I just hung out with colleagues from my 20s. We were all part of the early days at Citysearch. Back then, most people “dialed-up” the internet from landlines and the fastest connection gave you an incredible 56KB per second! And Austin, Texas, was the most connected city in the U.S. at a whopping 30% of the population online. 

All this to say, nobody knew much about the internet back then. Building a business on the back of it was absolutely not the norm. 

Also, at Citysearch:

  • They used made-up titles. I was an “Internet Business Advisor.”
  • They made the job descriptions up, too. (Actually, I don’t recall ever seeing one.)
  • Their performance metrics changed every six months or so. For example, the original goal was to sign up ten new accounts each week. Within a year, it was clear that the top performers could close more like two deals.
  • A new manager or executive showed up almost weekly.
  • Everyone shared what they knew with others and generally colored outside the lines.

It. Was. Great.

Back to the conversation with my former colleagues.

We laughed as we reminisced about the complete lack of direction. One person joked that the company motto should have been, “Why don’t you take a stab at that?” 


Because we were always trying to figure out what was next, how to do something, what the process should be, and how to get something “sorted.” The company leaders threw problems, projects, and new responsibilities at us with this assumption: you’re smart, and you’ll figure it out. 

Let me demonstrate how wild that assumption was. Before working at Citysearch, I had ZERO knowledge about the following things. (CS alum – I’d love to see your list. I’m guessing it’s equally insane.)

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  1. How to lease commercial real estate.
  2. How the P&L of a newspaper works.
  3. How to edit HTML code.
  4. How to build and test software.
  5. How to build and test office furniture.
  6. How to live on the road for two years and keep friends.
  7. How to hire people for jobs you just made up.
  8. How to train people for jobs you just made up.
  9. How to get up to speed on the potential needs of pretty much any small business you can imagine. EG. BBQ, Dentistry, Therapist, Mini Blind Broker, Art Dealer, Trucking. 
  10. How to convince a pair of police officers that they needed to give you and your friends a ride back to your apartment. (Oh, and by the way, your one friend is on crutches. So she needs to sit up front, meaning one of the officers needs to squeeze in the back with the rest of us. This same officer then finds out that yes, the backseat of a squad car is quite small and not very comfortable.) 

I gained all this experience because one of my managers asked if I’d “take a stab at it.”

I quickly figured out that the managers had no idea what the answer was either—but they trusted my front-line colleagues and me to figure things out and explain what we learned to them.

It. Was. Empowering.


If you’re in a leadership role (or hoping to get into one), part of your job is to empower your people, right? But since my days at Citysearch, I can count on one hand the number of times someone said, “Why don’t you take a stab at that?” to me. 

That question was empowering, even if the effect was accidental. Did our leaders question things? Yes, all the time. But instead of giving us directives or telling us that maybe we were wrong, they asked questions. The bottom line, they let us take a stab at it. And thanks to that, we learned the rules, came up with a framework and made recommendations. 

Empowering someone taps them into their potential.


There’s another truth to this story. Not everyone survived and thrived at Citysearch. 

At the time, I couldn’t help but notice the people who were following the rules—and rule-following perfectly. Sometimes these folks even delivered versions of “perfect” that turned out better than what our managers had asked of us. 

Did these people succeed in the short term? Yes. Did they survive and thrive? Not so much. 

This whole take-a-stab-at-it way of working is messy, risky, and fraught with failure. It doesn’t allow you to make “perfect” every single time.

On the upside, today, you see Citysearch alumna all over the place. Yes, the executives have gone on to bigger and better things. Even more impressive is the people from the front line who’ve taken their work to the next level. 

For example (and there are many more):

  • Rachel Francine – CEO of Musical Health Technologies. She’s helping grandmas and grandpas with dementia connect back to their memories. Seriously, go watch one of their videos on YouTube. I dare you not to cry happy tears.
  • Clint Smith – CEO of Emma. A self-described “accidental entrepreneur” who co-founded and led the Nashville-based company Emma, an email marketing software and services platform.
  • Jocelyn Mangan – CEO of Him For Her. A key player at Opentable, Jocelyn now engages leading “Hims” to introduce the world’s most talented “Hers” to board service.
  • Jeremy Liew – a Venture Partner at Lightspeed. He was one of the first investors to say yes to Snapchat. His portfolio includes companies like Bonobos and Jessica Alba’s Honest Company. 
  • Mandy Cole – Founder of the Rise Accelerator. Mandy tells us that “revenue solves everything,” and at her consulting firm, the team figures out how to make it happen.
  • Stephanie Eidelman – CEO of the IA Institute. A thought leader in the world of consumer debt, Stephanie built a media company around the industry 

Many of us have also whistled quietly under our breath as we’ve watched “Foley”, aka John Foley, the founder of Peloton, change the way we approach fitness.

If I pulled them all in a room, they’d all nod that the “Why don’t you take a stab at that?” culture at Citysearch was a big part of their professional growth. 

So whatever your ambition, take a page from their success. Be willing for things to get messy. Accept that taking stabs can be risky. And dance on the edges of perfect.


I suspect that many of you reading this relate to this story about the crazy times at Citysearch. If you’re an alumna of Yahoo, AOL, MySpace, and BlogHer, you might recognize the culture of “Figure it out, why don’t you?” that exists in any industry that’s building and figuring things out at the same time.

Why does this story matter now? Because we’re at the dawn of a new “why don’t you take a stab at that?” era. With artificial intelligence, machine learning, warm data, virtual and augmented reality, quantum computing, space tourism—and the list goes on—we all have an opportunity to build and figure out at the same time. 

And you’ve seen the professional trajectory of my Citysearch friends. Their stories are proof that learning how to build and figure out simultaneously has fantastic implications—especially if you’re working on the front line today. 

Ready to get started? Here are my recommendations.

As an individual, be on the lookout for opportunities to take a “stab” at things. Raise your hand when you see a chance to figure something out. The more you do it, the better you’ll become at it, and more opportunities will present themselves. It’s a bit of an opportunity circle.

As leaders, sometimes we don’t have all the answers. And allowing others to take “stabs at things” means everyone learns, including you. Isn’t this how you got your break? Be as generous as you can with this. Pro Tip – this is where diverse thinking has an impact. You want multiple perspectives when you don’t know the answer.

Finally, for all of us, our future success is closely linked to technology. Specifically, being able to work with technology rather than competing against it. And there’s a delicious paradox in this. By working with technology, we tap into our potential. And potential is a feature that’s uniquely human. 

You’re a human who thinks, not a robot who does. So, will you “take a stab” at leaning into building with technology while figuring things out—and grace us with your amplified human awesomeness?

Xo Joanna - orange.jpeg