The art of keeping creativity alive when you’re the boss

Photo credit: Eddy Klaus

A few years ago, a bad back left me unable to sit at a desk for more than an hour at a time. But with my company in growth mode, expanding by hundreds of employees, I had no choice but to spend long days at the office. My doctor recommended that, on top of improving my sleep and diet and doing yoga, I look at getting a standing desk.

I did some research online and experienced a bit of sticker shock. Models easily run into hundreds, if not thousands, of dollars – way more than I was prepared to spend. So I did what any self respecting-hacker would: grabbed a spare cardboard box and some duct tape and rigged myself up a really basic standing desk. I never would have guessed the impact it would have.

 Creative thinking is important in any organization, but it’s often overlooked in one of the most important places – at the top.

Creative thinking is important in any organization, but it’s often overlooked in one of the most important places – at the top. For CEOs, founders and leaders at all levels, it’s easy to get consumed with the demands of the day and the relentless cycles of business planning. This can leave little time for truly creative thinking and also sap energy from your work.

Often, you don’t even realize this is happening… unless you happen to be pulled away from the daily grind and given a fresh chance to flex your creative and entrepreneurial muscles. That’s exactly what happened to me, thanks to my jerry-rigged cardboard desk.

Almost immediately, people in my office started asking where they could get a desk of their own. Apart from being cheap, my little contraption was also super portable. It weighed about two pounds and didn’t require any assembly or furniture rearranging to set up. You could put it on your desk when you needed it, or fold it flat and store it away when you didn’t. I realized I might be onto something.

My entrepreneurial instincts kicked in. I contacted a pair of local designers and shared my concept. Together we began sketching out product designs and thinking about whether we could bring this idea to market.

Getting your entrepreneurial mojo back

The desk took shape literally off the side of my desk, but working on the project – even at a very high level – was a blast.

Before starting Hootsuite, I was a serial entrepreneur – running everything from a pizza restaurant to a digital media agency. The chaos and energy of starting a new venture is addictive. I realized that I missed it. That’s not to say that building Hootsuite hasn’t been rewarding. (Hands down, it’s the ride of a lifetime.) But, as companies reach a certain scale, there’s often less chance to exercise those basic entrepreneurial impulses. Things, of necessity, move at a more measured pace. Your role becomes more focused. And you’re farther from the customer.

This new side project was different. I was working directly with the management team to help get the desk to market. They were expert designers but had not had a lot of experience in building a business. As the team coalesced and was forced to learn on the fly, it gave me a chance to relive my own entrepreneurial journey through their experiences.

 I was reminded how, at core, great entrepreneurs have to be generalists.

They moved fast and handled everything on their own. If a new feature was needed – say a built-in ledge for keyboards – we talked it over and they got it done … in days, not weeks or months. At the same time, I was reminded how, at core, great entrepreneurs have to be generalists. Apart from product design, our tiny team had to think about marketing strategy, supply chain and distribution, market analysis, pricing, projected revenue, expenses, etc.

Not to mention, the feeling of vulnerability was a rush. Unlike in a larger company, we didn’t have a legal team to vet every decision, a PR firm to massage our product pitch or a C-suite of execs to corroborate our strategy. Yes, these are generally all good things to have, but working without a net again was exhilarating.

Benefits to the larger organization