Raking it in without
breaking your soul

No Regrets

This is going to sound like a bummer way to start but hang with me, it’ll be brief: My grandma passed to the other side recently. You don’t need to email me with condolences. It’s all good.

I didn’t realize, when I hung out with her the night before, that I’d be the last one to speak to her. She was retrospecting on life. I asked if she had any regrets. She broke out into a big smile and then fell asleep for a few minutes.

The same day I was visiting my grandma, Big Think published this article on the Harvard Study of Adult Development. The Harvard study and several others that track humans for decades produced similar findings: Life happiness is found in the quality of our relationships.

You’ve probably heard this before. If you’re like me, you’re already thinking “yeah, yeah,” with your hand on your mouse, ready to go scroll Instagram. Hold on.

If you want to be satisfied with your life, you’ve gotta invest in your family and friends. This is terrible news for people like me who have a hard time making new friendships as an adult.

The Big Think is careful to clarify that loneliness, which is what kills you, is “people who are more isolated than they want to be.” So if you LOVE being by yourself, do you, Boo. That’s a little freeing, right?

As long as you’re being honest.

If you think you’d like to be a little less isolated, let me tell you what I’ve been noticing.

People place bids.

Bids are tiny little invites to connect.

Perhaps a decade ago, I got new neighbors. They were from Montana. They raised backyard chickens that we’d watch when they went home for the holidays. She worked remotely and when she found out I was also typing away in my house all day, she said “Hey if you ever want to take a work break, hit me up and let’s go for a walk or something.”

Looking back now, I can see that was a bid.

I never took her up on it. I wanted to, sure. But there was always some Pressing Work Thing I needed to attend to instead. That’s what serious CEOs do. They don’t just vacate the office when there are Important Emails to be Answered.

A few years ago, they moved back to Montana because they missed the community.

Now I’m not saying I could have changed the course of their lives or something, but I definitely could have closed the laptop and enjoyed the company for 45 minutes once a week. You walk with someone for 5 years and you form a bond. (Also, just sayin, I coulda used the exercise.)

Work will always be there. The opportunity to create those life-satisfaction-building-connections will not.

I missed the bid and I regret it.

Now I look out for them and I intentionally bid all over the place. Lunch on Friday? Yes please.

Happiness requires a mindset shift for entrepreneurs.

There’s a very American work ethic we’re subscribing to, whether or not we’re aware of it.

Work hard now for future rewards.

Nose to the grindstone gets you a massive nest egg and a glorious retirement. Right?

Except whatcha gonna do with all that money and free time? Hang out with… who, exactly? Those friends you never nurtured along the way?

Please be cautious of promises of future reward.

Shifting our mindset would look like:

Blocking out four weeks of vacation in the year, even if you don’t have a destination in mind, even if you just stay home and enjoy the quiet time. Pick whole weeks or block out every Friday. You’ll figure out what to do with the vacation days, trust it.

Scheduling friend dates during the “work day.” Go for that walk, hit up that Indian buffet. I promise, you’ll feel like you had a good day.

Eating on the good plates and drinking out of the good cups. I know you normally reserve those for special occasions but I’m confident you can find something to celebrate every day, if you look for it. Today I finally took my dress to the tailor. Celebrate your accomplishments!

Giving people their flowers, while you can. Don’t wait until your colleague tells you she’s quitting to say “Oh shoot, I really like working with you.” Tell her now. Glow up that professional peer on your socials. Take a deep breath and tell your grandma exactly how she made your life better.

Let’s have faith in the fact that this isn’t going to turn into some YOLO sprint to bankruptcy court. You’re committed to growing your business and building a legacy.

It’s just that the legacy we leave for the next generation shouldn’t just be a big bank account. It should also be an example of a life well lived.

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