Entrepreneurial Insecurities and Failures — You’re Not Alone

“The following thoughts are my own experiences and opinions only. I am not a doctor or mental health professional. I am only sharing what I’ve been through, what I believe, and what’s helped me. My goal is that it may help someone else too.

“It must be nice to be Gary Nealon!”

It’s a running joke I have going with a couple of friends that I run into every now and again.

I never really thought much about it, until I was on a recent flight back home from California. I’m not sure why it stuck in my head this time, versus the other dozens of times that I’ve heard it, but for some reason it gave me pause for thought. I guess that’s what being stuck at 30,000 feet will do for you!

On paper, I’m someone who should have the perfect life. I recently exited a very successful business, launched a couple of new companies, great family, amazing network of friends, and genuinely get to spend my time working on things that I enjoy. I have had the privilege of working with high level e-commerce clients, often get invited to speak on big stages, travel extensively, and am well-connected in the business community. Most people on the outside looking in would think I’ve got it all.

So today, when I was filling out the bio form for a large event that I’m speaking at, I noticed it again. All of my answers were about my successes; my resume of awards and achievements. Nothing about my setbacks, failures, and certainly not my struggles. It’s all very one-sided, and you’d be forgiven for thinking that there’s nothing wrong in my life, that I’ve never reached rock bottom or even had a bad day.

In the business world, there’s an unspoken rule: we only talk about our successes.

Even when someone might be struggling to meet payroll, has just lost their biggest client, or is two weeks away from shutting down their business. We gloss over it, make a joke, or just don’t mention it at all.

If you are anything like me, this may be the approach that you take as well. It’s just easier, and in many ways comes naturally, only highlighting our best experiences or achievements, while burying the other, less-newsworthy ones.

The truth is, I have spent the last 11+ years of business avoiding anything negative or emotional in my life. When something painful or sad came up, I’d just double down on business. Work harder was my solution to everything.

I suspect it’s the same for many of us entrepreneurs.

Insecurities

When I sold my company last year, I ended up with a lot more free time on my hands.

This, of course, meant that it wasn’t as easy to simply hide behind the business anymore. Eventually, things came to a head and some of those emotions started coming out in unexpected ways. I finally had to deal with them.

So rather than pretending they don’t exist anymore, I thought I would share my struggles and biggest failures. It’s my hope that my experiences will help someone else as I firmly believe that it’s important to acknowledge our failures –as hard as it might be.

I’ve always tried to put others first, even to the point of negatively impacting my own happiness. Self-love, indeed even self-acceptance has long been a struggle for me.

A friend of mine had given me a book, The 3 Questions by Don Miguel Ruiz. I had been carrying it around in my backpack for months before I finally decided to crack the cover. And I’m glad I did. It turned out that it was exactly what I needed. Upon reading it, I was struck with the realization that I have never really been comfortable in my own skin, or happy with who I am.

From the time I was in high school, I’ve always been my own worst critic. When it came to goals, I would set such unrealistic expectations that I could never possibly achieve them. From basketball, to school, to business, even in success I would always view my achievements through a critical lens. There was always something that I could have done better or worked harder at. (Any of this sounding familiar?)

This combined with the fact that I’ve always stuck out in a crowd –and have never really been comfortable in my own skin, means that I’m in for a difficult time. I’m 6’7” and while most people see that as a huge asset (no pun intended) I was always uncomfortable with it. I hate being the center of attention, get anxious trying to have conversations in crowds, and have a hard time maintaining eye contact. I also downplay compliments, don’t place a high value on my own time, and you can forget about me initiating a conversation with someone I don’t know.

At this point you are probably thinking “How the hell did this guy EVER grow a massive business?!”

That’s a great question. The truth? I was able to build it without having to be the face of it.

The thought of spearheading anything as the front-lines spokesperson has always terrified me –even to this day (although I have been forcing myself to put myself out there recently). Lately, I’ve been trying to figure out why I keep pushing off new projects that deep down in my core I know will help a lot of people. Self-doubt always creeps in –“Who would anyone want to join my membership program if I built it?” “What value would anyone get out of my experience?” “Who would want to pay X for my time?”

Any of this sound familiar?

Self-doubt and a lack of self-love might be one of the most crippling games that our mind plays on us.

I would GUARANTEE almost every entrepreneur has dealt with it in some way, shape, or form –even if they haven’t yet admitted it themselves. In fact it hasn’t been until recently that I have been able to consciously catch myself in those moments of self-destruction and ask “Is that really true, or is it my mind just trying to sabotage me?”

Failures

In many ways, our view of failure is one of the worst aspects of the entrepreneurial community.

As entrepreneurs, it’s easy to talk about overnight successes, or the massive exits, or the “5 easy steps to earning a million dollars in your spare time.”

But nobody ever talks about the failures or the hard times. From the outside looking in, you would think that no one at these events has ever even had so much as a bad day in their lives.

I was having breakfast the other day with some friends and fellow business-owners, and this topic came up.

We were discussing the idea of shooting a video series that JUST talks about successful people’s biggest failures. Not in a judgmental way, but in a way that talks with straight up honesty about what happened –and what we can learn from it.

For a long time I carried my biggest failure with shame and guilt. I had a hard time even talking about it, for fear of judgement. But now that I have accepted it, and realize that I probably would never be where I am had it not happened. It has become part of my story and I’m sharing it now in the hope that it helps others who are struggling as well.

While I may have exited a $30 million+ business, my first venture was a complete disaster.

At the age of 29 I’d scraped up everything I had saved, found some investors, and bought a business. Within a year, though, I was filing bankruptcy on it. I’d lost everything I had except my townhouse –only because it was so leveraged the bank didn’t want it.

Self-doubt began to creep in and sabotage became the only solution that I saw.

A lack of self-love had led me to this point. One thought kept replaying in my mind: on paper, I was worth more dead than alive.

I thought the only way out was suicide. Luckily I am Irish, so clearly it takes more than a bottle of vodka and painkillers to take me out, but all jokes aside I have never felt as alone as I did at that point.

Interestingly enough, I’d never had thoughts like this prior to this, and I haven’t had them sense. But at that moment the stories running through my head were telling me that I had let everyone down.

From the day after and on, I just kept going on with my life like that NEVER happened. I don’t think I told anyone about it until years later, because of all the shame and guilt around failing and disappointing people. Knowing me now, most people have a hard time believing that I could ever have been at the point in life. I think there’s a lot to be said for the ability to open up and be honest with another person about what’s going on in our lives.

Statistics show that for every one person who goes through with suicide, there are another 280 people who think seriously about suicide but do not kill themselves.

I know there are more of us out there.

My story might sound tragic –but it doesn’t have to be. Because I believe that it’s what made me who I am today. I believe it has an important part in my story. And I believe that for those of who have faced our innermost demons, fought back and survived –we can even help to save lives.

❖

I’d like to say that there was a lightning-flash moment, and that some tremendously pivotal event that helped to transform me into who I am today, but there wasn’t. The truth is that these things rarely resolve themselves in that way. More often than not our journey out of the shadows is a cumulative series of small steps –rather than any one groundbreaking event. For me, it was a sudden resolution to make a series of changes in my life that spurred me onwards and upwards.

After my suicide attempt, I had a clear vision that I needed to seize life once more. I resolved to get a full-time job but knew I needed to figure out how to not have to work for anyone ever again. I also was determined to never get back to that point in life.

These days I’m doing my best –and working on accepting that at the end of the day, that’s all that’s needed.

I don’t necessarily have a daily routine. But I’ve spent the last year getting back in shape, eating healthy, practicing self-gratitude, and reading.

Perhaps most importantly, if a negative or deflating thought occurs I’ve learned to question it, rather than accepting it as fact.

. . .

I firmly believe that each and every one of us has had our own share of struggles.

Whether it’s a fleeting brush with suicide, constant recurring struggles with our own thoughts and inner demons, or a long-term mental health struggle –the fact remains that we are not alone in our fight –so why do we pretend to be? Why live alone with our own thoughts if we don’t have to?

What can we do about the rampant insecurities and failures that are so prevalent in the business world?

I don’t claim to have all the answers, I only know what helped others and helped me.

But I do think that first and foremost, we should try to be more open.

While everyone’s story looks different, and some may indeed benefit from keeping silent –I believe that those of us who can talk, should share our stories. The more we talk about it, the less stigma will surround it. The more open we are about our struggles, the less others will feel tremendous pressure to keep up with an unrealistic image or perfection –a facade.

I commend NBA player Kevin Love for publishing his own thoughts on mental illness –in his post Everyone is Going Through Something. In it, he bravely speaks of his own battles, and touches on the fact that in professional sports (much like my experience with the business world) mental illness just isn’t talked about.

“Mental health isn’t just an athlete thing,” he writes. “What you do for a living doesn’t have to define who you are. This is an everyone thing.”

Times are changing –and staying quiet about our own struggles is no longer the only way. Talking about our struggles is no longer being seen with the same stigma that it once was. Speaking up or sharing as we feel comfortable is probably one of the best ways to address these issues. After all, once their out in the open they can no longer elude us anymore.

At the end of the day, we can learn more from our failures than our successes. As for our circumstances, we can either grow through them, or hide them away until they eventually consume us. The choice isn’t always easy, but it’s one that matters –a lot.

Please feel free to share this write-up with anyone that you know who may be struggling, or in any entrepreneurial circles where this topic doesn’t get shared enough. Shining light on these issues is important, and raising awareness is a great first step.

And if you’re struggling yourself, please reach out — either in the comments or via a private message. I want you to know that you’re not alone.