July 21, 2023

Knowing When to Stop

It’s been interesting to write the last few pieces on my personal site. Not only is the tone one that’s a little different from my norm, there’s no real purpose other than to…just…write. My objective goes no further than taking some thoughts out of my head, putting them on paper, and maybe making a little more sense of each as I do.

But without a clear finish line for these, what’s been interesting is that the hardest part hasn’t been writing each one, it’s been finishing each one.

It feels sort of like going for a run without a route or adding seasonings without a recipe or playing a game without a set of rules. Without a point on a map or finite list to check off or a rule for winning…

…where do you stop?

The thing that’s wandering around in the back of my head as I type this are careers. Some people want to become Director of Marketing. That’s their finish line. So if they can’t get promoted internally? Welp, it’s time to move on. Maybe at their new job they want to become CMO. That’s their new finish line. So seeing a gray-haired marketing executive above you with 10 years until retirement? Welp, maybe it’s time to move on. Or perhaps get better at product launches. So when a company decides to lock down their current lineup? Welp, maybe it’s time to move on.

Whether it’s the size of a company or the role or managing a team, there are lots of ways that a career can grow and evolve and change and progress. All of these things could represent finish lines to both work toward and, once passed, mark a moment when it’s time to not only pat yourself on the back, but also start a new path.

As I’ve written about, balancing practical needs with less-practical dreams has been a challenge as I’ve navigated my career.

And I wonder if maybe, just maybe, my efforts to feel content in my job have left me with very little to work toward and, like running or cooking or a new game, have put me in a place where I simply can’t see a clear finish line. A place where there isn’t a moment to put my hands on my knees for a moment, celebrate the journey, and ask:

That was fun, what’s next?

More Thoughts & Such

How do you check prospects’ websites for specific code, technology, and software?
April 30, 2024   Read this post →

How to Subscribe to Blogs / RSS Feeds via Email
February 16, 2024   Read this post →

A Little of Both
January 3, 2024   Read this post →

Put it On Paper
November 3, 2023   Read this post →

An Ode to Awe
October 16, 2023   Read this post →

Change Has to Be Sold
September 27, 2023   Read this post →

Knowing When to Stop
July 21, 2023   Read this post →

The Language of Uncertainty
July 21, 2023   Read this post →

July 7, 2023   Read this post →

Who am I? Who do I want to be?
June 29, 2023   Read this post →

Hi, I'm Gregg.

I'm a SaaS marketer and maker.


Never heard of me? All good, these days I don't chase influence as much as I do balance. By day I run marketing for Inntopia and evenings see me building SendView, but my happy place is playing in the mountains with my family.