There's an old Haitian expression that translates roughly to: "beyond the mountains, more mountains," which I think should be the everyday motto of all good entrepreneurs because it's a spot-on description of the basic fact of life in a startup. The battle never really ends, iteration and constant forward motion are critical to any real success, momentary "success" is just a way station in the struggle and there's absolutely no finish line. My experience is that every time you think you can take a break, catch your breath, or that you've reached the top, is actually the time when the real climbing begins. This is not exactly a Sisyphean exercise because it's neither pointless, eternally frustrating, or free of any real progress-- that's just the way it can feel sometimes.

Every once in a while, though, you actually do pull off a huge win, a game-changing triumph, or the sale to end all sales. But then the question of how you and your people handle those highs will be just as critical as your ability to handle bumps in the road and hard times that also come with the territory. What you do after you win a big one is important to moving the business ahead and keeping the team together and focused on the next few hurdles. It's even more important than how good you are at picking yourself up off the floor and getting back in the game after getting punched a few times by a client or a competitor-- or one of your own folks. Especially when, as Steely Dan sung, you've got to Do It Again.

In Chicago, no one's had a bigger recent victory than the Cubs in winning the World Series after a mere 108 years. I had the chance to sit down recently with several senior members of the Cubs organization to ask them how they've tried to handle being champions. Some of the basic ideas and approaches we discussed are certainly worth sharing. I've noted that the Cubs' turnaround journey is like the trials and tribulations of a startup in many ways and the resemblance remains clear even in the new season. (See How the Cubs, a 140-Year Old Baseball Team, Operate Like a Startup.)

Here are a few of the most salient ideas to keep in mind:

1 Take Some Time to Celebrate and Say Thanks

Entrepreneurs generally enjoy the process and the journey more than the celebration and the hoopla at the end of the path. This is due at least in part because they always retain the knowledge (and stomach-churning fear) that any success is fleeting and can disappear or be overtaken just as quickly as it is sometimes secured. As a result, they run scared. They also don't understand that not everyone in the place is like them. So, they focus on getting right back to work. (See Why Entrepreneurs are Really Terrible at Saying Thank You.) However far you've come, the trip has been tough on everyone, with sacrifices being made in varying degrees all around. So it's important to acknowledge the win, the effort that it took to get there, and to give everyone and their families time to bask in the spotlight before getting back to business and starting to climb the next mountain.

2 Don't Move the Goal Posts Too Far Too Fast

In the heat and excitement of success it's easy to get too full of yourself, too aggressive in your plans, and too far out over your skis. Aiming high never hurts because feasibility will compromise you soon enough, but no one gets to heaven in a heartbeat these days. Everything takes longer than you think--although the long run is often shorter than we expect given the accelerating rate at which technologies are changing our lives. Good things simply don't happen overnight. A baseball season, especially at the start, can look like it's gonna last forever. So setting some early, modest hurdles is not a bad idea, before everyone starts talking about going for the gold. A little caution and some patience and maybe jogging a bit before racing headlong ahead into the mists makes a lot of sense and leads consistently to better outcomes. (See Slow Down, It Might Save Your Business.) "Does it better" always beats "does it first." The last thing you want is a disaster on your way to building your dynasty.

3 New Numbers Are Not Enough-- People Need a New Vision

The right metrics always matter, but no one ever invested financially or emotionally in a set of numbers. If you want them to sign up for the ride they need to believe and buy into a story about the next journey and be shown a realistic path to get there. Pie in the sky doesn't win pennants. The path doesn't have to be certain or easy. You can talk as much about the players' contributions and commitments as about what the team is going to achieve, but the message has to come through loud and clear. One thought that crosses the plate is better than three left on base. True motivation comes from inspiration, which comes from within. (See Trying to Motivate Your Employees? Forget It.) And while the message is gonna vary in every case, the fundamental content is almost always the same: it always has a lot less to do with more and much more to do with better. Because better beats more every time. It's not enough to be good if you could be better and it's not enough to be very good if you could be great.

4 Don't Play It Safe-- Failure is a Fundamental Part of the Process

I've discussed every aspect of failure in this blog and how it bears on startups. In baseball, even the best hitters fail 7 out of 10 times. So, failure is a given and a necessary evil that everyone needs to get comfortable with. The key is to build a resilient culture that gives your team permission to fail without accepting failure as a given. Playing it safe-- trying to avoid mistakes or being embarrassed-- isn't a formula that works for anyone these days. In many young businesses and in businesses with young players and employees, too many folks start out depending on talent alone. You can do that in the minors, but as you "grow up" in sports or in any other line of work, the mental game is every bit as important as the physical skills and talents. Only the players who master both sides of the equation become all-stars in the long run. Failing early and figuring out how to handle it is a much better approach than risk avoidance, which basically limits your upside opportunities without really providing any downside protection. Playing it safe today is risky.

Published on: Sep 12, 2017
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