Your child (company) will someday grow up and move away
I founded Acquia in 2007 by teaming up with Dries Buytaert. And in the years since then, we've succeeded in building up a really great team, forming a really great business, with amazing customers. As with many founding CEOs, there came a time for me to hire a CEO with experience in bigger companies and organizations, and when the time came I happily brought Tom Erickson into that role. And it's been good since then for me; Tom has respected my ability to continue to add value in the company by introducing new products, bringing the company to new markets, and generally accelerate growth.
But at some point, I had to realize that I'm a startup-type guy. I like the early days, when everything has to be figured out. I feel comfortable being involved in decisions about what the go-to-market strategy should be for a given product; how to work closely with early first customers to find traction quickly. Though it might actually be larger because of sheer company size, my sense of personal impact on the company seems more diffuse, and I like the direct, focused impact that comes in those early, smaller team days.
This moment becomes like that moment when a parent must send their child off to grow up. No longer is the child something you can hover over day after day; it's now up to the child - in this case, the management team under somebody else's control - to grow without your daily involvement.
The ultimate send-off is a wee bit reverse from sending a child off; in this case, the founder is the one that walks out the front door while the child stays behind to flourish. For me, that was Monday afternoon, 22 October 2012. The day I left my child to continue on without me being there daily. Happily, I think the child will do really well from here on.
But that literal action of walking away from the front door of the building, with your company at your back, hits you pretty hard. Though my wife & I don't have children, I think I just sensed a very similar feeling to the child send-off. I can see why it's such an emotional moment for parents, filled with pride in the child, pride in having helped make that happen, and uncertainty about what lies ahead - for both your child, and you.
I recommend the experience for all founders.