Why Self-Care Is a Critical Startup Investment

I had a client who was drowning in the details of his business.

He was either micromanaging or heavily involved with everything (you could call it either one, depending on your perspective).

But he was getting married, and there was a very clear expectation from his wife that they'd go on their honeymoon for two weeks after the wedding.

This wasn't optional. This was a life event that mattered deeply to both of them.

And he was terrified. Because in his mind, taking two weeks away meant everything would fall apart.

So we worked for months leading up to that honeymoon to hand stuff off and delegate.

It was an incredible forcing function that transformed the way the team and organization operated.

He had to hire people.

He had to let go of things.

He had to shift his role from being in the weeds doing everything to a much higher level of leading and orchestrating.

The irony? Preparing to step away made him more valuable to his company than any hour he'd spent buried in the work.

So what keeps most founders from making this shift?

Why Founders Believe They Can't Step Away

One of the biggest myths in startups is that success requires sacrifice. That it's either you thrive as a person OR your company thrives as a business.

It's this zero-sum mindset where you see lots of founders who used to have regular exercise habits, hobbies, time with friends.

But they let all that stuff go on the altar of startup success because they believe that's what it takes.

There's this default belief: "I have to give all my time to my startup. That's what my employees expect. That's what my investors expect."

And so founders end up operating in a way where they're draining their battery, burning themselves out, trying to push beyond their natural human limits.

They convince themselves that last marginal hour of grinding is what's going to make the difference.

Managing Your Energy, Not Your Time

But here's what that misses: "One cannot drink from an empty cup."

From this sacrifice mindset, a lot of founders end up operating at a suboptimal state. They're not actually their most effective as a leader. They're not as creative as they could be. They're reactive.

But most of us have experienced the opposite. Coming back from the gym way more energized. Way more clear-headed. Having breakthrough insights. Being able to inspire and motivate people more effectively.

What I think is so exciting as a possibility is a win for all: you invest in your own state by exercising, keeping up hobbies, doing things that energize you, spending time with people you love.

And then when you're focused on the startup, you just have more to give.

You end up being way more productive, more effective, a better leader. Also better as a spouse, parent, or friend.

There was an article years ago called "Manage Your Energy, Not Your Time." If you think about your energy being the most important contributor to startup success, it changes how you think about using your time.

I think the truth is, what people really expect and want from you as the founder or CEO is to bring your best self, not to maximize the quantity of hours you give.

And we don't bring our best self by sacrificing ourselves.

The human body works in cycles. Our heart opens and closes. We have circadian rhythms. We need sleep. There are different seasons.

When we try to just work linearly and ignore our body's natural limits, we're not actually maximizing our energy or our effectiveness.

Vacation as a Forcing Function

Let me be grounded in reality. Building a startup is very demanding.

There are times when there are critical deadlines based on the market, customers, and partners.

But as Clayton Christensen said in "How Will You Measure Your Life?": Life is a series of extenuating circumstances. And especially a startup is a series of extenuating circumstances.

What that means is it never feels like the right time.

There's always something: "I can't right now because we're launching next month." "I can't right now because the team is understaffed." "I can't right now because we're in the middle of this pivot."

The vacation becomes a forcing function. This is what happened for my client.

If you're gone for a week (or in his case, two weeks) you really get to see what falls apart. You have to think about who you can delegate to, how to delegate well, what context to give people. Or if there's no one you can delegate to, that tells you something about your hiring.

And here's what that reveals: as the founder or CEO, there are very few things only you can do. One of those is thinking about the future.

Most people are in the business, thinking day-to-day. You're one of the only ones who can really think long-term, strategically about what's happening in the industry. Raising money. Hiring senior executives.

There are a few critical things. But most founders are doing many other things than that.

I like challenging my founders to hire themselves out of a job. I want them to be bored for a little bit.

Most founders think that's absurd at first, but that's the goal: hire and delegate so your team runs the business day-to-day, and you can step back and really work ON the business versus IN the business.

Feeling the Fear and Letting Go Anyway

Here's the hardest part: it's scary to let go. Your mind will tell you stories that things will fall apart and unravel.

Generally, those stories aren't true.

And even if it's true that you'd do a better job than someone on your team for now, the only way to get leverage and scale is to let people learn by doing.

Maybe they won't do it as well as you the first couple times. Maybe they'll make mistakes and fail. But they'll learn from those mistakes and failures and get better.

Think of it like an investment. The gap between your performance and theirs is the short-term cost for the future gains of them being able to do it as well or better than you, so you're no longer having to do all those things.

Making that investment requires expanding your capacity to be with intense feelings. Being willing and able to just feel that fear and let go.

And one of the best ways to let go? Go on vacation. Not be on all day, every day. Actually take time off and don't focus on work for a little while.

You may need to show your nervous system that things don't fall apart. I've seen a lot of founders find a lot of freedom when they come back after a week and find things are still running okay.

People stepped up in surprising ways. Yeah, maybe a few things slipped through the cracks, but they're not existential things.

Operating From a Full Cup

So what happened when my client left for his two-week honeymoon?

Things didn't fall apart.

His company didn't just survive. It was stronger. The organization evolved, people stepped up, and the systems he'd been forced to create actually worked.

And when he came back, he wasn't micromanaging details anymore. He was actually leading.

The work he did to prepare for those two weeks (the delegation, the hiring, the letting go) had transformed him into the visionary his company actually needed.

He'd proven to himself that the story wasn't true. Everything didn't collapse without him.

If not for that honeymoon, I think he'd still be micromanaging and in the weeds today.

That honeymoon was the forcing function he didn't know he needed.

That's the shift: from "I have to sacrifice myself for my startup" to "investing in myself IS investing in my startup."

Because when you're operating from a full cup, everyone wins.

Which brings me to why I'm hosting the Sun Valley Founders Retreat this January.

Yes, it can feel hard to take time off like that.

But it won't only be a really powerful forcing function, it will be the kind of deep work that allows you to go from being stuck in some local maximum to actually having a quantum leap of performance.

So investing those couple of days is an incredible investment in future effectiveness.

Even if you lose four days of productivity, the percentage increase in how effective you'll be in the years after becomes a no-brainer ROI in terms of your time.

With love,

- Dave Kashen

P.S. If it feels impossible to step away right now, that's exactly when it would serve both you and your startup most. Learn more about the Sun Valley Retreat here >>​