Reflecting on my cloud career journey, I've realized that there are several things I would approach differently if I were to start again.

Firstly, I might have delayed diving into cloud technology. In the late 90s, I leapt into cloud computing when Application Service Providers (ASPs) were just emerging. While it was an exciting time, I would focus more on identifying and developing new and groundbreaking concepts.

Secondly, I would have been more cautious with high-risk opportunities, such as working for startups. I also allowed some business relationships to continue longer than they should have. In future endeavors, I'd aim to balance ambition with caution to mitigate risks.

Vetting business relationships more carefully would have been another priority. Ensuring that partnerships align with my values and objectives is crucial for long-term success.

In hindsight, I might have been less influenced by industry hype and crowds. Making decisions based on solid information rather than trends can prevent unnecessary distractions and setbacks.

Finally, I wouldn't allow myself to be pressured or bullied by industry expectations. Whether it's debates over microservices, cloud portability, or cost issues, I've learned to stand my ground for the benefit of my followers and clients, even if it risks my career. Prioritizing their needs over the interests of employers or cloud providers is something I believe in strongly today.