shifted. They held me in my endings and through extended periods of lostness.

They gave me the practices to heal and recalibrate my inner compass. Parts work, Zazen, somatic experiencing, breathwork, and other methodologies have become my toolkit for doing this work. These tools don’t give you answers—but they help you listen more deeply. They help you see where your compass still needs recalibrating.

This is how it’s meant to be. We’re not meant to move through life alone, especially when in transition. We need mirrors—people who reflect back the parts of ourselves we can’t yet see. We need guides who have walked the path before. We need people to hold us lovingly and nonjudgmental so that we can learn to hold ourselves in the same way.

It’s also helpful to have others by our side who are lost in the jungle too. Trust me, you are not alone.

A final thought…

If you’re in the midst of a transition, or standing on the precipice of your abyss, the most important thing I can tell you is this:

You don’t need to have it all figured out.

The answers aren’t waiting out there—they’re already inside you. The real work isn’t in mapping the future, but in unlearning the stories that have kept you from hearing yourself.

Start by listening. What’s the right next step?

If you’d like to embark on this journey with the support of Downshift coaches and other journeyers, Applications for the Spring 2025 Downshift Decelerator are now open!

This cohort kicks off on March 18th. Applications are due February 27th (early bird until Feb 14th for $500 off).

1. I’m continuing to learn what felt misaligned for me at that time. I still find I’m deeply curious about community, but what I now know is that the form it was taking was lacking a level of depth and heart that I yearned for. The corporate nature of my work was killing my soul. And I longed for a deeper form of service, which I later found with coaching. Now I’m weaving a lot of my passion for community facilitation in with deeper coaching and healing work and BOY is it feeling good (so far).