Chris Dixon has written a great post about pivoting:
Ask yourself: if you started over today, would you build the same product? If not, consider significant changes to what you are building. The popular word for this today is “pivoting” and I think it is apropos. You aren’t throwing away what you’ve learned or the good things you’ve built. You are keeping your strong leg grounded and adjusting your weak leg to move in a new direction.
I suggest the same line of reasoning should apply to your career. Ask yourself: if you were starting out today, would you work at the same company? Would you even be in the same business?
As I look back on the last ten years or so of my career, I see a set of such pivots that took me from content management and syndication (at Vignette) to enterprise RSS (at NewsGator) to one-way Atom and calendar feeds (at Spanning Partners) to GData and two-way feeds (with Spanning Sync) and now cloud-based feeds, API’s, storage, and compute (with Spanning Backup).
I’ve also progressed through the org chart, first as an engineer, then in presales, then sales, then product management, then up the chain as a director, then VP, and finally a co-founder. (That being said, the last title on that list is both the lowliest and best job I’ve had.)
Unsurprisingly, I’ve had more than one hiring manager raise an eyebrow when looking at my resume. Admittedly, it can look like I’ve taken a random walk through the technology industry. But in fact it’s the result of doing exactly what Chris recommends: “keeping your strong leg grounded and adjusting your weak leg to move in a new direction”.
It will be interesting to discover what pivot is next. But I’m in no rush.