Revisiting the hero's journey

Why does it call us, and who do we become?

Forth Eorlingas!
- Battle Cry of Rohan

It is March 2024, and I’m hyped as I record a Loom video for my remote team.

Our situation is both dire and exciting. We have just launched our new product — “pagerduty for data” — as our last attempt to save the business.

And the early results are promising: More than 25 customers — real businesses and teams, not one-off data engineers tinkering — have signed up for the product, successfully onboarded, and are being alerted by our system.

These clients are, for the most part, brand new. They are excited about the product and providing feedback that it solves acute problems. Many of them have indicated that this version, or a future iteration, is 10X better than other options on the market. They are generally aligned on our roadmap.

I am hyped, as this all feels different. It no longer feels like we are pushing a product that no one wants. It no longer seems like we have a solution looking for a problem. We are finally solving a problem data teams care about, and have the start of product-market fit and genuine customer pull.

But here is the rub: the last week has been slow. We had come out of the gate hard and fast, sometimes onboarding 2-3 new clients per day, but we are losing pace and momentum.

So I am recording this video, urging my team to keep pushing forward. I am nearly out of cash, and just 30 days away from a deadline to pull together a last minute rescue financing.

“Two things could happen,” I tell my team. “We could continue to push and onboard new clients, see the pace accelerate, and the company will have a future. Or we allow this slowdown to continue, and it will be our end.”

Why we laud heroes

The hero’s journey is a classic narrative structure that speaks to humans almost universally. What does it look like?

A protagonist goes on a perilous quest, overcomes obstacles, and comes home transformed. The hero is called to adventure, often initially resisting. The hero meets a mentor who offers training, guidance, and knowledge, and the confidence to pursue a big goal. Harrowing challenges then test the hero, who makes new friends and builds alliances. And in most narratives, the hero overcomes seemingly insurmountable obstacles, wins the day, and returns home transformed.

There are many examples: Frodo the Hobbit, Katniss Everdeen, King Hal, Lieutenant John F. Kennedy, Beowulf.

One of these might call to you more than the others. And there is something seemingly masculine about "hero worship."

But anyone can go on a quest; the hero’s journey is for everyone. We live in an age where women serve in combat roles. It was not just Eomer who charged the Pelennor Fields; there was also Lady Eowyn, shieldmaiden of Rohan, who rode alongside him and killed the Witch-king of Angmar.

While the hero’s journey resonates because we seek the acclaim of victory, we are more strongly drawn to crucible moments for their transformative power. The thrill and adrenaline of near-death strips us down to our raw essence, revealing who we truly are.

Most heroes are slain

While we best remember those who survive their trials, most heroes do not.

For every man rescued at Dunkirk, countless more English soldiers died in the battles before and after. For every Lady Eowyn, there is a King Theoden. For every Harry Potter, there is a Cedric Diggory.

So while we most often welcome the hero's journey for its promise of fame and glory, we do not think of the vast majority of us that are slain. We ignore that embarking on a perilous journey likely means we may very well be among the fallen.

I am aware that, as a high-achieving tech founder and operator, referring to myself as having “come through the hero's journey” or having “been slain” may seem dramatic. However, for a founder, whose life force becomes bound up in what they build, this all does feel like life and death. When I was navigating our company's crucible moment, recording motivational videos, and urging my team forward, I envisioned myself as blowing the metaphorical war horns of our victory.

But I did not emerge, like Lady Eowyn, wounded yet glorious; that version of myself, and of our company, instead lay slain.

The hero's journey transforms us

Yet nearly a year later, if you ask me if I regret our journey, I will tell you that the unequivocal answer is no.

I wish our outcome had been different, of course. As I listen to the stories of other successful founders and how they overcame their crucible moments, I feel deep-seated envy. I feel the sicknesses in me rising up, and my most base and difficult urges threatening to overwhelm my better angels.

But I also emerge a founder who knows they left it all on the metaphorical field, and feels transformed. Transformed by the training, transformed by the challenge we sought out, transformed by the spiritual nature of looking death in the face and then stepping across that threshold to what lies beyond.

While a large part of me wishes that I had been transformed by overcoming our crucible moment, I do not wish for who I was beforehand.

The journey made me into a better person. It turned me into a better husband. It created in me a better father. It forged in me a better, wiser, and more mature businessperson. It instilled in me a true sense of who I am, what I care about, and why I do what I do.

Here I lie

I urged my team that morning and in all the ones that came, and we played out our final hand to the bitter end. In the 30 days of operating that remained, we onboarded another 20 clients — bringing our total to almost 50 in less than 60 days from launch.

And while this was huge, the harsh reality was this: we had been forced into giving away this new product for free. The slowdown in our second month of onboarding made us wonder whether the product was a must-have. We had spent 4 years and $7M building the company. There were too many questions, and we had just not accomplished enough to create the conviction to continue the fight. Workstream.io, including me, my co-founder and my entire team, lay slain.

So what should we all take away from our journey, if anything? Should founders become fatalists? I don’t think so.

Instead, founders should ask: why does the hero's journey call me in the first place? What should I expect of myself in my crucible moment? And which new version of myself will emerge?

Ultimately, what matters is not whether you survive your journey — what matters is who you become as a result of it.