How to Do Hard Things

A therapy practice helped me face my struggles as a founder

DALL-E/Every illustration.

If you’re a founder, dealing with stress and uncertainty is an inevitable part of your day-to-day life—but that doesn’t mean burnout and misery have to be. When Casey Rosengren discovered acceptance and commitment therapy (ACT), an evidence-backed tactical framework from behavioral psychology, his entrepreneurship was transformed. We’re delighted to republish Casey’s first—and most popular—piece for Every, about how ACT helped him confront his perceived weaknesses as a founder.

Mindfulness is one of the easiest ways to build up the skills described in this piece, so if you’re interested in developing this practice for yourself, sign up for his new course The Hidden Discipline. The cost is normally $1,000, but Every subscribers can register now for just $699. —Kate Lee

When I started a company in my early twenties, I didn't have a great way of dealing with uncertainty and stress. Even though we bootstrapped the company to an exit, I was miserable a lot of the time and, when I finally moved on, I wasn't sure I'd ever want to start another business.

Entrepreneurship felt like a calling, yet my lived experience had often been quite painful. I spent years in traditional talk therapy and reading self-help books to try and make sense of my life, but I still felt stuck. I couldn't see myself being happy starting another company, but I couldn’t see myself doing anything else.

I'd always been a bit of a psychology nerd—I originally got into meditation after reading a meta-analysis of its positive effects. So, one day, I stumbled upon a book, Values in Therapy, that explored a little-known framework from behavioral psychology. That was a lightbulb moment for me. I suddenly understood why I was so unhappy while running my last company, and I began to see how I might be able to approach the stress and uncertainty of entrepreneurship in a new way: one that was life-giving instead of soul-sucking.

The framework is called acceptance and commitment therapy (ACT), and even though it's backed by evidence from 800-plus randomized controlled studies, it is relatively unknown outside of therapy circles. This article explains the basics of ACT, how it has impacted my life, and how you can begin to apply it, too.

At a high level, ACT (pronounced "act," not "A-C-T") looks at how our thoughts influence our behavior, and offers tools for self-correction when our minds get us stuck. In my case, it helped me recognize where my mind was compounding the stress inherent in running a company, and how that additional stress had gotten in the way of finding meaning and enjoyment in my work.

In talking with friends—both founders and non-founders—I realized that a lot of people go through what I went through. I started devouring books and research on ACT, and eventually trained in how to use it with others in a coaching context (when it's not therapy, we call it acceptance and commitment training and still abbreviate it as "ACT").

In this piece, I'll explain the basics of ACT and explain how this tactical framework can help you operate more effectively and stay connected to meaning when doing work that matters to you. By the end, you'll have an understanding of how you can use ACT to adjust your behavior, and hopefully,  live a more meaningful and productive life.

Let's begin.

How to find ‘psychological flexibility’

The ultimate goal of ACT is to help us move closer to what we care about in life.

From an ACT perspective, the main thing that gets in the way of this is when our behavior becomes primarily about avoidance. When we’re focused on avoiding difficult thoughts and feelings, we’re not focused on moving toward what we care about.

Where other psychological approaches might try to resolve challenging thoughts and feelings by rationally reframing them or exploring childhood memories, ACT doesn’t see difficult internal experiences as problems in and of themselves—they are only seen as problematic to the degree that they interfere with living a meaningful and engaged life in the present.

Thus, much of ACT is about helping us change how our thoughts and feelings influence our behavior. Essentially, ACT teaches us how to stay oriented toward what we care about even in the face of negative thoughts and feelings—because those are a normal part of life.

ACT calls this ability "psychological flexibility" because when we're caught in avoidance, our behavior tends to narrow and become inflexible. It outlines six core skills that we can practice to help ramp up the thoughts that bring meaning to our work and disengage from the thoughts that take us off-course. They are:

  • Experiential avoidance → Willingness
  • Fusion → Defusion
  • Past-future preoccupation→ Present-moment contact
  • Rigid stories → Flexible perspective-taking
  • Lack of direction → Clear values
  • Inaction → Committed action

These processes are all interconnected, but we'll talk about each and show how mastering one can lead you to the next.

Experiential avoidance → Willingness

When challenging thoughts and feelings come up, our tendency is to avoid them—or situations that might cause them. In ACT we call this experiential avoidance.

The problem is that difficult thoughts and feelings come up all the time, and often in situations that we don't really want to get away from. What we want to learn to do is contact discomfort when it's in service of doing things that we care about. In ACT, we call this willingness.

A mentor of mine likes to talk about experiential avoidance as a sort of "reverse compass." When we notice the desire to avoid something, it may actually be telling us what we need to move toward the discomfort. Of course, you shouldn’t move toward things that might actually harm you, but many of the things we avoid in life are simply unpleasant and are not actually dangerous.

For example, in my first startup, marketing was the area of the business where I felt least comfortable. I often procrastinated on growth-related tasks, and would spend my time instead working on our product, where I felt more confident. As a result, we probably didn't grow as fast or as large as we could have.

To try and grow as a founder, after exiting the company, I took a full-time growth role at a tech-focused fund. For the first several weeks, I was consumed by the fear of failure and letting people down. However, marketing was my whole job now–I could no longer avoid it. Even as alarm bells were going off in my head, I started trying different growth experiments. While the first few things we tried didn’t work, eventually one of our experiments got moderate traction, and something funny happened: Marketing suddenly became a lot less scary.

It turned out that the product skillset actually translated quite well to growth, and that I had simply never focused on marketing long enough to push through my initial discomfort and start to see results. For more than a year, I worked full-time growing the fund’s portfolio companies, and today, marketing no longer feels as scary or challenging.

Even though a lot of career advice preaches "playing to your strengths," sometimes the path to the life we want lies on the other side of what we find difficult.

Willingness can be developed through formal mindfulness practice: sitting in silence while allowing difficult thoughts and feelings to be present. It can also be developed informally whenever we stop trying to get rid of painful thoughts and feelings and instead open up to them as part of the path toward what we care about.

To help home in on experiential avoidance in our lives, Tara Brach, the meditation teacher and author of Radical Acceptance, offers a simple question: "What are you unwilling to feel?"

Whatever the answer, this becomes the focus of our work. The more we practice opening up to it in our lives or through formal mindfulness practice, the more we'll be able to stay connected to what we care about rather than getting lost in avoidance.

Now, gaining clarity about where avoidance shows up in our work is just the first step. Once we understand this, our next move is to look at how to work with the thoughts that come up that perpetuate avoidance. This is the process of moving from fusion to defusion.

Fusion → Defusion

When we’re caught in avoidance, we tend to see our thoughts as "true." ACT calls this process “fusion.” When we are fused, we react to a thought as if it were an external reality, as opposed to a cognitive and physiological experience happening inside of our mind and body.

Here are a few examples of thoughts people can fuse with with:

  • Reasons: "I can't do X because..."
  • Judgments: "People always are only looking out for themselves."
  • Rules: "I shouldn't feel Y" or "I have to work harder than others to be successful."

Defusion, on the other hand, is about noticing our thoughts are simply thoughts. When we can experience our thoughts as events happening inside our awareness, rather than taking whatever our mind says as reality itself, we can choose to pay attention to the thoughts that are more "workable" in moving us toward where we want to go in life.

As an example, in school, I picked up the rule that "mistakes are bad." If I got something wrong on a test, it meant that I hadn't properly studied—that I had done something wrong.

Later in life, when I started a company, I still had to contend with this belief. When a growth experiment didn't work, or a strategic decision didn't pan out, I felt it viscerally: "I did something wrong. I must be bad at this."

In real life, however, and especially in entrepreneurship, we aren't taught the right answers before we're faced with a challenging situation. Even though the context of my life had changed from school to entrepreneurship, this thought was still popping up as a guide rail for my behavior. The problem was that it was hard for me to enjoy work when I often felt like I was doing something wrong. It caused me to avoid doing things where I might mess up—and that’s a precarious way to run a company, because those situations are a constant part of life.

Thus, an ongoing practice of defusion for me has been to notice when the "mistakes are bad" rule shows up in my work, and to notice when that's leading me to avoid certain tasks or to over-analyze a situation. The more I've practiced this, the sooner I've been able to catch these thoughts and behaviors and to get back into action toward my goals, even if that might mean getting something wrong.

A quick exercise you can do at home to practice defusion is to raise your hand in the air, start waving it back and forth, and at the same time say out loud, "I'm not waving my hand back and forth." Somewhat silly, I know, but it's a simple way to short-circuit the part of your brain that unconsciously buys into your thoughts.

To summarize: Defusion is about seeing thoughts as real, but not necessarily true, and about choosing to give weight to the thoughts that help us move toward the lives we want to live.

Now that we’ve covered fusion and defusion, we'll explore two common types of fusion that ACT treats as important categories of their own: past-future preoccupation and rigid stories about self and other.

Past-future preoccupation → Present moment contact

Past-future preoccupation is a type of fusion that describes what happens when we get lost in our thoughts about the past or future, and we lose contact with what is happening right now, in the present.

For me, this would often come up when we were in a tight spot in the business. As a bootstrapped company, cash flow was always stressful, and when sales for a trip were slow, my mind would start imagining a future where we would run out of money.

In three years of running the business and nearly 30 trips, this never happened. Yet when the fear of going bankrupt arose, it was hard for me to focus on anything else. My behavior would become primarily about trying to avoid this imagined future state, and I'd lose touch with the parts of my work that were intrinsically rewarding.

Now, to some degree, it's useful to be able to imagine and plan for what might go wrong in the future, or recall lessons from a painful moment in the past. The stress response is built to get us out of danger. In the words of Andy Grove, "Only the paranoid survive." However, there comes a point where ruminating about the past or worry about the future no longer pays dividends, making it hard to find meaning in one's work in the present.

When we find ourselves stuck in the past or future, the step toward flexibility is to gently yet intentionally bring our attention back to the present moment. This can be hard to do when we're really stuck, but is also a skill that can be developed over time through formal and informal mindfulness practices.

One practice you can try at home is to bring your attention to the stimuli coming in through your five senses. The body lives in the present, so when you're noticing a lot of past- or future-oriented thinking, coming back to your various senses is a powerful way to return to the here and now.

You don't have to "meditate" or sit in a special position. All you need to do is to pause for a moment wherever you are and turn your attention toward physical sensations, sounds, smells, sight, and taste. Eventually, as your awareness develops, you can also turn your attention to the felt sense of thoughts and emotions as they arise in your experience.

Ultimately, thoughts about the past or future are not reality. They are cognitive events happening in the present. If we can notice them as such, we can stay oriented toward the joy, meaning, and opportunity available in our lives at this moment, rather than being guided by our thoughts and feelings about other times and places.

Even if we’ve unstuck ourselves from thoughts about the past or the present, there’s another major type of fusion that often gets us bogged down: rigid stories about ourselves and others. In ACT, when we notice these kinds of stories coming up, we practice flexible perspective-taking to help loosen their grip on our minds and behavior.

Rigid stories → Flexible perspective-taking

Rigid stories about others often come up in interpersonal conflict. When we get stuck in judgments that another person is "irrational" or "misinformed," we lose touch with who they are as whole, complex human beings.

Likewise, it's possible for us to get stuck on rigid stories about ourselves. Imposter syndrome is a prime example of this, and can show up as self-labels around being "broken," "deficient,'' or "incompetent." These negative self stories cause us to shield ourselves from the world, lest others discover the "truth" of who we really are.

For me, this often showed up through comparison: having thoughts that I was a bad founder compared to other folks in the space who were raising lots of money. This narrative wasn't always alive for me, but when it did arise, it felt like there was something others had that I was lacking, like I had somehow missed out on some important key to success in life and was thus doomed to toil away in mediocrity and failure.

Melodramatic, I know, but that's how minds work.

In retrospect, I'm glad we didn't raise money. Bootstrapping allowed me to exit the business after three years and provided me with the financial cushion to move onto projects that I found more interesting. However, in the moment, these narratives could be quite painful and felt very real. When stuck in one of these stories, it was hard to access a broader perspective: that everything I was going through was part of the messy path to maturing as a person and a founder.

Moving toward a flexible sense of self and others is about recognizing that any story we tell, good or bad, is not the whole truth about a person, and is only true within a given context. We can identify as a son or daughter, an athlete or an artist. We can tell stories about our childhood dreams, our first kiss, or a book that changed our lives, and while these are all part of our lived experience, they're not all of who we are. No label or story can fully capture the complexity of a human life.

Ultimately, flexible perspective-taking points toward a sense of self that transcends our experiences and our life history. It points toward a sense of "I" that is the container for all of our experiences: the "I" that has been aware of everything that has happened throughout the course of our lives.

While this all might sound a bit esoteric, the way we practice it is by noticing when we're flattening ourselves or others into two-dimensional caricatures, and seeing if it's possible to see them as multi-faceted humans with strengths, flaws, hopes, and fears. At our best, we may even try to put ourselves in their shoes and take on their perspective, exploring what the world might look like through their eyes.

Once we’ve learned we can effectively use skills like present moment contact and perspective taking to loosen the hold of fusion on our behavior the question then becomes: How do we want to behave in any given situation? 

In ACT, we figure this out by clarifying our values. 

Lack of direction → Clear values

Many of us experience aimlessness or a lack of meaning at various points in our lives. We might be able to talk about things that once excited us in the past, but when we look around at our lives and the choices available to us in the present, we don't actually feel a sense of vitality or enthusiasm.

Often, this is because we are caught in avoidance or fusion, making it hard to access meaning. This is why in ACT we’ll often start with the processes above, even though values represent the ultimate goal of our work.

Moving toward values is about reconnecting our day-to-day activities to the things that matter most to us. It's about clarifying for ourselves what a life well-lived would look like, and then intentionally bringing those qualities into our life and work in the present.

For me, two of my values are "love" and "play." If I think about looking back at my life from my deathbed, I sense that I'd feel content to look back on a life filled with these kinds of moments.

In my founder-coaching practice in the present, I try to cultivate these qualities in how I show up with a client. When I notice my mind getting overly analytical or even wanting to say something clever, I try to come back to the intention to be loving and playful. It's not about getting somewhere else; it's about seeing this session and this moment as an opportunity for both myself and the client to contact what's deeply important to us. When I approach coaching from this place, I enjoy it more, and I think I’m better at it.

It's important to note that values are different from goals. Goals are discrete milestones that either exist in the future or the past. Values, on the other hand, are ways of being and doing that are intrinsically meaningful, can never be "finished," and are only accessible in the present.

For example, if someone values "being a loving parent," there are a number of things they might do to express that value, like reading to their child at night or saving up for their college fund. The value of "being a loving parent" is what gives meaning to the act of reading or saving, and it doesn't go away when the child no longer wants a bedtime story or grows up and graduates college. The value simply finds new ways of expression as the child grows.

ACT often evokes mortality as a way of contacting what deeply matters to us. Awareness of death has a powerful way of bringing into focus what's truly important and highlighting ways we might be living out of alignment with our deepest yearnings.

A simple exercise you can use to explore values in your life through this lens is called the tombstone exercise

To do this exercise, first take a moment to reflect on what you might want your tombstone to say at the end of your life—maybe something like “was a loving parent” or “helped a lot of people”—and write it down.

Then, take a moment to think about what your tombstone might say if you died in your sleep tonight. If the tombstone was an honest reflection of your life to date, what might it say?

This exercise can be particularly powerful, because in addition to helping clarify what you might want your life to be about, it also shines a light on the gap between that ideal and how you are currently living. That gap, painful as it might be, can be highly motivating when doing the hard work of behavior change.

If you find yourself getting stuck around values, you may need to do more work around the other core processes—defusion, willingness, present-moment awareness, and flexible-perspective taking—to be able to get back in touch with meaning.

You can almost think of all the other psychological flexibility skills as clearing the way for us to contact our values, and values as being what makes all that hard work worthwhile.

Finally, now that we’ve covered the five psychological flexibility processes above, it’s time to turn to the sixth and final process: committed action.

Inaction → Committed action

Clarifying our values and learning a new relationship with our thoughts and feelings is great, but if we don't do anything differently, our lives ultimately won't change.

Committed action is about finding places in our lives where we might shift our behavior to be more aligned with our values. It's about using the skills above to work with whatever thoughts and feelings are sustaining unhelpful behaviors, and then taking small steps in new directions.

Russ Harris, author of several popular ACT books, offers a framework of seven Rs that can help support action in its early stages:

  • Reminders: Using apps, timers, or other means to remind us of the new behavior
  • Records: Keeping track of our behavior throughout the day
  • Rewards: Giving ourselves positive reinforcement for engaging in a behavior
  • Routines: Building the new behavior around an existing daily habit
  • Relationships: Finding a friend to do the new behavior with, or who you can talk to about the progress you’re making
  • Reflecting: Taking time to reflect on the progress you’re making through journaling, discussion with a friend, or in your mind
  • Restructuring: Making changes to the environment to make it easier to do the new behavior (i.e., throwing out unhealthy food or preparing at night for a morning run)

Behavior change is often fragile toward the beginning, so the goal of the list above is to provide scaffolding for new behaviors until they start to become self-reinforcing. Ultimately, we want the new behavior to be intrinsically rewarding enough that it continues on its own.

In my own life, I often had the desire to write more, but it would fall to the wayside when I got busy with other projects. I would write in fits and starts, and when I started missing writing sessions, it was hard to pick back up again. I'd go long stretches without writing anything at all, and when I did write, my writing skills were so rusty that it was hard to get in flow.

Then, toward the end of last year, I was talking with Dan Shipper, and it turned out that we both wanted to bring more consistency to our writing process. We decided to start meeting daily in the mornings for two-to-three hours of writing, and it turned out to be a game changer for both of us. Even when we’d miss a day, since we enjoy hanging out, we’d show up the next day  and push through the resistance to starting again.

Now, several months later, writing has become intrinsically rewarding: I enjoy it enough that I'll write even if we don't have a session on the calendar.

Over time, committed action is about creating larger and larger patterns of behavior in the service of our values. What starts out one day as putting on running shoes and going for a walk could eventually turn into training for a half marathon. Perhaps what has started out as Dan and I writing together on weekday mornings will someday turn into one of us writing a book.

When working with committed action, there are no "right" or "wrong" behaviors, and no step is too small—anything done in service of your values is a step toward building a life that matters to you. Living fully is the ultimate goal, and looks different for each and every person.

To explore committed action in your own life, you might ask, what small behavioral shift could I make in service of moving toward what matters in my life? And how might I support it with the scaffolding above?

Whatever the answer, this is what ACT is all about—living life from the feet up.

Want to read more?

Congrats! If you've made it this far, you now have a basic understanding of ACT and how it can benefit your work and your life.

If you're interested in learning more about ACT, here are a few places I’d recommend getting started:

  • Steve Hayes, one of the founders of ACT, has a wonderful TED talk explaining the basics of ACT and how he developed it through his own experiences dealing with panic attacks.
  • A Liberated Mind, also by Steve Hayes, is a self-help book that gives a more in-depth overview of the ACT model and includes a number of exercises to do on your own. If you'd like to get a taste of what the book is like, there are a number of exercises you can try on his site.
  • Values in Therapy, by Jenna LeJeune and Jason Luoma, is my favorite book on ACT, and explores the processes in this piece with a focus on how they all relate to values. Although this book is meant for clinicians, I've found it accessible for anyone interested in ACT.
  • There are also many posts on Every that directly, or indirectly, reference the principles of ACT, like Dan's piece on panic attacks.

Casey Rosengren is a founder and executive coach based in New York. If you’d like to learn more about coaching or his new course, The Hidden Discipline, drop him a note.

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