Sitting in the Gap

The period between identities is lonely, disorienting, and the most important work you'll do.

Several years ago, when I was in an operating executive role at a startup, one of many I’d held, doing what had become almost rote for me, I started looking at other jobs in industries I’d never worked before.

Not seriously. More like job window shopping. Reading descriptions for roles entirely out of my lane in terms of background and experience, exploring threads of interest.

Even though I had just started my current role a few months earlier, something didn’t feel right; it felt all too familiar in the wrong ways. I’d heard what I wanted to hear from my CEO when he convinced me to join the company, but not what the situation was actually telling me. Despite a funding round and announcement of all they were now ready to accomplish, the company wasn’t ready to go to market; instead of building product they were cutting staff. Customer logos that ran across the homepage had already churned or were about to. The numbers they were certain to hit at the end of the year were, I was starting to realize, fantastical; an assumed outcome based on nothing historical, just upon the hire of myself and an experienced sales leader.

The company was performing growth. That wasn’t a crime, but the miscasting was. I was told I would get to build a team and a strategy. Instead I was playing a cameo, versus a leading role. The company didn’t need a leader; it needed to check boxes for its board, to appear like its stall out was handled. Hire former operator who’d taken a company through to exit: Check. Hire someone who could speak fluently to a board: Check. Anything I had actually done to check these boxes was besides the point.

I was miscast, not as an operator with lived experience, but as a magic bean.

I knew that the miscasting problem would not get solved simply by jumping to another role; I was a known entity in a system that was not structured to accommodate what I needed from it. Startups were always resource strapped and borrowed experience for equity because they couldn’t pay for it outright. In situations where the organization did pay for it, the payee was expected to justify the cost by playing several roles–not just as strategist but as executioner, coach, and in extreme cases therapist.

One of my CEOs likened my role to that of the quarterback, which, while initially complimentary, became a convenient justification for asking me to both throw and receive all my passes.

For my part, I didn’t have a clear narrative to explain what I did for organizations beyond my former roles and companies; flawed proxies for my unique strengths and contributions. This lack of clarity allowed all kinds of operational riff raff to be thrown on my plate–firing people I never hired, signing up for numbers made in rooms I wasn’t in, delivering on strategies I was not bought into. Another role would likely be a repeat of the one before it.

I’d become a high-functioning professional Swiss Army knife, constantly deployed to deliver certainty without the authority to achieve it.

The most satisfaction I ever had in a role had been in a container I’d built autonomously as an equal, committed member, completely outside of the system but undeniable to it. And yet, years later, I found myself frantically drafting poor facsimiles of it within a new system, disappointed for not manifesting that same sense of agency.

I knew where I no longer wanted to be, but not where I wanted to go; I also knew for certain that nothing short of blowing up the path I’d forged over years would get me there. Like with my ideal role I had inhabited many years ago I would have to build the bridge to it, over what felt like a chasm a mile deep, using tools I didn’t yet have.

It felt hopeless, like a bridge too far.

So I stayed on the familiar side, filling in crumbling holes, even while knowing the ground would eventually give way. I rationalized that I had responsibilities on this side–a mortgage, childcare–and my days of bridge building without a net were long gone.

Numerous times the ground under my feet crumbled as expected, but I wasn’t ready to build a bridge, so I looked for familiar roles in familiar situations, buying myself time but also hoping these roles would serve a dual purpose of supporting my bridge. Some roles left clues for me, reminding me of what I was good at; some were solving problems in areas that called to me and offered glimpses into bigger problems no one was yet grappling with, but I wanted to solve.

On occasion I’d get cosmic whacks in the head that I didn’t see for the gifts that they were, bringing me closer to my mission: The funding rounds that were late or never happened, forcing me to break my habit of going where the funding, not my intuition, took me. The disappointed people I encountered along the way who were so smart but thrown off-course from their own intuitions, or stuck working within systems that diluted it; they became generous beta testers of my thinking around the future of work. The mission-rich, executionally challenged visionaries who needed my sensemaking brain to plot out the steps. They helped me plot new options.

I leveraged these roles to keep me legible in the system, knowing full well that eventually I’d have to show up differently, likely outside of it.

I got to the point where a few even asked: What are you building over there?

Nothing, I told them. In my mind I wasn’t lying; The bridge would only exist when the destination was reached.

But it does exist. It has existed quite literally for years. I’ve been protecting it, and maybe myself, waiting for the right moment to show it off, make you all think it just appeared–perfect, sound, safe–leading to a destination that had already been charted.

I had hoped to not spend on this transformation out of pocket, with time and expense I’d earmarked for retirement; with just the legitimacy I’d built to date. But my accumulated tools weren’t enough.

I’d hoped the bridge would build itself, and the world would read my mind and offer up the opportunities to fulfill them without my asking. But the universe said–as my co-founder Lisa used to say when someone made silly requests based on sillier assumptions–And I want a pony.

This is what a dear friend of mine, an executive coach, calls The Gap. The period in between identities, before we fully own our new selves, and we have to occasionally drum up faith from thin air that we’re heading in the right direction, not because it comes with any old world legitimacy; more a hunch.

Gaps are strange things. We tend to look back on them fondly because we can see growth we can’t when we’re in them. Oftentimes it sucks, which is why we do anything to avoid them–take on roles we don’t want; absorb toxic work situations. We’re drafting off the fumes of a world we know will go away, hoping it will sustain our journey. Until it doesn’t.

Some days it feels like sitting in the eye of a hurricane–eerily quiet while watching the rest of the world race by. Any step you make you know will sweep you into it, and so you wait. You prepare. But it’s lonely.

Some days it feels like sitting on the pulse of the world, feeling its heartbeat in a way you simply couldn’t while in the throes of operating.

The signals are different and more nuanced--a text asking how you are doing, a note of understanding and appreciation for your work lands more than outreach by peers or recruiters who are interested in meeting with the old you.

I long to describe in vivid detail what I’m seeing on the other side of the bridge, but it’s still hazy, like a watercolor painting. I can’t quite make out what is there. I suppose this is why I’ve sat on this essay; I’ve been waiting to tell a fully realized story.

But that IS the story; it ends in the middle, with the realization that, as much as I would have loved to have been airdropped into my future, my story cannot have an ending without accepting the bridge.

My story is quieter, and not at all anticipated by anyone other than myself. I wish I could say there’s been an everpresent pull of certainty, but instead I’ve found clues:

New faces responding to my ideas.

Old faces responding differently, indicating they appreciate my journey.

Deep annoyance with friends who attempt to draw maps on my behalf, and then guilt for seeming ungrateful, and then annoyance with myself for not articulating my journey well enough.

Entirely new KPIs: not revenue closed but heads nodding. Not business won, but inklings pursued.

I know that eventually I’ll have to build a new dashboard to show I’ve moved the needle in one direction or another, and show receipts for how others can follow a similar path without getting dizzy.

But today, not being done is enough.