Do You Need a Niche or Specialization to be Successful?

Is there such a thing as a successful generalist?

Jason Weiland
6 min readDec 19, 2023
Image created in Medjourney

Really? Is there such a thing as a successful generalist?

Okay, I’m sorry. This started all wrong. Allow me to unscrew myself.

We shouldn’t start an article about success unless we talk about the nature of success and what it means. I shudder to discuss it because it means something different to everyone.

For some, it’s money. Lots of it. For others, it’s love and a good relationship. A job? Travel? Luxuries? What about having a good family?

Take me for instance. I am 55 years old, and I’ve led a difficult life. Let’s just say a combination of being neurodivergent and mentally ill made it impossible for me to do what “normal” people do with their lives. I didn’t go to college out of high school. I spent a few years climbing the corporate ladder, but my illness and lack of a degree held me back.

This year I graduated college, and I am looking to find my version of financial success after finding the love of my life and having a family for a second time.

Am I a success because I have a good woman and a family who loves me, or am I not because I am broke and looking for financial freedom?



Jason Weiland

Personal essays and articles from a guy who never tires of writing about his life -