I think you and I spoke when I first left the agency world, right after you left Edelman. That was when I took the plunge and left what had been considered a stable gig for the world of start‑ups. It’s been about six years, and it has been anything but easy.
The hardest part—something I could never have predicted—was shedding the image of who I was and the mental models I used to approach work. I was no longer in the director’s seat, orchestrating within a system with well‑defined rules. I learned very quickly, as I descended into startup land, that my mental model for solving early‑stage problems was off by orders of magnitude. Swallowing that pill was tough: my ego was still back in the orchestration of launching vehicles around the globe, while reality was screaming, “We need product‑market fit, and you have to get us there alone because we’re not capitalized for a team.”
That was my crossing of the chasm, so to speak. I had to strip every initiative down to its irreducible core and rebuild it around the resources I actually had—my own time, skills, and readily available tools—instead of the team I wished I had.
In hindsight, it was the best decision of my life because it forced me to ask, “What can I accomplish without anyone else?” In the process, I returned to my roots of design and prototyping, pushing myself to build repeatable tools at every turn. It sounds cliché, but embracing the 10× mindset started the day I realized I had a choice: slog through the trough of despair and emerge an entrepreneur, or retreat to the comfort zone I once knew.
To my fellow Gen Xers—whether you’re being pushed down this path or can already see the new world taking shape—don’t fear change. Accept that it will be hard for a while, but remember: we’ve never before witnessed such a complete rewriting of the rules in our careers. The only real limit now is our imagination.
Thanks so much for sharing these incredible insights around your journey Dirk. That crossing of the chasm is so critical as is the stripping down of so many of the methods we used when we had vast teams and resources at our disposal. It’s like returning back to our early career years in some ways. Also, I appreciate that we’ve connected a few times during these post Covid years. Let’s do so again
We as a collective have been shaping what people have experienced digitally for the last 20 years because we were inventing alongside the technology. I think the gates are just dropping to shape the next wave.
This is spot on. I often discuss the invisible nature of Gen-X with my two sisters (all three are more senior Gen-X, our brother is "boomer.") I lead a small team, and half the team is older, there are two millennials, and I am on the cusp of hiring my first Gen-Z. It is interesting to see the differences in outlook and expectations across the range. Gen-X is the true "middle child" of the group. Often times invisible, under-rated, but should never be under-estimated.
Absolutely! And you are working in a true multi generational workforce! This is an area where I think GenX can be a huge asset and use our powers if invisibility for the benefit of the organization (and our teammates)!
Hey David,
I think you and I spoke when I first left the agency world, right after you left Edelman. That was when I took the plunge and left what had been considered a stable gig for the world of start‑ups. It’s been about six years, and it has been anything but easy.
The hardest part—something I could never have predicted—was shedding the image of who I was and the mental models I used to approach work. I was no longer in the director’s seat, orchestrating within a system with well‑defined rules. I learned very quickly, as I descended into startup land, that my mental model for solving early‑stage problems was off by orders of magnitude. Swallowing that pill was tough: my ego was still back in the orchestration of launching vehicles around the globe, while reality was screaming, “We need product‑market fit, and you have to get us there alone because we’re not capitalized for a team.”
That was my crossing of the chasm, so to speak. I had to strip every initiative down to its irreducible core and rebuild it around the resources I actually had—my own time, skills, and readily available tools—instead of the team I wished I had.
In hindsight, it was the best decision of my life because it forced me to ask, “What can I accomplish without anyone else?” In the process, I returned to my roots of design and prototyping, pushing myself to build repeatable tools at every turn. It sounds cliché, but embracing the 10× mindset started the day I realized I had a choice: slog through the trough of despair and emerge an entrepreneur, or retreat to the comfort zone I once knew.
To my fellow Gen Xers—whether you’re being pushed down this path or can already see the new world taking shape—don’t fear change. Accept that it will be hard for a while, but remember: we’ve never before witnessed such a complete rewriting of the rules in our careers. The only real limit now is our imagination.
Thanks so much for sharing these incredible insights around your journey Dirk. That crossing of the chasm is so critical as is the stripping down of so many of the methods we used when we had vast teams and resources at our disposal. It’s like returning back to our early career years in some ways. Also, I appreciate that we’ve connected a few times during these post Covid years. Let’s do so again
We as a collective have been shaping what people have experienced digitally for the last 20 years because we were inventing alongside the technology. I think the gates are just dropping to shape the next wave.
Lets do connect soon.
This is spot on. I often discuss the invisible nature of Gen-X with my two sisters (all three are more senior Gen-X, our brother is "boomer.") I lead a small team, and half the team is older, there are two millennials, and I am on the cusp of hiring my first Gen-Z. It is interesting to see the differences in outlook and expectations across the range. Gen-X is the true "middle child" of the group. Often times invisible, under-rated, but should never be under-estimated.
Absolutely! And you are working in a true multi generational workforce! This is an area where I think GenX can be a huge asset and use our powers if invisibility for the benefit of the organization (and our teammates)!
Wow…relate to this completely and living it. Great writing my friend
I see you!