Why You Keep Making It Harder Than It Has to Be

My client Jed had been working around the clock and was constantly stressed.

He committed to carving out time to go to the gym in the morning. Yet every time we spoke, he said there was too much to do and he just couldn't get there.

Jed thought the problem was his workload. At the same time, he knew, consciously and rationally, that he'd perform better if he took that time.

Underneath, he saw self-care and the parts of his job that came easy to him as less worthy of a CEO, a distraction from the "hard work" he believed was required to succeed.

Together, we uncovered one of his limiting beliefs: Success requires sacrifice.

It's among the most pervasive beliefs I see in founders: "it's supposed to be hard. I have to sacrifice in order to achieve."

And beliefs like that one tend to create the results that prove them right.

But when you see how that happens, you get to choose how hard building has to be.

How "It Has to Be Hard" Keeps Itself True

You might be thinking, "But building a company is hard."

If hard means long hours, think about the guy who started the local auto mechanic shop in your town, who created maybe a couple hundred thousand dollars of value. Then think about Elon Musk.

Did Elon work a billion times harder than that guy? Did he put in a billion times more hours? Certainly not. It's clearly not just about time.

When I say hard, I mean struggle and suffering. You could work a hundred hours in a week in a state of flow and have it feel like play and joy and enlivening. You could work thirty hours and have it feel like a grind.

So what makes building feel like struggle and difficulty? Often, it's the belief itself.

Because Jed believed startups require sacrifice, he saw his tasks as challenging and struggled through them. He spent his time on the hardest, least enjoyable tasks to make sure he was sacrificing enough.

That way of working created his results. He was stressed, unhealthy and, ironically, often unproductive. His team members absorbed his stress and were depleted.

His work felt really hard, which reinforced the belief he started with.

There's a distinction I learned from the Conscious Leadership Group: you can know your commitments by your results, not by what you say your commitments are. Someone who says they want to be fit but never works out is unconsciously committed to not being fit.

By that measure, Jed was unconsciously committed to it being hard.

And the startup world makes this commitment easy to keep. It doesn't just tolerate the grind. It rewards it, romanticizes it and treats exhaustion as a merit badge.

That's why the belief rarely gets questioned. It's worth looking for it on purpose.

How to Loosen the Belief That It Has to Be Hard

1. Find it and own it.

Finish these sentence stems with whatever comes to mind first, without overthinking:

• Startups are…
• Hiring is…
• Fundraising is…
• Sales is…
• Managing a team is…
• Life is…

One founder I did this exercise with realized she had the belief that fundraising is hard and stressful.

If any of your answers make it sound hard, own it. Say it out loud as a commitment. For her, that would be: "I'm committed to fundraising feeling hard and stressful." Repeat it until you feel yourself own it.

Owning it moves the hardness from something that's happening to you to something you're doing. And what you're doing, you can change.

2. Trace where it came from.

Ask yourself: When did you first take on this belief? Who did you get this belief from?

Seeing where it came from helps you see it as an adaptive strategy for situations that occurred in the past, not an eternal truth about yourself or the world.

3. Ask what you're afraid of, then look for the opposite.

Simply asking "Is this belief true?" often doesn't work. If it's felt hard, that's been your truth. We're not denying it.

Instead, ask: "What am I afraid would happen if I let go of this belief?" Then ask: "How might the opposite of this belief be just as true?"

In that same exercise, the founder realized she loved sales because, in her words, "It's an opportunity to connect someone with something that they'll benefit from." Then she exclaimed, "What if I looked at fundraising the way I think about sales?"

4. Create the evidence.

One of the best ways to gather evidence to disprove a limiting belief is to create that evidence.

For Jed, it was scary to let go of believing that work had to be hard. Still, he began to experiment with delegating tasks he didn't want to be doing.

Many clients assume that I'm advocating for them to work fewer hours and with less intensity. I'm not. If you want to work 80 or 90 hours, great. But if you think those hours have to be a struggle, I just think that's not true.

Admittedly, I have seen many founders who start working from flow reduce the number of hours they work. This is usually caused by a massive increase in effectiveness and a realization that they were operating in a way that wasn't authentic for them or aligned with their values.

As you work through these, you might feel some shame, like there's something wrong with you for not having figured this out already. Just don't go making yourself wrong for any of it.

When Building Gets Easier

Jed, the founder who couldn't make time for the gym, or for himself, found a different way to work.

As he let go of the belief that it had to be hard, he made space for the aspects of the work he most enjoyed and was uniquely good at. He took better care of his health and well-being.

His team stepped up in surprising ways and exceeded his expectations. With more time for reflection, he created a clearer, more effective vision and strategy for the company.

Once he saw the company's performance actually improve, he began gathering evidence for a new belief: that he could be successful and enjoy the journey.

Building doesn't have to be as hard as it's been. I want you to have the freedom to choose.

Jed didn't spot his belief on his own. We found it together.

At the third annual Sun Valley Founders Retreat, January 20 to 24, 2027, you'll work with eleven other founders and a team of coaches whose job is to see what you can't.

Over four days, you'll uncover the beliefs that have been making building harder than it has to be. Then you'll practice letting them go, so you can build a thriving company without having to sacrifice your life for it.

If you're a founder who wants to build with more ease, I'd love for you to join us.

​Click Here To Learn More And Apply>>​

With love,

Dave Kashen

P.S. If you have any questions about the retreat, just hit reply.