How the psychology of pivots holds us back

Pivoting is a personal and emotional act

At Workstream, we went through two major pivots and three core products.

A pivot from “Invision for FP&A” to “Zendesk for Data” in our first year; and a hail mary to “Pagerduty for Data” in our final months.

I often hear praise for our willingness to pivot and our competency in navigating these changes. “What amazing founder hustle!” “What a testament to your and Chris’ resiliency!” “That’s how you have to do it; you just ran out of time!” Indeed, there is much I am proud of in our work.

But when reflecting on our pivots today, I am mostly filled with regret. Not regret that we made them or brought the products we did to market—but regret that we didn’t pivot more.

I regret that, in our first pivot, we didn’t consider options further removed from our original vision. I regret that we didn’t make our second pivot sooner. Shifting twelve to eighteen months earlier could have made all the difference for our final shot, which appeared to hit the goal.

I regret all the days when, instead of trying something new, we clung to the status quo. And I try to understand why, in those moments, I often chose evolution, instead of full scale revolution.

Knowing How to Pivot is Only So Helpful

Most technology founders know what a pivot is and how to execute one.

There are many excellent resources on the topic. This morning, I stumbled across The Art of the Pivot by Lenny Rachitsky, as well as Dalton Caldwell’s All About Pivoting talk at YC. These are solid resources from people who have studied hundreds of early-stage founders.

But as I reflect, I am also struck by how these resources, while tactical, do not address the underlying psychology of pivots that make them so difficult.

Dalton explains “why people take too long to pivot,” citing reasons like loss aversion and the belief that persistence will eventually yield results. He identifies the “death zone” for high-performing individuals turned founders: having just a little traction. We lived there ourselves for years. He advises, with empathetic and encouraging intentions, that pivoting shouldn’t feel like a “momentous decision.” Pivoting is a common path to success—just look at the famous examples—because it gives founders another shot at finding something that works.

I understood that pivoting quickly and ruthlessly was necessary, and we did it. But each time, it hurt. It felt momentous. Even contemplating a pivot when the product was clearly not working was hard.

Why? I believe the answer lies deep in the mentality of founders and at the core of what drives us forward.

Pivoting is Emotional and Personal

I recently spoke with a potential founder who asked me what motivated me to start Workstream.

My answer: I had experienced a problem and discovered a market gap that I believed represented a significant opportunity. I also felt a deep restlessness to strike out on my own. Most founders can relate: they see a problem and become determined to solve it.

Pivot maximalists might dismiss this, saying, “It’s just an idea!” But to a founder, the idea is yours.

You take possession of it, and it you. You project the future of that product, and of the business, and of you behind it all. You inhabit and covet that world, even in those first days when it is just you daydreaming at your computer. This process changes you, even if all you have so far is a slide deck, or wireframes. The idea you gave birth to becomes personal and emotional.

In The Lord of the Rings, Galadriel describes how Sauron poured “his cruelty, his malice and his will to dominate all life” into the One Ring. Similarly (though with hopefully better intentions), founders pour their life force into what they build. We do this with the ideas we form around the ones we pivot into.

So merely saying, as Dalton from YC does, that “pivoting should not feel like a momentous decision” feels like a woefully out of touch piece of investor advice. It fails to understand the mentality of founders.

Pivoting feels consequential because it is deeply personal. Founders experience acute emotions when faced with a pivot, clouding our otherwise logical judgement.

Pivoting Kills Part of You

Our personal connection to what we build is both a founder’s greatest strength and weakness.

Emotion and passion imbue us with a reality distortion field to build the future. It allows us to excite investors and raise millions of dollars of capital. It drives us to recruit employees, convincing them to take enormous risks to join the “rocketship.” It whispers encouragement as we fight through the many “no’s” from prospects. Each step redoubles our emotional commitment to this future, and our role in it.

We often pay lip service to the sunk cost fallacy, and believe ourselves logical enough to avoid throwing good money after bad. But when your life force has become bound in your product, it is not simple to fold your hand and move on.

For many, walking away from burned money is hard. But the emotional toll of admitting failure is far harder.

To pivot, you must first admit to yourself that you were wrong. Then you must admit it to your co-founders, and your entire team. If it is a hard pivot – where you already have a product and customers – you must admit failure to your user base. You must admit to your investors that the only hope is to move on. Each admission sacrifices social and emotional capital, even if pivoting is a logical and expected part of the startup journey.

Pivoting forces you to kill the part of yourself that now lives in your product, for you too have poured part of your life force into it.

Does this all sound overwrought and dramatic, and not at all logical? That is because it is.

A Founder’s First Insight Should Be About Themselves

Every founder believes that they have a unique insight into the market that presents an opportunity.

But given how common pivoting (and failure) is, these initial insights are often false signals. They are just the first of many we work through on the path to building something great.

Instead, early stage founders should recognize that the act of founding reveals only one true insight: one about ourselves. Starting something reveals we are obsessed with striking out on our own, and possess the unique mix of drive and madness required to try. Founding is, at its core, an illogical, emotional act.

We start companies not because of a market need, but because it is what we need. A need to be our own boss; a need to fulfill our illusions of grandeur; a need to become insanely wealthy. The pursuit of these rewards is in itself deeply fulfilling.

Recognizing this helps us understand why pivoting — an act that often undermines our sense of self-worth — is so hard.

Serve Others By Pivoting

How do we address these feelings that hold us back?

Founders should recognize that while founding is selfishly-motivated, success comes from serving others. If we can truly embrace this, perhaps we can better manage our troubling emotions when forced to pivot.

Instead of focusing on what we might lose, we might start to think: by pivoting, I can best serve my team through gainful and meaningful employment. By pivoting, I can best serve my customers by offering a critical, enduring solution. By pivoting, I have a better shot at creating a substantial return on capital for our investors.

And it strikes me that perhaps the best way to start any business is by merely recognizing that you have the motivation to do so. To resist the urge to start a company with any specific product in mind – and instead start with a passion to serve a specific customer and market. And from there to pursue a mindset of tireless curiosity and service to build the top problem that your client must have solved.

And so thus I will leave you, and say with love:

If you are a founder emotionally struggling to pivot, I truly get it. It feels like a big decision, and it is. Just remember: the voice holding you back is likely your ego. To properly serve it, you must serve others first.