What career emergence actually feels like

A few weeks ago, I wrote about an idea I’ve come to call career emergence over on Lenny’s Substack. Career emergence borrows from emergence in nature, where individual parts—bees, starlings, ants—follow simple local rules and, together, create complex patterns like beehives and murmurations that no individual could design or predict. The career version is the idea that instead of trying to design your career toward a clear long-term plan, you can clarify your principles, focus on the right next step, and trust that something you could never have planned might emerge. This isn't the same as drifting—you may not have a destination, but you do have a way of deciding what to do next.

As I worked on that piece with Lenny's team, I kept thinking about the last five years of my own career—both the magic of career emergence and how absolutely terrible it can feel while you’re in the middle of it. So I wanted to add just a little color and normalize the fact that not having a plan can be incredibly powerful—and can also occasionally feel like being stabbed with dull spoons while wandering through a tunnel in the dark.

My last five years have been a great example of emergence—lotta wandering, no plan, strong principles, and some real magic. So I thought I’d share the three lessons I wish I’d known ages ago using examples from this most recent phase in my career:

1. You need a compass when you don’t have a map.

Five years ago, I left my last full-time COO role knowing I was ready for something different. I was a bit burnt out, so I knew much more about what I didn’t want than what I did.

I had three theories: take a C-level job at a big company, probably Chief People Officer; take a CEO role; or start something myself. I started with the first two because starting something myself felt the least energizing or clear.

Looking back, it’s so obvious that I was running away from my past roles rather than running toward something I was excited about. (Thinking a CPO job sounded relaxing is probably the clearest sign, lol.) I ended up in some really wonderful conversations, but I was interviewing for jobs I knew I’d be great at and feeling so, so drained. Eventually I had to admit that I had run out of energy to manage up.

I explored the CEO path too and quickly realized it wasn’t for me. (My basic assessment of most take-over CEO jobs: someone takes a shit all over a business, hands it to you and says, “Oh good, you’re here to clean it up.”)

Ok, lotta detail Molly, pick up the pace.

So I started building, somewhat begrudgingly. If you'd asked me four years ago what I was building, I would have told you I wanted to build the McKinsey for tech—a powerful consulting firm that helped founders build better companies.

Meanwhile, somewhat randomly, I started two communities. Glue Club came out of an email from a CEO asking me to meet with one of his leaders. I couldn’t meet with everyone individually, but maybe I could create a group where they could learn from each other? I put up a LinkedIn post, and Glue Club was born. Around the same time, I was noodling on another idea: a community for women leaders built around actual friendships. A friend suggested I just “throw one weekend retreat and see how it goes.” That became the Guild.

Btw, I was also very spastically and sporadically writing on LinkedIn and Substack. There was no content strategy or grand plan here, I promise. I just liked sharing things with the world, so I kept doing it.

It took me about a year to realize I didn’t actually want to build the McKinsey for startups. I got much more energy from working with leaders and building these communities. So, slowly—so slowly—I started moving my time toward them.

The only clear theme through all of this is that I kept trying to follow my energy. I didn’t know where any of these choices were leading. I just knew they were giving me information about the kind of work that brought out the best in me.

At some point, I started using the word “Joy” as my compass: the work I would want to do even if no one was noticing. That sounds slightly woo-woo, but it became incredibly practical. COO jobs drained me: stop. Working with leaders gave me energy: do more. Building communities made me happy: keep going. Writing made me feel connected to people I wanted to help: keep doing that too.

If you’re going to give up the map, you need something else to navigate by. Find your version of “joy.” It might be learning, impact, craft, autonomy, or the people you want to be around. In the language of career emergence, these become your “local rules”—the principles you use to make the next decision when you don’t know where it’s ultimately leading. You need to know yourself well enough to define them, and then actually listen to them.

2. Not knowing where you’re going feels fucking terrible.

I feel like this gets left out of every story about career reinvention. In retrospect, I can make these five years sound charmingly experimental. I followed my energy! I built some communities! I wrote things!

That is not what it felt like.

Remember those C-level jobs I walked away from? There was one in particular that I still think about because I know how much I would have learned by doing it. And that would have been enough 10 or even 5 years earlier, but it wasn’t anymore.

To turn it down, I took a lot of walks with myself repeating, “What does this get you that you don’t already have?” Eventually, I hit send on the “I’m out” email. I felt good for a bit, and then was hit with a wave of regret. I almost went back and took that job four times over the following 12 months. Not even exaggerating.

And that was kind of what this whole period felt like. Murky and scary and confusing. I watched other people take big jobs with impressive titles while I struggled to explain what exactly I was doing with my time. Honestly, when someone asked me, “So what are you doing these days?” or “How’s Molly Inc.?” it felt like being stabbed in the heart with a bunch of dull knives.

The hardest part was that I had no external evidence that I was going in the right direction. There was no promotion or title or salary increase telling me, “Good job, keep going.” I had to trust my own compass—which sounds lovely when I write it now and felt fucking terrible at the time.

And I think there’s a particular danger in this phase: when you feel lost, you really, really want to stop feeling lost. So you’re tempted to make a big decision that gives you an answer.

I had plenty of opportunities to do that. I could have done something like raised VC money for Glue Club. Taken a big shiny job. I’ve watched a lot of friends get overwhelmed and grab on to the first “life raft” that someone throws them. It is so important to be wary of decisions that are a “one-way door” (hard to take back) in the wandering phase. Anything reversible is your friend; anything permanent might just be a temporary fix for your anxiety, not a long-term happy place.

The hard part, of course, is that this means you have to get better at tolerating being lost. The wandering is, unfortunately, the point. You have to resist the urge to turn uncertainty into certainty before you actually have enough information to make a great decision.

This is also why I’m SO GLAD I hired a coach during this period. Vanda gave me somewhere to go when I was scared and confused without immediately trying to make the uncertainty go away. She helped me stay in the wandering instead of trying to solve it. She also helped me come up with a better answer to “What are you doing these days?” Instead of trying to explain what I was building—which I genuinely did not know—I learned to talk about what I was learning. I wish I’d figured that one out three years earlier.

I think this is the part you have to be prepared for if you’re going to pursue a more emergent career: you can be going in the right direction and still feel completely lost. Being lost isn’t necessarily a problem you need to solve. Sometimes you need to give yourself enough time and space to wander your way through it.

3. You cannot plan for what doesn’t exist yet.

A couple of years into this wandering, a friend organizing a new TED conference asked if I wanted to give a talk. A TED talk had always been on my list, and the conference was focused on an audience I’d come to think of as “my people”: mid-career leaders. It felt like a full-body yes.

A couple of months earlier, I’d turned down a fun-sounding but ultimately misaligned speaking opportunity in Bhutan. Who doesn’t want to go to Bhutan?? But it wasn’t a full-body yes, so I said no. I didn’t know what I was making room for. It turned out to be TED.

My only goal for the talk was to learn as much as I could and create something I was proud of. I had no particular plan for what would happen afterward.

About a year later, I got a call from Valentina, one of the people at TED who had helped curate my talk. She said, “Molly, have you ever thought about doing a podcast?”

I said, “Valentina, do we need more podcasts?”

That conversation eventually led to TED offering me the opportunity to take over as host of WorkLife, the podcast they’d built with Adam Grant over the previous seven years.

WorkLife was not unlikely to be in my five-year plan. It was impossible to be in my five-year plan.

Five years ago, I didn’t know TED. I wasn’t really a writer. I had never built a community or even considered it. I was a COO who knew she didn’t want to be a COO anymore.

But the offer from TED changed the way I saw the previous four years. The TED team saw something in me that I couldn’t yet see in myself. You know that feeling when you’re staring at something that doesn’t make sense, and then someone turns it 90 degrees, and suddenly you can see what it is? That’s what this felt like. My random collection of projects, scattered in what felt like haphazard piles, suddenly looked like a sculpture that had almost been intentional.

Looking backward, I could suddenly see a pattern that had been completely invisible to me while I was creating it.

And once I saw it, I realized this wasn’t the first time. I can tell a version of this story about almost every major moment of emergence in my career. Lots of wandering, following what felt interesting or important, and then a new path appearing that I never could have planned for.

There was no way I could have drawn a line from COO to WorkLife five years earlier. All I could do was pay attention to what gave me energy, say no when something felt wrong even when I couldn’t fully explain why, and keep choosing the next step that felt right.

And then, eventually, the pattern emerged.

Looking backward, I can see it clearly. Looking forward, I never could.

And, btw, I still have no idea where I’m going.

The difference is that I don’t think I need to know anymore.

I know what my compass is—my local rules. I trust myself to figure out the next step. And I have a little more faith that if I keep doing that, more magic is waiting somewhere around the corner—or maybe down a steep, bumpy hill full of mud and rocks.

I guess I’ll find out when I get there.

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What else?

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