Lifers and Leavers: Our Opportunity as Business Owners 

When we opened Cat & Cloud we hired eight people. It wasn’t a stretch for me to look at those eight people and imagine that one day they could retire with us. I wasn’t sure how it would work, but it felt reasonable—if they grew as the organization grew, they could have lifelong careers with us.

Six years later our upper leadership team is exactly eight people. Two of them have been with us since day one but most of them were brought into the fold at different points on our journey.

We currently have seventy employees, and it’s much more difficult for me to look at those seventy people and imagine they could all retire with us. Not because of some size cap we have but because our pace of growth considering our resources (we don’t have huge amounts of external funding), and standards (quite high), make us more of the tortoise than the hare.

It’s tempting to try and solve the lifelong career equation. What kind of growth would be necessary to provide an A-Z path for everyone on staff at all times? Since that equation spins the growth flywheel, it’s easy to see how the numbers scale exponentially—if we solve for seventy, we’re faced with a problem of hundreds and then thousands.

This also makes a lot of assumptions. It assumes that everyone who experiences what we have to offer would decide to stay. That every person, each one with their own hopes and dreams, will discover that the best place to bring their dreams to life is with our organization. As business owners we tend to be proud of what we’ve created, and rightfully so, but it’s a bit egomaniacal to think this way.

Shuffling the Deck

Although people start companies, I’ve always found individuals to be far more interesting than organizations. Maybe it’s the compromises that come with the realities of business or that chasing popularity and growth tends to (counterproductively) water down a strong point of view. I feel a world in which more people are speaking directly about what they believe in and can do it in a financially viable way is richer than a world in which we all work for “Big Corporation X”.

Don’t get me wrong, there’s a place for the big. I like that Disney has the resources and team to be able to create Frozen II, but for me, this is more of an exception than the rule. Small is personable, small has a point of view, small is nimble, and small in size doesn’t mean small in impact.

Taking into account all of the above, it’s clear what our opportunity is.

We can choose to be a place of growth. A place where people can learn about themselves, learn skills that will help them on their journey, and learn what it means to be of service. A place where people can see the magic of their contribution and begin to realize their potential.

For most people who walk through our doors, we’re more of an incubator than a forever home. This isn’t a trivial role to play—the experiences we create for the people around us shape our lives and theirs. The journey matters.

A certain percentage of people will stay. The journey on offer and the journey they’re looking for will be a perfect fit. This blows me away. The fact that we’ve created a place that someone wants to make their forever home is incredible.

People will always leave. As business owners, part of our challenge is to embrace the fact that keeping people isn’t as important as helping them find their voice and ultimately their happiness.

If we’re doing it right, every time the deck shuffles we’ll draw a better hand than before.

Chris Baca