Uncomfortable Entrepreneurship

Uncomfortable Entrepreneur: What to build

This year I’m back making businesses. For me that’s software. It’s been software since I was a teen (20 odd years).

And here I am again, back in that deeply uncomfortable place. When you have a business to grow, whether it’s new or established, the path is pretty straightforward: start working, keep growing, keep improving.

The same applies if you’re employed.

After selling my company over 5 years ago I was employed to keep running ZBS CRM for 3 years. Last year I took a year out to build a cabin in the woods, recharge.

This year back to it. Back to that uncomfortable place. I’m running lots of experiments – I’m back in the lab.

And yet, eight months into the year, nothing has ‘popped’ yet.

Uncomfortable Entrepreneurship: When nothing is working

This post serves as a note to myself—and perhaps to you.

This space between ‘vehicles’ of work—between gigs, ideas, or businesses—is profoundly uncomfortable.

The compulsion to create is raging inside me.

My ideas spreadsheet is massive, filled with possibilities. But I’m reluctant to start building just based on that list. I want to solve a real, existing problem in the market—something tangible, something needed.

I go on sales safari’s. I leverage gummy search. I get familiar with v0 and cursor ai. I wonder whether all work is from now on is prompting a console.

I have my intentions. I know the direction I want to head in. I’m doing my best to manifest it.

But still, this existential crisis swarms me.

What to make.

What to make that matters.

What to make that will produce profits.

What to make that isn’t just facilitating human spam.

What to make that feels good to work on, that adds genuine value.

What the f*ck is my ikigai?

… I know only fragments of the answer. I’m showing up every day to work on it. I will endure through the unknown lands between businesses/outlets. I will keep trying stuff and I will sustain belief that this will eventually capture grace. I won’t fall into the trap of feeds and make stuff for the sake of it.

Keep. Going.


What’s your approach to choosing what’s next? Tweet me.

Let’s make mad sh*t.

I’ve made a lot of things in my life, and I intend to make a lot more. My biggest goal is to make a good and happy life.

Join my journey to authentic autonomy; let’s make craft software make money!

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