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What would you do if you were not afraid?

“What would you do if you were not afraid?”

I hadn’t even had my first sip of coffee yet, and our seven-year-old was coming in particularly hot this Monday morning.

“Well, I would tell you all about it, but I am afraid we’re going to be late to school if I do, so go brush your teeth and let’s get going.”

I dropped the kids off at school and my daughter’s question bounced around my brain.

Beyond thinking about the crazy stunts I’d try if there was no consequence of facing physical pain and or my own mortality (I’ve always wanted to go skydiving, but my wife has lovingly told me it is strictly forbidden!), I decided to let my mind wander a bit down the road of deeper, psychological fears.

I did a quick inventory of some of the big, gnarly emotional fears that were top of mind for me and which many of you (especially you fellow entrepreneurs out there) may face…

Was I afraid of rejection? Not really—the four years I spent post-college working in commission-based sales roles and the hundreds of hours of cold-calling I had to do pretty much got that fear out of my system. 

Was I afraid of living an inauthentic life? Thankfully, not. When I mustered up the courage to come out as a 23-year-old, I was fortunate enough to have the support of so many friends and family members and was a part of an amazing gay community in Chicago. My coming out experience and life with my wife of nearly 13 years have given me the confidence to step forward into my true self,and never look back.

Was I afraid of making mistakes? Nope, I make enough mistakes every day to make it seem rather commonplace and, relatively speaking, a rather benign thing to be afraid of in my line of work, where I do not have to engage in matters of life and death.

Taking it one notch further…was I afraid of failure? Now, this was a tricky one that required a little bit more digging.

A deep dive into the fear of failure

Growing up playing sports taught me to learn from failure. To shake off a bad play or a bad loss. To pick yourself up off the ground, dust yourself off, and try again. To persist. I had a lot of success as a student-athlete but equal amounts of failure, and ultimately, I made it through the other side with more strength and confidence.

But here I was now, a mother of three and an entrepreneur, and I suddenly realized I wasn’t so sure of myself. I had successfully launched a new business and in just six months had an amazing roster of clients with whom I was producing meaningful results. By all accounts, I should be striding confidently forward, but as I tried to do this, there was this slight headwind pushing against me —oh crap, I realized…I am afraid of failing!

Where did this fear come from? What had changed in me or in my context to bring it on? I took the time to reflect.

After college, I left the friendly confines of “safe failure” which playing sports provided and then entered into the world of Corporate America for the next 15 years. While I learned a lot in this world, I never really experienced what it meant to take risks or to fail. The great corporations I worked for and with operated (for the most part!) with established systems of checks and balances and had abundant resources and processes in place–all things that served as buffers for failure. These buffers do not exist when you’re starting your own business.

So, I was finally ready to answer my daughter: “I think I am afraid of my business failing.” Yikes. There it was.

Now that I faced and named my fear in business, I was able to begin to dig deeper and uncover my approach to “flop the flip” and turn things around. What would and could I be doing if I was not afraid?

The answer was simple: if I was not afraid of failing as an entrepreneur, I would be investing to grow my business.

Overcoming fear to make a bigger impact

Over the past six months since launching, I have been laser-focused on ensuring that my amazing clients receive the best level of service and support while simultaneously grappling with setting up and operationalizing my business. And, with the exception of the support of a few brilliant freelancers here and there, I have been going at it all alone.

I have been overly focused on “internal” matters, and less focused on “external” matters (i.e. prospecting, business development, and attending events). These external matters are most critical to growth, and these are actually the things I love to do. I just haven’t been prioritizing them. Until now.

It’s important to note that failure, success, and creativity tend to go hand-in-hand-in-hand. As Elizabeth Gilbert explores in her Ted Talk  (one that has resonated with well over 5 million viewers) there tends to be an interesting dance between the three. She suggests that both success and failure can breed uncertainty, throw us off balance, and keep us in fear of creating our next best piece of work (or, in my case, my newest career move). What brings us back “home” to a place of authenticity and forward momentum, is a focus on something outside of ourselves, a greater purpose, a North Star, 

As I look to the next six months to a year, I am choosing to combat my fear of failure with a relentless pursuit of growth and willingness to invest in this growth, both from a time standpoint and a financial and resourcing standpoint. My obsession with sustainable growth will be the tailwind that will outmatch that nagging headwind of fear.

Get to know your fear

So, what are you afraid of? What fear is holding you back? Are you willing to chase it down and dig deep into it? To pick it apart and understand its components? To put it back together into something you can manage rather than be stifled or paralyzed by it?

How do you start? Take time to reflect on what you are afraid of. Write it down. Do a mind-dump of all the things you’ve been putting off in your life and business, and try to find a common theme and then take action.

If you’re having a hard time getting your thoughts out, try starting with something more basic: go for a walk. Did you know that walking can actually help you process emotions and ideas? And, walking can have a positive effect on creativity – which is exactly what you need to pinpoint your fears and create solutions to overcome them. 

Take the time to identify the type of fear that’s holding you back from going after your goals more whole-heartedly.  Then, imagine and create a world in which this fear does not exist. Hold on to this vision as you continue to chase and grow your big, bold, life-altering dreams.

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