Startup hell: How to get through the 'messy middle' period

Everyone loves a success story. But there’s one big problem... You rarely hear about the “messy middle”: the part where everything nearly collapsed under the weight of obstacles.

In 2006, Scott Belsky founded a company called Behance to connect professional creatives. After a five-year bootstrap, he raised VC investment and Adobe bought the business in 2012. Sounds pretty straightforward, right?

In reality, there were so many headaches that Behance almost fell apart along the way. That middle stage of the journey is what makes or breaks you. It inspired Belsky to write a book about surviving it called The Messy Middle – and this is what he learned…

Resourcefulness beats resources. Don’t assume that hiring someone is the most efficient shortcut. First question the adequacy of your tools and processes. This will boost productivity and will likely create a more efficient environment in the long term.

You should be frugal with lots of things, but not your workspace or your team. Your staff will spend a heck of a lot of time in their chairs, for example, so make productivity easier – don’t scrimp. That applies to salaries, too: you must reflect your team’s value back to them.

How do you stay motivated when there are no rewards on the horizon? Get creative by creating a short-term rewards system. Belsky set intermediate goals like getting Google to stop auto-correcting Behance to “enhance” – which he celebrated with (cheap) champagne.

Stay self-aware. Navigating the ups and downs of running a company will have all sorts of consequences for you as a person: the ego swells when the going is good, and insecurities pop up when things get tough. Both will blind you to valuable feedback.

When you’re in it for the long haul, focusing on day-to-day productivity is shortsighted. Like relationships, most ideas take time to pay off. A crucial part of “the messy middle” is sticking around long enough to watch the seeds you’ve planted grow.

Never lose your edge. The closer you get to the finish line, the more risk-averse you become. But an experimental mindset is probably what got you that far in the first place, so don’t compromise that attitude of openness just because the stakes are higher.

Bottom line: The classic business story arc of idea -> hard work -> success is misleading. That middle part involves countless challenges. But if it doesn’t work out, don’t just jump to the next thing – own the outcome with grace; be accountable. Your reputation depends on it.