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Make today uncomfortable

The most memorable moments involve some sort of discomfort; the greatest achievements celebrated because they’re a result of sacrifice and trial. Think: marathons, diplomas, childbirth. Edmund Hillary and Tenzing Norgay’s Everest ascent. Malala Yousafzai. Countless others.

“Great achievement is usually born of great sacrifice, and is never the result of selfishness.” – Napoleon Hill

Don’t shy away from the difficult. When you find yourself struggling, uncomfortable, even angry, run into it.

Hard times are gifts.

There are moments you’re sick or tired or bored.

You’re not sure whether to stick or quit. It’s unclear whether progress is being made. Patterns seem hardwired, destined to repeat. Nothing makes sense, and the future is uncertain.

You’re questioning your work, your decisions, the motives of people around you. You’re questioning yourself.

These are the defining moments. This is when you find your passion and what really matters.

How I screwed up (anxieties of an entrepreneur)

The following is taken from an interview with Jahan Mantin. For the original article, click here.

In the beginning I didn’t have my story straight. I knew there was value in getting certain people into a room to share and learn from each other, but I didn’t know how to articulate it. In my mind, the story and its importance was perfectly clear. My intuition of human dynamics and relationships was always on target. But the business side was lacking. I had to thrash and experiment and test formulas to make it sustainable. It didn’t happen overnight.

I didn’t come from a business background. I had a lot to learn and made a lot of mistakes. This is part of it. You have to go through it, do the work and press on.

Overcoming anxiety 

When I first started hosting dinners I was absolutely petrified. I’d give myself pep talks on the train before every event. The fact that I managed to convince these incredibly smart, brilliant, talented people to come meet each other in a secret room became a tremendous burden. I put intense pressure on myself to organize unforgettable evenings. My anxiety was through the roof. “What if no one shoes up? What if plates come crashing down off the walls? What happens if someone becomes angry and storms out? If I forget someone’s name? If someone drinks too much and stumbles down the stairs?”

Eventually I realized my fears were mostly irrational. Thankfully, I got to a place where I could recognize that these dinners are beyond me. Yes, I still get nervous, but I can manage my anxiety with the understanding that my responsibility is to provide the platform for people to come together and meet and enjoy. The rest is ultimately up to them.

The pressure of being an entrepreneur

We spend most of our young lives being told what to do. School is laid out for us, and certain milestones seem preordained — job, college, house, friends, relationship. When you start your own business, there is no set plan. There’s a sense of leaping, falling, an uncertainty of what’s to come.

For me, this levity was accompanied by obligation, a duty to see it through. It’s easy to shy away from fear like a fire, but these scary moments show us who we are.  When we are petrified and allow ourselves to be vulnerable, we grow.

Why do so many people become entrepreneurs when it feels like such a big risk?

At first glance, entrepreneurship doesn’t seem safe. Safety is 9 – 5, a steady paycheck and stock options. But if you think about it, freedom and creative independence can provide more security than any job. At any point you can be fired. When you create your own business/service/product, the power is in your hands.

Entrepreneurship isn’t for everyone. Not everyone wants to run their own show; it’s demanding and tough. But you owe it to yourself to sit down and ask, “What do I want? What do I want to contribute to the world? What brings me the most joy?”

When do you know you’re ready?

You have to be honest, ask hard questions and give yourself the time to go through the process of identifying your values and priorities, your skills and talents, what you’re really good at.

If you wait for the right moment, the right time, you’re never going to ship. You’re never going to put work out into the world. You’ll never create art (of which the most interesting and successful is far from perfect). You have to reach the point where it’s good enough, where you can feel satisfied and confident. “Done” is better than perfection.

There are always edits to be made. It can — and probably will — be improved. But your work has to make it out into the world.

Power pack: 5 questions

I use questions to help my clients uncover their best selves, whether it is work or personal goals they are after. I’m sharing five here in hopes they spark your own journey:

  1. How are you different, what can you do that no one else can?
  2. What do people ask from you? (clients, family, friends, organizations, managers)
  3. What one word embodies your vision, your company, your principles?
  4. What top two dreams are current priorities?
  5. Tomorrow you wake up and everything is as it should be — simply perfect. What does this look like? From relationships to work to home to money. Get specific.

The rebellion of questions

As a school girl, I found myself in detention for asking questions. I was threatened to be kicked out of academic programs for challenging authority. You were permitted one question after your name was called, and superiors always had the last word. Too many questions meant insolence, disrespect and delinquency.

The problem is the greatest inventions arise from asking questions. When we dare to ask why, archaic systems can improve and new ways of doing things emerge.

Questions can take courage, and perseverance is sometimes needed to find the right answers. Honest leadership will welcome such speculation and discussion.

Surefire ways to get attention

I spent a good chunk of my early career worrying about finding the right kinds of business, attracting smart clients, generating the best PR. I’d worry if my work was good enough, if my talents and skills were evident, if my angle was unique.

Through trial and error, I realized there are two surefire ways to catch the attention of an audience (they’re fickle and quick to move on, so you have to be powerfully concise and to the point):

1. Show “why you.”

Behave in a way that gives me no choice but to see you. Your track record is an active testament to your character and to your work as a professional. I don’t care what is listed on your resume. I want projects and completed work that demonstrate your capabilities and promise as a leader.

2. Ask a question that can’t be avoided.

Put something in my head I can’t ignore. You’re here as a professional, so ask me something that proves you are what you say. You’re not here to be ordered about. Create an itch that leaves me wanting more.

Make me care.