How to Find Freedom Under Pressure

A founder’s guide to liberation amid stress and uncertainty

Midjourney/prompt:”a graphic of chains breaking apart, symbolizing liberation from the constraints of fear and stress that hold people back”

After leaving my company in 2018, I ran a small retreat for exited founders who were exploring their next move. To a person, we were all sitting with the same basic question:

Am I really going to do that again?

Starting a company is hard. By choosing to do it, we invite stress and uncertainty into our lives—and the pressure and responsibility only increases as a company grows.

However, one’s experience as a founder isn’t only dependent on external circumstances. While the pressure doesn’t go away, there are more and less skillful ways of dealing with it. And if you don’t learn to perform and live well under stress, your life becomes driven by it.

I learned this the hard way in my first company, which became all-consuming. It was a travel company—an operationally intense business with low margins—and we were always six months away from running out of cash. Most of the time, it felt like some aspect of the business was on fire.

I reacted to this stress by focusing on the short term. I spent my days responding to momentary crises and immediate threats, rarely thinking more than 3-6 months in the future. While this kept the company afloat, it also meant that I lost touch with a long-term vision for our work. I didn’t exercise or date for several years—it was hard to focus on life amid the stress of work.

In the language of behaviorism, we’d say that my life fell under “aversive control.” In other words, I was making decisions driven by fear of bad outcomes, not inspired by the call of something greater. And fear is a lousy foundation for making good choices.

But there are ways to maintain our focus on what matters and the future we hope to create, no matter how stressful our environment. Through a few core practices, we can cultivate a mental and emotional freedom, such that stress doesn’t drive our decision-making. 

And that’s liberation: the ability to perform well, think long-term, and craft a life of meaning—regardless of the stressors that surround you. In this piece, we’ll cover the skills you need to access that kind of freedom.

A behavioral look at liberation

B.F. Skinner, the father of modern behaviorism, taught that we act either to move toward pleasure or away from pain. Everything we do in life comes down to one of these two motivations.

Even what you’re doing right now—reading this article—falls into one of these two categories. Perhaps you love learning, and reading this essay is a way to connect with your core values. Or maybe you’re experiencing stress at work, and you’re hoping that this article might provide some relief. Or it could be that you’re simply bored and looking for distraction. Either way, it all boils down to one of two drives: pleasure or pain.

In behaviorism, when someone is acting to avoid pain, we call it “aversive control.” We use the word “control,” because their behavior is being shaped by the unpleasant elements in their environment. This was what happened to me in my first startup—the fear of running out of cash was so salient that it became the underlying motivation for everything I did.

On the other hand, when someone is acting to seek pleasure, we call it “appetitive control.” In this case, their actions are being shaped by the enjoyable and meaningful aspects in their surroundings. This is often the initial mindset founders have as they embark on a new project, energized by the creative process and the project’s potential impact.

“Liberation,” viewed through a behavioral lens, is the ability to orient toward what’s appetitive (i.e., pleasant or meaningful), even in an environment full of aversive stimuli. For me, this has meant learning to stay connected to a larger vision and the joy of creativity, even during difficult times.  

Yet, this is hard to do. When we perceive a threat in our environment, our evolutionary instinct is to run, fight, or hide. This worked for our ancestors, who were dealing with predators like lions and tigers.  However, as founders, we primarily deal with psychological threats, like fear, uncertainty, and self-doubt. Unlike with physical threats—which you can escape from—we carry these around with us wherever we go, so can get perpetually stuck in aversive control.

So how can we learn to focus on what matters even in the face of what’s hard? The behavioral tradition offers a few core skills to help make the shift.

Notice when you’re running

The first step toward freedom is to notice when you’re falling into aversive control. In other words, you can’t stop running until you realize that you’re doing it.

For example, as you’re joining a meeting or beginning work on a task, you could ask yourself, “At this moment, am I oriented toward what matters or away from pain?” Sometimes, this question alone is enough to shift from aversive to appetitive control.

However, it’s hard to always be fully aware of what’s driving us, so it can be helpful to familiarize yourself with what aversive control feels like on the inside. It shows up a bit differently for everyone, but there are some commonalities

Generally, your body will release adrenaline, empty the stomach, and push blood to your extremities—preparing you to fight or flee. Your vision will narrow, and you may feel tightness in your throat or chest, as well as an overall sense of restlessness.

These physical sensations are uncomfortable, and are part of what we avoid and try to find relief from. If you can notice when these sensations are present, that’ll help you recognize when you’re running so you can shift toward what matters.

Another way to catch when you’re in aversive control is to notice the things you do to avoid pain or discomfort. For example, if I’m reading the news or checking email during my morning writing hours, it’s likely that I’m feeling stressed or avoiding something.

Maybe for you, this looks like going to the gym, checking Twitter, playing video games, or hopping on your phone to start the day instead of meditating. Whatever you do, once you’ve noticed that you’re running, the next step is to make space for what you’ve been avoiding.

Make space for what’s hard

We can’t point ourselves toward what matters until we stop running. And when we stop running, we come into contact with whatever it is we’ve been running from.

When I look back at the things I’ve felt pulled to avoid—difficult conversations, key decisions, important but challenging tasks—these are often connected to some root fear, like the fear of failure, rejection, or making mistakes.

Through a behavioral lens, these fears show up as thoughts, feelings, memories, and urges. Here are examples of what they could look like for a founder when a big deal falls through:

  • Thoughts—“What will happen if I can’t make payroll?”
  • Feelings—tightness in chest and throat, queasiness in stomach
  • Memories—thoughts about past decisions around cash flow that led to this point
  • Urges—to reach for distraction, obsessively check email, etc.

In the above example, what sends this founder into aversive control is the thought of their company going bankrupt—which may or may not map to reality—and the unpleasant feelings, memories, and urges associated with it. 

When we come face to face with these thoughts and feelings, it’s painful. We don’t run from things because they’re wonderful and joyous; we run from them because they hurt. And our natural inclination when we experience pain is to try and make it go away. 

Yet there is pain and difficulty inherent to life as a founder. So in order to find freedom amid discomfort, we have to learn to make space for what’s hard instead of always running from it.

Making space means having the willingness to allow your thoughts, feelings, memories, and urges to be there, without doing anything to try and get rid of them. In essence, you don’t do anything to them, nor do anything because of them. You don’t have to “accept” or “enjoy” them. All you need to do is stop trying to escape and instead, allow yourself to experience what’s hard.

Now, this is often easier said than done. With something evocative, like the fear that your company might fail, you may have to practice making space over and over again. We don’t open up to discomfort once and then live happily ever after—it’s an ongoing practice, and a choice we make about how we will relate to difficulty so that it doesn’t take over our lives.

As you work on making space for what’s hard, the final step toward liberation is to let go of aversive control and reorient your actions toward appetitives—that which you find pleasant, meaningful, and engaging.

Reorienting toward appetitives

When you’re caught up in stress and avoidance, it can be hard to connect with the life-giving parts of the world around us. Good food, friendship, and the parts of work we typically enjoy can all feel inaccessible as we get trapped in doom spirals in our head. 

There was a particularly stressful period at my first startup where we thought we might go bankrupt. A natural disaster had hit Peru right as we were starting a trip there, and we didn’t have enough cash on hand to issue refunds if everyone had demanded their money back. 

I was so caught up in the stress of the situation and playing out different scenarios in my head that I was barely paying attention to the world around me. I only noticed how absent I was when I finished some takeout from one of my favorite restaurants and couldn’t remember what I’d just eaten.

This is an example of how stress can narrow your focus. So, after we’ve created space for what’s hard, we want to try and broaden our world back up again. 

We do this by fattening up the environment with pleasant stimuli, so you can shift from aversive to appetitive control. You might start simply, by cooking your favorite food from childhood and seeing if you can slow down and really taste it. Similarly, you could put on a favorite song or TV show and do your best to take it in.

If you can do this with the small pleasures in the world around you, it’s more likely you’ll be able to connect with the more subtle qualities you find enjoyable or meaningful at work, like banter with a teammate or the challenge of solving a complex problem.

It’s important not to do this as a way to try and replace or get rid of what’s hard. That would only serve to keep you under aversive control. Instead, we want to make space to feel what’s difficult and open back up to what’s pleasant and life-giving in the world around us.

As we do this practice, we can start to expand our view of what’s possible. We can become more skilled at finding and acting on what’s meaningful, engaging, or important—even in an environment full of aversive stimuli.

Finding liberation

No matter how experienced we get, stress and uncertainty will always be a part of our lives as founders. We don’t always get to choose our circumstances, but with a bit of practice, we can make choices about how we relate to the challenges and opportunities we’re presented with.

By becoming aware of when you’re running, making space for what’s hard, and reorienting yourself back toward pleasure, you can access a kind of liberation that allows you to create a meaningful life—even in the most intense of contexts. 

This is the wonderful thing about entrepreneurship: It’s a high-pressure environment for learning how to skillfully relate to stress and difficulty. In many ways, it serves as a crucible for developing as a person. You either adapt and grow, or you burn out.

My hope is that I’ve provided you with the necessary support for meeting that crucible with grace, so that you can bring forth that which is within you and craft the future you truly desire.


Casey Rosengren is a founder and executive coach based in New York. If you’d like to learn more about ACT and values-oriented coaching, drop him a note.


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Eric Kerr 27 days ago

Good read! However, you could easily swap out “founder” for “human,” as these insights are universal, and your suggestions would be appreciated by many.

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