Lesson 4: How to Deal with Failure

This week I’m reflecting on this year so far, how my past failures have shaped who I am and what I’m doing and, of course, gushing over my favourite podcast: How to Fail With Elizabeth Day.

The day after I moved into this apartment, I sat down at this desk and wrote in my journal. I listed my new year’s resolutions and goals for 2023.

As I wrote at the time: I don’t think you need a new year for a new beginning; you don’t even need a new week or a new day. But, sometimes, the feeling of a fresh number to write in your journal helps, just a little.

I should mention, it was January 1st, and the end of 2022 had been difficult for me. I was ready to turn over a new leaf with some pretty bold resolutions, and one goal stood above the rest. 

Start a Magazine.

(Yes, so important that it was capitalised.)

This was the first time I had ever written anything down about Outloud (working title at the time: Project Avenida). I had been speaking about it for months and thinking about it for even longer, but this was the first time I had actually made a tangible declaration.

The reason I’m feeling a little nostalgic this week is because I’m moving out. I’m actually going to move back into the apartment I lived in when I first had the idea for Outloud, which makes me feel better about leaving this space behind.

Now, I’m not here to brag, but I have honestly never worked this hard in my life. Outloud is just a baby and we’re not making any revenue yet, so I’m still working to provide myself with a full-time income whilst I run this show.

I’m not ashamed to say that I’m exhausted, and only recently, for the first time in months, have I taken a couple of weekends off. Except for running our social media accounts. (Which doesn’t count, right? Although I have never hidden the fact that it’s my least favourite thing to do!)

The only problem is that instead of resting on weekends, like maybe I ought to, I’ve been going to dance events, travelling, and generally staying out later than I should. As you might have gathered, I’m not the kind of person that can sit still. (Unless I’m on the beach. Then you might not see me move for hours).

I’ve spent so much time sitting at this desk, I don’t want to let it go. In fact, I always imagine this exact desk when I’m picturing what life will be like after I move, even though I’m not taking it with me. (What does it say about me that, when I’m picturing my gorgeous new apartment, I’m still thinking about work?!)

My work station has evolved over the months, from a plastic chair and my laptop to a two-screen setup, a proper office chair (how old do I sound when I say this did WONDERS for my back?!), and scribbles all over the walls. (On paper, of course… I didn’t write on the actual walls.)

Anyway, I haven’t decided what the point of this article was yet, if not to document the last five months of my life. Everything was created here. I spent countless hours slaving over the website, practically reducing myself to tears with frustration, having video calls with writers, creating these articles for my column, and developing a flow of operations that, magically, now runs like clockwork.

I was sitting right here when the website went live, when I tweeted our first tweet, when I had my first epic failure.

Okay, here we go.

I think I might have just stumbled upon the point of this week\’s article.

It always comes to me eventually!

How to Fail With Elizabeth Day

Without spoiling too much of one of the best podcasts I have ever listened to, one thing stuck with me, and stays with me today. Justin Basini (I thought briefly about referring to him as ‘Elizabeth Day’s husband’ to subvert the trends of the patriarchy… but let’s not fight fire with fire) says that many venture capitalists in Silicon Valley won’t invest in a CEO until they have already had two failures. (This is me crudely paraphrasing, please listen to the podcast.)

I thought about my own failures. The four blogs I had before I started Outloud, and the failure of the most recent one, which was almost successful. The theatre company I ran with an old friend that collapsed during Covid.

1… yep, that’s 2 failures for Isabella.

And then, before I’d even started wireframing our website, I was determined that this would be my success. Either a success in itself, or another gigantic stepping stone on my way there, worthy of mention on a podcast some day.

I told all of this to the entrepreneur I went on a date with. I think he thought it was cute that this was all new to me, but he told me about his failures nonetheless. Then we ate ice cream on the beach and dated for the next three months, during which time we both launched new businesses. Talk about a stressful relationship.

Anyway, back to failure.

Elizabeth Day has revolutionised what it means to fail, and has truly changed the way I perceive myself when something doesn’t go to plan. For every set back I have, I think: “I’ll know how to do it better, next time.”

What podcast changed your life? 

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