I’m Suffocating Under This Mask (Part 2)

Don’t Let Anyone Find Out

This is a four-part blog post. If you missed Part 1, go here.

But why? Why didn’t I let my true feelings show? Well, for two reasons.

For one thing, no one else seemed to be struggling like me. I mean, there were definitely conversations I had with other entrepreneurs where we exchanged war stories about the brutal gauntlet of trying to build a successful company, but those conversations never went that deep. More times than not we stayed above the surface, sticking to safe and seemingly relatable topics, like difficulties fundraising, or how to best convince rising tech talent to come work for us, rather than The Big Five.

And sure, I wanted to go deeper at times. But I was absolutely terrified. I was terrified, because I never really heard other entrepreneurs speak about their personal struggles, so I thought maybe these were just my issues. Maybe all of the back-and-forth self-talk and recurring doubts taking up residency in my head was just something unique to me. Maybe the swinging door of emotions was a sign that I really wasn’t cut out for success in this field.

But I honestly didn’t buy that. I could sense that there were other entrepreneurs out there like me too. I mean it wasn’t rocket science. You could clearly see the huge bags under their eyes, or hear through the grapevine that yet another investor passed on their idea and they were pinching pennies to keep it together. But why wasn’t anyone saying anything? They’re obviously going through difficult stuff too, but they’re not uttering a word about it. So really, what place do I have to complain? This is clearly a club that doesn’t have room, or time, for pity. I better buck up and follow suit — quick.

And so that’s how it went. Rather than glue and paper, us entrepreneurs crafted our masks with pride and ego. And everyday, we wore these masks out into the world, even when interacting with each other. With our masks on, we felt stronger. With our masks on, no one could see through to our scars. And what others couldn’t see, couldn’t hurt us — right?

The second reason I never said anything about my personal struggles as an entrepreneur is because I was afraid it would negatively impact the image valued stakeholders would have of me and/or my company. As an entrepreneur, you have to believe in yourself more than anyone else does. It’s an old saying, but one I’ve found to be true time and time again: investors often times invest in you, the individual, more than they do your idea.

So just think. If there’s a founder that’s displaying signs of insecurity, doubt, or fear, it’ll more than likely cost her the deal. Quite understandably, it’s just not a good business move for an investor. As a founder, an investor needs to know that you are confident enough to recruit a capable team, smart enough to develop a quality product, and stable enough to weather any storm, no matter how tumultuous things get — and they know better than anyone, that things will get rocky. That means there’s little or no room as an entrepreneur to show weakness. Given this reality, many entrepreneurs actually have a second mask, specifically for investors. But this mask’s not just made out of pride and ego; it’s adorned with charisma and charm, as well.

So where am I at today?

Two years have passed since I was operating my tech startup. It’s fair to say my life and mindset is significantly different now. Thanks to the support and guidance of my life coach, doing the daily work of investing in my own personal development, and taking a break from the startup grind and all the pressure that comes along with it (we closed up shop in the fall of 2013, and I accepted a leadership role at another organization), I can honestly say I am stronger than I’ve ever been.

Today, I am equipped with a sturdy toolbelt of resources and strategies that help me keep my insecurities, doubts, and fears at bay and allow me to navigate the world and my role in it with a brighter perspective, a stronger mentality, and true belief that no matter what happens, I will be able to handle it. I work hard to call “BS” on my own perfectionism, and I try to approach the ups and downs of life with significantly more acceptance and self-love.

And for those who may be thinking it: No, I’m not saying that the only way to come out stronger is to walk away from your startup. As you’ll see in Post 3 tomorrow, I’m not advocating for that at all. This is simply my story, these are just my personal experiences, and that’s the only truth I can tell.

But despite how far I’ve come, I can’t seem to forget about those few years in my life when things were really bad for me. I haven’t been able to forget, because although my role has changed, my frequent contact with other entrepreneurs has not. Every year, I meet hundreds of entrepreneurs, who like me, are not necessarily coping well with the incredible challenges of building a successful business from scratch. Entrepreneurs, like me, who are hiding behind a mask of security and confidence, appearing to have it all together, but silently, secretly hurting inside.

I feel so deeply for these entrepreneurs, because I know that wearing a mask sheds a dark shadow over you, dimming your inner light, and restricting your ability to breathe freely and flow naturally in the world. Day by day, little by little, the fact that you are hiding what’s really going on inside of you, the fact that you feel like you can’t show people who you really are — the good, the bad, and the “I’m just trying to figure it all out” side of you — that stuff can really eat away at you. It can breed an abnormal level of inauthenticity that leads to serious internal tension and unhappiness. In fact, it can be so detrimental that some people even turn to suicide as a way to escape the pain.

Continue to Part 3.