The Challenges Of A Smooth-Sailing Startup

Every CEO wants the venture they lead to succeed. But many envision success as something it’s not — smooth sailing and the end of stress.

Success presents its own challenges. And this kind can be even more worrisome than the ones you have to navigate in the company’s early stages.

Things are easier when you have more mission-critical challenges to contend with.

When you’re busy solving problems and coaching your teams through tough times, you’re focused on one thing: survival. You’re too preoccupied with problems to be nervous.

But once your company starts on a winning streak, you suddenly have more to lose. Expectations compound. You realize every decision falls on you. And this breeds a different kind of stress—a worry of blowing it or letting your team down.

Paradoxically, almost everything is easier when you’re in survival mode.

This must be teleological, wired deep in all of us. Humans progress forward through problem solving.

What strengthens teams is something I called P-squared: pain times proximity.

In other words, the greater the proximity and pain, the more bonded the team. Working hard to solve difficult problems brings people together and strengthens the company culture.

So when you and your team are firing on all cylinders trying to make something work, trying to fix a critical tool or application, you’re working in a state that’s more natural than the set of actions that come with a certain level of success.

As CEO, your stress levels get higher as things become “smoother.”

With increased success comes increased expectations.

And as expectations rise, so does pressure. You start thinking, “What if I make a mistake? What if I blow it? What if I lead the company in a way that doesn’t live up to everyone’s expectations? What if we F — up?”

In addition to this sort of natural pressure, success unearths another unfortunate fact about running a company. There is an ever-widening array of important decisions that you, as CEO, have to make — decisions that often define the fate of your company.

And you have to make these decisions alone.

In the beginning, when you and your early team members are scrapping and struggling to survive day-to-day, you’re all essentially on one set path. There are less critical decisions to make. Your goals are simple: complete this research, build this model, or win this investor — and then keep going. Every day.

But as you continue down this road, and your company grows and thrives, you’ll find that suddenly you have many different paths you could at any time take. And the correct path won’t always be obvious. Combine this with the fact that you are the single point of failure for all bad decisions your company makes. Suddenly, you’ll find yourself terrified.

As CEO, you are judged on the outcomes of the decisions you make — not the logic of the decisions as informed by the information you had at the time.

For example, imagine your drug company has the option to partner with a pharmaceutical company to bring your product to market. On one hand, the potential partnership could be beneficial, because it will help validate what you’re developing in the eyes of the market and industry, and it will allow you to grow without having to raise money on your own.

But at the same time, by entering the partnership, you’re also giving away a percentage of your equity — meaning if the drug you’ve developed proves successful, you’ll have left a massive amount of money on the table.

Do you roll the dice knowing that in order to make it work, you have to raise hundreds of millions of dollars on your own? Or do you go the safe route, opting with the security of the partnership? Do you even really have these choices or are you deluding yourself?

What choice do you make? And how can you be sure which is the right one? The uncertainty always weighs on the mind.

The truth is, you can never be sure which choice is correct.

You can’t know for sure if any given decision was the right one until you know the outcome.

The example above was derived from an experience one of my employees had at her old company. The CEO, in that case, decided to roll the dice. And if her company’s drug had proven popular and effective, she would have been a hero. But the drug failed. Now, she’s remembered as the catalyst for a disaster.

Ultimately, you just have to make the best decision you can with the information at your disposal. This is a huge source of stress because of how much is at stake, and how singularly you’ll be judged for the outcome.

And that’s why people say a CEO’s job is not only stressful, but lonely.

Despite the challenges, you can manage this—you just have to control your psyche.

At the end of the day, you have no choice but to accept the increased consequences and isolation that come with momentum.

But it doesn’t have to be crippling, though it never goes away.

In my own life, as the years have gone by, I’ve become better at articulating why I’m making certain decisions at any given point, along with what exactly is informing my thinking. This is in direct contrast to the way I felt when we first started gaining momentum, when the nature of the challenges we faced changed from survival to simply stressful.

The more decisions you make, the more expertise and experience you acquire, the more capable you’ll become. Humans soak in knowledge and transform it into judgement at an astounding rate. You can take advantage of that.