My BIGGEST Regret In My First 10 Years of Entrepreneurship
Every so often, I take personal time to reflect on the inevitability of my death.
I know. That sounds horribly grim. But this little ritual never fails to bring my short time on earth into the proper perspective.
My daily concerns and challenges just seem so petty and miniscule when compared to the grand scheme of life God has created for us.
And it seems many other people feel the exact same way, particularly those who are near the tail end of their life…
In her best-selling book, The Top 5 Regrets of The Dying, Bonnie Ware (a Palliative Nurse) recorded the most common regrets shared by her patients while facing their impending demise.
Out of the 5 regrets, there was one in particular which really hit home with me:
“I wish I hadn’t worked so hard.”
Ouch! As a 24/7 hustlin’ entrepreneur, this one sentence reached out from the page on which it laid and slapped me across the head.
Many of the patients — especially the men — felt they had not spent nearly enough quality time with their family and missed a lot of their kids’ childhood.
Do you ever fall into this trap?
I believe a lot of well-intentioned people do. In western society, our identities are tightly entwined with our careers and businesses outside of the home.
For instance, when meeting someone for the first time, what’s one of the most common “ice-breaker” questions to be pulled from your conversational repertoire?
“So Bob, what do you do for a living?”
Yep…me too. Guilty as charged.
To make matters worse, we’re bombarded with constant marketing messages designed to brainwash us to believe more “stuff” will make us happy. And only grinding harder and longer in our work will get us to this so-called “promised land”.
Well, I don’t know who the Joneses are, but trying to keep up with them will NOT bring you ultimate happiness.
So then, what will exactly?…
We should refer to the insightful, experienced men and women interviewed on their deathbeds. The wonderful souls unshackled from the trivial affairs of daily life.
Their answer?
People. Relationships. Personal connections. These are what TRULY matter to God—and to us, since we’re made in His image.
Yes, we are called to work diligently and work faithfully. As it says in Colossians 3:23,
“Whatever you do, work at it with all your heart, as working for the Lord, not human masters….”.
Yet, NOT at the expense of our closest relationships. In fact, our closest relationships can enhance the happiness and joy we derive from our vocation.
My daily work is much more rewarding when I share it with others. My business partner, Shaun. Our amazing team. And most importantly (for me), my beautiful wife, Kathy, and son, Zachariah.
So as we celebrate another Labor Day holiday today, we should all reflect on how to best AVOID this unnecessary regret during our final days on Earth.
My TOP 3 regret-eliminating recommendations are (drum roll please):
- Establish strict work schedule boundaries.
- Purposefully plan time with loved ones.
- And be present in the moment when you’re with them.
From what I hear, you won’t regret any of these choices.
Ryan “Life is More Than Business” Colby


