When You Plateau, So Does Your Company

A founder's guide to expanding your comfort zone

Midjourney Prompt: "Create an illustration representing the idea "When you plateau so does your company: Avoid becoming the bottleneck in your business and life"

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I didn’t fully understand how detrimental avoidance could be as a founder until after I’d exited my first startup and began working at a fund that acquired and operated SaaS companies.

There, I was involved with 4-5 acquisitions of businesses with $1-10M in annual revenue, and I noticed an interesting pattern; nearly all of the companies we acquired had been run by product-focused founders who had avoided sales and marketing.

Each of them had gotten quite far by being first to market and offering a quality product; yet over time, they had all hit a plateau. They spent years trying to grow the business through yet-another-feature launch. When they did invest in sales or marketing, it was usually a half-effort led by a junior employee and constrained by the founder’s discomfort around growth.

This was fine for the first years of the company—but then revenue stalled, the founders burnt out, and they decided to sell their businesses. After seeing this pattern, I realized I had been guilty of the same behavior in my previous startup.

This is one of the beautiful and painful parts of building a company–at some point, your comfort zone becomes the bottleneck in your business. Either you grow as a founder (and a person), or the company plateaus. Whether you're just starting out or are running a billion-dollar business, success depends on your ability to tolerate discomfort. 

In this post, we'll break down what a comfort zone is through the lens of Acceptance and Commitment Therapy (ACT) and discuss several ways to intentionally expand it so you're less likely to cause your life and projects to underperform.

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Comfort Zones: An ACT Perspective

A comfort zone represents a set of behaviors that feel safe to us. Our brains believe that if we step outside that zone, something bad might happen, so we experience discomfort. To avoid it, we move back toward what feels safe.

You can think of it like an electric dog fence. While the border might be invisible to others, when you venture near it, you get a shock that sends you back toward safety.

Rather than the physical shocks used when training dogs, our brains use aversive thoughts and feelings to keep us in line. When we start to venture beyond our comfort zone, we experience things like fear, doubt, anxiety, and self-criticism—pushing us right back towards safety.

For example, when a product-focused founder starts doing sales and marketing, they might get hit with a wide array of aversive internal experiences:

  • Thoughts: “This won’t work” or “I don’t know where to start.”
  • Self-stories: “I’m no good at this.”
  • Feelings: fear, shame
  • Memories: past experiences of rejection or failure
  • Urges: to distract oneself or work on something easier (like developing another feature)

If the founder gets hooked on these experiences, they are likely to retreat back to the comfort zone of product development in order to avoid discomfort. This is how a friend of mine ended up with, in his words, “18 microservices and not a single user.”

From an ACT perspective, comfort zones themselves are not a problem—they are only problematic in as much as they get in the way of doing what we care about. Much of the time, there may not be much of a cost to staying in your comfort zone. However, choosing to pursue a meaningful life at times requires us to venture beyond its borders… or shrink our lives to fit what feels safe.

Now that we understand the concept of comfort zones and their potential impact on our lives, let's explore how we can expand them to achieve our goals. 

Expanding Your Comfort Zone

When we leave our comfort zone, it may feel like we're a pinball hitting a bumper. Without even thinking, we end up right back where we started. 

However, it is possible to stretch and expand your comfort zone. From an ACT perspective, there are four key aspects to consistently getting out of your comfort zone in service of building a life that matters:

  • Clarify what’s important
  • Ramp up the costs
  • Build discomfort tolerance
  • Create commitment scaffolding

Let's dive briefly into each one.

Clarify What’s Important

When first stepping out of our comfort zone, it will be uncomfortable. So to begin, it often helps to start by reflecting on why we’re willingly choosing to open ourselves up to discomfort.

It’s kind of like you’re sitting on an island surrounded by a swamp. All else being equal, it makes sense to stay on dry land. However, if there is a mountain you want to climb on the other side of the swamp, then you might be willing to get your feet wet.

When we are unsure about what we truly care about, it’s easy to default to familiar and comfortable behaviors. On the other hand, when we know what our discomfort is in service of, we experience that suffering as meaningful and are more likely to stay the course.

When we talk about what's important in ACT, we're often talking about values. Values are about what we'd choose our lives to be about, if we could choose anything.

Here are a few questions to help connect with your own willingness to go beyond your comfort zone:

  • What is the “mountain” I want to climb that makes the “swamp” worthwhile?
  • If I wasn’t bothered by fear/doubt/shame, what would I do? What would I want my life and work to stand for?

Ramp up the Costs

Staying in our comfort zone has short-term benefits and long-term costs. 

On any given day, it may feel easier to prioritize engineering instead of sales, or to eat a cookie instead of going to the gym. However, a life spent avoiding sales and eating cookies may not be the life we ultimately want to look back on from our deathbeds.

By reflecting on the costs of staying in our comfort zone, we realize that “playing it safe” has its own costs—and these costs are often worse than the discomfort we experience when trying something new.

Here are a few questions to help connect with your own willingness to go beyond your comfort zone:

  • If someone were to replace me in my life/work tomorrow, what would they do differently? (the Andy Grove question)
  • If I were to live the rest of my life in the way I’m doing now, would I be content?

You might also check out our earlier piece on the tombstone exercise, which explores questions like these in further detail.

Build Tolerance for Discomfort

From a behavioral perspective, a few things happen in a typical comfort zone cycle:

1. We reach the edge of our comfort zone and experience discomfort

2. We experience an urge to move toward safety

3. We move towards safety

4. We experience relief

While it's difficult or impossible to prevent feelings of discomfort from arising at the edge of our comfort zones, we can learn how to open up to those feelings and urges without acting on them.

Below are a few practices that can help you build up this muscle.

Be-still Meditation

The first practice is a simple exercise called the “be-still meditation," developed by psychologists Robyn Walser and Darrah Westrup. All you need to do is close your eyes and sit still for a few minutes, noticing the sensations of your body. Shortly after beginning, you’ll likely notice some physical discomfort—maybe an itch or a small ache somewhere in the body. 

Your only job in this practice is to sit still and open up to the sensations without acting on them. It might feel excruciating at first, as we’re so conditioned to feel discomfort and immediately act upon it. However, after a little bit of time, you’ll notice that you can have an itch on the edge of your nose and just sit there and watch it, without moving. 

Emotions are ultimately physical sensations in the body that we have named, so building our capacity to sit with small amounts of discomfort in meditation can help prepare us to work with challenging feelings when they arise in our everyday lives.

Practicing Opposites

Another way to build tolerance to discomfort is by “practicing opposites,” an exercise developed by ACT founder Steve Hayes. This practice involves becoming aware of our urges to move toward safety, and using those very urges as a trigger to move toward what feels uncomfortable.

For example, a founder who has the urge to develop one more feature before launching a product might interpret that urge as a signal to launch the project as is. Similarly, a person who is just beginning to exercise might use the urge to delay or cancel a workout as a cue to get up and go to the gym.

In the world of addiction, this is called urge surfing. When we feel an urge and do the opposite, we learn that we have agency to act no matter how strong our cravings are. 

Over time, we may find that an urge that once activated comfort-seeking behavior can become a trigger for leaning into discomfort—like a reverse compass, telling us what’s important. 

Exposure Ladders

In traditional therapy, exposure ladders are used to help people gradually open up to increasing levels of discomfort.

For example, someone who has a fear of snakes might go through a process like:

  • Saying the word “snake”
  • Looking at a picture of snake
  • Watching a video of a snake
  • Being in a room next to a room with a snake
  • Being in a room with a snake at a distance
  • Gradually decreasing the distance between them and the snake
  • Touching the snake
  • Briefly holding the snake
  • Holding the snake for increasing periods of time

If you put them in a room with a snake right off the bat, it might be overwhelming. However, if you slowly acclimate them to each phase, you can gradually expand what they’re able to tolerate. 

While most of us don’t have full-on phobias, a similar approach can work to help gradually expand our comfort zone. 

For example, if an exposure ladder for a software founder who tends to avoid sales might be:

  • Watching a video on sales techniques
  • Role-playing a sales pitch with a trusted friend or colleague
  • Sending a cold email to a potential customer
  • Watching a friend or teammate do a sales call
  • Taking a sales call alongside a teammate or trusted advisor
  • Taking a sales call alone
  • Attending an event or conference and networking alongside a colleague
  • Attending an event or conference and networking alone

Similar to the snake example, we start with a small and manageable step and gradually expand the comfort zone from there. You can do the same thing with whatever it is that is outside your comfort zone—bite off a small chunk, and create a map of how to expand slowly from there.

This doesn’t mean it won’t be hard at each stage; exposure is uncomfortable throughout the process, and often needs to be repeated to maintain gains. However, if you put in the work over time, you can fairly reliably extinguish fears.

If you want to learn about exposure, this is a good overview. It’s important to note that exposure can bring up strong emotions, and self-guided exposure is only suited for self-improvement, not for treating trauma or mental illness. If your experience becomes overwhelming, you may want to find a therapist to support you in the process.

Creating Scaffolding for Commitment

Even if we do the above, it can still be hard to consistently get out of our comfort zone. Avoidance can be sneaky, and we may not even notice the ways we subtly evade the things we fear in life and work.

Thus, it can be useful to create structures that help us to consistently lean into discomfort in service of what we care about. I call these structures "commitment scaffolding."

One example of scaffolding is body doubling. A personal favorite, body doubling is where we take an unpleasant task and do it alongside someone else, making the overall experience more pleasant and tolerable.

This is often used with kids who have trouble in school—simply having a supportive adult sit with them can make it easier for them to focus and do their homework. In my own experience, meeting a friend for in-person writing sessions was critical when I was first building the writing habit. On my own, I would avoid writing like the plague, but together I found I was able to push through the discomfort and write for hours at a time.

To make body doubling work for you, choose a task you tend to avoid and invite a friend or teammate to work alongside you. I often frame these as “deep work sessions,” and you can work on the same thing or on separate projects. 

I’ve found these work best in-person and with someone you know and like, but there are also a number of options for doing them online with strangers.

Other forms of commitment scaffolding are:

  • Deadlines—e.g. committing to a regular publishing deadline or picking a date to present sales numbers to an investor or advisor
  • Regular metrics reviews—e.g. tracking time spent writing each day or number of customer conversations per week
  • Classes and workshops—e.g. taking an improv class to challenge your comfort zone around public speaking

Whenever I see clients struggling to maintain some form of discipline on their own, I think about how to help them lean on their environment to support change rather than their willpower. 

Over time, you may find you can do more and more without the external scaffolding. However, it is invaluable at the start when new behaviors are just beginning to take flight.

A Lifelong Process

We spend most of life in our comfort zone, and that's normal. Some things outside our comfort zone are unsafe, and other things cause discomfort while providing little to no benefit.

However, comfort zones can also be a trap, keeping us from pursuing our long-term goals. In particular, when running a company or launching a new creative project, the critical path often lies beyond what feels safe. Unless we can expand our ability to tolerate discomfort, we'll get constantly bogged down on the path, distracted from what really matters. 

By using the practices above, we can slowly but surely expand our comfort zones and access new opportunities in life and in work. It may not always be easy, but if you persist over time, you can do things you previously would have thought were impossible.

In the end, expanding your comfort zone is a lifelong process. There will always be new challenges and opportunities that require you to step outside what feels safe. But with the right tools, you can continue to grow and meet life on your own terms. And who knows? You may just surprise yourself with what you’re capable of achieving.

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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