Six Things Entrepreneurs Will Never Admit To
Truth #1 - It’s OK to be doing badly.
Struggling and doing badly is out of fashion for entrepreneurs. Admit difficulty at your peril. At all times you must put on a brave face and tell your coffee meetings how much you are “Killin’ it, bro”. It seems to be unacceptable to be doing badly at work. It’s an unspeakable horror if your company isn’t making as much money as you need to survive. It’s a shocking headline if you fought with your spouse and are on the verge of breaking up. Don’t talk about doing badly.
It’s pretty much impossible to be a regular human person with troubles and hardships.

Troubles don’t get likes, folks. Difficulty isn’t cool. You can’t market or promote your bad day or struggling business. We’re systematically being trained to hunt likes which validate our actions and feelings and it’s mostly the proud, amazing, fun, exciting, jealousy inducing moments that get the most likes and make us feel the most validated. Nobody is jealous of my struggle and I have been trained to show no weakness or fear being cut down and destroyed.
The thing is, some of my most valid feelings are the dark ones. The ones that make me introspective, the one that make me really think about my existence and the things I choose to spend my time on. It’s the feelings that put me into a state of anxiety and panic that make me question my choices that I admire the most once they have passed. It’s easy to promote a happy life. It’s easy to only show people the side of you that makes you the most comfortable.
Some of my most valuable days as a write and entrepreneur have been the bad ones when nothing went my way. These days tested me and brought me forward once I managed to overcome them or they overcame me and I started again. Embrace the bad because you never know what will emerge from it.
Truth #2 - You’re allowed to take lunch, watch a video, see your partner and go to gym.
It’s impossible to work 80 hour weeks indefinitely. You are going to crack and your work is going to suffer. It’s OK to take a walk and let your mind drift occasionally.
I have a rule that when I’m eating lunch in the office everyone needs to leave me alone. As long as I’m eating, I want to be alone and think, browse twitter or read up on some interesting topic that isn’t work related. It helps my mind clear and brings me back to a state where my work can become optimal.
I wrote more about this topic here, but in short — give yourself permission to take a break and find the magic in the moments between work.
Truth #3 - Nobody knows what they are doing.
As you sit reading this, take a look around you. Feels like everyone knows what they’re doing and has a plan, right? Not so much.
The truth is that at every level there are people (most people) who don’t know what they are doing. You think Elon Musk knows what he’s doing? Probably. But there is a chance that most of the time he’s guessing using as much information as he can from the smart people around him who also don’t know what they’re doing.
If you haven’t heard about this before, it’s called Imposter Syndrome. The feeling that in spite of external validation, you don’t belong where you are or deserve what you have.
Everyone feels this way. Every person in the world (if they are not psychopaths) who has a teeny bit of self-awareness has felt that they don’t belong in that big meeting, at the grown up’s table, in the boardroom at the big meeting or that they are actually the age that they are. I felt like a very incapable 25 year old when I was 25. I still feel like a very incapable 35 year old right now.
Truth #4 — It’s OK to have sad days.
I’m not sure when it happened in human culture but being sad has been stricken from the list of topics that are OK to discuss with others. Perhaps when Facebook hit 1 billion users, bought Instagram and folded Whatsapp into the mix people started being aware that “all their friends look happy” so they should too. I don’t know.
I have never adhered to the saying which urges us to avoid discussing religion and politics. Recently it seems like all we can do is discuss these important topics, and that’s great but we’ve started to avoid talking about sadness like it’s going to unleash some kind of kraken that we’ll never be able to tame.
Sadness is as fleeting an emotion as happiness, anger or any of the others. If everything is going right for you but you’re still sad, that’s OK. You can verbalise it and it will likely lessen the burden. Trust your spouse or friends with your feelings and they will more than likely embrace your feelings and help you through them. If they don’t, then fuckem, find new friends or leave your spouse.
Truth #5 - We fuck up all the time.
Failure is inevitable. Hell, I bet you’ve failed at something today already. But that’s OK. Humans fail a lot. We fail at everything we try all the time. It’s how we learn. Unfortunately of late failure has become a very big negative and something to avoid talking about and learning from.
I propose that you reframe failure. Instead of looking at failure as an end point, I’d like you to look at failure as a through-point. Failure should be something you work through to get to the next iteration of your relationships, projects, game progress or whatever it is you’re working towards.
Imagine playing Fortnite but being too scared to move or fire your gun in case you miss and your opponent kills you. Why bother playing?
I am more in awe of the people who throw themselves at tasks with calculated enthusiasm and risk.
Stop, think, plan, execute, fail, re-plan, try again.
Or, as I said in my book: DO. FAIL. LEARN. REPEAT.
Truth #6 - We don’t celebrate our wins enough.
Building anything of value and meaning is really difficult. There are people who make you feel like it should be easy but I promise, building stuff is hard.
So when you encounter a victory of some kind, don’t belittle it, don’t put it down and don’t ignore it. Celebrate the victories when you have them because at times they will be few and far between.
When you sent your first invoice out to a customer that wasn’t your mom, did you celebrate? I bet not. When you hired your first team member, did you take them out for lunch to celebrate your business growing? I doubt it. When you received your first piece of media coverage did you share it all over your social media with pride and tell the world how excited you were? Maybe, but perhaps not with enough enthusiasm.
Forget about what other people might think, forget about what it might look like to celebrate small things and just do it. You’ll be grateful one day that you are in the habit of celebrating.
I’d love to hear about the things that you hate to admit to. Sign up to me newsletter below and drop me a mail or write a response to this article and let me know.
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Photo by Gift Habeshaw on Unsplash