CEO’s — You just might be a bit too generous

Those greedy CEOs, they are to blame for this, if they were just more generous, people would be more / less _____________.

Given how I run my company, I tend to attract a certain type of conversation with other leaders who reach out for coffee. They see that I work hard to be transparent about my journey, and I seem generous with my team and they are trying to replicate it in some way.

So a lot of CEO friends ask me how I’m so happy, motivated to keep working, when I don’t have to, enduring the day to day people-based headaches, pains, and to be honest, heartbreaks — all of which are on top of just trying to run the business.

First it is that in Jeff, Emily, Crystal, Larry, and Steve I have a brick house of a leadership team that have a combined 60 years-ish working with me.

Your generosity when it comes with strings attached, even if unsaid, will cause you heartbreak.

Overly Generous CEOs can set themselves up for depression, I’m seeing it with a few friends I’ve recently chatted with. They are giving more and more, taking more personal sacrifices, and finding out the hard way that sacrificing comforts at home, time with family, etc isn’t getting them a thank you when that generosity is expressed, much less long term loyalty, leading to some serious disappointment.

The year I had my highest profit distribution, was the same year I had my highest turnover.

Yeah, let that sink in for a minute. They year I set a record for highest % of profits and raw # of $ given to the team in profit share was was same year I set a record for people leaving Seer.

It’s interesting how we have this belief that a CEO who is transparent, generous, etc will have coworkers who reward that generosity with loyalty.

I didn’t go into my profit share expecting new found loyalty, I also didn’t expect to set turnover records (in the mid 20’s I think).

As I write this, I think when you are generous you really should be signaling at best to a small group of people, not expecting some “across the team” loyalty.

The Key: Securing your mask before helping others

As a CEO or an owner of a business, you need to first define what “enough” money for you and your family looks and feels like. Then you need to secure your “mask” and the “mask” of your family as soon as humanly possible. Run to that enough point.

This isn’t a cop-out for not being generous today.

I believe CEOs who wake up with a generous mindset are almost always too generous early on and sacrifice putting on the mask for them and their families. Once you give something to your team, you can’t take it back without pain. I’ve been there, the one day I didn’t feel like going into work was the result of me giving an employee who left a bonus 4 months after they left the company (when we were under 10 people).

For me, securing my mask wasn’t about some big, lofty, fancy life. It was about:

• Paying off my house
• Afford the best roofer (House had mad leaks for 5 years)
• Buying a nice car with great tech
• Taking vacations w/ my family (mostly as part of my business travel, and also use my status / points to fly my family for free)
• Have a nanny who could travel with us (which allows my wife and I to both work)
• Tuition for my kids so I can continue to live in the city and get them a great education
• Fix stuff at my parents / in laws houses

To me (and only me) these weren’t crazy indulgent luxuries, they were about security, peace of mind, and some joy for me and my family.

I know CEOs that haven’t made money in six months and haven’t been able to give raises to their people in two years. When they finally have a good quarter or a good year, they’re much more likely to give those people raises than they are to take care of themselves. That is how many generous CEOs act, however it comes at a cost.

Expecting Loyalty + Not Securing Your Mask = Depression, Resentment, Frustration.

Here’s the kicker: when CEOs make day-to-day sacrifices for their team, they often develop expectations around their generosity.

You start believing the hype that if you aren’t like those CEOs who compensate themselves in ways like the above your employees would be more sticky that just is the wrong way to look at it.

I chatted with Khe Hy (worth a follow) who helped me see this through the lens of Buddhism — he told me that we don’t have the right to expectations on the fruits of our generosity. If you’re going to be generous with your team, just do it. But do it without expectation.

“You have a right to perform your prescribed duties, but you are not entitled to the fruits of your actions. Never consider yourself the cause of the results, and never be attached to not doing your duty.”

This quote highlights the idea that when you give or act with generosity, you should let go of any attachment to the outcome or the recipient’s actions.

In Buddhism, this concept is often referred to as “dana” (generosity) without attachment.

You give with expectations when you haven’t secured the mask…

However, that’s really hard to do when you haven’t secured the mask for you and your family.

I just wish THEY knew the sacrificing I am making

It’s not your employees job to know your personal sacrifices for them / their families well being. It is your job to make sure you have secured or are on a strong path to secure) the mask for you and your family, so you can be OVERLY generous later without expectations and resentment.

Your personal sacrifices for your team will cause you to resent them

Every single day, you’re reminded of those daily frustrations, every day I heard a dodge charger rip down I-95, I was reminded that I had “bad windows and that I was woken up because of them”. So when you don’t get those thank-yous for your generosity, the sting is so much deeper. You start thinking “wait, do I not have good windows, so I can give out bonuses, just for this lack of thank you’s for what I’m doing?”

What is “life changing” money?

Very quickly, I started realizing that there was no more joy to be unlocked. I tried to figure out how my life would change with more money, and didn't like what I came up with, so I didn’t do those things. That is when I knew I secured the mask for me and my family. I will say, I will spend insane amounts of money on vacation to have someone else care about me having a good time to the nth degree.

I’m always gonna be that guy who uses points to try to upgrade, but has no problem flying coach. You have to go through imagining your liquid net worth being at increasing levels until it gets to a level at which you kind of feel that the things you are doing are ridiculous. That’s when you know what your line is.

Generosity Without Strings

You set yourself up for disappointment and even resentment when you’ve given out bonuses or raises while you know you haven’t taken one in years. How many of us tell our teams “unplug on vacation”, but recognize that maybe if we do and that deal doesn’t get closed people might lose their jobs?

When my work life balance as a CEO could cause you to lose your job, would you still want me to “unplug”? That is what I thought.

When you walk out of that office door into your home and see the things you’re not doing for yourself or your family because of your generosity at the company, it can quickly turn into resentment. This can make you really not want to spend time at the company you built, with the people you deep down love and want great things for. But that is a YOU problem, no one said you had to be that generous, and now you can’t take it back so just be a bit smarter next time raises or bonus time comes.

So yes, we should always strive to be generous as CEOs. But we need to do it without attaching our self-worth or happiness to the reactions of others. Don’t give people power over your generosity by having expectations.

Remember, we don’t have the right to the fruits of our generosity. But we do have the power to create a culture of genuine care and generosity, both in our companies and in the world at large. So secure your mask, define your ‘enough,’ and then secure others masks, there’s real joy in knowing that your generosity will help others do good for their families and loved ones.