Your Awkward Phase, And Why You Should Love It

All growing companies eventually reach an adolescence - a no man's land between scrappy startup and big, established company. It may make you feel like an overwhelmed teen again. Don't let it.

- Leigh Buchanan, illustrations by Paul Blow

PHIL LIBIN LIKED IT better when all he had to worry about was survival.

“It is very clarifying and liberating—and in hindsight, kind of fun—when the challenges facing you are making payroll and keeping the lights on,” says the co-founder— and, until recently, the CEO—of productivity juggernaut Evernote. “You don’t feel like it’s a luxury when you are in it. But it feels like a luxury afterward.”

“Say what?” gasp entrepreneurs clinging to crumbling cliffs while hungry tigers snarl below. “A founder with 400 employees and a billion-dollar valuation is telling us that life post-startup gets harder?”

Not exactly. But running a business in the foothills of the middle market is dramatically different. Between startup and maturity,companies navigate a period of adolescence that—like its biological counterpart—is awkward and uncertain. If you’re reading this because you’re among the 2015 Inc. 500, congrats on growing up so quickly. Now prepare for escalating customer expectations, relentless operational demands, and starkly different leadership requirements from those that got you of the ground. (You know how you’ve liked to joke that you don’t know what you’re doing? Now you scare people when you say it.)