Stressed to Impress: Don’t Get Derailed by Insecurity

Originally posted on FounderDating


I couldn’t sleep a wink. I was pissed. It was ten years ago. I was the Founding CEO of my last company (Jive Software) and was attending one of the many navel-gazing, Insertbuzzword 2.0 industry conferences.

That day, I talked to a “friend” who was the CEO of a company in a related space. With all the subtlety of a Sicilian stuck in traffic, he let on that his company was going to do in sales that year. And it was twice what we were going to do. I couldn’t believe it. I had worked so hard to crank out our revenue engine. And now we were getting passed. I couldn’t let it go. I decided to get hyper-focused on tripling our sales number for the next year and surpassing that Tool and his company.

Problem was, the whole idea of comparing myself to some adjacent company was ridiculous. Never mind that we had just moved the company from New York to Portland, hired a brand new team and bootstrapped the whole thing. I felt like I was losing a race in my mind, and I obsessed about it. Which was ridiculous. I might as well have been losing sleep over the Bennifer breakup (this was 2004 mind you).

Looking back on that period, it seems obvious: There’s nothing wrong at all with being passionate and focused on the next mountain to climb. The problem for me (and I suspect many first-timers) is that underneath that obsessive focus is intense insecurity that clouds judgment.

dog with frisbee quote


In the early days the misguided motivation was wanting to hire superstars. Then it was big sales numbers. Then it was raising capital from a top firm. More growth, board members, positioning for an acquisition, IPO, blah, blah. Anything impressive.

By themselves, these big goals are not really a problem. But if the outcomes you seek come from an insecure place of wanting to seen and be impressive, you either a) focus on the wrong goals, or b) neglect the work that best supports those desired results for those outcomes themselves.

Some examples of how the insecurity derailed me along the way:

  1. I took shortcuts to the goals. For instance, hiring people to do big deals but who, in my gut, I knew weren’t a cultural fit (and who ultimately blew up).
  2. I made it difficult for employees to confide in me because I had a hard time hearing anything but progress.
  3. I had a hard time enjoying the ride. You always feel like a better life is right around the corner, after you hit your goal, which is never the case. If you don’t hit it, you get deflated and feel like you’ve lost. And if you do, you realize it hasn’t changed things much and you sit in a vacuum while you find something else to take its place.

I see this insecurity in a lot of first-time entrepreneurs who want to prove themselves. Not only in their bragging about investors and customers, but even the way they think about the business. Like putting an “Exit Strategy” slide on a pitch deck. Seems innocuous, but what it often says is that the entrepreneur is unnaturally focusing on the outcome, likely because they equate it with their own worth as an entrepreneur. The reality of “exits” is that opportunities will abound if you build a great company, but focusing on the exit is the tail wagging the elephant. And it’s only going to cause you and your company pain along the way.


This time around as a startup CEO, I’m trying to save myself the pain. Knowing where you’re going and having Big Hairy Audacious Goals is important, but checking your ego and building out systems and processes form the basis for greatness. Focusing on things like:

  1. Doing amazing work every day. “Leaving it on the field”.
  2. Building out the infrastructure to keep your customers thrilled and your employees thriving.
  3. Becoming a true servant leader who is “cloaked” in the needs of the business.
  4. Thinking about process and system goals more than your big company goals, and celebrating those successes along the way.

Thanks to a little help from friends and colleagues back in 2004, I ultimately realized that trying to triple sales to one-up another company was not the move of a stable leader. Over the next few years, we built out a pretty rugged framework for business planning that put the needs of the business and the process goals up front. If we got all the that stuff right, sales would follow.

Usually people who preach to me about being “in the present” and “the journey not the destination” make me want to punch them. Especially non-entrepreneurs. But I’m chilling out in my “over 40” years, and now realize there’s some truth in that overused maxim: fully immersing yourself in the work itself, separating your ego from the equation and focusing on systems and process goals ultimately leads to better outcomes…and a healthier relationship with your company. You know, more like Ben and Jen.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s