When Laurie Voss (COO of npm, Inc.) goes to talk at coding bootcamps, people often ask him how did he get started in web development. Voss's answer is that he got started at the same time as web development. He was able to learn web development by having different web technologies accumulate around him.
Voss acknowledges that this strategy for learning doesn't really help a person starting a web development career in 2019. These days the world of web technologies is huge and it's complex. Even though the access to learning materials and the quality of developer tools have improved, it will take longer for beginner developers to comprehend the full capabilities of web now than it took 20 years ago.
You can look up to Voss as inspiration and you can learn from him. But you can't walk the same path as he did and expect to end up where he is now.
When HubSpot was founded in 2006, it was competing with 13 other marketing software products. In 2018, that same market consisted of over 6,000 products. HubSpot's CEO Brian Halligan knows this and says that the web will treat your startup differently than it treated HubSpot back in the day.
As a final piece of great non-advice, Hank Green (YouTube vlogger, entrepreneur, author, and co-creator of VidCon) says that the best way to get a large audience on YouTube is to start in 2007. That way you will have a somewhat established reputation when the masses arrive on the platform.
Voss, Halligan, and Green didn't get lucky. Things weren't easier for them. They still had to show up and do the work. They had to invest time on things and ideas that were unproven or contested.
We can continue to learn from the most influential people in our fields. But we also need to find people who are a little closer to where we are now.
We can continue to learn the fundamentals of the web and further improve our current skills. But we also need to open our eyes and observe what exactly is happening around us.