Dabbling Again: Revisiting An Old Project With New Perspective

Photo by Dimitar Belchev on Unsplash

Making The Tigger Tendency Work For You

As a self-proclaimed “Professional Dabbler,” I often find myself jumping from one interest to the next. Oftentimes, those interests seem completely unrelated. I’m sure others scratch their head when they observe what appears to be a nonlinear and chaotic path that I follow.

One of the inherent risks with living a Dabbler lifestyle is the so-called “Tigger Tendency” (aptly named after the bouncy character of A.A. Milne’s Winnie-The-Pooh), as described by author Benjamin Hoff in his book, The Te of Piglet.

“The final problem we might mention about the Tigger Tendency is that the worthwhile and important things in life — wisdom and happiness in particular — are simply not the sorts of things one can Chase After and Grab. They are instead the sorts of things that come to us where we are, if we let them — if we stop trying too hard and just let things happen as they need to. Tigger found this out when he discovered What Tiggers Like Best…”
 — The Te of Piglet by Benjamin Hoff

During the course of my nonlinear career thus far, I’ve confirmed that the problem is not in the tendency of jumping around, but rather in the intent of why people zig-zag in the first place. If it’s to chase after and grab happiness, the prize is elusive and the experience can be quite frustrating. Case in point, at the start of my career, “chase and grab happiness” was my intent and I found myself jumping around in circles and often getting lost.

I hope the following example will help reassure other Dabblers. Despite the naysayers and other challenges along the way, dabbling can be a good thing and there’s a reason why we should let the moment draw us in, even when it doesn’t seem to make a lot of sense at the time.

Coming Full Circle

“We shall not cease from exploration
And the end of all our exploring
Will be to arrive where we started
And know the place for the first time.”
 — T.S. Eliot, Four Quartets

In 2001, I launched a website as a business. My goal: to help engaged couples find resources when planning their wedding in Chicago. (I was working as a wedding DJ living in Chicagoland at the time.) Similar to how this Dabbler publication on Medium came about, it was not something I had planned to do. It unfolded at the moment as inspiration struck. With a lot of effort, but mostly by sheer luck and timing, it actually did well for quite a while and made a decent profit from vendor advertising.

When I first got ChicagoWeddingServices.com up and running, I worked intensely. Almost non-stop every day, I enthusiastically taught myself everything I needed to know while simultaneously applying what I learned to build and optimize the site. Although I paid a hefty price in terms of life balance and family time, it became a springboard for the beginning of a new career.

One thing led to another and the experience eventually landed me many years in executive management as a digital marketer. Because the demands of corporate life didn’t leave me much time to continue with the Chicago Wedding Services side-hustle, the site went downhill and just flew on autopilot for more than a decade.

As life would have it, I’m out of corporate again. Recently, with the COVID-19 circumstances, I’ve had the time and opportunity to revisit ChicagoWeddingServices.com as a project. This go-around, I see things in a new light and am enjoying the process in a much more balanced way. Applying everything I learned the first time and since then, I’m also better able to avoid my earlier mistakes and bad assumptions.

This time around, I’m not chasing the attention or the money of a successful, high-traffic website. If that happens again, great. If it doesn’t, that’s fine too. The project, in and of itself, has reignited a fire within that was beginning to flicker away. I can get lost for blissful hours of tinkering and developing. Reacquainting myself with a forgotten friend, the process brings my passion for digital creation to life. At the same time, I can still easily walk away from it when it’s time to walk the dog, cook dinner for the family, or simply just rest. I couldn’t do that before.

This is just one example of countless lessons I’ve learned from living life as a Dabbler and coming full circle.

Dabble in interests that really bring out your passions, not just the next new shiny object. Go all in, but don’t lose your balance. Get lost in the moment but stay connected to reality. Do it for the love of the game and not just the final score.

I’ve found pleasure and happiness in the act of becoming rather than focusing too much on what I will become. Joy has come to me from bridging the gap between who I already am with who I might be someday. This has helped me stop feeling like an inadequate imposter in a world where being someone well-known and important is an admired thing.

If you’re a natural dabbler, be comfortable in your own skin by accepting your inner Tigger. It’s okay to jump around and explore. Understand why you bounce and enjoy the journey. You’ll eventually get to where you need to go. But remember that happiness is already where you are.


Photo by Dimitar Belchev on Unsplash

Original post from The Dabbler publication on Medium.