005. The Art of Dabbling - Why Career Jumping isn't All That Bad

When I’m asked about my work experience, I prime them with something to the effect of “It’s been a little all over the place.” 

I wasn’t one of those kids who had their career path mapped out from the age of 15. If you had asked me then, I would soon be a professional baseball player. A few surgeries later that was out of the question. 

At 20, I set my sights on becoming a medical doctor. However, after a couple rounds of the MCAT and a rejected application, I crossed medicine off the list. 

By 22,  I was aiming for a career as a hospital administrator, as I was in graduate school for this specifically. Simultaneously, I applied for the Navy that same year. Well I didn’t finish school and the Navy told me no…so, on we go. 

At 24, I envisioned myself as an entrepreneur.  Several failed business ventures and a humbling move back to my parents' place, I questioned if I had it in me.

By 27, I just craved stability and a decent income, which I found in medical device sales.

At 28, I realized the entrepreneur desire never left and I was fixated on becoming a full time land investor, which I was dabbling with on the side. 

Now at 33, as a full time land investor, I’m still uncertain about my ultimate career destination. Perhaps I’ll own multiple businesses, or maybe I’ll delve deeper into note investing, or even explore starting a blog or media company. 

Reflecting on my meandering journey, I see a couple of through lines. 

Firstly, I crave financial freedom but value autonomy over mere profits. 

Secondly, I’m a seasoned dabbler. 

Some would call this job hopping, uncommitted, aimless wandering, but I prefer dabbling.

I was even denied a job once when the hiring manager looked at my resume and said, “I don’t know what Jake wants to do.” 

However, I see it as accumulating skills and traits from a wide array of experiences which shaped me into the professional I am today. Each endeavor has provided me with tools that I utilize daily in my work and relationships. They’ve given me insights into who I am and how I operate. 

So while it sounds nice to have a lengthy, tenured career in one field, if you’re anything like me - navigating from one pursuit to the next every few years (dabbling) - just know that you’re accumulating a wealth of universal experience that will serve you well in ways unforeseen down the line. 

Plus it’s just more fun to dabble… 

So. What’s your through line?