Founders: it doesn’t have to be this hard

Dave Kashen
19 min readJan 15, 2024

--

Note: If you want to be radically supported, join the next cohort of The Inner Game of Entrepreneurship, a 3-month transformational group coaching program for founders, starting on Tuesday 1/30

The idea that pain, insecurity and suffering are necessary ingredients for a founder to succeed is the most common and dangerous myth in the entrepreneurial community. Or more simply stated… it’s a bunch of bullshit.

Most people think that being a founder is inherently stressful. That the challenges of bringing something new into the world, raising capital, hiring and firing people, and scaling are anxiety-inducing by nature.

Further, many believe that in order to be successful, you must be driven by a deep need to prove something to the world. You’ve likely heard the quote: “Chip on your shoulder, chips in your pocket,” implying that the more a founder has to prove, the more successful they will be. You may have read Elon’s biography and assumed that he must be driven by the wounds of his father’s abuse, and that that’s why he’s been so impactful. I once had a founder/CEO client quote Captain Kirk: “I need my pain.”

So, why does the entrepreneurial journey feel so stressful for most founders?

Entrepreneurship requires extraordinary levels of motivation — both for the founder themselves and for their teams. Most founders, like most people, intuitively recognize that tension is a powerful motivator. Tension, by its nature, seeks to be resolved.

So they create tension based on lack or fear.

Lack is the sense that something is missing or you’re not where you should be. In essence, it’s resisting what is that creates the tension.

Fear is the sense that you are headed for a future you don’t want. In essence, it’s attachment to the future you want that creates the tension (between your desired future and the one you think you’re headed toward).

Lack and fear are based in perception and imagination, and not the reality of the present moment you are in. Lack and fear are toxic forms of tension that create the feelings of stress and anxiety that most founders and their teams experience.

The root causes of lack and fear are resistance and attachment. These are the only two things that actually cause stress:

  1. Resistance to what is
  2. Attachment to what you want

That’s it.

The external conditions don’t cause suffering. Our resistance or attachment does.

I need my pain.

At about this point in the conversation, most of my founder clients start to squirm a bit. They’re getting nervous because they see where we’re headed. I’m about to ask them to let go of their resistance and attachment. And they’re scared because they’ve been motivating themselves for most of their lives from a place of lack and fear. Letting go of that motivation feels like a leap into the unknown. And it is. Bear with me while I explain...

Resistance to letting go of resistance.

I ask my clients to let go of resisting what is, and accept everything about themselves, their lives and their business just as it is. Here’s what most of my clients say in response:

“If I just accept things as they are, what would motivate me to do anything?”

That’s the core fear. “Because I’ve been motivating myself for so long by telling myself a story that things are not the way they should be (or I am not the way I should be), I won’t be motivated without it.”

The sky shouldn’t be blue.

Here’s what’s crazy about this: telling yourself that things should be different than they are (we should have hit our sales targets, we should have closed our round by now, I should have lost 10 pounds, I should be more confident, I should know how to do this) is no different than telling yourself: “the sky shouldn’t be blue.” And that’s what you do, all day, every day. You go through the world saying the equivalent of “the sky shouldn’t be blue.”

Think about it. Imagine if you actually, really strongly believed that the sky shouldn’t be blue. You’d wake up in the morning and look outside and think “darn, it’s blue again!” You’d create so much needless frustration and suffering in your life. Can you see how you are essentially doing that?

Attachment to attachment.

I next ask my clients to let go of attachment to the outcome. The most confronting question I ask is typically this one: Are you willing to let go of being right that your company being successful would be better than your company failing?

This usually stops them in their tracks. Most founders have it as a hard and fast truth that their company being successful is the ‘good’ outcome and their company failing is the ‘bad’ outcome.

“Nope,” they often respond. “How could my company failing be a good thing?” But if I really press them, they start to say things like: “well, maybe I could move on and work on something even more meaningful” or “maybe I’d learn something from failing that will be key in whatever I do in the future.” An even deeper reflection leads to: “maybe it would help me release my ego attachment to success. That might be more valuable than my company succeeding…”

If you listened to my (quite vulnerable) interview on the Danny Miranda podcast, you’d have heard me describe how I lost nearly 70% of my net worth in 2022 (mostly crypto and tech stocks). Of course, it felt like a huge punch in the gut at first. I felt shock, and even more, shame. “How could I have let this happen? Why didn’t I sell? I should have known. You’re clearly not as smart as you thought.” And on and on went my inner critic.

But over time, as I let my waves of fear, nausea, and disappointment move through me, I started to realize something. Nothing was different. The thing that my mind said was one of the worst possible outcomes actually happened… and I was ok. While I might have told myself this (or told my clients this), the actual visceral experience of losing all that money and feeling, knowing in my bones that I was ok, was liberating. On a drive somewhere, my wife asked me: “What do you love about yourself that has nothing to do with your achievements or money?”

“I’m just a kind, caring, fun-loving guy, I replied” And in that moment, I knew that I was enough regardless of how successful or wealthy I was.

For years, I’d worked on letting go of my attachment to money, with modest success. And here, life had given me, a whack-you-upside-the-head version of a gift. The experience of losing money freed me. And that was more valuable than the millions I lost. My mind was certain that making money is better than losing money. And my mind was wrong.

And so is yours. Certain and wrong. My friends who have gone through AA tell me that they have an acronym for fear:

False
Expectations
Appearing
Real

If I had a nickel for every time my mind, based on fear, was certain and wrong about what would happen, well… I’d have the money I lost back.

Letting go of resistance and attachment.

As a thought experiment, see if, just for this now moment, you can let go of wishing anything about your current experience was different than it is. And, at the same time, let go of needing to control the future. Let go of any attachment to what you want to have happen. Notice how you feel.

If you’re like most people, you experience a deep sense of peace and calm. And that peace and calm is always available in any present moment by simply letting go of resistance and attachment.

“OK, so maybe, just maybe I could let go of resisting where we’re at and let go of attachment to my company being successful. But won’t that just lead to apathy? Why would I care or work so hard to make my company successful?”

Apathy v Non-attachment

This question leads us to a critical distinction:

Apathy = not caring.
Non-attachment = not believing your well-being depends on the outcome.

Attachment comes from believing that your and others’ well-being depends on a certain outcome (that’s why you believe it’s the ‘good’ outcome). A lot of my work as a coach is based on the conscious leadership framework, which distinguishes between being in a state of threat (seeing yourself as a victim and believing life happens ‘to me’) and a state of presence (seeing yourself as a creator and believing life happens “by me”). They call this distinction Above the Line (presence) and Below the Line (threat). This video on Locating Yourself explains the distinction in more detail.

The critical distinction I want to make here is that when you’re in a state of threat, you believe that your well-being is determined by external circumstances and conditions (that’s why you’re in a state of threat). When you’re in a state of presence, you believe that you are the creator of your well-being, regardless of external conditions. In fact, the practice of conscious leadership is, in essence, learning to be present in a wider variety of external circumstances so that your well-being is less and less dependent on anything outside of you.

“OK, but I still want my startup to be massively successful,” they say.

“Yes!!!” I respond. “I want that too. I want you to have what you want. I want you to play to win!”

And that might be the key word: play.

When you let go of attachment to being successful, the experience of building a company (or any pursuit, really) starts to feel more and more like a game. And, like most games, the more you play to win, the more fun it is, the more you grow and learn and the more likely you are to win. You can play to win and give it everything you have without being attached to the outcome.

Preference v. Attachment

This bring us to another critical distinction: preference v attachment.

Preference = wanting a certain outcome.
Attachment = believing your well-being is dependent on having that outcome.

You can want to win, play to win, leave it all out on the field, be that man or woman “in the arena whose face is marred by dust and sweat and blood… who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly…” without being attached to the outcome.

You can be an extraordinary entrepreneur without being attached to winning. I want you to play full out. I want you to give it everything you’ve got. I want you to win.

And here’s something interesting to reflect on:

The less attached you are to an outcome, the easier it is to create.

People often think of dating or a job interview as an illustration of this. You may have had a time when you felt kind of desperate. You got really attached to a date or job interview working out. How’d that go for you? How did your date or your interviewer respond when they sensed your clinging to the outcome? The same dynamic occurs in hiring, fundraising and sales. Non-attachment is a fundamental business skill!

A healthier, sustainable, non-toxic form of tension.

OK, so at this point maybe you’re convinced that letting go of wishing reality was different than it is, and letting go of attachment to outcomes is a good idea. Maybe you’ve even mustered up the courage to let go of those old ways of motivating yourself from lack and fear-based tension, and are ready to take that leap into the unknown. What’s on the other side, and how do you motivate yourself and your team now?

The answer is: Creative Tension.

Remember, tension is a powerful motivator because it seeks to be resolved by its nature. Creative Tension is a source of motivation that leads to inspired, creative action. It feels more like being pulled toward an inspiring future than being pushed or driven away from an unsatisfactory present. You’ve most likely experienced it or even created it at times. But if you’re like most leaders, you’re not yet clear on exactly how or what you did differently to inspire the team than other times where the team seems more driven out of fear. I’m going to teach you the critical leadership skill of generating Creative Tension so you can create it anytime you want to inspire yourself and your team. I’ll also teach you to quickly diagnose what likely went wrong if you or your team are experiencing stress instead of inspiration. Here goes…

How to generate Creative Tension.

Creative Tension is generated when you have two things present at the same time:

Current Reality + Desired Future.

That’s it. It’s that simple. Since a picture is worth a thousand words, here’s one that gives you a sense of the model (and may leave you grateful I became a leadership coach and not a designer):

Generating Creative Tension

Importantly, as we discussed above, you must be present to and grounded in Current Reality (face what’s true, accept it as it is, let go of wishing it was different) while at the same time imagining your Desired Future without getting attached to it (this is my preferred outcome, this is the game I’m playing, but I can’t know for sure that it’s the ‘right’ outcome).

So a more precise way to describe what’s required to generate creative tension is:

Current Reality (without Resistance) + Desired Future (without Attachment).

I think of this Creative Tension model as a core leadership fractal, in that it can be used in a wide variety of situations and at different scales. For example, in preparing for a team all-hands, you might structure it this way.

Current Reality: “Here’s where we are. We grew by X% and achieved Y% of our goals. We hired X people. We’ve been working really hard and a lot of you are feeling tired and disappointed that we didn’t launch ABC on time.”

Desired Future: “Here’s where I see us a year from now. We’ll have grown by X% and achieved $Y in revenue. We’ll have learned from our mistakes and gotten tighter on our operating efficiency and timelines. We’ll have had the most fun, energizing year since we started. I see all our efforts these last X years starting to bear fruit as we get the flywheel going and our launch of ABC will take the customer experience and value to the next level and be a catalyst for expanding into XYZ segment.”

Reflect on if you’ve been in or lead an all-hands meeting in which one of these was missing. Sometimes leaders will harp on the Current Reality, without ever creating a compelling future for the team to live into. Other times, leaders will go on and on about the amazing Desired Future without acknowledging the challenges the team is facing today. The vision won’t feel credible because of the lack of acknowledgment of Current Reality.

You can also use the Creative Tension model for a 1-on-1 conversation with a team member:

Current Reality: “You achieved X% of sales quota, about the middle of the pack.”

Desired Future: “I think you have everything you need to be one of our best salespeople. I see you in a year, crushing your numbers and being a mentor for some of the new sales team members, and ultimately moving into a sales manager role.”

And most importantly, you can use the Creative Tension model with yourself:

Current Reality: “Self, you are tired and stressed. This journey has felt like a huge emotional roller coaster ride, and you’re getting close to burnout. You’ve made some great progress building the team and acquiring customers, but it’s felt like such a slog every step of the way.”

Desired Future: “You’re going to stop motivating yourself from lack and fear, and start using the Creative Tension model to motivate yourself from creativity and inspiration. This will be the most fun, creative year you’ve had yet. You’re going to wake up excited to get started, and end each day feeling fulfilled. Your team will notice a palpable shift in your energy and it will trickle throughout the company, inspiring them to new levels of creativity and bold action.”

Common Pitfalls in Applying the Model

Since you’re about to start practicing a new way of leading, I’d like to make you aware of some of the most common pitfalls founders and leaders fall into when applying the Creative Tension model. You’ll likely notice how you’re already falling into some of these traps.

  1. Collapsing the Desired Future into the present
Collapsing the Desired Future into the present

Once we get clear about our Desired Future, a common trap is to collapse that Desired Future into the present by wishing we were already there. We tell ourselves: “I should be better at leading. We should have already achieved $X revenue or funds raised. I should have lost 20 pounds. I should be more courageous.” Instead of putting the Desired Future in the future where it’s possible and feeling inspired to create it, we focus on the gap and create suffering and frustration for ourselves. This is how we create a sense of lack or not enough — by comparing our Current Reality to some Desired Future that we think we should be experiencing now.

I had a client who was nearly out of cash (been there?) and feeling the weight of the world on his shoulders and the shame of failure looming. He was so frustrated that he had not been able to raise the money he had set out to raise, and kept ruminating on all the things he should have done differently in various fundraising meetings. “How could I have gotten here?” he kept berating himself. I explained this model to him and challenged him to shift his Desired Future (raising the capital he needed to continue on and build the team and product) out into the future where it belongs. Even if that future had to be 3 weeks away; that’s a lot better than wasting his energy wishing he was already there now. As a sports fan, we came up with a metaphor: “you’re in the fourth quarter of the game, there’s 5 minutes left and you’re down by 10.”

“Give me the ball coach,” he replied with a smile on his face. I had him envision winning the game - in this case 3 weeks in the future, having raised the money he needed. He felt the energy of imagining that victory and started getting creative. He brainstormed people from his past he hadn’t thought to ask for money. He made a list of possible angel investors, and got in action reaching out and setting up meetings. He showed up at his meetings energized and excited for the future ahead. Three weeks later, he had raised over $1mm to press on, and months after that a few million dollars more from institutional investors.

2. Focusing on the Undesired Future

Focusing on the Undesired Future

Too often, instead of focusing on the Desired Future, we focus on our Undesired Future. You’ve probably heard yourself or someone else say something like: “If we don’t hit these goals, we’ll have a terrible board meeting or run out of money or have to crush ourselves next quarter.” Or “if my startup fails, I’ll end up on the street, scared, hungry and alone…”

I’m told that when you go through training to drive a race car, they emphasize this point over and over: “Do not focus on the wall!” If you focus on the wall, you’ll hit the wall. Focus, instead, on where you want the car to go.

The same is true in business and life. Yet too often, our attention drifts from focusing on our Desired Future to our Undesired Future. This is how we create fear-based tension — by focusing on the Undesired Future.

“But focusing on all the bad things that might happen helps me avoid them,” many of my clients protest.

Scenario Planning v. Rumination

While it’s true that it can be useful to do some scenario planning and imagine all the things that could go wrong and what you might do about them, this is an intentional exercise you choose to sit down and do, once. What most people actually experience is their minds drifting to imagine the Undesired Future state again and again through the day. That’s rumination, not scenario planning. I recommend my clients who notice this pattern engage in this practice:

Anytime you notice you’re focused on your Undesired Future, shift your focus to your Desired Future instead. Imagine your Desired Future as vividly as possible. Imagine yourself there, experiencing what it’s like to be you in this future. Step into the body of your future self. Breathe through her lungs, see though her eyes. Notice what it’s like to be you. Notice what’s going on in your mind and what your body sensations feel like. Notice what you’re feeling. If we were looking at you from the outside, what would we notice? What’s your posture like? What’s the expression on your face?

The more vividly you imagine your Desired Future and your experience of being you in the Desired Future, the more you’ll feel (now) the feelings and sensations of that future you. You actually start to shift at the level of Being to become the person you’ll need to become to create that Desired Future State (more on this in another post).

I explained this model to a client who was founder of a nearly 1,000-person company that had raised hundreds of millions of dollars. Like so many, he was in a precarious position, having raised money at high multiples before the market conditions changed in 2022. He realized that he had been almost exclusively motivating team from fear, saying things like: “If we don’t achieve our goal, we won’t be able to raise the next round we need.”

The distinction between focusing on the Desired Future and the Undesired Future was a light bulb moment for him. He committed to focusing on the Desired Future from now on, and motivating his team that way. Within a few months, he saw the level of energy and creativity of his team increase dramatically. He himself was in an open, creative state instead of being stressed all the time. When he received a cold outreach from a potential customer in an industry the company currently didn’t serve (that he likely would have ignored in his stressed out state), he was curious and present enough to pursue it and connected to the potential customer. That one conversation let to the company doubling its revenue nearly overnight (which was already 9 figures) and becoming cash flow positive.

3. Extrapolate setbacks into the future

Extrapolate setbacks into the future

This is a slight derivation on focusing on the Undesired Future. You’ve generated Creative Tension, you’re going along on your way to creating your Desired Future, and you hit a setback. Something doesn’t go as you expected. A key team member quits. Fundraising falls through. A large customer churns. Our tendency is to extrapolate that setback into the future, and once again focus on our Undesired Future State. (I believe this is sometimes referred to as ‘envision’ in psychologist-speak). This often leads to us reacting out of fear of the Undesired Future, rather than creatively responding to the specific situation at hand in a way that moves us back toward our Desired Future.

Once again, the solution is to acknowledge the new Current Reality (accept it as it is; as my clients like to say: “it is what it is”) and then focus on your Desired Future.

Creating your Desired Future

One really important point: you don’t need to know how you’re going to get there to envision and share a Desired Future State. To some extent, generating Creative Tension is the how. By generating creative tension, you’re creating the conditions for creativity and bold action in the direction of your Desired Future. Our minds can’t really tell the difference between what we see/experience and what we envision. And our minds don’t like cognitive difference. By being present to both your Current Reality and your Desired Future, you create cognitive dissonance and your (and your team members’) subconscious minds will go to work on removing the cognitive dissonance by realizing the Desired Future. Further, our reticular activating system (fancy way of saying: the part of our brain that filters out what we do and don’t experience) gets attuned to our Desired Future so you may notice relevant ideas, opportunities and possibilities that you didn’t or couldn’t see before. (You may recall a time when you got a new car, and suddenly you saw that car everywhere. That’s your reticular activating system at work.)

One of the most famous examples of the Creative Tension model in action was when JFK announced “We’re going to put a man on the moon and return him safely to earth by the end of the decade” in the early 1960's. NASA scientists were apparently up in arms because they had no idea how they were going to achieve that. Technologies needed to be invented to invent still newer technologies to make it possible. Yet, on July 21, 1969, Neal Armstrong became the first person to walk on the moon (and returned safely to earth).

Sometimes clients ask how audacious v “realistic” to be in creating your Desired Future. There’s no ‘right’ answer here, but I’d use your body sensations to help answer the question for yourself. Choose a Desired Future that makes you feel most alive.

You could think of the ‘track’ between your Current Reality and the Desired Future in the drawings as a rubber band. If you set the Desired Future too conservatively, you won’t generate much Creative Tension. If you set the Desired Future too ambitiously (and you or others don’t actually believe it’s possible), the rubber band will snap and you won’t generate any Creative Tension. It’s a bit of a goldilocks approach — find the level of ambition that, when you envision it, you feel alive and inspired rather than daunted and overwhelmed. One of my goals with clients (and myself) is to expand their willingness to believe in greater and more ambitious possibilities by awakening them to how powerful, creative and resourceful they actually are (also, a subject for another post). A quote I love comes to mind here:

“The future belongs to those who believe in the beauty of their dreams.”
- Eleanor Roosevelt

Where to from here?

Practice, practice, practice. Practice generating Creative Tension for yourself and your teams. Notice when you’ve fallen into one of the traps, and shift back into Creative Tension.

If you want to be radically supported by me and a group of peers to shift how you motivate yourself, let go of limiting beliefs and show up as your most energized, confident, powerful, visionary self, join a group of like-minded founders:

Join the next cohort of The Inner Game of Entrepreneurship, a 3-month transformational group coaching program for founders, starting on Tuesday 1/30.

--

--