I was feeling sentimental, and a little nostalgic the other night as I walked home from the office.

I didn’t have time to start another podcast before getting home, but I wanted to listen to something.

In my nostalgic state, I found myself scrolling through old songs I had recorded years prior.

My Origin Story

My current role running a podcast agency was preceded by going to school to become an audio engineer and record producer.

My dream had always been to split my time between producing music for others, while also writing and recording music myself, a dream that never panned out but ended up leading to greater things.

The playlist of old recordings spanned a decade of sporadic work and meandering styles, from singer-songwriter to metal, to electronic to alternative rock to hardcore punk.

I wrote and recorded single songs, releasing a couple of them under different monikers, which maybe 15 people downloaded in total.

I envisioned these songs being the beginnings of larger projects, culminating in EPs or albums, but the closest I ever got was a few dozen songs existing in various states of completion on my hard drives.

Finish The Work?

In the world of creative work and entrepreneurship, there’s a huge emphasis placed on finishing or shipping the work.

As creatives, we can find ourselves endlessly tweaking our work, convinced that it could always be better, afraid of overlooking some glaring flaw for which we’ll be criticized and written off as just another amateur trying to pass ourselves off as a pro.

In such cases, I think the advice to just ship the work is valid and useful. But I don’t think it always is, and I think the sentiment can sometimes be downright unhelpful.

Permission To Explore

As I listened through the eccentric playlist, I started thinking about my larger trail of creative work that’s led me to where I am now.

Besides the decade’s worth of aforementioned music, there are the sketches and drawings from junior high, angsty high-school poetry, my photography blog, tens of thousands of photos, more than a few of which were actually paid work, my old travel blog, the short-lived travel vlog I started during my first year of full-time travel, my podcast blog, recent explorations into calligraphy and hand lettering, this blog (apparently I’ve started a lot of blogs…), podcasts created for myself and clients, and more.

As a kid, I even invented a new billiards-style game in my basement, printed off the rules and made my parents and friends play. I vaguely remember that the blue, black and purple balls were somehow important, and as such, I dubbed the game Bruises.

Thinking through my past creative endeavors, I realized that I had pursued many of them with a significant amount of dedication and seriousness. Some of them, such as photography and music I’m sure still have a place in my future.

And yet, even in those pursuits in which I really made a run at, I can’t say that I ever really finished any work to the extent that I would have liked.

Perhaps that’s why I never succeeded as a musician or photographer, but I also never quite felt the pressing need to finish in those fields.

One of the things I’ve come to most appreciate about myself is that I’ve started down many different, (mostly) unrelated paths, typically with a good deal of conviction and discipline, and then been fine dropping the pursuit and hopping over somewhere else once I lost interest or realized that the path didn’t lead quite where I thought it did.

Choose Your Dips Wisely

Most new pursuits are easy and exciting when you first start out. You’re able to put in work and see measurable improvement, maybe on a daily basis.

Ultimately, however, you reach what Seth Godin calls The Dip, the point at which something stops being easy and exciting, where you realize that to achieve mastery and further success you must work through what I think of as The Hard Stuff.

In thinking about my own creative history, I’ve recognized a pattern of starting things and sticking with them up to The Dip, before either petering out or dropping the pursuit immediately.

While I’m convinced that to become exceptional at anything you have to work through The Dip, none of us has the bandwidth to work through every Dip we come across. We need to be selective about the Dips we lean into, because each one might take months, years, or even decades to reach the other side of.

To discover the area in which we can do our best work, achieve the greatest fulfillment, and create the greatest impact, it’s essential that we start a lot of things, but finish only a few.

Only by reaching the various Dips can we look into their gaping chasms and ask ourselves whether this is where we want to invest our precious time and creative energy.

Most things we start won’t be.

In those cases, accept them for what they are. Content yourself with remaining a novice, with keeping it a hobby, or with dumping it altogether.

Forget finishing, ignore the sunk cost and move onto the thing that excites you.

Eventually, we each find a dip that’s worth bringing our full selves to, putting in the work, and finishing.

But until then, just get busy starting.

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