Oh my God, I’m feeling pangs of anxiety just writing this title.
Part of myself has been screaming at me to not do it. This little, but very loud internal voice keeps telling that I’m not wired for this. It tells me that if I was meant to have a business I would have done it already, that I have so much to lose, and that I’ll never have the willpower to get things done. It whispers these negative thoughts to me over and over again.
That little voice is pretty darn persuasive.
So much so that in the past three months I’ve flip flopped daily between thinking I can do this and browsing jobs on LinkedIn, hitting that apply button with ten different hiring companies. I could spend a day creating my business website (which you should totally go check out), and the next day interviewing at a company.
It took a long time to decide to shut off the voice, or at least try to make it quieter. So I’m happy to report today that I have finally decided to ignore it and take the chance to follow my dream of owning a successful business! This is probably the last chance I have to do so, and frankly, I can’t afford wasting time anymore.
Getting to this point, however, has not been easy. There’s an internal battle constantly raging in my head between my fears and my dream.
The fears
My panic and anxieties are rooted in fear. Some of these fears are legitimate, but others are irrational and need to be dealt with. Sometimes, I just wish I was overconfident, willing to jump off the deep end of the pool and not feel even a tiniest amount of doubt in my mind. But unfortunately (or fortunately?) I’m not that guy. As such, I need to learn to identify and face my fears if I’m going to make any progress.
Let’s take a look some of those fears that keep me up at night
The fear of failure
I have a few words in my head to qualify how terrifying it feels to think about stopping my job search. It’s brutal, paralyzing, and demoralizing. My brain conjures up images of myself living on the street and I keep thinking I’m letting my family down. To be fair, these images bubble up into my mind because I’ve conditioned myself to think like that as a way to motivate myself to work hard and show up to work every day. But now this is actually hurting me.
I recently watched season 3 of The White Lotus where one of the main characters is a successful businessman who brings his whole family for a week of relaxation at this beautiful hotel in Thailand. *Spoiler alert* However, while at the hotel, he learns that the FBI back home is running a sting operation against him and discovers the fraudulent and illegal activities he’s been up to. Our character then spends the whole week in paradise knowing that his life is over, that’ll he’ll spend his retirement in prison and his family will have no money when they return. But he stays silent and doesn’t tell his family the news, delaying the inevitable.
I couldn’t sleep that night. For me, that fear of failing and losing everything is pretty strong and that part of the show hit a little too close to home. I saw myself as that man, losing everything, including the respect of his loved ones.
But there is a way to rationalize this fear away! In today’s market, where jobs opportunities are rare, that fear is also present. So whether I’m starting a business or looking to work for the man, I still have to deal with this.
What’s more, I don’t have to lose everything. That fear is irrational. If the business doesn’t work out, I have other avenues to explore, including going back to working a job. Heck, I’ve failed once before when I started a small coffee shop, as I described in this post, and I’m still here today.
Performance anxiety
It’s not just the fear of not being up to the challenge that is hurting me. It’s also the fear of putting myself out there and risk failing in plain sight. Just as software engineers joke that you can’t have bugs if you never write any code, an entrepreneur could joke that you can’t fail if you never try. If my goal is to never look stupid, well I could easily achieve that by never doing anything. Although a point could be made that this would be pretty idiotic in itself…
In his rock climbing book “The Rock Warrior’s Way: Mental Training for Climbers“, Arno Ilgner mentions performance anxiety as a limiting factor in someone’s ability to climb. The fear of not being able to perform well on a climb can be a self-fulfilling prophecy! In the book, the author recommends re-framing a climb as a practice session, as a learning opportunity. If you’ve learned something on that climb, then you’ve succeeded, whether you have reached the top or not.
I think the stakes a bit higher when choosing to devote my life to run a business… Ah, gosh, my inner voice is getting the better of me again. Did you see that choice of words? “Devote my life.” Ha! Don’t be so dramatic, Louis!
If anything, starting my own company is going to be an amazing learning experience and I’ll be able to rely on my newfound skills to find work if it ever comes to that again.
Fear of being judged, of being disliked
A long time ago I wrote a tech blog that was published on an up-and-coming tech website, which means my posts had visibility. I always treated blogging as some kind of journal, so my posts were never very deep or thought out. I never spent the time to investigate what I wanted to talk about and relied mostly on my intuition.
Well, one day I wrote a polemical post, which angered a well known blogger. He came in and left a scathing comment about how none of my posts were ever well thought out, and that in this particular case I was super wrong and should be ashamed of myself for putting out such garbage. I argued my point in the comments, but internally I wanted to suddenly disappear from the face of the earth.
I think I deleted my account a few weeks later, after making sure never to blog again.
While I obviously got over that fear (you are reading this blog post after all), I’m not completely free of it. For example, when I created this website I did debate whether I should turn on the comments on my blog, and I’m nervous at the thought that this blog might one day get some traction and attract naysayers.
Skiing under the chairlift

“Riding the chairlift at Whistler” by Wildcat Dunny is licensed under CC BY 2.0
I used to ski regularly when I was young. But I never wanted to ski below the chairlift because I thought everyone going up the mountain on those chairs was looking at me and judging me, probably because I was doing that to others myself. Thankfully, a friend eventually shook me out of that fear.
I still think about that today, about how I use to fear being judged by people who don’t even know me. Sometimes, that’s still how I think. But to combat that I recently began telling myself to not be afraid to ski under the chairlift. It’s a good expression and mantra that will help me on this new chapter of my life.
The dream
Show me who your friends are and I’ll tell you who you are.
Apparently this is a Spanish proverb? I’m not sure where the phrase comes from exactly, or what the actual saying is, but I can tell you that it’s true.
A few years ago I lived in Corpus Christi. My wife and I had a circle of friends who were all entrepreneurs. They ran their own small local businesses or local communities. One person owned a design business and was married to an ear specialist running his own practice. Someone else ran a local newspaper with a freemium model, similar to the Austin Chronicle. A few folks ran their consultancy offices, one friend was an accounting freelancer, and another had an architecture firm. And we all knew each other because someone had started a group that met monthly to discuss and plan how to make our city better. We were all part of that group.
Being surrounded by entrepreneurs and motivated people had an effect on both me and my wife. Within two years we both started businesses. She opened a clothing boutique and I opened a coffee shop! It is incredible the effect these friendships had on us. Although our businesses failed and things at times were incredibly difficult, I still fondly remember this chapter of my life.
But that was at a different time and in a different city. I do not currently have friends like that, who can positively impact me. I’ll need to surround myself with people that have an entrepreneurial spirit and feed off that energy to keep me going through the inevitable challenges ahead.
The plan
The fears and anxiety are still there, even though I’m better equipped today to reason them away. But they are also a tremendous force of energy that I can channel positively.
When the fear comes, I will use it to push through.
When I feel anxious, I will use that to sharpen my plans and priorities.
I’ll show all these people up in the chairlift that I know how to ski!
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