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Entrepreneurial Cultures

I went to a conference on entrepreneurship recently called the World Domination Summit. The mission of the event is to empower you to have a remarkable life in a conventional world.  The founder Chris Guillibeau is a Portland local turned world traveler who has been to every country in the world (which is 193, by the way) and has a very popular blog called the Art of Non-Conformity.

Now, I don’t know about you, but most of these details do not describe me.

I reflected on what it means to live in a conventional world as I drove the 648 miles home from Portland back to Oakland. For me, conventional means my career is more like a job and my life is more like a script I act out, and not much of an adventure at all. I feel sad just writing these words.

Outside my window were beautiful snowcapped mountains and wide open plains. I thought, how can I have an adventurous life?  For many, the answer is often travel and dreams of working from a beach in an exotic place. That’s not realistic for everyone, and honestly I want to be near my family. What else can bring adventure to my work and life? Perhaps another option is entrepreneurship.

But what if, being an entrepreneur has too many risks. I don’t know about you, but I’d like to have the best of both worlds. Being an entrepreneur means no paid vacation, no healthcare, no 401(k), no free lunch or regular paycheck.

What if we could have the best of both worlds?  I believe it’s possible.

Create an entrepreneurial workplace culture right where you are.

I know what you are thinking – “My boss would never go for that,” or “How do I convince leadership to buy-in on THAT?”

The idea that we must wait for someone else to take action on improving our workplace culture is the exact reason why so many companies are not great places to work.

Everyone, everywhere can create a more entrepreneurial workplace culture wherever they are working. Yes, everyone.  

If you are excited by this, keep reading I’m going to share how you can do this. If you are skeptic and coming up with all the reasons why this is not possible – I want to tell you:

The first step of entrepreneurship:

  1. You must believe that the impossible is possible

Entrepreneurs believe that crazy ideas might actually have billion dollar potential. If you think its not possible to create an entrepreneurial workplace at your corporate, grey, sad workplace culture – then I must tell you: you are part of the problem.  But! You can be part of the solution by changing your belief about this. Change your belief by referring to yourself as an entrepreneurial person. Its totally ok to be entrepreneurial if you’re not ready or interested in saying you are an entrepreneur. Change your mindset as to how you think of yourself and things around you will start to shift. Try this, “I’m an entrepreneurial marketing coordinator” or “I’m an entrepreneurial human resources manager”.


  1. You must be courageous

Now, courage is a funny thing. It sounds like something brave people do, and that we must have a certain type of personality to be courageous.  This, of course, is just not true. Everyone has the abiltiy to be more courageous in their life.  The best way to be more courageous is by doing something that scares you. And entrepreneurial behaviors are scary. Which brings me to my next point.


  1. You must be creative

Entrepreneurship requires creativity. And to be creative we need to be courageous, and face our fears of standing out.

You are not meant to be like everyone else, you are meant to stand out! [Tweet This]

Creativity has many forms, and infusing your workplace with more creativity can be as simple as using colorful post-its and drawing. When we are kids using images and pictures to explain ideas is just how things work. As we grow older, this kind of creative activity is hammered out of us for more ‘mature’ things like PowerPoint decks and spreadsheets. Entrepreneurs know that to get buy-in you need a sexy term, so childhood doodling, wa-la you are now “Visual Storytelling”.  Bring your meetings to life by sharing ideas through visual storytelling. Have you ever drawn a stick-figure? Then you have visual storytelling abilities!


  1. You must look for opportunity beyond your job description

Entrepreneurs look for unmet needs in the market. Think of your workplace as ‘the market’ and look for unmet needs. Most entrepreneurs create ideas based off of problems that they have themselves. Which also means you show an interest in things that are ‘not your problem’ or part of your job, but that interest you anyway.

I love the story of Bevi, a smart water cooler that brings flavors, fizz, and eco-friendly fun to the workplace. This story of entrepreneurship started with when three friends, Sean Grundy, Eliza Becton, and Frank Lee, wondered why people prefer to buy bottled water over drinking tap water, and often trashing bottles after a single use. That question evolved into an idea of using design and technology to promote behavioral change. Inspiration can come from anywhere.

Now, you don’t need to look for business ideas around you – but you can look for opportunities to make the day to day workplace experience better. For example, if you feel its difficult to connect with people outside of your department, you could host a lunch-mingle.  At companies like Asana, they have a weekly practice to have lunch with someone new. They get groups together through a lottery system to create lunch tables of four people to eat together. Mingling with new people just for the sake of getting different perspectives is an entrepreneurial act. Give it a try!


  1. You must collaborate with people different from you

Building a business out of nothing requires a lot of skills, so entrepreneurs know they need to collaborate and create learning networks. Someone who is great at marketing, needs someone who is great at products, and they absolutely will need someone who is skilled in finance and budgets. If you are working on a project at work, infuse it with entrepreneurial action by looping in cross-functional colleagues. Add more diversity of thought and skills to your projects and seek to learn from each other.


There are dozens of other ways to create entrepreneurial workplace cultures, and I’ll be talking about that at the upcoming #MillennialTalk twitter chat on Tuesday, August 15th 5pm PST / 8pm EST.




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