Do What You Love or Try to Love What You’re Doing?
When I was a boy I loved LEGO. I mean I really loved LEGO. I was an only child and was often by myself; but I always had my LEGO. My mom accumulated literally two trash cans (well, those small 15 gallon ones anyway) full of the stuff over the course of 3 or 4 years. I could spend hours building things. I really liked starting from scratch and I had no interest in reading instructions. I just figured it out, that was my specialty.
Fast forward 30 years, I think I’d still probably enjoy playing with LEGO, and frankly I can’t wait until my son or daughter wants them, but I’m actually really still good at building things, and I love it. Over that time I’ve honed my skills and come to love building things both in the physical world as well as the virtual.
Enter software. In the 90’s I learned about software development and I came to love how things could be built so quickly and dynamically. I saw that whatever my imagination could dream up, I could create in software. I wasn’t limited by the physical building blocks Lego’s provided, and it certainly didn’t matter if I had enough little plastic hinges (FYI, the ultimate LEGO part as far as I could see), when it comes to software, I could just design a new hinge, and viola, there it is.
As the years passed I learned to build companies that built software, and I got pretty good at that too. But something has recently happened that has me re-examining what I really love to build. As my current company grew, I spent less time building and more time managing. I found myself spending half my time procuring little plastic hinges and less time figuring out what to do with them. I think I’ve come to the point where I just want to build things again. On top of that, there’s this whole mobile thing, a new medium to build things; one that really suits me and I just love.
So now I’m headed down that path as I slowly transition out of the company I spent seven years to create. I’m off to once again build something. But with more intelligence about who I am and what I like, I’m faced with a new challenge; a challenge to know what I should do next.
When I started on the entrepreneurial path I thought I was supposed to build companies; big companies. I thought I was supposed to accumulate massive riches and notoriety doing it. The truth is, I still want some of those things, but I’m not sure if that should be the primary motivator. I’m torn by whether I should just follow my passions and see where they take me, or should I try to find passion in what I think I should be doing?
I like the analogy of how many musicians live; they are simply passionate about making music. You might argue that the best, even most successful ones, don’t care about the results, they only care about the process of making music; and frankly most music goes unheard, but that doesn’t stop them.
My experience has been that everyone poses this question to themselves at some point in their life. Should I do what I love, or try to love what I’m doing. I think more people end up with the latter, and some end up pretty damn successful there. But I think I have a responsibility to ask myself that question and I have a feeling the answer might actually surprise me.









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Very insightful (and thoughtful) post. Best of luck as you figure this out — over the years, I’ve run into plenty of entrepreneurs and executives where it has gone many ways (massive riches and notoriety, but much unhappiness; no riches or notoriety, much happiness; and even much riches and notoriety with happiness). The difference (I agree with you) is the passion you bring to the table.
Ben, I always appreciate your comments. Of course the last of the results you stated sound the best, but my sense is that those who achieved that put passion on top, which lead to the other things falling into place.