How to Reach the World Series in Five Years

For longer than any of you currently reading this have been alive, this year’s World Series teams have been losers — sometimes lovable, legendarily cursed, often achingly close, but nonetheless, losers at the art of winning baseball’s top honor.

This year the Cubs, who last won the World Series in 1908, and the Indians, whose last victory was 1948, reached the peak of their sport. What can you learn from their successes to reach the peak of yours?

This terrific recap from Jarrett Seidler at Baseball Prospectus walks through Theo Epstein’s step-by-step transformation of the Cubs from consecutive last-place cellar dwellers to today’s dominant franchise. In just five years, he and his new team reached the World Series.

On the other side, the Cleveland Indians were largely pegged to be a mediocrity again this year — ESPN rated them 17th in their season preview.

That these two teams are now the greatest in the game is part of the magic of sports. It’s renewal, it’s redemption, it’s failing to remember the setbacks of last year as you pursue the glory of this one.

Perhaps that inspires us most about sports. It’s the constant reminder, amidst a tumult of statistics and trivia and rumor and egos, that we can overcome and we can emerge victorious, despite the odds.

And that reminds you that you, too, can overcome.

Whether you are charting your rocketship to the stars, or contemplating setbacks of your own, this year’s baseball drama is a reminder that five years can change everything. And the best way to change five years from now is to change this year. And the best way to change this year is to change today.

For sports team, picking the goal is easy — win the championship, raise your arms in victory, lift the trophy high.

For you, picking the goal is part of the freedom, and part of the curse, of having choice in your career.

What is your goal, your choice, your desire?

Is it getting to the next promotion? Or the promotion after that?
Is it getting into a more lucrative, more rewarding, or more fulfilling role in life?
Is it changing industries, changing fields, or changing cities?
Or is it just change, whatever form it may take? Change that takes you away from the drudgery of today and gets you to a new place in your career?

Whatever your goals, whatever your dreams, the best way to become the champion you want to be is to follow the same simple steps that transformed the Cubs and Indians:

1. Set your goal

What’s a thrilling place you’d like to be in five years? While the randomness of life means you probably can’t pick the title, the company, the place and the day — too much is out of your control — you can set simple goals. “Be a VP, Marketing” or “Manage a large team of software engineers” or “Progress my sales career to where I’m carrying a $10 mm book of business” all make sense as simple, easy-to-understand goals to aspire to.

2. Make the plan

Keeping it simple, what are the steps to getting there? The Cubs didn’t do it all in one year and neither can you. Break down your goals into something you can actually achieve each year — getting the promotion, or improving your results, or out-performing your boss’ expectations.

3. Go to practice

It’s remarkably simple to be successful, but hard to do. As Silicon Valley star Keith Rabois tweeted Saturday: “I have never met a single successful person who didn’t get there by outworking other (exempting VCs).”

4. Play like a champion today

Mixing sports inspiration, this Notre Dame football slogan captures the essence of being a winner. Every day, every meeting, every client call, every code review, every focus group, every industry conference, every slideshow, every day, you need to decide how much you want to be a champion.

If the answer comes back “very, very badly”, then your results will predictably follow.

So with the Cubs and the Indians in the World Series, Readers, it’s a sure thing that they can’t both lose.

But we can also say that they’ve both won already.

And for you too, the choice is yours. I’ll look forward to seeing you hold your championship trophy high.

I’m rooting for you!