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The Most Expensive Career Mistake Is Refusing To Let Go

On February 5th, 2019, construction workers in Seattle officially began to demolish a key highway that some called the most beautiful view in Seattle, the Alaskan Way Viaduct. If you’re not familiar, the Viaduct as we knew it in Seattle was a stretch of highway that connected Highway 99 through downtown Seattle and en route to South Seattle and eventually towards the airport. If you lived in Seattle, you used this highway almost daily, and if you were headed to the airport through the city, you most definitely took this road.

The Viaduct was a giant, ugly double-decker concrete structure that backed up on most days, it had minimal exit paths off of it, and if you were headed south, you prayed there was no fender bender because you were going to be stuck for a good hour.

If you were headed north, however, you were treated to one of the most beautiful views in Seattle. The concrete behemoth sat in this perfect section of downtown that gave you views to the water, the Space Needle, Alki Beach, and if you were driving on it when the sun was going down, then someone had their phone out to take pictures.

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So when Seattle leadership announced they were going to tear the highway down to make way for an underground tunnel and a waterfront beautification project, many Seattleites lost their god damn minds.

“How can you tear down this iconic piece of highway?”

The project was fraught with delays, political fights, budget overruns, and a rather forgetful period of time in which a boring machine was running into all sorts of stuff in the Seattle underground. Eventually, the viaduct came down, the tunnel was built, and the waterfront project was well underway.

I was one of those people who couldn’t figure out why they would go through all of this hassle to do this project. It made no sense. I was a die-hard Viaduct fan.

But all these years later, I can tell you it was the right decision. The tunnel is fast and efficient, and the new waterfront is absolutely beautiful.

I couldn’t see the vision all those years ago, and I chose to focus on the things that I wanted to hold onto rather than seeing the bigger picture. Sometimes it’s hard to step outside the vision we have for a situation and see the possibilities that could exist.

This is where what we do so often in our careers is that we fail to dream, we fail to see the possibilities, and therefore we fail to re-invent what we know as the world around us.

Sometimes we have to tear down some walls in order to build the next version of ourselves.

Most people spend their careers trying to preserve a version of themselves that made sense five years ago.

They hold onto a title that no longer excites them because they can’t see something bigger.

They stay in an industry they accidentally fell into, albeit they are miserable in it because it’s hard to imagine something different.

They keep managing the same team, selling the same product, or solving the same problems long after the challenge has disappeared.

The comfort of what you know is often what keeps you stuck, and the vision of seeing something bigger, new, different, and often uncomfortable is hard to imagine.

The irony is that the opportunities we want are usually hiding on the other side of something being torn down. A promotion often requires giving up the role you’ve mastered. A new company requires leaving the reputation you’ve built somewhere else. Starting a business means walking away from the safety net that helped you sleep at night. Every meaningful chapter of growth usually begins with demolition before construction.

What I have learned over the years is that vision is one of the rarest skills in business.

Plenty of people can identify problems. Plenty of people can tell you why something won’t work. Very few people can look at a pile of rubble and imagine what could exist in its place five years from now.

Those people are the ones who build companies, create movements, reinvent industries, and change the trajectory of their careers.

The next version of your career may require tearing down something that feels important today. It may be a title, a routine, a belief, a company, or a story you’ve been telling yourself for years. That process rarely feels comfortable in the moment. The people standing on the sidelines will question it. You may question it yourself.

Years from now, however, you might find yourself standing on a waterfront that didn’t exist before, wondering why you fought so hard to save a highway that was blocking the view.