By Bobby George, CEO of Montessorium.

There's a myth that startups are sexy. Work is conceived, not as a clock-in and clock-out enterprise, but rather as something that must accommodate our lifestyle: basically, a passion that you get paid to pursue because it encapsulates your vision of how the world could be improved and how you can go about changing it. You can change the world. Or at least, that's the argument (and perhaps underlying appeal) of startups.

The Modern Workspace

To reinforce this new lifestyle, working environments are often populated by extravagances from our everyday lives: slides, bicycles, even gardens or parks, gyms or meditation rooms. They feature anything to actuate our passions and continually nourish and rejuvenate our minds, making us forget the seriousness of the work that we face and the seemingly insurmountable tasks that lie ahead.

Said differently, companies build working environments to help us celebrate our unique cultures, equipping us to make them more cohesive. So as we venture out into unknown territory, we are unified in our quest and determination to push forward together. All of this is well and good until you consider the other, less "sexy" side of startups.


It's not always easy working so intimately with a group of singularly focused individuals. Things can get messy. It's also not always easy coming to work every day without a template by which to operate, or to rally around analytics or intuitions without a shared sense of commitment and excitement. It requires a lot of work.


Many startups consist of people asking questions that no one has asked before and then, on top of that, constructing possible answers by which to build upon. There are so many intangibles at play:

  • Have you asked the right questions?
  • Is the momentum of time on your side?
  • Do you have the perseverance to find out?

The list goes on and on.


Everyone knows the stakes. If we get it right, it could change everything. If we get it wrong, it could leave us longing for better days, wondering aloud in the narrow hallway of our lives what we could have done differently. If we had approached the problem a certain way, would it have made a difference? And why didn't we think to ask that question?

Imagine an island. The island is the challenge, the singular focus by which you need to create a map to reach. Now, imagine there are literally thousands of ways to get there, and you need to decide on the best approach. Will you go by land or sea, or is there another route you haven't considered yet? Is the map as accurately drawn on paper as it is outlined in your mind? One wrong calculation and you are caught in a history that no longer includes you.

We wish we had a miraculous story to share to help other companies -- one that includes a roadmap or guidebook. We wish we knew the answer that would help the most. The best advice that we can offer is that when faced with decisions, make sure everyone is aligned around those decisions. It'll take everyone to get where you are going.

The Bright Side

The real appeal of startups lies in their agility, naiveté and persistence. The characteristics of a good team is exemplified by their intuition, confidence and tireless pursuit of unsettled assumptions. There are no certitudes. Leaving aside the potential stress of investors, fundraising, obligations to banks or parents, mortgages, or pressure to think about exit strategies or acquisition offers, startups find innovative ways to shed these constraints and find a way to ask only the questions they know how to ask.

Why? Because if they are lucky, they have built a culture that will support their efforts, despite the outcomes. Successful teams find ways to shelter each other from particular stresses. What may affect one team member in a certain way may not affect another, or it may be a lesser burden to bear. The job of the team becomes one to alleviate each other's worries or concerns.

It's not all roses with startups. But it sure can be fun. When most of us think about startups, we think of the barrage of benefits, this seemingly glamorous lifestyle, and yet we somehow set aside the nature of the work -- the real, concrete challenges that companies face.

Companies are comprised of individuals and ideas, people who are trying to forge ahead despite the odds, the risks, and the naysayers. Here's to the odds -- to the fearless teams asking the big questions.

Bobby George is the CEO at Montessorium.

Published on: May 4, 2017
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