Making The Leap: Why I Hesitated

The ballistic vest rested heavily on my shoulders, and the mask I wore didn’t help. Time seemed to slow as took slow, intentional breaths. My mind cleared and my senses heightened. I felt a small squeeze on my shoulder — it was time.
Making The Leap: Why I Hesitated

My heartbeat quickened and I drew in a shaky breath of sticky Savannah air. It was so early in the morning, the sun hadn’t risen to burn off the dense fog. Sweat rolled down my back. The ballistic vest rested heavily on my shoulders, and the mask I wore didn’t help. Time seemed to slow as took slow, intentional breaths. My mind cleared and my senses heightened. I felt a small squeeze on my shoulder — it was time.

The weight of the ram in my hands seemed to lighten, and the grass squished beneath my feet as I glided across the soggy lawn. The men and women ahead of me moved soundlessly, weapons drawn and pointed at the darkened windows.

The walk took seconds, but felt like hours. The team leader pulled me towards the steel front door. Left foot on the sill. Right foot under my right shoulder. Someone knocks, but I don’t hear it. Someone shouts, “Police! Open the door!” but my ears are ringing. All I can see is that sweet spot right by the doorknob. Those two inches that will open the door to the unknown.


I heard that one. The 30-pound master key pulls back in a beautiful arc. Tick. Like a pendulum, the ram in my hands swings forward towards the door and connects. Tock. The waves from the impact ripple through my bones. The door flies open with a satisfactory thud.


What was on the other side of that door doesn’t matter. And, if I’m being honest, it didn’t matter in those moments leading up to the entry. Try as we may, our most complete intel was nearly always wrong about the inside. We’d have sketches drawn up from people who have been in there before, we’d stalk the internet for interior photos, and even contact city departments for historical renovation records and floor plans.

No matter what, I was nearly always surprised when that door opened. There would be furniture in the way or a wall mirror in a weird place throwing reflections that would make me jump. One time the door opened so easily I fell flat on my ass, and other times the door would so reinforced we’d have to find a different one.

And forget about the human factor. Try to predict whether a stranger will fight, flee or hide in that situation. Impossible.

So how were we able to open so many doors? How did I handle the my personal fear? How, day after day, were we able to step into the black, to take that leap of faith?

One word: confidence.

Confidence can’t come from prediction. And it certainly doesn’t come from knowing the right answers. I was confident because I knew that I possessed the toolset to respond to whatever comes next. I had prepared endlessly, physically and mentally, for a range of possibilities. And for those situations where I knew my skillset was lacking, I knew exactly who on my team to depend on.

For me, fear inspired preparation. Preparation inspired confidence.

But this confidence failed to translate in an incredibly important aspect of my life. You see, I was a police officer for five years. And I was good at my job. But somewhere between graduating from my academy class and chasing drug dealers with a multi-jurisdictional narcotics agency, an idea formed. And I sat on that idea, that dream of owning my own business, for years.

I wasn’t willing to take the leap. But now I think I know why.

Why people don’t leap.

If you’re like most people with entrepreneurial tendencies, you probably have an idea for a business rolling around in your head. And if you’re like most people, you haven’t taken action to make that idea real. If you’re like me, some of you may have a plan. But when it comes to taking action, we don’t.

What stops many of us is simply the fear of failure.

But failure means many different things when referring to your life’s work. It’s the cause and effect relationship between failure and other aspects of life that keeps us awake at night.

We fear failure because we cannot predict success

Not being able to predict a successful outcome was the biggest reason it took me so long to to make the jump. When you analyze the outcomes of any business venture, you realize that nothing is guaranteed. But the harsh reality is that nothing in life is ever guaranteed.

My job as a police officer was probably one of the most secure, recession-proof careers anyone could pursue. But all it takes is one mistake. Losing your temper once. Becoming complacent. Not following procedure. Once. And that could mean your job, or worse.

Once I realized this, it became easier to overcome my obsession with attempting to predict success. I still had a clear definition of what success was (something I want to cover in a different article), but I started to relax when I approached trying to figure out THE PLAN.

I stopped waiting for THE PLAN to fall in place and I simply started doing. I started reaching out to people, taking small jobs from online aggregators, and started relearning how to be a designer. And eventually, I realized that I didn’t have enough time in my day to get what I wanted to done. My full time job had become an obstacle instead of a safety net. That’s when I knew it was time to make a change.

Key point: You can’t predict the future. You can take action now.

We fear disappointing someone else

This was a big one for me. Disappointing other people was at the root of my fear of failure. I was terrified of telling my wife that we didn’t have enough money to pay our mortgage. I feared telling my father that I wasn’t good enough. I wasn’t scared of my mom at all, she’ll always love me, duh.

But those ones are standard. My fear of disappointing others went even deeper. I was scared of telling my sergeant that I was leaving his team to pursue an entirely different career. I was scared to tell my division leader that all the time, money and training they had invested in me was going to go to waste. I even feared disappointing potential clients that I had never met by not living up to their expectations.

One by one, I spoke to every person who I feared disappointing. And one by one, unanimously, they gave me their support. The first person I approached was my best friend, Smitty.

I can remember the conversation as clear as day. I paced back and forth in a little covered section of the parking lot at work during a torrential downpour. If you’ve never seen rain in Georgia, picture standing under a waterfall — it’s that heavy. I told him that I wasn’t sure if it was the right decision, that I didn’t know if I could succeed.

He responded, “Dude, no one knows that, and you’ll never know if you don’t try. But I know you, and I know you’re going to kill it.”

Now, being externally motivated is not always a good thing, but in this scenario, Smitty’s words were all I needed. It confirmed what I already knew: that the people who matter would always be there for me, win or lose. I made the decision, right there, in the rain, under that leaky canopy in a shitty parking lot in Savannah to jump.

Fearing other people’s disappointment is irrational. Ninety-nine percent of the time, their disappointment is your imaginary creation. If I had failed, I know my wife would been there for me — she would have thrown down, pulled extra shifts, done whatever she needed to do to help.

Key Point: You can’t control anyone else’s response. Don’t let your dreams die for fear of it.

We fear things we cannot control

Remember, you never know what’s on the other side of that door. You could step through and find no floor. It could be smooth sailing. But what stops a lot of people is being afraid of those things that they have no control over.

What I’m talking about here are things like market conditions, the next recession or housing crisis. A big one with a lot of people is a fear of competition. These are things that no one can control. Yep, we’re probably approaching the next housing crisis. And Landor will probably beat you for the next airline logo. Your target market may not respond well to your product or service.

“The oldest and strongest emotion of mankind is fear, and the oldest and strongest kind of fear is fear of the unknown”

– H.P. Lovecraft

What we must remember when facing this fear is that the only thing we can control is how we respond. Our response ability (whoa, responsibility). What would you do if the economy dropped again and companies stopped spending money on design? If you’re not gaining traction with your customers, how would you pivot your customers, service or engine of growth?

These questions are difficult to answer when an answer is required. Trying to answer them beforehand is nearly impossible. What helps overcome this fear is to remember those times that you were cornered. What did you do to move forward?

I remember when I discovered the passion for design. It was a little late in the game: junior year in college. With no time to switch my major and no money to pursue other education, I pivoted my method of education towards an internship. I showed up to my first interview with no work samples, in a suit and tie and absolutely bombed the questions. Within 24 sleepless hours, I was back in the Creative Director’s office with a brand new portfolio. I got the job.

Simply having that story in my back pocket, I was able to overcome my fear of uncontrollable forces. I know I can respond to the unexpected.

Key point: You can’t control anything except your ability to respond. Prepare, then have faith that you can react accordingly.

We fear discovering that we aren’t good enough

If I fail, what does that say about me? If my business fails, am I a failure? These are questions that I struggled with before and throughout the life of my studio. For those of us who are our worst critics (read: every designer), having an F on our life’s report card seems devastating.

I was scared to make that leap and fail because I didn’t want to learn that I couldn’t hack it. That I wasn’t as good as I thought I could be.

The inextricable intertwinement of creatives and their work has long been an issue for many of us. It rears it’s ugly head in things as large as a design consultancy shuttering and as small as negative client feedback on a piece of work.

I am not the shitty logos I designed in my early years. I am also not my greatest work.

What I’ve discovered is that I find immense self satisfaction in learning. And as long as I can learn from my mistakes and failures, I can be confident enough to limp into the next challenge.

To be honest, I didn’t really struggle with this one. I know from talking with many of you that it’s a big fear, so I don’t want to dismiss it. I totally have empathy for you guys, because it’s the real deal. But for some reason, this wasn’t the one that was holding me back. I think the reason why goes back to my parents. They pushed so hard to instill this strong sense of self confidence in me when I was young, that I literally believe I can go out and accomplish anything.

Key point: You are not your business. You are not your work. Don’t let your self worth depend on what you produce.

So what now?

Starting a business, launching that idea, might not be right for you. But inaction because of fear is stupid. I’m scared of a lot of things. In fact, I wrote a post specifically about how my two biggest fears are my driving force. But I’ve learned not to let fear stand in the way.

“Inaction because of fear is stupid.” — Tweet this!

Fear is a powerful thing. And it’s harnessable. Use fear to motivate action. Prepare as much as you can. Break that big goal into small ones. Trust in your ability to respond to the unknown. Then take one step across that threshold.