How to avoid chasing the rabbit, and the truth behind letting go of bad ideas

Reflections on what makes a for a good startup team.
Breena Fain
August 25, 2023

“Beginner’s mind” — I don’t know a more popular phrase among founders on the Internet. It’s like everyone listened to the same podcast and suddenly decided they wanted to apply Zen Buddhist teachings to their business. And while I whole heartedly believe in this concept of intellectual humility — in practice, most founders struggle to follow through with it.

I get it though. When you’re in the early days of a startup, chasing rabbits is exciting! After all, if you’re not sure what will work, how can you be certain what won’t? So we follow every idea to the bottom of the hole it came from and while we're down there, it's hard to find our way back. It's hard to let go of all the work we put in. So we stay there, in the dark, clinging to our bad, bad rabbit.

“What is beginner’s mind? It’s dropping our expectations and preconceived ideas about something, and seeing things with an open mind, fresh eyes, just like a beginner. If you’ve ever learned something new, you can remember what that’s like: you’re probably confused, because you don’t know how to do whatever you’re learning, but you’re also looking at everything as if it’s brand new, perhaps with curiosity and wonder. That’s beginner’s mind.”
Zen Habits

I’ve seen it countless times in startups I worked for as well as consulted. Founders have a hard time breaking away from their original execution plan. They grip so tightly to the how of their business that they dislodge themselves from the why completely.

They chase rabbits down their little rabbit holes. They abandon their team. And they lose track of where they’re going. It’s actually remarkable how many teams I’ve seen fall apart simply due to this Alice in Wonderland syndrome.

Of course, good leaders know how to corral, and accept, the chaos. Chasing bad ideas into the ground is part of the whole founder experience. But without a trusting team holding the rope, you may find yourself alone and out of luck in the dark.

As a team who moves quickly on multiple projects a day, trust is a big part of how we function. It is really difficult to know when to cut something loose and when to let our wandering spirit take the lead — trust helps guide us. It keeps our ego in check and fosters the kind of creativity and curiosity required to be successful.

To be honest, this whole founder experience feels like a comical paradox reflecting life itself...

How do we balance the creative spontaneity with the day-to-day minutia?
How do we balance past experience with open-mindedness to the new?
How do we let ourselves begin again, over and over and over, without losing sight of who we are and where we’re going?

I clearly don’t have all the answers. But I’ve spent over 15 years mediating conversations between founders — being an emotional counselor to some — and then running my own business for the last nine years. To be frank, it’s all hard. And no matter what they say on a podcast or quippy LinkedIn post, most founders are suffering from some sort of chronic illness alongside their pursuit of success. So take your own wellbeing into account when heeding advice, including this.

Here are some things I’ve learned help curb the rabbit chasing and keep your team anchored to your why:

Write the press release

I don’t know where this came from originally. I feel like the startup world is such an echo chamber of the same advice (including this post), but this one repeatedly surfaces for good reason. A press release is succinct. They are usually only one page, which means you have to be thoughtful about what words you choose. And when you’re that meticulous, you’re bound to find the nugget of your why.

This is also great because it doubles as a sort of manifestation practice. It’s aspirational. You can write a press release for a month from now or a year from now. No matter the date, it gives your entire company a peek into what leadership desires. There are no OKRs, there are no bulleted lists of what to do, it’s your vision in a single document.

Build a process that lets you brain dump

At PSV, we have an ongoing list of ideas in Notion we’d like to bring to the table. They are categorized as, surprise, “Ideas” and they stay there until we’ve decided they can move forward as a project we want to pursue. We had many meetings about what those parameters are, but we narrowed it down to 3-5 items that these ideas have to pass. There is some flexibility there, but we stick to principles similar to the Ikigai concept:

  • What are we good at doing?
  • What do we love to do?
  • What can we get paid for?
  • What does the world need?
  • The important thing is that you have a central place where you can brain dump anything and everything, then have a strong filter for when those ideas are allowed to move forward. You must decide these parameters as a team, before generating ideas. This allows for a democratic approach to the process, and more importantly, gives your entire team permission to hold leaders accountable when they stray from this agreed upon list of requirements.

Talk to your target customers early and OFTEN

This seems obvious, but it’s amazing how quickly startups lose sight of their own customers. They get a few nuggets here and there of validation, and they are off to the races! So it’s important that you keep talking to people. Nothing keeps an unruly founder in check more than customer feedback. It is another way your team can hold each other accountable if there’s a disagreement on how to move forward.

Allow for divergent conversations

This may seem counter-intuitive and contradictory to the previous advice, but stay with me. Similar to us braindumping ideas in Notion, our team also needs time to do so live. For the sake of our relationships and our business, we need to riff as a team. We need to co-create ideas, good and bad, in order to break out of any stiff routine we’ve developed over time. This is when we can find our way back to the beginning. It’s where new ideas can form.

And if you’re on a larger team, these conversations are where leadership should be signing permission slips to forgo unsuccessful ideas thus far. Management and individual contributors will run bad ideas to the depths of the earth if their founders tell them to do so. So release as much as you can during these conversations and make it clear that people are allowed to give honest feedback. But you better be able to actually hear it or else you will break their trust, and they’ll never give honest feedback again.

So schedule these conversations. Stick to the timeframe you allotted. And allow for open feedback and listen.

Don’t overcorrect

Sometimes divergent conversations help clarify, and sometimes they lead you straight into the darkness again. Just like with anything good in this world, it requires balance. You have to know how much rope to give so you don’t run out. So let your team sparkle with new ideas and insight, and then ground them with a process that helps them anchor it into your original why. (Reference the press release and the process to keep things under control.)

But if you recently experienced a failure with a feature, an idea, a bad hire, don’t overcorrect. You’ll just risk repeating it and confusing everyone in the process. Go slow and be methodical about a decision that didn’t work out. And most of all, be honest — even if it as the expense of your pride.

As you can see, there isn’t a perfect formula. Every situation is going to be different and depending on the stage, the people on your team, and likely a hundred other factors — what works for you will look different. But sometimes just knowing this can help. Good founders take advice as something to consider, not assign.

So I’ll leave you with this — don’t take any of this so seriously. This will be your downfall (another life lesson I’ve learned). If you can admit when you’ve gone too far or that you’ve chased a bad rabbit idea into the ground, that is more than most can do. So build a process that helps pull you out when needed, trust that your colleagues may know more than you, and allow for curiosity (and fun) to guide you when it feels right as a team.

Be kind, stay open. And most of all, remember you chose this path so you might as well enjoy the ride. ✌️

Thanks for reading!

Breena Fain

Breena Fain is Head of Marketing at Plain Sight Ventures. In her free time, you can find Breena in the garden, at the clay studio, or gabbing with neighbors over coffee at Blackbird Bookstore.

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