Points of failure: Stopping

For a few years now I've kept a notebook where I log my attempts at building what I call a "clever living.” I define it as a lifestyle where I work for myself and earn a reasonable income based on my own ideas and creations.

That notebook is where I sketch out plans and revise them, where I ask myself questions and monitor my level of enthusiasm for a given project. It's where I keep track of what has and hasn't worked in business or art.

It's where I hold myself accountable.

Finding something to dedicate myself to is not so black and white for me. I never developed one single creative and remunerative skill like many of my peers who make a living independently; visual designers, architects, sound engineers, web developers, studio musicians, and more.

Instead, I've always had multiple interests and steady jobs that support them. Ironically, the one creative area where I've spent the most time and energy, writing and performing music in a band, has had very little commercial value so far.

It stings, but it's true. The data is in the notebook.

On the very first page there is a list of everything I remember trying:

VHS rentals to classmates in 6th grade

Guitar teacher starting in high school

T-shirt brand after college

Door-to-door salesman

Advertising for local businesses

Concert promoter

Record label owner

Multiple attempts at e-commerce

A van rental business for bands

The list is over 30 attempts long and growing.

Lately, I spend a lot of time on those pages. I'm trying to be intentional about what I want to dedicate the second half of my life to. One afternoon last month, while taking this bird's-eye view of my efforts, I saw an uncomfortable pattern:

I stop too much.

It's a painful realization because I pride myself on being disciplined. In fact, I know I am. But perhaps I've been more disciplined about changing course than sticking with one.

I immediately recalled moments of quitting:

• Scrapping the t-shirt line when the designer became a parent and lost interest

• Stopping a profitable online store when my main supplier disappeared and I didn't seek a new one

• Quitting the van rentals after multiple mechanical problems

Hell, even this newsletter almost suffered the same fate recently.

All of these were opportunities to pivot and push through, but I didn't want to. My interest in the project wasn't strong enough to withstand the headwinds. Instead, I would quickly move on to something else, thinking I would find my niche with the next thing, or the one right after that.

But now I see how easily I could go my whole life like that.

Contrast this to my job, where I've been promoted for three straight years. I've mentioned before that this is my tenth year there. I often wonder why by many metrics I've been successful in my professional life but haven't been able to replicate it outside of work.

So I made a list:

• Stick it out for the long run

• Show up every day even when you don’t want to

• Take the next best step

• Don't quit

 It turns out to be pretty simple.

Now, as I wonder which of my interests are worth pursuing, there's one question I'm going to start with: Am I willing to do this for the next ten years?

That's the level of commitment I'm going to need if I want to achieve the lifestyle I desire. When things get uncomfortable is when the urge to quit gets strongest, but I need to know what lies on the other side of that discomfort. I want to choose only the things I feel truly aligned with, I already know what happens when I don't.

I got a notebook full of those.

I'm not quite sure what the final answer to my ten-year question is, but I get the feeling that writing about what I learn along my path will have something to do with it.

If my modest two years writing publicly have shown me anything, it's that even when I'm not sure what to write next, or when imposter syndrome creeps in and I want to quit, eventually the words unfold right before my eyes, so long as I sit down and keep at it.

Here's to another year of failing publicly. Thank you for following along.