how to be an entrepreneur

My Biggest Challenge as an Entrepreneur (and how I overcome it)

entrepreneur challenges


I’m going to tell you a quick personal story. I have two sons, a 3-yr-old and a 1-yr-old. Yesterday, I put them both in the pool (not at the same time, but one after the other with some help, of course). BTW they make the most amazing “swimmies” nowadays that go completely around the child’s arms and waste.

Wait. Sorry, I’m going off track.

Anyways the most remarkable thing happened. My 1-yr-old let go of me completely and calmly floated away smiling like he was experiencing weightlessness for the first time. Then what did he do? He naturally without any prompt started kicking his legs and moving his arms around – no sign of fear at all.

My 3-yr-old was an entirely different story. He’s taken two rounds of swimming lessons and has been in and out of pools for the past two summers. He dug his nails into my arms and begged me not to let him go. And, the one time I did try to let him go, he screamed so loud that even the seniors at the other end of the pool doing water aerobics (eerr…under water) could hear him.

The thing is I know he can do it. He fully understands what he’s supposed to do and is more coordinated than half the kids his age (in my humble mommy opinion), but he just can’t get over the fear of letting go. I don’t blame him. I remember doing the exact same thing as a kid. I was athletic, but often doubted my ability. I can remember my coaches telling me, “Get out of your head. You’re in your own way.”


It has a way of sneaking up on me just when I’m about to hit cruise control. It’s the number one challenge I have as an entrepreneur. Anytime I’m faced with being uncomfortable, I hesitate. I mean, doesn’t everybody? The thing is with running your own business, you sort of get comfortable being uncomfortable, and it’s scary as sh*t, but worth it.

A couple of months ago I pitched my business to a group of students at Harvard Business School for an internship program. I couldn’t breathe, but I knew it was something I had to do for my business.


It’s paralyzing sometimes. It’s an amazing motivator, but I think a negative one. It’s the one thing that can keep us all from achieving greatness.

One of my favorite entrepreneurs today, Marc Cuban says, “A major problem for entrepreneurs is getting stuck, and this is often a result of “fear of the unknown.” The only people who find success are those who take that next step, go out there and see what happens.”

It is so true – you can’t get ahead by sitting still. I can’t let fear prevent me from living life to its full potential. If I want my business to be successful, then execution is crucial. Without execution, you just have ideas that aren’t worth anything really.


There is an art to it. Just like there’s an art to letting go….and holding back.

How I Push Through the Fear

There are three things that help me push through that lump in your throat, can’t breathe kind of fear on a daily basis:

  1. Folder Naming – I use power words and phrases to name the folders I use most. This might not work for everyone, but I usually have 1-2 folders on my desktop that I use almost everyday. I choose strategic names for these folders that encourage and inspire me as I work. It’s almost a sneaky way to influence my subconscious mind throughout the day. Here’s a snapshot of my desktop as an example of the ones I’m using right now.

entrepreneur folders


  • Keep Swimming – Upcoming personal projects, and well you can read why I named this folder, “Keep Swimminghere.
  • Mompreneur – projects I’m currently working on for my own brand
  • Believers – projects that I’m currently working on for my clients

They’re just words, but I believe they can actually shift my attitude sometimes.

2. Music Playlists – Music has a way of motivating me like nothing else. I do my best work while listening to music, but I’ve learned it has to be a certain type of song. The song has to resonate with me in some way and get me moving – no classical focus music here! I love making marketing playlists, which I share every month with my subscribers. The songs I choose keep me performing at optimal levels and I refresh them every few weeks!

music for entrepreneurs

3. Community – I have strategically surrounded myself with some very talented people that I admire. Whether it’s a blog that I subscribe to, an influencer I follow on social media or a fellow entrepreneur who I check in with regularly, I lean on my network to get through any doubts that I might have. I like to follow other successful people and watch what they’re doing to find my own success. I have to admit, there’s a role model that I follow for everything from fitness to style, marketing to entrepreneurship.

As a business owner, you might face a hundred challenges in one day, but…


Fear is the product of the thoughts that you create. To quote President Franklin Roosevelt, “The only thing we have to fear is fear itself.”

Find a way to face it head on, and don’t be afraid to jump in the water, breathe deep and let go.

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