Accepting “Congratulations” for the Road Less Traveled

Andy Silber | August 6, 2019

Road Less Traveled
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A year ago, my wife and I decided to uproot our family and move to Ireland, where we have citizenship through her grandfather. She had bicycled around the island in the 1990s, but I had never even visited. As of this writing, we have no place to live or jobs, just a flight landing in Dublin at the end of this month. Yet, when we tell people our plans, the typical response is “Congratulations.”

At first, this response surprised me, since I think of congratulations as something you say to someone who has just completed a significant task like graduating from college or getting married. We haven’t accomplished anything yet. Once we’ve successfully settled there, I can see someone offering their congratulations, but why now? What have we done so far?

Then, I realized we have accomplished something significant—we made the decision to do something hard.

Staying in Seattle would have been easy. We both had good jobs, our beautiful house, amazing friends, and proximity to our families. Nothing forced us to make a change. We just looked at the balance sheet of living in the two countries and decided we’d rather live there. I think people have been congratulating us for not being complacent.

Human nature often makes us follow the easy path, to do what’s expected of us. However, interesting things happen when you don’t follow that path. Entrepreneurs like Elon Musk are famous for not following the rules. This is not always a good thing (e.g., the fines with the SEC over his tweets), but as a whole, the world is better off with Tesla and SpaceX.

The biggest difference between a startup and an established company is their approaches to the road less traveled. Established companies have ways of doing things that have worked in the past and allocate their resources to strengthen their previous successes. Startups are founded by people who recognize they can only compete with the established companies by forging a new path. This situation was described in The Innovator’s Dilemma, one of my favorite business books. The book is filled with examples where small, innovative companies replace established players. Often the established players got to their position of dominance by being a scrappy startup in the previous cycle.

Established companies from Amazon to Disney talk about innovation, but how do you break from complacency? You can just go with your gut, but that doesn’t always work out so well; lawyers and PR firms make a good living cleaning up the messes these decisions leave behind.

When things go south (as they often do), how do you explain the wasted resources and opportunities to your stockholders? You can’t just go with your head, because there’s never enough information to make a purely rational decision: the road less traveled is, by definition, filled with unknowns and risks. A head-based approach will typically lead to complacency.

You have to start with your gut, and then challenge your decision by continually asking yourself, “What if I’m wrong?”

For our big move, I assumed I’d be able to find a job in Ireland. Then, I followed up that assumption by connecting with recruiters in Ireland and applying for jobs. The message I kept hearing was “We’re desperate for people with your skills, and once you get here, you’ll find a job.” My family also took a trip to Ireland, visiting different cities and constantly asking ourselves, “Can we imagine living here?”

One of the things that Amazon founder Jeff Bezos talks about is differentiating between decisions that are reversible (two-way doors) and those that aren’t (one-way doors). Walking through a door that stays open is different from walking through one that locks behind you.

For us, we can return to the United States if things don’t work out. We’ll be out the cost of moving and need to find a new home and jobs, but we’re not renouncing any citizenships and our friends and family will still be here.

At a company, if someone has an out-of-the-box idea, you can start by putting together a list of reasonable assumptions, ballpark estimates on development costs and schedule, and a list of risks. If things look promising, start with a proof-of-concept project that has just enough resources (the equivalent of a trip to Ireland) to determine if the idea is plausible and your assumptions are sound. By using a stage-gate process, you can follow a path less traveled without risking the company, making the decision easier to make.

When people say that we’re brave, I disagree. We did a lot of work to reduce the risk. We’re traveling to a country where we are citizens, speak the language, and know there are well-paying jobs. We actively chose to follow a less-trodden path, but one we’re confident will be rewarding. At the worst, we’ll spend some time living abroad and return with a greater appreciation for what we had left behind.

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