An Unsettling Lie about Entrepreneurship

I've just finished my 41st birthday. And felt I should clear the air - at least with myself.

Today, my second venture (the first to be successful), an agency - Digital Street - turns 6 years old. And instead of sharing my lessons, I need to come clean about how I'm doing.

Something has been bothering me for some time and I've not really taken steps to address it properly.

My wife says I should write more honestly - that makes me think I share cliched pieces of my journey - the things that might get likes or validation.

Seems sensible and safe.

What I should be doing is be transparent and upfront about what my journey is really like.

About the true nature of what I'm going through and to see if I'm just really bad at it.

And if you read my last piece, which is more a celebration of my prophetic foresight and propensity to see opportunity where chaos resides, then you should know the truth behind it.

So here goes...

About 3 weeks ago I stumbled across a video of Dr. Scott Galloway [watch at the 22 min mark]. In it, he articulates similar advice I was given by the person I get my best advice from, my wife and inspiration.

He says that the advice about following your passion is bullshit you are fed by people who don't have to worry about money. That passion, is the result of doing something with focus and determination, then becoming really good at it. Not the other way around.

And on some deep levels, it makes sense.

Following this, I see a friend of mine post a comment about how a lot of people seized the 2020 shitstorm and turned it into an all-out 'How I won the worst year of our lives' yarn, with me being one of them.

And that becomes the tipping point, initiated by my wife, reinforced by Dr. Galloway, and followed through by my friend, Riaz.

See, I wake up every morning and sell myself this bullshit strawberry Alka Seltzer that "I'm so excited about the challenges today will present me with."

Mind you, my mental sentences aren't that well-formed or eloquent as my written ones.

The truth is a kicker;

I am really stressed out. Almost all the time.

And I actually wake up thinking, "What puddle of sh*t is today going to throw at me?".

• Will I lose another account for my agency, which I am also trying to transition out of to focus on my new venture?
• Will another potential investor tell me "NO!" because I'm too early stage or haven't demonstrated enough "commitment".
• Will I find out about another expense I cannot pay, while I'm struggling to keep my team and sanity together?
• Will another client squeeze and abuse my services with scope creep, while flexing their "financial muscles"?
• Will another employee have an existential crisis and leave when you need them most?

Then, an idea enters my head, and I draft a possible article to carve out 'a keen lesson I'm getting from it' so I can share it with you - my network of friends, colleagues, and well-wishers.

But I don't complete it.

Because instead of being truthful about the hardship-in-progress, I find that I cannot justify sharing the half-baked wisdom that hasn't really gotten me the success I expect or crave.

Instead, I wallow in some form of self-deprecating pity which then affects my mood and the rest of my day. And sometimes leaks into my personal life, which I fight to avoid.

And because of this, I have anxiety. Almost all the time. And that's the most real thing.

So, I often catch myself biting my nails; a nervous tick I've had since I was a kid, but also a sign of restlessness.

As a kid, I would be threatened by an an aunt of mine, saying she'll pour red chilies over my damaged cuticles.

She wasn't kidding but I never really stopped; biting my nails or being anxious.

But from what do I have anxiety, you may ask? I have a seemingly well-put-together life and a successful career/journey as an entrepreneur.

While some of this is true, it's also heavily curated so that I appear well-put-together.

It's not.

The reality is that more than often it feels like I'm barely holding together. But that's not the truth I want to motivate myself with when I go to sleep at night and wake up to in the morning.

So I forge a lie to myself about how well I'm doing and that tomorrow is going to be an even better day! At the same time, I wonder if I should go back to a full-time job and a steady paycheck.

After all, if this is part of the sexy of entrepreneurship, then maybe I was wrong about my grit and resilience.

It's taking a toll on my mental and physical well-being that probably isn't good for me and may have lasting effects.

Some mild forms of depression will mask themselves as motivational adrenaline - shots of imaginary dopamine - to keep holding on. No one can tell me how long for though.

Unsettling, isn't it? And it's not an exaggeration either.

And the worst part is that I often catch myself in the lie of imagining myself being successful - because I can somehow afford to still get groceries while my business struggles to manage its vital cash-flow and operating capital requirements.

But that's because it's true what Dr. Galloway says -- I am fortunate and comfortable with some personal finances that cushion me from the harsh reality most other entrepreneurs have to deal with fully, without a plan b.

And that's ok because everyone takes a start from different stages.

But even my plan b has real limits and I'm worried about reaching mine sooner than I expected. Worrying mainly about the severe consequences of real failure (not the 'rite of passage for entrepreneurs' kind) and risk to my family's well-being.

I'm sure there's advice from a Steve Jobs or Warren Buffet about how the absence of a plan b is why sincere struggling entrepreneurs will actually make it - because they have nothing to fall back on.

How entitled am I, right? A plan b AND a dilemma of personal suffering.

What I should be doing is talk about how vulnerable I really am and that the difficulties are not fun or aspirational - some of which may even feed struggle porn.

For once, I have no moral or lesson to share. I only have a personal struggle that I need to find a way through, sensibly.

Because I can't be a good role model for my son if I am not actually a successful person in my own eyes.

Let's take it one real step at a time. Solve cash-flow, pay salaries on time, find investors, build a product, pivot the company, and so on.

Now I am working on my third venture, which you will learn about soon enough.

Until then, the journey, and its painful reality, continues...